1877
Pathway
L-Arabinose Degradation I
L-arabinose enters E. coli unphosphorylated via a low-affinity proton-driven transporter (AraE) or a high-affinity ATP-driven system (AraFGH). Following entry, it is converted to L-ribulose-5-phosphate by an isomerase and kinase. L-ribulose-5-phosphate is then converted by an epimerase to the pentose phosphate pathway intermediate, D-xylulose-5-phosphate. D-xylulose-5-phosphate then enters metabolism pathways to become precursor metabolites, reducing power and metabolic energy.
Metabolic
PW002103
Center
PathwayVisualizationContext2390
1750
1951
#000099
PathwayVisualization1861
1877
L-Arabinose Degradation I
L-arabinose enters E. coli unphosphorylated via a low-affinity proton-driven transporter (AraE) or a high-affinity ATP-driven system (AraFGH). Following entry, it is converted to L-ribulose-5-phosphate by an isomerase and kinase. L-ribulose-5-phosphate is then converted by an epimerase to the pentose phosphate pathway intermediate, D-xylulose-5-phosphate. D-xylulose-5-phosphate then enters metabolism pathways to become precursor metabolites, reducing power and metabolic energy.
Metabolic
3
109769
113174
SubPathway
109273
691
Compound
3956
24586851
1877
Pathway
279749
11102706
Schleif R: Regulation of the L-arabinose operon of Escherichia coli. Trends Genet. 2000 Dec;16(12):559-65.
1877
Pathway
1
Cell
CL:0000000
2
Platelet
CL:0000233
5
Hepatocyte
CL:0000182
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
7
Epithelial Cell
CL:0000066
3
Escherichia coli
562
Prokaryote
23
Pseudomonas aeruginosa
287
Prokaryote
1
Homo sapiens
9606
Eukaryote
Human
2
Bacteria
2
Prokaryote
Bacteria
12
Mus musculus
10090
Eukaryote
Mouse
17
Rattus norvegicus
10116
Eukaryote
Rat
19
Schizosaccharomyces pombe
4896
Eukaryote
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
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
5
Bos taurus
9913
Eukaryote
Cattle
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
1
Cytosol
GO:0005829
3
Mitochondrial Matrix
GO:0005759
5
Cytoplasm
GO:0005737
14
Mitochondrial Outer Membrane
GO:0005741
2
Mitochondrion
GO:0005739
15
Nucleus
GO:0005634
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
7
Endoplasmic Reticulum Membrane
GO:0005789
10
Cell Membrane
GO:0005886
27
Peroxisome Membrane
GO:0005778
31
Periplasmic Space
GO:0005620
11
Extracellular Space
GO:0005615
35
Chloroplast
GO:0009507
12
Mitochondrial Inner Membrane
GO:0005743
32
Inner Membrane
GO:0070258
19
sarcoplasmic reticulum
GO:0016529
24
Mitochondrial Intermembrane Space
GO:0005758
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
2
Endothelium
BTO:0000393
1
Liver
BTO:0000759
72
9
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
25
Intestine
BTO:0000648
8
Blood Vessel
BTO:0001102
74
11
28
Stomach
BTO:0001307
155
26
117
1
3
1
PW_BS000117
322
1
23
1
PW_BS000024
2
1
1
1
PW_BS000002
4
3
1
1
PW_BS000004
8
5
1
1
PW_BS000008
16
2
1
2
PW_BS000016
22
14
1
1
PW_BS000022
13
1
2
1
PW_BS000013
32
1
15
1
5
PW_BS000032
5
4
1
1
PW_BS000005
39
7
1
1
3
PW_BS000039
3
2
1
1
PW_BS000003
18
13
1
1
PW_BS000018
10
1
7
1
1
PW_BS000010
49
7
1
1
PW_BS000049
14
10
1
PW_BS000014
58
1
14
1
1
PW_BS000058
59
27
1
1
PW_BS000059
27
15
1
PW_BS000027
46
1
1
4
PW_BS000046
29
1
1
1
PW_BS000029
66
18
5
1
8
PW_BS000066
72
5
1
3
PW_BS000072
61
25
1
7
PW_BS000061
51
8
1
PW_BS000051
23
15
1
1
PW_BS000023
31
1
5
1
1
PW_BS000031
91
8
5
1
1
PW_BS000091
54
1
3
1
5
PW_BS000054
89
2
PW_BS000089
26
1
1
1
5
PW_BS000026
7
1
1
PW_BS000007
97
1
5
2
1
PW_BS000097
100
5
2
1
PW_BS000100
104
14
3
1
PW_BS000104
101
5
3
1
PW_BS000101
111
5
12
1
PW_BS000111
112
2
12
1
PW_BS000112
103
3
3
1
PW_BS000103
118
1
17
1
PW_BS000118
120
3
17
1
PW_BS000120
129
1
5
12
1
PW_BS000129
132
1
12
1
PW_BS000132
133
3
12
1
PW_BS000133
135
5
17
1
PW_BS000135
108
1
3
PW_BS000108
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
107
31
3
PW_BS000107
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
188
1
18
PW_BS000024
160
1
18
1
PW_BS000160
199
14
18
1
PW_BS000024
205
5
6
1
PW_BS000024
206
2
6
1
PW_BS000024
210
13
18
1
PW_BS000024
213
7
18
1
PW_BS000024
211
10
18
PW_BS000024
198
5
18
1
PW_BS000024
216
4
18
1
PW_BS000024
217
15
18
PW_BS000024
218
15
18
1
PW_BS000024
163
2
18
1
PW_BS000163
222
3
4
1
PW_BS000024
190
11
18
PW_BS000024
225
35
4
1
PW_BS000024
277
1
2
18
PW_BS000024
170
18
PW_BS000170
281
1
25
1
PW_BS000024
164
4
PW_BS000164
285
10
4
1
PW_BS000024
226
4
4
1
PW_BS000024
290
5
49
1
PW_BS000024
223
12
4
1
PW_BS000024
308
10
1
1
PW_BS000024
315
1
23
PW_BS000024
318
31
23
PW_BS000024
253
5
4
1
PW_BS000024
134
12
12
1
PW_BS000134
329
14
12
1
PW_BS000028
333
1
2
12
PW_BS000028
336
1
12
1
PW_BS000028
332
1
7
12
1
PW_BS000028
350
1
14
12
1
PW_BS000028
128
15
12
1
PW_BS000128
351
15
12
PW_BS000028
353
25
12
7
PW_BS000028
335
27
12
1
PW_BS000028
115
10
12
PW_BS000115
130
13
12
1
PW_BS000130
331
7
12
1
PW_BS000028
334
4
12
1
PW_BS000028
368
3
60
1
PW_BS000028
184
1
2
1
PW_BS000024
119
2
17
1
PW_BS000119
1
1
PW_BS000001
124
1
5
1
PW_BS000124
94
3
PW_BS000094
388
1
6
1
PW_BS000112
109
32
3
PW_BS000109
122
5
5
1
PW_BS000122
406
3
5
1
PW_BS000115
407
2
5
1
PW_BS000115
382
14
5
1
PW_BS000100
412
1
2
5
PW_BS000115
429
1
5
1
PW_BS000115
123
1
7
5
1
PW_BS000123
433
1
14
5
1
PW_BS000115
408
4
5
1
PW_BS000115
410
15
5
1
PW_BS000115
125
13
5
1
PW_BS000125
383
7
5
1
PW_BS000100
405
10
5
PW_BS000115
422
27
5
1
PW_BS000115
435
15
5
PW_BS000115
399
14
17
1
PW_BS000113
446
1
2
17
PW_BS000115
464
1
17
1
PW_BS000115
447
1
7
17
1
PW_BS000115
468
1
14
17
1
PW_BS000115
374
4
17
1
PW_BS000053
444
15
17
1
PW_BS000115
136
13
17
1
PW_BS000136
398
7
17
1
PW_BS000113
376
10
17
PW_BS000053
472
25
17
7
PW_BS000115
375
27
17
1
PW_BS000053
470
15
17
PW_BS000115
297
5
10
1
PW_BS000024
479
3
10
1
PW_BS000115
299
1
10
1
PW_BS000024
481
2
10
1
PW_BS000115
484
14
10
1
PW_BS000115
485
15
10
1
PW_BS000115
300
13
10
1
PW_BS000024
495
7
10
1
PW_BS000115
478
10
10
PW_BS000115
491
27
10
1
PW_BS000115
499
15
10
PW_BS000115
501
3
6
1
PW_BS000115
389
14
6
1
PW_BS000112
516
15
6
1
PW_BS000115
395
13
6
1
PW_BS000113
390
7
6
1
PW_BS000112
209
10
6
PW_BS000024
508
27
6
1
PW_BS000115
517
15
6
PW_BS000115
15
11
1
PW_BS000015
47
19
1
4
PW_BS000047
313
23
PW_BS000024
17
12
1
1
PW_BS000017
42
24
1
1
PW_BS000042
70
28
5
1
1
PW_BS000070
105
11
3
PW_BS000105
157
2
24
1
PW_BS000157
159
24
PW_BS000159
152
8
4
PW_BS000152
187
31
18
PW_BS000024
219
31
4
PW_BS000024
220
1
4
PW_BS000024
212
1
7
18
1
PW_BS000024
162
12
18
1
PW_BS000162
224
2
4
1
PW_BS000024
195
13
18
PW_BS000024
249
13
4
1
PW_BS000024
286
36
4
1
PW_BS000024
287
53
4
1
PW_BS000024
227
34
4
1
PW_BS000024
294
11
4
1
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
293
4
1
PW_BS000024
114
11
12
PW_BS000114
327
1
1
12
5
PW_BS000028
347
1
3
12
5
PW_BS000028
345
24
12
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
409
11
5
PW_BS000115
424
1
1
5
5
PW_BS000115
425
1
3
5
5
PW_BS000115
418
24
5
1
PW_BS000115
384
12
5
1
PW_BS000100
137
11
17
PW_BS000137
459
1
1
17
5
PW_BS000115
460
1
3
17
5
PW_BS000115
454
24
17
1
PW_BS000115
121
12
17
1
PW_BS000121
483
11
10
PW_BS000115
489
24
10
1
PW_BS000115
480
12
10
1
PW_BS000115
208
11
6
PW_BS000024
506
24
6
1
PW_BS000115
391
12
6
1
PW_BS000112
505
L-Arabinose
HMDB0000646
L-Arabinose is a pentose with a sweet taste and one of the most abundant components released by complete hydrolysis of non-starch polysaccharides (NSP) of vegetable origin. However, NSPs are complicated compounds from the point of view of both physical structure and chemical composition, and they include cellulose, hemi-cellulose, pectin, and oligosaccharides. It is well-recognized that NSPs are resistant to the digestive enzymes and pass to the hind-gut where microbial degradation takes place. When L-arabinose is ingested in a digestible form, it is absorbed from the intestinal tract at a lower rate than glucose. A portion of the ingested L-arabinose is excreted in the urine. Although widely present in nature, L-arabinose is rarely used, and its physiological effects in vivo have received little attention. L-Arabinose selectively inhibits intestinal sucrase activity in a noncompetitive manner and suppresses the plasma glucose increase due to sucrose ingestion. Because the intestinal absorption of sucrose is inhibited in the presence of L-arabinose, the absorption of sucrose should be reduced by arabinose ingestion. Most of the studies reported so far on the absorption and utilization of L-arabinose relate to omnivore animal species other than humans. In a rare case of two autistic brothers that were not associated with any known metabolic disease, it was found the median value for their urine samples was 179 umol/mmol creatinine of L-arabinose, nearly six times greater than normal children (PMID: 11238761, 8931641, 1390604, 7628083). L-Arabinose is found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism.
87-72-9
C00259
439195
17535
388335
DB03246
O[C@H]1COC(O)[C@H](O)[C@H]1O
C5H10O5
InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5?/m0/s1
SRBFZHDQGSBBOR-HWQSCIPKSA-N
(3R,4S,5S)-oxane-2,3,4,5-tetrol
150.1299
150.05282343
0.91
4
L-arabinopyranose
0
0
FDB012306
Arabinose;L-(+)-arabinose;L-arabinopyranose;L-arabinose
PW_C000505
Ara
6825
117
43770
322
1863
L-Ribulose
HMDB0003371
Ribulose is a ketopentose- a monosaccharide containing five carbon atoms, and including a ketone functional group. It has chemical formula C5H10O5. Two diastereomers are possible, D-ribulose (D-erythro-pentulose) and L-ribulose (L-erythro-pentulose). D-ribulose is an intermediate in the fungal pathway for D-arabitol production.
551-84-8
C00508
439204
16880
L-RIBULOSE-5-P
388344
OCC1(O)OC[C@@H](O)[C@@H]1O
C5H10O5
InChI=1S/C5H10O5/c6-2-5(9)4(8)3(7)1-10-5/h3-4,6-9H,1-2H2/t3-,4+,5?/m1/s1
LQXVFWRQNMEDEE-OVEKKEMJSA-N
(3S,4R)-2-(hydroxymethyl)oxolane-2,3,4-triol
150.1299
150.05282343
0.94
4
(3S,4R)-2-(hydroxymethyl)oxolane-2,3,4-triol
0
0
FDB023156
L-erythro-pentulose;L-Arabinoketose;L-Arabinulose;L-Riboketose
PW_C001863
L-Rbose
414
Adenosine triphosphate
HMDB0000538
Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).
56-65-5
C00002
5957
15422
ATP
5742
DB00171
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-2.05
7
adenosine triphosphate
0
-3
FDB021813
5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid
PW_C000414
ATP
9
2
21
4
60
8
266
16
414
22
478
13
733
32
799
5
934
39
976
3
2105
18
2112
10
2146
49
2156
14
2160
58
2405
59
2434
27
2726
46
2812
29
3029
66
3163
72
3616
61
3617
51
4399
23
4474
31
4768
91
4864
54
5032
89
5035
26
5155
7
5205
97
5215
100
5250
104
5291
101
5313
111
5346
112
5390
103
5406
117
5430
118
5443
120
5542
129
5556
132
5569
133
5603
135
5621
108
5846
143
5854
146
5876
107
5897
147
5924
151
6048
155
6109
161
6230
166
6493
178
6839
188
6870
160
6976
199
7157
205
7184
206
7209
210
7225
213
7229
211
7298
198
7302
216
7390
217
7408
218
7432
163
7481
222
7499
190
8186
225
11847
277
11903
170
12010
281
12039
164
12178
285
12578
226
12691
290
13264
223
15327
308
42326
315
42621
322
42694
318
77028
253
77218
134
77233
329
77468
333
77632
336
78037
332
78041
350
78168
128
78214
351
78240
353
78411
335
78494
115
78850
130
78865
331
78919
334
80028
368
80046
184
80674
119
85629
1
94826
124
113234
94
113282
388
116280
109
119914
122
119992
406
120154
407
120245
382
120362
412
121246
429
121392
123
121397
433
121471
408
121974
410
122065
125
122079
383
122083
405
122402
422
122444
435
122919
399
123009
446
123816
464
123951
447
123956
468
124029
374
124527
444
124616
136
124630
398
124634
376
124943
472
124972
375
125011
470
125304
297
125371
479
125392
299
125515
481
125595
484
126123
485
126220
300
126234
495
126240
478
126547
491
126596
499
126913
501
127123
389
127731
516
127781
395
127796
390
127801
209
128119
508
128167
517
40862
L-ribulose 5-phosphate
OCC(=O)[C@@H](O)[C@@H](O)COP([O-])([O-])=O
L-ribulose 5-phosphate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. In Escherichia coli, RpiA catalyzes the interconversion of ribose-5-phosphate and ribulose-5-phosphate and is a key enzyme in the pentose phosphate pathway. (PMID 12182339) Interconversion of D-ribose-5-phosphate (R5P) and D-ribulose-5-phosphate is an important step in the pentose phosphate pathway. (PMID 18640127) A key player in LPS synthesis is the enzyme D-arabinose-5-phosphate isomerase (API), which catalyzes the reversible isomerization of D-ribulose-5-phosphate to D-arabinose-5-phosphate, a precursor of 3-deoxy-D-manno-octulosonate that is an essential residue of the LPS inner core. (PMID 20954237) Dihydroxybutanone phosphate synthase (DS) catalyzes a commitment step in riboflavin biosynthesis where ribulose 5-phosphate is converted to dihydroxybutanone phosphate and formate. (PMID 11053863) Ribose-5-phosphate isomerase A (RpiA) plays an important role in interconverting between ribose-5-phosphate (R5P) and ribulose-5-phosphate in the pentose phosphate pathway and the Calvin cycle. (PMID 19214439) (from ECMDB)
58226
OCC(=O)[C@@H](O)[C@@H](O)COP([O-])([O-])=O
C5H9O8P
InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/p-2/t4-,5+/m0/s1
FNZLKVNUWIIPSJ-CRCLSJGQSA-L
(3S,4S)-1,3,4-trihydroxy-5-(phosphonatooxy)pentan-2-one
228.094
228.004601408
-0.63
3
L-ribulose 5-phosphate(2-)
-2
-2
PW_C040862
LR5P
1034
Adenosine diphosphate
HMDB0001341
Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.
58-64-0
C00008
6022
16761
ADP
5800
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
XTWYTFMLZFPYCI-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
427.2011
427.029414749
-2.12
6
adenosine-diphosphate
0
-2
FDB021817
Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acid
PW_C001034
ADP
23
4
134
8
415
22
482
13
801
5
963
15
978
3
1061
14
1518
2
1901
49
2104
18
2113
10
2161
58
2408
59
2435
27
2728
47
2736
46
2855
29
3165
72
3635
61
4400
23
4476
31
4770
91
5036
26
5157
7
5208
97
5217
100
5315
111
5349
112
5392
103
5446
120
5544
129
5572
133
5624
108
5741
117
5764
101
5849
143
5856
146
5878
107
5899
147
5926
151
6050
155
6111
161
6231
166
6495
178
6700
94
6841
188
6872
160
7159
205
7187
206
7208
210
7226
213
7231
211
7300
198
7303
216
7391
217
7410
218
7433
163
7483
222
8187
225
11851
277
11905
170
12013
281
12180
285
13262
223
15329
308
42328
315
42398
313
42622
322
42696
318
77029
253
77087
132
77216
134
77306
329
77472
333
77663
336
78039
332
78043
350
78170
128
78215
351
78244
353
78414
335
78495
115
78705
331
78849
130
78920
334
80030
368
80622
118
80651
135
80676
119
94827
124
113283
388
116204
109
119944
122
119994
406
120156
407
120318
382
120366
412
121248
429
121394
123
121399
433
121472
408
121899
383
121976
410
122064
125
122085
405
122405
422
122445
435
122973
399
123013
446
123818
464
123953
447
123958
468
124030
374
124452
398
124529
444
124615
136
124636
376
124947
472
124975
375
125012
470
125334
297
125373
479
125492
299
125517
481
125645
484
126125
485
126219
300
126235
495
126242
478
126550
491
126597
499
126915
501
127733
516
127780
395
127797
390
127803
209
128122
508
128168
517
128313
389
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
691
Xylulose 5-phosphate
HMDB0000868
Xylulose 5-phosphate (Xu-5-P) is a metabolite of the hexose monophosphate pathway that activates protein phosphatase 2A to mediate the acute effects of carbohydrate feeding on the glycolytic pathway, as well as the coordinate long-term control of the enzymes required for fatty acid and triglyceride synthesis. Xu-5-P is the signal for the coordinated control of lipogenesis. Feeding carbohydrate causes levels of liver glucose, Glucose-6-phosphate (Glc-6-P), and Fructose-6-phosphate (Fru-6-P) to rise. Elevation of Fru-6-P leads to elevation of Xu-5-P in reactions catalyzed by the near-equilibrium isomerases of the nonoxidative portion of the hexose monophosphate pathway (ribulose 5-phosphate (Ru5P) epimerase [EC 5.1.3.1], ribose 5-phosphate (Rib5P) isomerase [EC 5.3.1.6], transaldolase [EC 2.2.1.2], and transketolase [EC 2.2.1.1]). The elevation of Xu-5-P is the coordinating signal that both acutely activates phosphofructokinase [PFK; EC 2.7.1.11] in glycolysis and promotes the action of the transcription factor carbohydrate responsive element binding protein (ChREBP) to increase transcription of the genes for the enzymes of lipogenesis, the hexose monophosphate shunt, and glycolysis, all of which are required for the de novo synthesis of fat. (PMID 12721358).
60802-29-1
C00231
439190
16332
XYLULOSE-5-PHOSPHATE
388330
DB04034
OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O
C5H11O8P
InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5-/m1/s1
FNZLKVNUWIIPSJ-RFZPGFLSSA-N
{[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid
230.1098
230.01915384
-0.95
5
ribulose-5-phosphate
0
-2
FDB022290
D-xylulose 5-po4;D-xylulose 5-phosphate;D-xylulose-5-p;D-xylulose-5-phosphate;Xu-5-p;Xylulose 5-phosphate;Xylulose-p;Xylulose-phosphate;5-o-phosphono-d-threo-pentos-2-ulose;5-o-phosphono-d-xylulose;D-xylulose 5-phosphoric acid;D-xylulose-5-phosphoric acid
PW_C000691
Xyl-5-P
1776
2
13294
225
13298
151
77178
132
122188
124
124740
118
126348
299
127910
388
5943
L-arabinose isomerase
P08202
Involved in L-fucose isomerase activity. Catalyzes the conversion of L-arabinose to L-ribulose.
araA
b0062
AP009048
3
5.3.1.4
5945
Ribulokinase
P08204
Involved in phosphotransferase activity, alcohol group as acceptor. ATP + L(or D)-ribulose = ADP + L(or D)- ribulose 5-phosphate.
araB
b0063
AP009048
3
2.7.1.16
6583
L-ribulose-5-phosphate 4-epimerase sgbE
P37680
Involved in metal ion binding. Catalyzes the isomerization of L-ribulose 5-phosphate to D-xylulose 5-phosphate. May be involved in the utilization of 2,3- diketo-L-gulonate.
sgbE
b3583
AP009048
3
5.1.3.4
6852
Arabinose-proton symporter
P0AE25
Involved in transmembrane transporter activity. Uptake of arabinose across the boundary membrane with the concomitant transport of protons into the cell (symport system).
araE
AE005174
3
8915
109
4096
L-arabinose isomerase
25
PW_P004096
11114
5943
6
6821
117
4097
L-ribulokinase
25
PW_P004097
11115
5945
2
6822
117
1413
L-ribulose-5-phosphate 4-epimerase
3
PW_P001413
1645
6583
4098
arabinose:H+ symporter
25
PW_P004098
11116
6852
1
6824
109
6132
false
PW_R006132
Both
25087
505
1
Compound
false
25088
1863
1
Compound
false
6093
4096
5.3.1.4
6133
false
PW_R006133
Right
25089
1863
1
Compound
false
25090
414
1
Compound
false
25091
40862
1
Compound
false
25092
1034
1
Compound
false
25093
40034
1
Compound
false
6094
4097
2.7.1.16
2714
false
PW_R002714
Right
10655
40862
1
Compound
false
10656
691
1
Compound
false
2703
1413
5.1.3.4
515
PW_T000515
Active
656
505
1
Compound
107
117
Right
657
40034
1
Compound
107
117
Right
444
4098
2015-10-14T11:10:02-06:00
2015-10-14T11:10:02-06:00
109
71706
505
3
false
592
550
10
regular
100
100
71707
1863
3
false
592
900
10
regular
100
100
71718
414
42
false
542
1035
10
regular
50
30
71719
40862
3
false
900
1100
10
regular
100
110
71720
1034
43
false
800
1220
10
regular
50
30
71721
40034
55
false
780
1041
10
regular
78
78
71730
691
3
false
1345
1100
10
regular
100
110
71734
505
117
3
false
593
190
10
regular
100
100
71735
40034
107
55
false
504
456
10
regular
78
78
71736
40034
117
55
false
503
286
10
regular
78
78
32846
5943
17
false
552
730
8
subunit
regular
180
85
32850
5945
6
false
564
1117
8
subunit
regular
160
80
32853
6583
2
false
1095
1120
8
subunit
regular
150
70
32855
6852
109
76
false
567
375
8
subunit
regular
150
70
27578
4096
1861
32527
32846
27582
4097
1861
32531
32850
27585
1413
1861
32534
32853
27587
4098
1861
32536
32855
101775
M642 650 C642 680 642 700 642 730
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101776
M642 900 C642 870 642 845 642 815
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101789
M642 1000 C642 1030 644 1087 644 1117
5
false
18
101790
M592 1050 C634 1054 644 1087 644 1117
5
false
18
101791
M900 1155 C870 1155 772 1155 724 1157
5
false
18
true
M 420.85675967136467 246.00930085119703 L 405.9099046271998 244.74774455490098 L 412.29079234838565 258.3228788779793
false
101792
M825 1220 C825 1190 806 1157 724 1157
5
false
18
true
M 420.85675967136467 246.00930085119703 L 405.9099046271998 244.74774455490098 L 412.29079234838565 258.3228788779793
false
101793
M819 1119 C818 1153 771 1156 724 1157
5
false
18
true
M 420.85675967136467 246.00930085119703 L 405.9099046271998 244.74774455490098 L 412.29079234838565 258.3228788779793
false
101802
M1000 1155 C1019 1156 1075 1155 1095 1155
5
false
18
101803
M1345 1155 C1315 1155 1281 1155 1245 1155
5
false
18
true
M 420.85675967136467 894.6579411403923 L 405.9099046271998 893.3963848440962 L 412.29079234838565 906.9715191671746
false
101809
M642 550 C642 520 642 475 642 445
83
false
18
true
M 1057.5 362.0096189432334 L 1065 375 L 1072.5 362.0096189432334
false
101810
M643 290 C643 320 642 345 642 375
83
false
18
false
false
101811
M582 495 C630 496 642 475 642 445
83
false
18
true
M 933.5 353.0096189432334 L 941 366 L 948.5 353.0096189432334
false
101812
M581 325 C624 325 642 345 642 375
83
false
18
false
false
3658725
M1395 1100 C1395 1071 1395 1053 1395 977
5
false
18
true
M 2760.5 1189.9903810567666 L 2753 1177 L 2745.5 1189.9903810567666
false
20791
1861
6132
80780
71706
101775
Left
80781
71707
101776
Right
20962
6093
27578
20795
1861
6133
80793
71707
101789
Left
80794
71718
101790
Left
80795
71719
101791
Right
80796
71720
101792
Right
80797
71721
101793
Right
20966
6094
27582
20796
1861
2714
80798
71719
101802
Left
80799
71730
101803
Right
20967
2703
27585
973
515
1861
2389
71706
101809
Left
2390
71734
101810
Right
2391
71735
101811
Left
2392
71736
101812
Right
725
27587
444
109438
109769
1861
14
false
1320
907
16
regular
106137
71730
3658725
Left
186334
784
502
1.1
1.1
0
2
92
479
481
3627
M125 225 C125 175 175 125 225 125 C680 125 1271 125 1726 125 C1776 125 1826 175 1826 225 C1826 619 1826 1131 1826 1525 C1826 1575 1776 1625 1726 1625 C1271 1625 680 1625 225 1625 C175 1625 125 1575 125 1525 C125 1131 125 619 125 225
1
true
6
1701.0
1500.0
3628
M427 513 C427 463 477 413 527 413 C800 413 1154 413 1427 413 C1477 413 1527 463 1527 513 C1527 730 1527 1012 1527 1229 C1527 1279 1477 1329 1427 1329 C1154 1329 800 1329 527 1329 C477 1329 427 1279 427 1229 C427 1012 427 730 427 513
1
true
6
1100.0
916.0