114583
Pathway
Rhamnolipid Biosynthesis RL(14:1(3-OH,5Z)/6:0(3-OH))
Rhamnolipids (RL) consist of a fatty acyl moiety composed of a 3-(3-hydroxyalkanoyloxy)alkaloid acid (HAA) and a sugar moiety composed of one or two rhamnose sugars. Rhamnolipids function as surfactants and virulence factors and are involved in biofilm formation and cell motility. The rhamnose sugar component is produced via the dTDP-L-rhamnose biosynthetic pathway which forms dTDP-L-rhamnose from glucose 6-phosphate (G6P) in five steps. First, glucose 6-phosphate is converted into glucose 1-phosphate (G1P) via the enzyme phosphoglucomutase (AlgC). Second, glucose 1-phosphate is converted into dTDP-D-glucose via the enzyme glucose-1-phosphate thymidylyltransferase (RmlA). Third, dTDP-D-glucose is converted into dTDP-4-dehydro-6-deoxy-D-glucose via the enzyme dTDP-glucose 4,6-dehydratase (RmlB). Fourth, dTDP-4-dehydro-6-deoxy-D-glucose is converted into dTDP-4-dehydro-L-rhamnose via the enzyme dTDP-4-dehydrorhamnose 3,5-epimerase (RmlC). Fifth, dTDP-4-dehydro-L-rhamnose is converted into dTDP-L-rhamnose via the enzyme dTDP-4-dehydrorhamnose reductase (RmlD). The HAA component is synthesized from 3-hydroxyacyl-[acyl-carrier protein] diverted from fatty acid biosynthesis via the enzyme 3-(3-hydroxydecanoyloxy)decanoate synthase (RhIA). The final step in rhamnolipid biosynthesis is the formation of the glycosidic link between the rhamnose sugar component and the HAA component. This is accomplished by two rhamnosyltransferases (RhlB and RhlC) which catalyze sequential glycosyl transfer reactions to first form mono-rhamnolipids (via RhIB) and then di-rhamnolipids (via RhIC). RHlA, RHlB, and RHlC are associated with the inner membrane.
Metabolic
PW123743
Center
PathwayVisualizationContext124019
1200
3900
#000099
PathwayVisualization114446
114583
Rhamnolipid Biosynthesis RL(14:1(3-OH,5Z)/6:0(3-OH))
Rhamnolipids (RL) consist of a fatty acyl moiety composed of a 3-(3-hydroxyalkanoyloxy)alkaloid acid (HAA) and a sugar moiety composed of one or two rhamnose sugars. Rhamnolipids function as surfactants and virulence factors and are involved in biofilm formation and cell motility. The rhamnose sugar component is produced via the dTDP-L-rhamnose biosynthetic pathway which forms dTDP-L-rhamnose from glucose 6-phosphate (G6P) in five steps. First, glucose 6-phosphate is converted into glucose 1-phosphate (G1P) via the enzyme phosphoglucomutase (AlgC). Second, glucose 1-phosphate is converted into dTDP-D-glucose via the enzyme glucose-1-phosphate thymidylyltransferase (RmlA). Third, dTDP-D-glucose is converted into dTDP-4-dehydro-6-deoxy-D-glucose via the enzyme dTDP-glucose 4,6-dehydratase (RmlB). Fourth, dTDP-4-dehydro-6-deoxy-D-glucose is converted into dTDP-4-dehydro-L-rhamnose via the enzyme dTDP-4-dehydrorhamnose 3,5-epimerase (RmlC). Fifth, dTDP-4-dehydro-L-rhamnose is converted into dTDP-L-rhamnose via the enzyme dTDP-4-dehydrorhamnose reductase (RmlD). The HAA component is synthesized from 3-hydroxyacyl-[acyl-carrier protein] diverted from fatty acid biosynthesis via the enzyme 3-(3-hydroxydecanoyloxy)decanoate synthase (RhIA). The final step in rhamnolipid biosynthesis is the formation of the glycosidic link between the rhamnose sugar component and the HAA component. This is accomplished by two rhamnosyltransferases (RhlB and RhlC) which catalyze sequential glycosyl transfer reactions to first form mono-rhamnolipids (via RhIB) and then di-rhamnolipids (via RhIC). RHlA, RHlB, and RHlC are associated with the inner membrane.
Metabolic
23
112600
2233
SubPathway
112182
203
ElementCollection
316
335140
16160828
Soberon-Chavez G, Lepine F, Deziel E: Production of rhamnolipids by Pseudomonas aeruginosa. Appl Microbiol Biotechnol. 2005 Oct;68(6):718-25. doi: 10.1007/s00253-005-0150-3. Epub 2005 Oct 13.
114583
Pathway
335141
10521708
Deziel E, Lepine F, Dennie D, Boismenu D, Mamer OA, Villemur R: Liquid chromatography/mass spectrometry analysis of mixtures of rhamnolipids produced by Pseudomonas aeruginosa strain 57RP grown on mannitol or naphthalene. Biochim Biophys Acta. 1999 Sep 22;1440(2-3):244-52. doi: 10.1016/s1388-1981(99)00129-8.
114583
Pathway
335142
30919102
Gutierrez-Gomez U, Servin-Gonzalez L, Soberon-Chavez G: Role of beta-oxidation and de novo fatty acid synthesis in the production of rhamnolipids and polyhydroxyalkanoates by Pseudomonas aeruginosa. Appl Microbiol Biotechnol. 2019 May;103(9):3753-3760. doi: 10.1007/s00253-019-09734-x. Epub 2019 Mar 27.
114583
Pathway
335143
28599506
114583
Pathway
335144
18326581
114583
Pathway
1
Cell
CL:0000000
2
Platelet
CL:0000233
5
Hepatocyte
CL:0000182
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
7
Epithelial Cell
CL:0000066
1
Homo sapiens
9606
Eukaryote
Human
3
Escherichia coli
562
Prokaryote
12
Mus musculus
10090
Eukaryote
Mouse
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
2
Bacteria
2
Prokaryote
Bacteria
17
Rattus norvegicus
10116
Eukaryote
Rat
5
Bos taurus
9913
Eukaryote
Cattle
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
23
Pseudomonas aeruginosa
287
Prokaryote
19
Schizosaccharomyces pombe
4896
Eukaryote
25
Escherichia coli (strain K12)
83333
Prokaryote
5
Cytoplasm
GO:0005737
3
Mitochondrial Matrix
GO:0005759
1
Cytosol
GO:0005829
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
14
Mitochondrial Outer Membrane
GO:0005741
2
Mitochondrion
GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
25
Golgi apparatus
GO:0005794
10
Cell Membrane
GO:0005886
27
Peroxisome Membrane
GO:0005778
15
Nucleus
GO:0005634
26
Golgi apparatus membrane
GO:0000139
35
Chloroplast
GO:0009507
11
Extracellular Space
GO:0005615
12
Mitochondrial Inner Membrane
GO:0005743
34
Plant-Type Vacuole
GO:0000325
31
Periplasmic Space
GO:0005620
6
Lysosome
GO:0005764
16
Lysosomal Lumen
GO:0043202
18
Melanosome Membrane
GO:0033162
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
40
Periplasm
GO:0042597
19
sarcoplasmic reticulum
GO:0016529
24
Mitochondrial Intermembrane Space
GO:0005758
32
Inner Membrane
GO:0070258
33
Outer Membrane
GO:0043165
2
Endothelium
BTO:0000393
1
Liver
BTO:0000759
72
9
7
Nervous System
BTO:0001484
5
cardiocyte
BTO:0001539
8
Blood Vessel
BTO:0001102
74
11
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
28
Stomach
BTO:0001307
155
26
11
Heart
BTO:0000562
73
10
8
5
1
1
PW_BS000008
4
3
1
1
PW_BS000004
16
2
1
2
PW_BS000016
2
1
1
1
PW_BS000002
26
1
1
1
5
PW_BS000026
5
4
1
1
PW_BS000005
18
13
1
1
PW_BS000018
22
14
1
1
PW_BS000022
39
7
1
1
3
PW_BS000039
3
2
1
1
PW_BS000003
21
5
1
1
4
PW_BS000021
46
1
1
4
PW_BS000046
49
7
1
1
PW_BS000049
43
25
1
1
PW_BS000043
14
10
1
PW_BS000014
10
1
7
1
1
PW_BS000010
59
27
1
1
PW_BS000059
23
15
1
1
PW_BS000023
29
1
1
1
PW_BS000029
7
1
1
PW_BS000007
31
1
5
1
1
PW_BS000031
91
8
5
1
1
PW_BS000091
54
1
3
1
5
PW_BS000054
56
26
1
1
PW_BS000056
104
14
3
1
PW_BS000104
111
5
12
1
PW_BS000111
112
2
12
1
PW_BS000112
103
3
3
1
PW_BS000103
147
1
24
1
PW_BS000147
151
1
4
1
PW_BS000151
155
3
24
1
PW_BS000155
161
3
18
1
PW_BS000161
166
1
1
PW_BS000166
178
3
21
1
PW_BS000178
164
4
PW_BS000164
160
1
18
1
PW_BS000160
199
14
18
1
PW_BS000024
205
5
6
1
PW_BS000024
206
2
6
1
PW_BS000024
213
7
18
1
PW_BS000024
211
10
18
PW_BS000024
214
25
18
1
PW_BS000024
216
4
18
1
PW_BS000024
198
5
18
1
PW_BS000024
222
3
4
1
PW_BS000024
132
1
12
1
PW_BS000132
210
13
18
1
PW_BS000024
225
35
4
1
PW_BS000024
249
13
4
1
PW_BS000024
288
14
4
1
PW_BS000024
226
4
4
1
PW_BS000024
290
5
49
1
PW_BS000024
285
10
4
1
PW_BS000024
308
10
1
1
PW_BS000024
133
3
12
1
PW_BS000133
329
14
12
1
PW_BS000028
336
1
12
1
PW_BS000028
334
4
12
1
PW_BS000028
335
27
12
1
PW_BS000028
115
10
12
PW_BS000115
331
7
12
1
PW_BS000028
356
25
12
1
PW_BS000028
130
13
12
1
PW_BS000130
368
3
60
1
PW_BS000028
184
1
2
1
PW_BS000024
372
10
2
PW_BS000028
118
1
17
1
PW_BS000118
135
5
17
1
PW_BS000135
15
11
1
PW_BS000015
253
5
4
1
PW_BS000024
51
8
1
PW_BS000051
383
7
5
1
PW_BS000100
27
15
1
PW_BS000027
223
12
4
1
PW_BS000024
390
7
6
1
PW_BS000112
398
7
17
1
PW_BS000113
406
3
5
1
PW_BS000115
122
5
5
1
PW_BS000122
382
14
5
1
PW_BS000100
407
2
5
1
PW_BS000115
408
4
5
1
PW_BS000115
124
1
5
1
PW_BS000124
429
1
5
1
PW_BS000115
419
25
5
1
PW_BS000115
125
13
5
1
PW_BS000125
405
10
5
PW_BS000115
422
27
5
1
PW_BS000115
120
3
17
1
PW_BS000120
399
14
17
1
PW_BS000113
119
2
17
1
PW_BS000119
374
4
17
1
PW_BS000053
464
1
17
1
PW_BS000115
455
25
17
1
PW_BS000115
136
13
17
1
PW_BS000136
376
10
17
PW_BS000053
375
27
17
1
PW_BS000053
297
5
10
1
PW_BS000024
484
14
10
1
PW_BS000115
479
3
10
1
PW_BS000115
481
2
10
1
PW_BS000115
482
4
10
1
PW_BS000115
299
1
10
1
PW_BS000024
495
7
10
1
PW_BS000115
490
25
10
1
PW_BS000115
478
10
10
PW_BS000115
491
27
10
1
PW_BS000115
300
13
10
1
PW_BS000024
389
14
6
1
PW_BS000112
501
3
6
1
PW_BS000115
502
4
6
1
PW_BS000115
388
1
6
1
PW_BS000112
507
25
6
1
PW_BS000115
209
10
6
PW_BS000024
508
27
6
1
PW_BS000115
395
13
6
1
PW_BS000113
158
34
24
1
PW_BS000158
6
1
3
1
PW_BS000006
32
1
15
1
5
PW_BS000032
89
2
PW_BS000089
101
5
3
1
PW_BS000101
117
1
3
1
PW_BS000117
108
1
3
PW_BS000108
107
31
3
PW_BS000107
188
1
18
PW_BS000024
163
2
18
1
PW_BS000163
306
35
51
1
PW_BS000024
17
12
1
1
PW_BS000017
315
1
23
PW_BS000024
318
31
23
PW_BS000024
128
15
12
1
PW_BS000128
134
12
12
1
PW_BS000134
170
18
PW_BS000170
1
1
PW_BS000001
384
12
5
1
PW_BS000100
391
12
6
1
PW_BS000112
410
15
5
1
PW_BS000115
121
12
17
1
PW_BS000121
444
15
17
1
PW_BS000115
485
15
10
1
PW_BS000115
9
6
1
1
PW_BS000009
28
1
16
1
1
PW_BS000028
95
1
7
2
1
PW_BS000095
123
1
7
5
1
PW_BS000123
100
5
2
1
PW_BS000100
141
1
7
19
1
PW_BS000141
157
2
24
1
PW_BS000157
224
2
4
1
PW_BS000024
298
1
7
10
1
PW_BS000024
322
1
23
1
PW_BS000024
332
1
7
12
1
PW_BS000028
113
6
12
1
PW_BS000113
347
1
3
12
5
PW_BS000028
94
3
PW_BS000094
425
1
3
5
5
PW_BS000115
126
6
5
1
PW_BS000126
447
1
7
17
1
PW_BS000115
460
1
3
17
5
PW_BS000115
443
6
17
1
PW_BS000115
480
12
10
1
PW_BS000115
13
1
2
1
PW_BS000013
20
4
1
1
1
PW_BS000020
33
18
1
1
PW_BS000033
24
4
10
1
1
PW_BS000024
60
25
1
PW_BS000060
70
28
5
1
1
PW_BS000070
72
5
1
3
PW_BS000072
61
25
1
7
PW_BS000061
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
97
1
5
2
1
PW_BS000097
105
11
3
PW_BS000105
110
2
3
1
PW_BS000110
127
1
16
5
1
PW_BS000127
114
11
12
PW_BS000114
129
1
5
12
1
PW_BS000129
140
10
3
PW_BS000140
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
159
24
PW_BS000159
180
2
21
1
PW_BS000180
152
8
4
PW_BS000152
207
6
6
1
PW_BS000024
215
6
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
190
11
18
PW_BS000024
162
12
18
1
PW_BS000162
277
1
2
18
PW_BS000024
281
1
25
1
PW_BS000024
286
36
4
1
PW_BS000024
287
53
4
1
PW_BS000024
227
34
4
1
PW_BS000024
65
11
1
PW_BS000065
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
301
6
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
294
11
4
1
PW_BS000024
293
4
1
PW_BS000024
333
1
2
12
PW_BS000028
337
1
16
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
343
18
12
1
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
360
4
10
12
1
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
232
40
3
PW_BS000024
412
1
2
5
PW_BS000115
409
11
5
PW_BS000115
415
18
5
1
PW_BS000115
414
1
5
5
1
PW_BS000115
434
4
10
5
1
PW_BS000115
436
25
5
PW_BS000115
446
1
2
17
PW_BS000115
137
11
17
PW_BS000137
448
1
16
17
1
PW_BS000115
451
18
17
1
PW_BS000115
450
1
5
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
483
11
10
PW_BS000115
487
18
10
1
PW_BS000115
208
11
6
PW_BS000024
504
18
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
513
1
7
6
1
PW_BS000115
35
5
19
1
4
PW_BS000035
42
24
1
1
PW_BS000042
187
31
18
PW_BS000024
219
31
4
PW_BS000024
220
1
4
PW_BS000024
195
13
18
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
327
1
1
12
5
PW_BS000028
345
24
12
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
109
32
3
PW_BS000109
424
1
1
5
5
PW_BS000115
418
24
5
1
PW_BS000115
459
1
1
17
5
PW_BS000115
454
24
17
1
PW_BS000115
489
24
10
1
PW_BS000115
506
24
6
1
PW_BS000115
317
32
23
PW_BS000024
321
33
23
PW_BS000024
314
40
23
PW_BS000024
313
23
PW_BS000024
323
15
23
1
PW_BS000024
319
36
23
PW_BS000024
189
32
18
PW_BS000024
316
10
23
PW_BS000024
423
Magnesium
HMDB0000547
Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.
22537-22-0
C00305
888
18420
13-HYDROXY-MAGNESIUM-PROTOPORP
865
DB01378
[Mg++]
Mg
InChI=1S/Mg/q+2
JLVVSXFLKOJNIY-UHFFFAOYSA-N
magnesium(2+) ion
24.305
23.985041898
0
magnesium(2+) ion
2
2
FDB003518
Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+
PW_C000423
Mg2+
86
8
227
4
268
16
476
2
727
26
811
5
819
18
883
22
936
39
983
3
992
21
1167
46
1483
49
1529
43
1764
14
2124
10
2411
59
2942
23
3126
29
3373
7
4540
31
4774
91
4869
54
4974
56
5253
104
5329
111
5356
112
5376
103
5906
147
5934
151
6038
155
6094
161
6250
166
6484
178
6594
164
6881
160
6979
199
7170
205
7194
206
7227
213
7233
211
7250
214
7310
216
7313
198
7473
222
11763
132
11843
210
12312
225
12324
249
12513
288
12581
226
12729
290
15275
285
15337
308
77137
133
77236
329
77937
336
78393
334
78417
335
78489
115
78522
331
78536
356
78574
130
80020
368
80045
184
80048
372
80623
118
80654
135
80865
15
80965
253
81841
51
93832
383
94900
27
108596
223
110559
390
115687
398
119974
406
120070
122
120247
382
120702
407
120981
408
121181
124
121265
429
121319
419
121924
125
122086
405
122408
422
122759
120
122921
399
123307
119
123546
374
123835
464
123889
455
124477
136
124637
376
124978
375
125447
297
125598
484
125669
479
125777
481
125921
482
125947
299
125973
495
126000
490
126243
478
126553
491
126753
300
127125
389
127164
501
127380
502
127407
388
127451
507
127804
209
128125
508
128347
395
1083
Glucose 6-phosphate
HMDB0001401
Glucose 6 phosphate (alpha-D-glucose 6 phosphate or G6P) is the alpha-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Glucose 6 phosphate is an ester of glucose with phosphoric acid, made in the course of glucose metabolism by mammalian and other cells. It is a normal constituent of resting muscle and probably is in constant equilibrium with fructose-6-phosphate. (Stedman, 26th ed). Glucose-6-phosphate is a phosphorylated glucose molecule on carbon 6. When glucose enters a cell, it is immediately phosphorylated to G6P. This is catalyzed with hexokinase enzymes, thus consuming one ATP. A major reason for immediate phosphorylation of the glucose is so that it cannot diffuse out of the cell. The phosphorylation adds a charged group so the G6P cannot easily cross cell membranes. G6P can travel down two metabolic pathways, glycolysis and the pentose phosphate pathway. In addition to the metabolic pathways, G6P can also be stored as glycogen in the liver if blood glucose levels are high. If the body needs energy or carbon skeletons for syntheses, G6P can be isomerized to Fructose-6-phosphate and then phosphorylated to Fructose-1,6-bisphosphate. Note, the molecule now has 2 phosphoryl groups attached. The addition of the 2nd phosphoryl group is an irreversible step, so once this happens G6P will enter glycolysis and be turned into pyruvate (ATP production occurs). If blood glucose levels are high, the body needs a way to store the excess glucose. After being converted to G6P, phosphoglucose mutase (isomerase) can turn the molecule into glucose-1-phosphate. Glucose-1-phosphate can then be combined with uridine triphosphate (UTP) to form UDP-glucose. This reaction is driven by the hydrolysis of pyrophosphate that is released in the reaction. Now, the activated UDP-glucose can add to a growing glycogen molecule with the help of glycogen synthase. This is a very efficient storage mechanism for glucose since it costs the body only 1 ATP to store the 1 glucose molecule and virtually no energy to remove it from storage. It is important to note that glucose-6-phosphate is an allosteric activator of glycogen synthase, which makes sense because when the level of glucose is high the body should store the excess glucose as glycogen. On the other hand, glycogen synthase is inhibited when it is phosphorylated by protein kinase a during times of high stress or low blood glucose levels. -- Wikipedia.
56-73-5
C00092
5958
4170
GLC-6-P
5743
OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O
C6H13O9P
InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1
NBSCHQHZLSJFNQ-GASJEMHNSA-N
{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
260.1358
260.029718526
-0.92
6
glucose 6-phosphate
0
-2
FDB021818
D(+)-glucopyranose 6-phosphate;D-glucose 6-phosphate;D-glucose-6-dihydrogen phosphate;D-hexose 6-phosphate;Glucose 6-phosphate;Glucose-6-phosphate;Robison ester;A-d-glucose 6- phosphate;Alpha-d-glucose 6- phosphate;Alpha-d-glucose 6-phosphate;Alpha-d-hexose 6-phosphate;6-o-phosphono-d-glucopyranose;Glc6p;D-glucopyranose 6-phosphoric acid;D-glucose 6-phosphoric acid
PW_C001083
Gluc-6P
1118
8
1804
2
2381
18
3125
29
5898
147
5925
151
6065
158
6871
160
7403
198
11912
164
12577
225
77086
132
77936
336
77949
130
78164
111
120824
122
121172
124
121200
125
121264
429
123409
135
123744
118
123770
136
123834
464
125815
297
125938
299
127267
205
127398
388
1207
Glucose 1-phosphate
HMDB0001586
The direct product of the reaction in which glycogen phosphorylase cleaves off a molecule of glucose from a greater glycogen structure. It cannot travel down many metabolic pathways and must be interconverted by the enzyme phosphoglucomutase in order to become glucose 6-phosphate. Free glucose 1-phosphate can also react with UTP to form UDP-glucose. It can then return to the greater glycogen structure via glycogen synthase.
59-56-3
C00103
439165
16077
GLC-1-P
388311
OC[C@H]1OC(OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O
C6H13O9P
InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1
HXXFSFRBOHSIMQ-GASJEMHNSA-N
{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
260.1358
260.029718526
-0.91
6
glucose 1-phosphate
0
-2
FDB021830
Cori ester;D-glucopyranose 1-phosphate;D-glucose 1-phosphate;D-glucose-1-p;D-glucose-1-phosphate;Glucose 1-phosphate;Glucose monophosphate;Glucose-1-phosphate;Glucose-1p;A-d-glucopyranosyl phosphate;A-d-glucose 1-phosphate;Alpha-d-glucopyranosyl phosphate;Alpha-d-glucose 1-phosphate;Alpha-d-glucose-1-phosphate;Alpha-delta-glucopyranosyl phosphate;Alpha-delta-glucose 1-phosphate;Alpha-delta-glucose-1-phosphate;Delta-glucopyranose 1-phosphate;Delta-glucose 1-phosphate;Delta-glucose-1-p;Delta-glucose-1-phosphate;1-o-phosphono-d-glucopyranose;Glc-1-p;D-glucopyranose 1-phosphoric acid;D-glucose 1-phosphoric acid
PW_C001207
Gluc1P
1120
8
1505
2
3117
29
5690
6
5909
147
5939
151
6887
160
12576
225
77101
132
77926
336
78401
111
120826
122
121186
124
121254
429
123411
135
123757
118
123824
464
125817
297
125953
299
127269
205
127412
388
1035
Thymidine 5'-triphosphate
HMDB0001342
"Thymidine 5-triphosphate, also known as TTP or DTHD5'ppp, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. Thymidine 5-triphosphate is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Within the cell, thymidine 5-triphosphate is primarily located in the mitochondria, nucleus and cytoplasm. Thymidine 5-triphosphate exists in all living organisms, ranging from bacteria to humans. In humans, thymidine 5-triphosphate is involved in the pyrimidine metabolism pathway. Thymidine 5-triphosphate is also involved in several metabolic disorders, some of which include Beta ureidopropionase deficiency, the mngie (mitochondrial neurogastrointestinal encephalopathy) pathway, UMP synthase deficiency (orotic aciduria), and dihydropyrimidinase deficiency. Outside of the human body, thymidine 5-triphosphate can be found in a number of food items such as nopal, saskatoon berry, grass pea, and sourdock. This makes thymidine 5-triphosphate a potential biomarker for the consumption of these food products. Thymidine 5-triphosphate or TTP is one of the four nucleoside triphosphates that make up DNA. It can be used by DNA ligase to create overlapping ""sticky ends"" so that protruding ends of opened microbial plasmids maybe closed up."
365-08-2
C00459
64968
18077
TTP
58493
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O
C10H17N2O14P3
InChI=1S/C10H17N2O14P3/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(24-8)4-23-28(19,20)26-29(21,22)25-27(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,21,22)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1
NHVNXKFIZYSCEB-XLPZGREQSA-N
{[hydroxy({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid
482.1683
481.989262798
-1.79
6
dTTP
0
-3
FDB022565
2'-deoxythymidine 5'-triphosphate;2'-deoxythymidine triphosphate;5'-ttp;5-methyl-dutp;Deoxy-ttp;Deoxythymidine 5'-triphosphate;Deoxythymidine triphosphate;Ttp;Thymidine 5'-triphosphate;Thymidine mono(tetrahydrogen triphosphate);Thymidine triphosphate;Dttp;Dthd5'ppp;Pppdt;Thymidine-5'-triphosphate;2'-deoxythymidine triphosphoric acid
PW_C001035
Tm5TP
2771
2
12760
151
78750
132
122240
124
124793
118
126403
299
127966
388
1024
dTDP-D-glucose
HMDB0001328
Deoxythymidine diphosphate-glucose is an intermediate in the nucleotide sugar metabolism pathway (KEGG). It is a substrate for the enzyme dTDP-D-glucose 4,6-dehydratase which catalyzes the reaction: dTDP-glucose = dTDP-4-dehydro-6-deoxy-D-glucose + H2O.
2196-62-5
C00842
439324
35248
DTDP-D-GLUCOSE
388455
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O2)C(=O)NC1=O
C16H26N2O16P2
InChI=1S/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/t7-,8+,9+,10+,11+,12-,13+,15?/m0/s1
YSYKRGRSMLTJNL-KFQCIAAJSA-N
{[hydroxy({[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy}({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid
564.329
564.075755818
-1.70
8
dtdp-D-glucose
0
-2
FDB022557
Dtdpglucose;Mono-a-d-glucopyranosyl ester;Mono-alpha-d-glucopyranosyl ester;Mono-alpha-delta-glucopyranosyl ester;Tdp-d-glucose;Tdp-glc;Tdp-delta-glucose;Tdpg;Thymidine 5-diphosphate-d-glucose;Thymidine 5-diphosphate-delta-glucose;Dtdp-d-glucose;Dtdp-glucose;Dtdp-delta-glucose
PW_C001024
dTDPDG
170
Pyrophosphate
HMDB0000250
The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.
14000-31-8
C00013
644102
18361
PPI
559142
DB04160
[O-]P([O-])(=O)OP([O-])([O-])=O
O7P2
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4
XPPKVPWEQAFLFU-UHFFFAOYSA-J
(phosphonooxy)phosphonic acid
173.9433
173.911925378
4
pyrophosphoric acid
0
-3
FDB021918
(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ion
PW_C000170
Ppi
12
2
35
4
63
8
429
23
735
32
882
22
1217
3
1620
49
2410
59
2815
29
4175
14
4868
54
5034
89
5252
104
5294
101
5409
117
5424
103
5433
118
5458
120
5548
111
5559
132
5584
133
5606
135
5655
108
5879
107
6239
166
6978
199
7073
188
7134
163
7272
160
7312
198
7318
213
8275
151
8283
210
11869
161
12002
222
12041
164
12315
225
12323
249
12512
288
12579
226
12695
290
15219
306
15375
18
34760
17
42561
315
42697
318
77235
329
77317
128
77635
336
78416
335
78928
331
79153
112
79950
134
79958
130
80047
372
80417
170
85630
1
94786
384
94814
125
94819
382
98678
223
110634
391
113270
395
113275
389
115527
136
115532
399
119934
122
120017
124
120032
406
120330
410
120936
407
121261
429
121341
121
121486
383
122407
422
122985
444
123502
119
123831
464
124044
398
124977
375
125324
297
125395
299
125410
479
125597
484
125656
485
125876
481
126552
491
126869
205
126935
388
126950
501
127337
206
128124
508
721
NAD
HMDB0000902
NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).
53-84-9
C00003
5893
15846
NAD
5682
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H28N7O14P2
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
664.433
664.116946663
-2.59
8
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-1
FDB022309
3-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nad
PW_C000721
NAD
140
4
150
3
353
8
651
10
1114
2
1134
43
1273
5
1466
54
2229
49
2779
17
2835
29
3107
9
4807
18
4813
18
4819
28
4902
6
4960
31
5167
95
5238
103
5334
111
5360
112
5469
123
5482
125
5590
135
5610
118
5696
100
5738
108
5827
141
5912
147
5942
151
6024
155
6072
157
6076
161
6385
1
6469
178
6772
117
6890
160
7012
188
7097
163
7174
205
7197
206
7405
198
7459
222
8241
226
8359
225
9085
224
11819
216
12322
249
13006
298
13018
300
13256
223
42404
322
42619
315
77104
132
77120
133
77209
134
77370
331
77650
336
77667
334
77702
332
77709
130
77915
113
77983
347
78406
356
80006
368
80690
119
93825
124
110552
388
112750
166
112853
94
119929
122
119952
406
120171
407
120834
419
120984
408
121159
425
121242
126
121259
429
121817
383
122614
384
122742
120
123130
447
123141
136
123419
455
123549
374
123731
460
123812
443
123829
464
124370
398
125187
121
125319
297
125342
479
125530
481
125806
299
125825
490
125924
482
126515
495
126765
480
126885
501
127278
507
127383
502
128089
390
128360
391
128428
395
42658
dTDP-4-dehydro-6-deoxy-D-glucose
HMDB0060081
dTDP-4-Dehydro-6-deoxy-alpha-D-glucose, also known as dTDP-4-dehydro-6-deoxy-D-galactose or dTDP-6-deoxy-D-xylo-4-hexulose, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. dTDP-4-Dehydro-6-deoxy-alpha-D-glucose is soluble (in water) and a moderately acidic compound (based on its pKa). dTDP-4-Dehydro-6-deoxy-alpha-D-glucose can be biosynthesized from dTDP-D-glucose. Outside of the human body, dTDP-4-dehydro-6-deoxy-alpha-D-glucose can be found in a number of food items such as ohelo berry, kelp, almond, and silver linden. This makes dTDP-4-dehydro-6-deoxy-alpha-D-glucose a potential biomarker for the consumption of these food products.
C[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@@H](O)C1=O
C16H24N2O15P2
InChI=1S/C16H24N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-10,12-13,15,19,21-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8+,9-,10-,12+,13-,15-/m1/s1
PSXWNITXWWECNY-UCBTUHGZSA-N
{[(2R,3R,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid
546.3137
546.065191132
-1.68
6
[(2R,3R,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy({hydroxy[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methoxyphosphoryl}oxy)phosphinic acid
0
-2
PW_C042658
D4D6DDG
1420
Water
HMDB0002111
Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).
7732-18-5
C00001
962
15377
937
O
H2O
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
18.0153
18.010564686
1
water
0
0
FDB013390
Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;Wasser
PW_C001420
H2O
55
8
94
9
109
5
139
4
151
3
162
14
481
13
526
15
624
28
652
10
691
20
770
33
823
18
838
2
1094
31
1377
49
1465
54
1590
43
2018
24
2532
22
2678
60
2727
46
2778
17
2805
29
3143
70
3164
72
3634
61
4598
36
4727
37
4941
93
5030
27
5156
7
5195
97
5214
100
5227
94
5236
103
5297
105
5319
111
5343
113
5355
112
5402
110
5470
123
5483
125
5492
126
5507
127
5534
130
5537
114
5541
129
5591
135
5608
118
5622
108
5691
6
5759
140
5778
101
5841
143
5853
146
5877
107
5890
95
5910
147
5940
151
6032
155
6059
157
6087
161
6123
163
6133
159
6215
1
6218
166
6477
178
6507
180
6600
152
6713
117
6840
188
6888
160
7162
205
7181
207
7193
206
7211
211
7228
213
7238
214
7243
215
7295
198
7350
216
7388
210
7401
212
7467
222
7492
224
7500
190
7588
170
8201
225
8237
226
8414
162
9265
26
11850
277
11922
164
12011
281
12213
285
12250
286
12264
287
12327
249
12520
227
12632
65
12693
290
12705
291
12715
292
13007
298
13019
300
13025
301
13037
302
13261
223
13327
294
15340
308
42327
315
42695
318
43691
322
76914
293
77019
253
77102
132
77131
133
77215
134
77378
331
77397
332
77471
333
77516
115
77536
334
77628
336
77722
337
77759
341
77816
343
77982
347
78071
329
78235
352
78242
353
78270
356
79113
360
80014
368
80039
370
80591
228
80656
119
93830
383
94794
384
110557
390
110639
391
115844
398
119879
232
119915
122
119963
406
120008
407
120046
408
120113
124
120365
412
120430
405
120438
409
120606
415
120794
414
121158
425
121240
429
121351
121
121381
419
121607
434
122118
382
122384
436
122753
120
122797
374
122804
443
123012
446
123064
376
123072
137
123131
447
123142
136
123162
448
123231
451
123384
450
123730
460
123810
464
123940
455
124165
469
124670
399
124938
471
124945
472
125305
297
125353
479
125386
481
125424
482
125480
299
125682
483
125707
478
125745
487
126054
490
126238
495
126273
484
126764
480
126896
501
126963
502
127017
388
127177
208
127199
209
127227
504
127506
507
127576
515
127836
389
128082
395
128176
513
44520
dTDP-4-dehydro-β-L-rhamnose
dTDP-4-Dehydro-beta-L-rhamnose, also known as dTDP-4-oxo-6-deoxy-L-mannose or dTDP-4-oxo-L-rhamnose, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. dTDP-4-Dehydro-beta-L-rhamnose is soluble (in water) and a moderately acidic compound (based on its pKa). Outside of the human body, dTDP-4-dehydro-beta-L-rhamnose can be found in a number of food items such as chickpea, pepper (c. pubescens), gram bean, and bayberry. This makes dTDP-4-dehydro-beta-L-rhamnose a potential biomarker for the consumption of these food products. A dTDP-sugar having 4-dehydro-β-L-rhamnose as the sugar component. It is an intermediate in dTDP-rhamnose biosynthesis.
C00688
45868
C[C@@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@H](O)C1=O
C16H24N2O15P2
InChI=1S/C16H24N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-10,12-13,15,19,21-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8-,9+,10+,12+,13+,15+/m0/s1
PSXWNITXWWECNY-LPVGZGSHSA-N
{[(2R,3R,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid
546.3137
546.065191132
-1.68
6
dtdp-4-keto-L-rhamnose
0
-2
dTDP-4-dehydro-beta-L-rhamnose;dTDP-4-dehydro-6-deoxy-beta-L-mannose;dTDP-4-oxo-6-deoxy-L-mannose;dTDP-4-oxo-L-rhamnose
PW_C044520
D4DβLR
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1
ACFIXJIJDZMPPO-NCHANQSKSA-N
{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
745.4209
745.091102105
-2.14
9
[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
0
-4
FDB021909
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reduced
PW_C000146
NADPH
185
8
190
3
778
10
796
5
821
18
837
2
1609
29
1615
49
4687
31
4793
14
4797
14
5310
111
5789
108
5972
147
6128
159
6271
35
6779
117
7068
188
7103
163
7154
205
7205
160
7315
213
7345
210
7559
212
7591
170
8194
225
8219
151
8421
224
11812
198
11893
211
12006
222
12150
164
12245
286
12596
226
12648
249
42343
315
43746
322
76911
293
77166
132
77385
331
77394
332
77460
130
77504
112
77511
115
77623
336
80712
119
113164
94
120105
407
120425
405
120452
122
120616
123
121141
125
121275
429
121402
124
121483
383
123059
376
123086
135
123241
447
123712
136
123846
464
123961
118
124041
398
125472
481
125696
297
126214
299
126529
495
127009
206
127572
388
128101
390
40034
Hydrogen Ion
HMDB0059597
Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])
C00080
1038
15378
1010
[H+]
H
InChI=1S/p+1
GPRLSGONYQIRFK-UHFFFAOYSA-N
hydron
1.0079
1.007825032
0
hydron
1
0
H+;H(+);Hydrogen cation;Hydron;Proton
PW_C040034
H+
215
4
670
8
753
15
788
31
848
3
1116
2
1463
26
1464
54
2231
49
2780
17
4250
22
4254
42
4547
10
4576
18
4694
70
5241
103
5327
111
5353
112
5626
108
5639
107
5699
100
5720
105
5742
117
5963
147
6037
155
6070
157
6093
161
6130
159
6232
166
6483
178
6601
152
6692
101
6843
188
6910
187
7100
163
7168
205
7191
206
7453
219
7454
220
7472
222
7525
213
7532
210
7558
212
7572
160
7590
170
8195
225
8218
151
8243
226
8413
162
8420
224
9139
195
9155
249
11915
164
12015
281
12181
285
12246
286
12266
287
12521
227
13257
223
13325
294
15330
308
42329
315
42354
318
42401
322
42405
312
42454
320
76912
293
77136
133
77210
134
77372
331
77804
114
77955
132
77990
327
77991
347
78379
345
79929
130
80019
368
80387
310
80388
304
80722
119
93823
124
94823
383
110550
388
112855
94
113280
390
115537
398
115539
118
115856
336
116205
109
119973
406
120193
407
120549
122
120593
409
121170
424
121171
425
122569
418
122615
384
122687
125
122758
120
123183
135
123218
137
123742
459
123743
460
125141
454
125188
121
125273
136
125359
479
125550
481
125730
483
125736
297
125809
299
126517
495
126717
489
126766
480
126823
300
126902
501
127213
208
128308
506
128361
391
128430
395
143
NADP
HMDB0000217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O17P3
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
744.4129
744.083277073
-2.27
9
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-3
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
2734
dTDP-β-L-rhamnose
HMDB0006354
Deoxythymidine diphosphate (dTDP)-l-rhamnose is the precursor of l-rhamnose, a saccharide required for the virulence of some pathogenic bacteria. In gram negative bacteria such as Salmonella enterica, Vibrio cholerae or Escherichia coli 075:K5, l-rhamnose is an important residue in the O-antigen of lipopolysaccharides, which are essential for resistance to serum killing and for colonization. In gram positive bacteria, such as streptococci, the capsule is a recognized virulence factor, for example, l-rhamnose is known to be present in the capsule of Streptococcus suis, a causative agent of meningitis in humans. In Streptococcus mutans, l-rhamnose containing polysaccharides have been implicated in tooth surface colonization and adherence to kidney, muscle and heart tissues. In mycobacteria, l-rhamnose is fundamental to the structural integrity of the cell wall since it connects the inner peptidoglycan layer to the arabinogalactan polysaccharides. dTDP-l-rhamnose is synthesized from glucose-1-phosphate and deoxythymidine triphosphate (dTTP) via a pathway involving four distinct enzymes. Whereas common sugars such as glucose, fructose and mannose are all D-configured, bacteria commonly utilize the L-configured carbohydrates in pharmacologically active compounds and in their cell-wall structures. The bacterial cell wall is unique to bacteria; neither the cell wall nor the enzymes and chemical intermediates in its formation have analogues in humans. The enzymes involved in dTDP-l-rhamnose synthesis are potential targets for the design of new therapeutic agents. (PMID: 10802738, 12773151).
2147-59-3
C03319
439975
35452
DTDP-RHAMNOSE
388998
C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@H](O)[C@H]1O
C16H26N2O15P2
InChI=1S/C16H26N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-13,15,19-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8-,9+,10+,11-,12+,13+,15?/m0/s1
ZOSQFDVXNQFKBY-CZRCVJRHSA-N
{[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid
548.3296
548.080841196
-1.68
7
dtdp-L-rhamnose
0
-2
FDB023902
Deoxythymidine diphosphate-L-rhamnose;Thymidine diphosphate rhamnose;Thymidine diphosphate-l-rhamnose;Dtdp-6-deoxy-l-mannose;Dtdp-l-rhamnose;Thymidine 5'-(trihydrogen diphosphate), p'-(6-deoxy-beta-l-mannopyranosyl) ester;Thymidine 5'-(trihydrogen diphosphate), p'-(6-deoxy-b-l-mannopyranosyl) ester;Thymidine 5'-(trihydrogen diphosphate), p'-(6-deoxy-β-l-mannopyranosyl) ester;Thymidine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-b-l-mannopyranosyl) ester;Thymidine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-beta-l-mannopyranosyl) ester;Thymidine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-β-l-mannopyranosyl) ester
PW_C002734
dtDP-Rh
108440
HAA(14:1(3-OH,5Z)/6:0(3-OH))
HAA(14:1(3-OH,5Z)/6:0(3-OH)) belongs to the class of compounds known as 3-(3-hydroxyalkanoyloxy)alkanoic acids (HAAs). HAAs consist of two 3-hydroxy fatty acids of varying length linked to each other via the carboxyl group of the first chain and the beta-hydroxyl group of the second chain. HAAs are the precursors of rhamnolipids. HAA(14:1(3-OH,5Z)/6:0(3-OH)), in particlular, is composed of one chain of 3-hydroxy-5Z-tetradecenoic acid linked to the beta-hydroxyl group of 3-hydroxyhexanoic acid.
3-3-HAAs
CCCCCCCC\C=C/C[C@@H](O)CC(=O)O[C@H](CCC)CC(O)=O
C20H36O5
InChI=1S/C20H36O5/c1-3-5-6-7-8-9-10-11-12-14-17(21)15-20(24)25-18(13-4-2)16-19(22)23/h11-12,17-18,21H,3-10,13-16H2,1-2H3,(H,22,23)/b12-11-/t17-,18-/m1/s1
VOFMRINYAJRIPQ-SKFQIZJUSA-N
(3R)-3-{[(3R,5Z)-3-hydroxytetradec-5-enoyl]oxy}hexanoic acid
356.503
356.256274259
-4.55
2
(3R)-3-{[(3R,5Z)-3-hydroxytetradec-5-enoyl]oxy}hexanoic acid
0
-1
HAA(14:1(3-OH,5Z)/6:0(3-OH));HAA(14:1/6:0);HAA(14:1n9/6:0);HAA(14:1w9/6:0);HAA(20:1);C14:1-C6;3-(3-Hydroxy-5Z-tetradecenoyloxy)hexanoic acid;(R-R)-3-(3-Hydroxy-5Z-tetradecenoyloxy)hexanoic acid;3-(3-Hydroxyalkanoyloxy)alkanoic acid;3-(3-Hydroxyalkanoyloxy)alkanoate;HAA
PW_C108440
108521
monoRL(14:1(3-OH,5Z)/6:0(3-OH))
monoRL(14:1(3-OH,5Z)/6:0(3-OH)) belongs to the class of compounds known as monorhamnolipids (monoRLs). The monorhamnolipids is one of two main classes of rhamnolipids and consists of a fatty acyl moiety composed of a 3-(3-hydroxyalkanoyloxy)alkaloid acid (HAA) and a sugar moiety composed of one rhamnose sugar. The other class of rhamnolipids, the dirhamnolipids, have a sugar moiety composed of two rhamnose sugars. Rhamnolipids (RL) function as surfactants and virulence factors and are involved in biofilm formation and cell motility. monoRL(14:1(3-OH,5Z)/6:0(3-OH)), in particular, is composed of one rhamnose sugar linked to to the beta-hydroxyl group of 3-hydroxy-5Z-tetradecenoic acid whose carboxyl group is linked to the beta-hydroxyl group of 3-hydroxyhexanoic acid.
Mono-Rhamnolipids
[H][C@@]1(O[C@H](C\C=C/CCCCCCCC)CC(=O)O[C@H](CCC)CC(O)=O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
C26H46O9
InChI=1S/C26H46O9/c1-4-6-7-8-9-10-11-12-13-15-20(17-22(29)34-19(14-5-2)16-21(27)28)35-26-25(32)24(31)23(30)18(3)33-26/h12-13,18-20,23-26,30-32H,4-11,14-17H2,1-3H3,(H,27,28)/b13-12-/t18-,19+,20+,23-,24+,25+,26-/m0/s1
HPRSPHNLKRKXRE-OEJJHEJXSA-N
(3R)-3-{[(3R,5Z)-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetradec-5-enoyl]oxy}hexanoic acid
502.645
502.314183061
-3.73
4
(3R)-3-{[(3R,5Z)-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetradec-5-enoyl]oxy}hexanoic acid
0
-1
monoRL(14:1(3-OH,5Z)/6:0(3-OH));monoRL(14:1/6:0);monoRL(14:1n9/6:0);monoRL(14:1w9/6:0);monoRL(20:1);Rha-C14:1-C6;L-Rhamnosyl-3-hydroxyhexanoyl-3-hydroxyhexanoic acid;Rhamnosyl-β-hydroxyhexanoyl-β-hydroxyhexanoic acid;Rhamnosyl-beta-hydroxyhexanoyl-beta-hydroxyhexanoic acid;Monorhamnolipid;Mono-rhamnolipid;monoRL
PW_C108521
987
dTDP
HMDB0001274
dTDP, also known as deoxy-tdp, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside diphosphates. These are pyrimidine nucleotides with a diphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. dTDP is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, dTDP is primarily located in the mitochondria, nucleus and cytoplasm. dTDP exists in all living organisms, ranging from bacteria to humans. dTDP participates in a number of enzymatic reactions. In particular, dTDP can be converted into thymidine 5'-triphosphate; which is mediated by the enzyme nucleoside diphosphate kinase. Furthermore, dTDP and undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate can be biosynthesized from undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate and TDP-fuc4nac; which is mediated by the enzyme 4-acetamido-4,6-dideoxy-D-galactose transferase. Finally, dTDP and undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate can be biosynthesized from undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate and TDP-fuc4nac through its interaction with the enzyme 4-acetamido-4,6-dideoxy-D-galactose transferase. In humans, dTDP is involved in the pyrimidine metabolism pathway. dTDP is also involved in several metabolic disorders, some of which include Beta ureidopropionase deficiency, UMP synthase deficiency (orotic aciduria), dihydropyrimidinase deficiency, and the mngie (mitochondrial neurogastrointestinal encephalopathy) pathway. Is an intermediate in the Thymidylate kinase (EC 2.7.4.9; ATP:dTMP phosphotransferase) catalyzes the phosphorylation of dTMP (to form dTDP) in the dTTP synthesis pathway for DNA synthesis. (OMIM 188345 )
491-97-4
C00363
164628
18075
TDP
144320
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O
C10H16N2O11P2
InChI=1S/C10H16N2O11P2/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(22-8)4-21-25(19,20)23-24(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1
UJLXYODCHAELLY-XLPZGREQSA-N
{[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}phosphonic acid
402.1884
402.022932388
-1.76
5
dTDP
0
-2
FDB022528
Deoxy-tdp;Deoxythymidine 5'-diphosphate;Tdp;Thymidine 5'-diphosphate;Thymidine 5'-pyrophosphate;Dtdp;2'-deoxyribosylthymine 5'-(trihydrogen diphosphate);Thymidine-5'- diphosphate;2'-deoxyribosylthymine 5'-(trihydrogen diphosphoric acid)
PW_C000987
dTDP
2770
2
12759
151
78749
132
122239
124
124792
118
126402
299
127965
388
108602
diRL(14:1(3-OH,5Z)/6:0(3-OH))
diRL(14:1(3-OH,5Z)/6:0(3-OH)) belongs to the class of compounds known as dirhamnolipids (diRLs). The dirhamnolipids is one of two main classes of rhamnolipids and consists of a fatty acyl moiety composed of a 3-(3-hydroxyalkanoyloxy)alkaloid acid (HAA) and a sugar moiety composed of two rhamnose sugars. The other class of rhamnolipids, the monorhamnolipids, have a sugar moiety composed of one rhamnose sugar. Rhamnolipids (RL) function as surfactants and virulence factors and are involved in biofilm formation and cell motility. diRL(14:1(3-OH,5Z)/6:0(3-OH)), in particular, is composed of two rhamnose sugars linked to to the beta-hydroxyl group of 3-hydroxy-5Z-tetradecenoic acid whose carboxyl group is linked to the beta-hydroxyl group of 3-hydroxyhexanoic acid.
Di-Rhamnolipids
[H][C@@]1(O[C@@H]2[C@H](O)[C@@H](O)[C@H](C)O[C@@]2([H])O[C@H](C\C=C/CCCCCCCC)CC(=O)O[C@H](CCC)CC(O)=O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
C32H56O13
InChI=1S/C32H56O13/c1-5-7-8-9-10-11-12-13-14-16-22(18-24(35)43-21(15-6-2)17-23(33)34)44-32-30(28(39)26(37)20(4)42-32)45-31-29(40)27(38)25(36)19(3)41-31/h13-14,19-22,25-32,36-40H,5-12,15-18H2,1-4H3,(H,33,34)/b14-13-/t19-,20-,21+,22+,25-,26-,27+,28+,29+,30+,31-,32-/m0/s1
VDDIRRLFDRNWOU-SMPQSQOUSA-N
(3R)-3-{[(3R,5Z)-3-{[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}tetradec-5-enoyl]oxy}hexanoic acid
648.787
648.372091863
-3.53
6
(3R)-3-{[(3R,5Z)-3-{[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}tetradec-5-enoyl]oxy}hexanoic acid
0
-1
diRL(14:1(3-OH,5Z)/6:0(3-OH));diRL(14:1/6:0);diRL(14:1n9/6:0);diRL(14:1w9/6:0);diRL(20:1);Rha-Rha-C14:1-C6;L-Rhamnosyl-L-rhamnosyl-3-hydroxyhexanoyl-3-hydroxyhexanoic acid;Rhamnosyl-rhamnosyl-β-hydroxyhexanoyl-β-hydroxyhexanoic acid;Rhamnosyl-rhamnosyl-beta-hydroxyhexanoyl-beta-hydroxyhexanoic acid;Dirhamnolipid;Di-rhamnolipid;diRL
PW_C108602
203
(3R)-3-Hydroxyacyl-[acyl-carrier protein]
ProteinComplex
ProteinComplex
PW_EC000203
C01271
KEGG Compound
33HACP
518
[Acyl-carrier protein]
ProteinComplex
ProteinComplex
PW_EC000518
C00229
KEGG Compound
[ACP]
23139
Phosphomannomutase/phosphoglucomutase
P26276
Highly reversible phosphoryltransferase. The phosphomannomutase activity produces a precursor for alginate polymerization, the alginate layer causes a mucoid phenotype and provides a protective barrier against host immune defenses and antibiotics. Also involved in core lipopolysaccaride (LPS) biosynthesis due to its phosphoglucomutase activity. Essential for rhamnolipid production, an exoproduct correlated with pathogenicity (PubMed:10481091). Required for biofilm production. The reaction proceeds via 2 processive phosphoryl transferase reactions; first from enzyme-phospho-Ser-108 to the substrate (generating a bisphosphorylated substrate intermediate and a dephosphorylated enzyme), a 180 degree rotation of the intermediate (probably aided by movement of domain 4), and subsequent transfer of phosphate back to the enzyme (PubMed:11716469, PubMed:16880541, PubMed:16595672, PubMed:22242625).
algC
23
5.4.2.2;5.4.2.8
137990
312
23148
Glucose-1-phosphate thymidylyltransferase
Q9HU22
Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis.
rmlA
23
2.7.7.24
137991
312
23149
dTDP-glucose 4,6-dehydratase
Q9HU24
rmlB
23
4.2.1.46
137977
312
23150
dTDP-4-dehydrorhamnose 3,5-epimerase
Q9HU21
Catalyzes the epimerization of the C3' and C5'positions of dTDP-6-deoxy-D-xylo-4-hexulose, forming dTDP-6-deoxy-L-lyxo-4-hexulose.
rmlC
23
5.1.3.13
137992
312
23153
dTDP-4-dehydrorhamnose reductase
Q9HU23
Catalyzes the reduction of dTDP-6-deoxy-L-lyxo-4-hexulose to yield dTDP-L-rhamnose.
rmlD
23
1.1.1.133
137978
312
137979
317
137980
321
137981
198
137982
211
137983
314
137984
313
137985
323
137986
315
137987
319
137988
322
137989
23
23155
3-(3-Hydroxydecanoyloxy)decanoate synthase
Q51559
Required for rhamnolipid surfactant production (PubMed:15126453). Supplies the acyl moieties for rhamnolipid biosynthesis by competing with the enzymes of the type II fatty acid synthase (FASII) cycle for the beta-hydroxyacyl-acyl carrier protein (ACP) pathway intermediates. Catalyzes the formation of one molecule of beta-hydroxydecanoyl-beta-hydroxydecanoate from two molecules of beta-hydroxydecanoyl-ACP. Is the only enzyme required to generate the lipid component of rhamnolipid. In vitro results establish that RhlA is highly selective for 10-carbon acyl-ACP intermediates and thus functions as the molecular ruler that controls the acyl chain composition of rhamnolipids. Cannot use beta-hydroxydecanoyl-CoA as substrate (PubMed:18326581). Rhamnolipid production plays an important role in swarming motility (PubMed:15126453).
rhlA
23
2.3.1.-
137994
312
138235
189
138238
317
23156
Rhamnosyltransferase chain B
Q9HYD1
rhlB
23
2.4.1.-
137995
312
138236
189
138239
317
23157
Rhamnosyltransferase 2
Q9I4K5
rhlC
23
2.4.1.-
137996
312
138237
189
138240
317
13647
Phosphomannomutase/phosphoglucomutase
23
PW_P013647
23521
23139
1289
423
13714
Glucose-1-phosphate thymidylyltransferase
23
PW_P013714
23605
23148
6535
dTDP-glucose 4,6-dehydratase
23
PW_P006535
14255
23149
1298
721
13715
dTDP-4-dehydrorhamnose 3,5-epimerase
23
PW_P013715
23606
23150
6306
dTDP-4-dehydrorhamnose reductase
23
PW_P006306
13977
23153
1299
423
1
13717
Rhamnosyltransferase subunit A
23
PW_P013717
23608
23155
13718
Rhamnosyltransferase subunit B
23
PW_P013718
23609
23156
13719
Rhamnosyltransferase subunit C
23
PW_P013719
23610
23157
187153
PW_R187153
Both
709208
1083
1
Compound
false
709209
1207
1
Compound
false
176944
13647
5.4.2.2
187268
PW_R187268
Right
709585
1035
1
Compound
false
709586
1207
1
Compound
false
709587
1024
1
Compound
false
709588
170
1
Compound
false
176992
13714
2.7.7.24
212123
false
PW_R212123
Right
815111
1024
1
Compound
false
815112
42658
1
Compound
false
815113
1420
1
Compound
false
201774
6535
187269
PW_R187269
Both
709589
42658
1
Compound
false
709590
44520
1
Compound
false
176993
13715
5.1.3.13
183799
false
PW_R183799
Right
695420
44520
1
Compound
false
695421
146
1
Compound
false
695422
40034
1
Compound
false
695423
143
1
Compound
false
695424
2734
1
Compound
false
173638
6306
1.1.1.133
212289
PW_R212289
Right
815942
203
2
ElementCollection
false
815943
1420
1
Compound
false
815944
108440
1
Compound
false
815945
40034
1
Compound
false
815946
518
2
ElementCollection
false
201940
13717
2.3.1.-
212290
PW_R212290
Right
815947
2734
1
Compound
false
815948
108440
1
Compound
false
815949
108521
1
Compound
false
815950
987
1
Compound
false
815951
40034
1
Compound
false
201941
13718
2.4.1.-
212291
PW_R212291
Right
815952
2734
1
Compound
false
815953
108521
1
Compound
false
815954
108602
1
Compound
false
815955
987
1
Compound
false
815956
40034
1
Compound
false
201942
13719
2.4.1.-
3076602
423
312
9
false
520
457
10
regular
100
25
3076603
1083
312
3
false
300
450
10
regular
100
110
3076604
1207
312
3
false
750
450
10
regular
100
110
3076605
1035
312
3
false
800
305
10
regular
100
110
3076606
1024
312
3
false
1200
454
10
regular
100
100
3076607
170
312
45
false
1148
374
10
regular
63
43
3076608
721
312
9
false
1425
451
10
regular
100
25
3076609
42658
312
3
false
1650
437
10
regular
100
130
3076610
1420
312
49
false
1601
337
10
regular
78
78
3076611
1420
317
49
false
2189
826
10
regular
78
78
3076612
44520
312
3
false
2100
442
10
regular
100
120
3076613
423
312
9
false
2325
453
10
regular
100
25
3076614
146
312
62
false
2200
389
10
regular
50
30
3076615
40034
312
55
false
2191
289
10
regular
78
78
3076616
40034
317
55
false
2509
826
10
regular
78
78
3076617
40034
317
55
false
2954
683
10
regular
78
78
3076618
40034
317
55
false
3444
682
10
regular
78
78
3076619
143
312
61
false
2505
390
10
regular
50
30
3076620
2734
312
3
false
2550
445
10
regular
100
110
3076621
2734
317
3
false
3103
791
10
regular
100
110
3076622
108440
189
3
false
2553
929
10
regular
100
120
3076623
108521
189
3
false
3053
928
10
regular
100
120
3076624
987
317
3
false
2963
803
10
regular
100
100
3076625
987
317
3
false
3453
802
10
regular
100
100
3076626
108602
189
3
false
3503
927
10
regular
100
120
23194
203
144
316
false
2078
944
12
regular
150
70
23195
518
144
317
false
2493
729
12
regular
150
70
1185021
23139
312
2
false
495
472
8
subunit
regular
150
70
1185022
23148
312
2
false
950
470
8
subunit
regular
150
70
1185023
23149
312
2
false
1400
466
8
protein
regular
150
70
1185024
23150
312
2
false
1850
467
8
subunit
regular
150
70
1185025
23153
312
2
false
2300
468
8
subunit
regular
150
70
1185026
23155
317
2
false
2305
942
8
subunit
regular
150
70
1185027
23156
317
2
false
2753
942
8
subunit
regular
150
70
1185028
23157
317
2
false
3253
941
8
subunit
regular
150
70
932480
13647
114446
312
1180733
1185021
37919
3076602
4192231
Cofactor
932481
13714
114446
312
1180734
1185022
932482
6535
114446
312
1180735
1185023
37920
3076608
4192238
Cofactor
932483
13715
114446
312
1180736
1185024
932484
6306
114446
312
1180737
1185025
37921
3076613
4192244
Cofactor
932485
13717
114446
317
1180738
1185026
932486
13718
114446
317
1180739
1185027
932487
13719
114446
317
1180740
1185028
4192230
M2078 979 C2048 979 2067 979 2037 979 C2037 955 2036 871 2036 850 C2014 850 2024 850 1998 849
5
false
18
true
M 2075.0096189432334 986.5 L 2088 979 L 2075.0096189432334 971.5
false
4192231
M195 7.5 L195 57.5 L245 7.5 z
10
true
18
4192232
M400 505 C430 505 465 507 495 507
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4192233
M750 505 C720 505 675 507 645 507
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4192234
M900 360 C899 465 920 505 950 505
5
false
18
4192235
M850 505 C880 505 920 505 950 505
5
false
18
4192236
M1200 504 C1170 504 1130 505 1100 505
5
false
18
true
M 455.94685504416486 321.261556296296 L 441 320 L 447.38088772118584 333.5751343230783
false
4192237
M1148 395.5 C1150 471.5 1130 505 1100 505
5
false
18
true
M 455.94685504416486 321.261556296296 L 441 320 L 447.38088772118584 333.5751343230783
false
4192238
M1595 456.5 L1595 506.5 L1645 456.5 z
10
true
18
4192239
M1300 504 C1330 504 1370 501 1400 501
5
false
18
4192240
M1650 502 C1620 502 1580 501 1550 501
5
false
18
true
M 628.9468550441649 300.261556296296 L 614 299 L 620.3808877211858 312.5751343230783
false
4192241
M1601 376 C1600 472 1580 501 1550 501
5
false
18
true
M 628.9468550441649 300.261556296296 L 614 299 L 620.3808877211858 312.5751343230783
false
4192242
M1750 502 C1780 502 1820 502 1850 502
5
false
18
true
M 1151.9468550441647 287.261556296296 L 1137 286 L 1143.380887721186 299.5751343230783
false
4192243
M2100 502 C2070 502 2030 502 2000 502
5
false
18
true
M 1151.9468550441647 287.261556296296 L 1137 286 L 1143.380887721186 299.5751343230783
false
4192244
M2495 358 L2495 408 L2545 358 z
10
true
18
4192245
M2200 502 C2230 502 2270 503 2300 503
5
false
18
4192246
M2250 404 C2249 471 2270 503 2300 503
5
false
18
4192247
M2269 328 C2265 400 2270 503 2300 503
5
false
18
4192248
M2505 405 C2504 473 2480 503 2450 503
5
false
18
true
M 1657.9468550441647 297.261556296296 L 1643 296 L 1649.380887721186 309.5751343230783
false
4192249
M2550 500 C2520 500 2480 503 2450 503
5
false
18
true
M 1657.9468550441647 297.261556296296 L 1643 296 L 1649.380887721186 309.5751343230783
false
4192250
M2228 979 C2258 979 2275 977 2305 977
5
false
18
4192251
M2267 865 C2267 947 2275 977 2305 977
5
false
18
4192252
M2553 979 C2523 979 2485 977 2455 977
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false
18
true
M 2024.9468550441647 615.261556296296 L 2010 614 L 2016.380887721186 627.5751343230784
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4192253
M2509 865 C2502 972 2485 977 2455 977
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false
18
true
M 2024.9468550441647 615.261556296296 L 2010 614 L 2016.380887721186 627.5751343230784
false
4192254
M2493 764 C2491 901 2485 977 2455 977
5
false
18
true
M 2024.9468550441647 615.261556296296 L 2010 614 L 2016.380887721186 627.5751343230784
false
4192255
M2650 500 C2655 643 2723 977 2753 977
5
false
18
4192256
M2653 979 C2683 979 2723 977 2753 977
5
false
18
4192257
M3053 978 C3023 978 2933 977 2903 977
5
false
18
true
M 2404.9468550441647 509.261556296296 L 2390 508 L 2396.380887721186 521.5751343230784
false
4192258
M2963 853 C2965 939 2933 977 2903 977
5
false
18
true
M 2404.9468550441647 509.261556296296 L 2390 508 L 2396.380887721186 521.5751343230784
false
4192259
M2954 722 C2955 832 2933 977 2903 977
5
false
18
true
M 2404.9468550441647 509.261556296296 L 2390 508 L 2396.380887721186 521.5751343230784
false
4192260
M3203 846 C3205 932 3223 976 3253 976
5
false
18
4192261
M3153 978 C3183 978 3223 976 3253 976
5
false
18
4192262
M3503 977 C3473 977 3433 976 3403 976
5
false
18
true
M 2703.9468550441647 575.261556296296 L 2689 574 L 2695.380887721186 587.5751343230784
false
4192263
M3453 852 C3455 957 3433 976 3403 976
5
false
18
true
M 2703.9468550441647 575.261556296296 L 2689 574 L 2695.380887721186 587.5751343230784
false
4192264
M3444 721 C3441 865 3433 976 3403 976
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false
18
true
M 2703.9468550441647 575.261556296296 L 2689 574 L 2695.380887721186 587.5751343230784
false
907696
114446
187153
3699203
3076603
4192232
Left
3699204
3076604
4192233
Right
862808
176944
932480
907697
114446
187268
3699205
3076605
4192234
Left
3699206
3076604
4192235
Left
3699207
3076606
4192236
Right
3699208
3076607
4192237
Right
862809
176992
932481
907698
114446
212123
3699209
3076606
4192239
Left
3699210
3076609
4192240
Right
3699211
3076610
4192241
Right
862810
201774
932482
907699
114446
187269
3699212
3076609
4192242
Left
3699213
3076612
4192243
Right
862811
176993
932483
907700
114446
183799
3699214
3076612
4192245
Left
3699215
3076614
4192246
Left
3699216
3076615
4192247
Left
3699217
3076619
4192248
Right
3699218
3076620
4192249
Right
862812
173638
932484
907701
114446
212289
3699219
3076611
4192251
Left
3699220
3076622
4192252
Right
3699221
3076616
4192253
Right
22413
23194
4192250
Left
22414
23195
4192254
Right
862813
201775
932485
907702
114446
212290
3699222
3076620
4192255
Left
3699223
3076622
4192256
Left
3699224
3076623
4192257
Right
3699225
3076624
4192258
Right
3699226
3076617
4192259
Right
862814
201776
932486
907703
114446
212291
3699227
3076621
4192260
Left
3699228
3076623
4192261
Left
3699229
3076626
4192262
Right
3699230
3076625
4192263
Right
3699231
3076618
4192264
Right
862815
201777
932487
112327
112600
114446
14
false
1848
814
16
regular
275
23194
4192230
Right
468149
3039
293
0.8
0.8
0
2
92
479
481
465004
M226 325 C226 275 276 225 326 225 C1311 225 2591 225 3576 225 C3626 225 3676 275 3676 325 C3676 491 3676 708 3676 874 C3676 924 3626 974 3576 974 C2591 974 1311 974 326 974 C276 974 226 924 226 874 C226 708 226 491 226 325
1
true
6
3450.0
749.0
465005
M125 226 C125 176 175 126 225 126 C1271 126 2630 126 3676 126 C3726 126 3776 176 3776 226 C3776 453 3776 748 3776 975 C3776 1025 3726 1075 3676 1075 C2630 1075 1271 1075 225 1075 C175 1075 125 1025 125 975 C125 748 125 453 125 226
1
true
6
3651.0
949.0
868763
15
Cytoplasm
340
743
20
2.2
2.2
160
15
868764
15
Inner Plasma Membrane
339
887
20
2.2
2.2
160
15