590
Pathway
Fucose and Rhamnose Degradation
In E. coli, L-fucose and L-rhamnose are metabolized through parallel pathways. The pathways converge after their corresponding aldolase reactions yielding the same products: lactaldehye. Proton symporter can facilitate the import of alpha-L-rhamnopyranose, methylpentose and beta-L-rhamnopyranose into cell for further metabolism, which allow E.coli to grow with carbon and energy. For alpha-L-rhamnopyranose, it is isomerized by a l-rhamnose mutarotase resulting in a beta-L-rhamnopyranose which is then isomerized into a keto-L-rhamnulose by a l-rhamnose isomerase. The keto-L-rhamnulose spontaneously changes into a L-rhamnulofuranose which is phosphorylated by a rhamnulokinase resulting in a L-rhamnulose 1-phosphate. This compound reacts with a rhamnulose-1-phosphate aldolase resulting in a dihydroxyacetone phosphate and a lactaldehyde. For beta-L-rhamnopyranose, it is isomerized by a L-fucose mutarotase resulting in a alpha-L-fucopyranose. This compound is then isomerized by an L-fucose isomerase resulting in a L-fuculose which in turn gets phosphorylated into an L-fuculose 1-phosphate through an L-fuculokinase. The compound L-fuculose 1-phosphate reacts with an L-fuculose phosphate aldolase through a dihydroxyacetone phosphate and a lactaldehyde. Two pathways can both be used for degrading L-lactaldehyde, which the aerobic pathway facilitates the conversion from L-lactic acid to pyruvic acid via L-lactate dehydrogenase, and the anaerobic pathway facilitates conversion from lactaldehyde to propane-1,2-diol via lactaldehyde reductase. Under aerobic conditions, L-lactaldehyde is oxidized in two steps to pyruvate, thereby channeling all the carbons from fucose or rhamnose into central metabolic pathways. Under anaerobic conditions, L-lactaldehyde is reduced to L-1,2-propanediol, which is secreted into the environment.
Metabolic
PW000826
Center
PathwayVisualizationContext1113
2970
3400
#000099
PathwayVisualization574
590
Fucose and Rhamnose Degradation
In E. coli, L-fucose and L-rhamnose are metabolized through parallel pathways. The pathways converge after their corresponding aldolase reactions yielding the same products: lactaldehye. Proton symporter can facilitate the import of alpha-L-rhamnopyranose, methylpentose and beta-L-rhamnopyranose into cell for further metabolism, which allow E.coli to grow with carbon and energy. For alpha-L-rhamnopyranose, it is isomerized by a l-rhamnose mutarotase resulting in a beta-L-rhamnopyranose which is then isomerized into a keto-L-rhamnulose by a l-rhamnose isomerase. The keto-L-rhamnulose spontaneously changes into a L-rhamnulofuranose which is phosphorylated by a rhamnulokinase resulting in a L-rhamnulose 1-phosphate. This compound reacts with a rhamnulose-1-phosphate aldolase resulting in a dihydroxyacetone phosphate and a lactaldehyde. For beta-L-rhamnopyranose, it is isomerized by a L-fucose mutarotase resulting in a alpha-L-fucopyranose. This compound is then isomerized by an L-fucose isomerase resulting in a L-fuculose which in turn gets phosphorylated into an L-fuculose 1-phosphate through an L-fuculokinase. The compound L-fuculose 1-phosphate reacts with an L-fuculose phosphate aldolase through a dihydroxyacetone phosphate and a lactaldehyde. Two pathways can both be used for degrading L-lactaldehyde, which the aerobic pathway facilitates the conversion from L-lactic acid to pyruvic acid via L-lactate dehydrogenase, and the anaerobic pathway facilitates conversion from lactaldehyde to propane-1,2-diol via lactaldehyde reductase. Under aerobic conditions, L-lactaldehyde is oxidized in two steps to pyruvate, thereby channeling all the carbons from fucose or rhamnose into central metabolic pathways. Under anaerobic conditions, L-lactaldehyde is reduced to L-1,2-propanediol, which is secreted into the environment.
Metabolic
3
109709
677
SubPathway
109209
1134
Compound
117
109788
549
SubPathway
109297
164
Compound
2236
Escherichia coli and Salmonella: Cellular and Molecular Biology (EcoSal). Online edition.
590
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
2
Platelet
CL:0000233
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
7
Epithelial Cell
CL:0000066
6
Myocyte
CL:0000187
3
Escherichia coli
562
Prokaryote
23
Pseudomonas aeruginosa
287
Prokaryote
1
Homo sapiens
9606
Eukaryote
Human
12
Mus musculus
10090
Eukaryote
Mouse
2
Bacteria
2
Prokaryote
Bacteria
24
Solanum lycopersicum
4081
Eukaryote
Tomato
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
17
Rattus norvegicus
10116
Eukaryote
Rat
5
Bos taurus
9913
Eukaryote
Cattle
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
19
Schizosaccharomyces pombe
4896
Eukaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
11
Extracellular Space
GO:0005615
31
Periplasmic Space
GO:0005620
1
Cytosol
GO:0005829
3
Mitochondrial Matrix
GO:0005759
5
Cytoplasm
GO:0005737
2
Mitochondrion
GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
12
Mitochondrial Inner Membrane
GO:0005743
14
Mitochondrial Outer Membrane
GO:0005741
24
Mitochondrial Intermembrane Space
GO:0005758
13
Endoplasmic Reticulum
GO:0005783
35
Chloroplast
GO:0009507
4
Peroxisome
GO:0005777
10
Cell Membrane
GO:0005886
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
15
Nucleus
GO:0005634
27
Peroxisome Membrane
GO:0005778
19
sarcoplasmic reticulum
GO:0016529
25
Golgi apparatus
GO:0005794
6
Lysosome
GO:0005764
16
Lysosomal Lumen
GO:0043202
18
Melanosome Membrane
GO:0033162
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
40
Periplasm
GO:0042597
1
Liver
BTO:0000759
72
9
28
Stomach
BTO:0001307
155
26
8
Blood Vessel
BTO:0001102
74
11
2
Endothelium
BTO:0000393
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
25
Intestine
BTO:0000648
4
Adrenal Medulla
BTO:0000049
71
8
11
Heart
BTO:0000562
73
10
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
105
11
3
PW_BS000105
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3
PW_BS000107
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1
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PW_BS000108
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PW_BS000024
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1
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PW_BS000024
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PW_BS000008
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PW_BS000015
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PW_BS000002
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1
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PW_BS000115
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40957
α-L-rhamnopyranose
Alpha-L-Rhamnose, also known as α-L-rha or alpha-L-rha, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Alpha-L-Rhamnose is soluble (in water) and a very weakly acidic compound (based on its pKa). Alpha-L-Rhamnose may be a unique E.coli metabolite.
27907
[H][C@@]1(C)O[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O
C6H12O5
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6+/m0/s1
SHZGCJCMOBCMKK-HGVZOGFYSA-N
(2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol
164.1565
164.068473494
0.70
4
α-L-rhamnopyranose
0
0
6-deoxy-α-l-mannopyranose, α-l-mannomethylose, isodulcit
PW_C040957
αLR
5722
105
5723
107
5724
108
42427
318
42428
315
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
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111
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112
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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
40958
β-L-rhamnopyranose
β-L-rhamnopyranose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. β-L-rhamnopyranose is soluble (in water) and a very weakly acidic compound (based on its pKa). β-L-rhamnopyranose may be a unique E.coli metabolite.
27586
C[C@@H]1O[C@H](O)[C@H](O)[C@H](O)[C@H]1O
C6H12O5
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6-/m0/s1
SHZGCJCMOBCMKK-YJRYQGEOSA-N
(2S,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol
164.1565
164.068473494
0.70
4
β-L-rhamnose
0
0
PW_C040958
βLR
6451
107
6452
108
42612
318
42613
315
40959
keto-L-rhamnulose
keto-L-rhamnulose belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. keto-L-rhamnulose is soluble (in water) and a very weakly acidic compound (based on its pKa).
CC(O)C(O)C(O)C(=O)CO
C6H12O5
InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h3,5-8,10-11H,2H2,1H3
QZNPNKJXABGCRC-UHFFFAOYSA-N
1,3,4,5-tetrahydroxyhexan-2-one
164.157
164.068473486
0.37
4
fuculose
0
0
PW_C040959
KLR
40960
L-rhamnulofuranose
L-Rhamnulofuranose belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. L-Rhamnulofuranose is very soluble (in water) and a very weakly acidic compound (based on its pKa). L-Rhamnulofuranose may be a unique E.coli metabolite. L-Rhamnulofuranose can be converted into L-rhamnulose 1-phosphate; which is mediated by the enzyme L-rhamnulose kinase.
CC1OC(O)(CO)C(O)C1O
C6H12O5
InChI=1S/C6H12O5/c1-3-4(8)5(9)6(10,2-7)11-3/h3-5,7-10H,2H2,1H3
CJJCPDZKQKUXSS-UHFFFAOYSA-N
2-(hydroxymethyl)-5-methyloxolane-2,3,4-triol
164.157
164.068473486
0.85
4
2-(hydroxymethyl)-5-methyloxolane-2,3,4-triol
0
0
PW_C040960
LR
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
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
40961
L-rhamnulose 1-phosphate
L-rhamnulose 1-phosphate is soluble (in water) and a very weakly acidic compound (based on its pKa). L-Rhamnulose 1-phosphate has the chemical formula C9H19O5P, and an average molecular weight of 238.22. L-Rhamnulose 1-phosphate is involved in the Fucose and Rhamnose Degradation Pathway.
58313
CC(O)C(O)C(O)C(=C)COP(C)(O)=C
C9H19O5P
InChI=1S/C9H19O5P/c1-6(5-14-15(3,4)13)8(11)9(12)7(2)10/h7-13H,1,3,5H2,2,4H3
QRXAIBTYLQNPRQ-UHFFFAOYSA-N
methyl(methylidene)[(3,4,5-trihydroxy-2-methylidenehexyl)oxy]phosphinous acid
238.22
238.09701071
-1.34
4
methyl(methylidene)(3,4,5-trihydroxy-2-methylidenehexyl)oxyphosphinous acid
0
0
L-rhamnulose-1p, l-rhamnulose-1-p, 6-deoxy-l-fructose 1-phosphate
PW_C040961
LR1P
1134
Dihydroxyacetone phosphate
HMDB0001473
Dihydroxyacetone phosphate, also known as 3-phosphate, dihydroxyacetone or 3-hydroxy-2-oxopropyl phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Dihydroxyacetone phosphate has been detected in multiple biofluids, such as saliva and blood. Within the cell, dihydroxyacetone phosphate is primarily located in the peroxisome, mitochondria and cytoplasm. Dihydroxyacetone phosphate exists in all living organisms, ranging from bacteria to humans. In humans, dihydroxyacetone phosphate is involved in cardiolipin biosynthesis CL(i-13:0/i-21:0/a-17:0/i-14:0) pathway, cardiolipin biosynthesis CL(i-14:0/a-13:0/i-19:0/a-25:0) pathway, cardiolipin biosynthesis CL(i-12:0/i-13:0/i-17:0/i-12:0) pathway, and cardiolipin biosynthesis CL(a-13:0/18:2(9Z,11Z)/i-20:0/i-22:0) pathway. Dihydroxyacetone phosphate is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(8:0/a-21:0/13:0) pathway, de novo triacylglycerol biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(i-20:0/i-21:0/19:0) pathway, and de novo triacylglycerol biosynthesis TG(i-22:0/17:0/i-14:0) pathway. Outside of the human body, dihydroxyacetone phosphate can be found in a number of food items such as towel gourd, boysenberry, jujube, and prunus (cherry, plum). This makes dihydroxyacetone phosphate a potential biomarker for the consumption of these food products. Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.
57-04-5
C00111
668
16108
DIHYDROXY-ACETONE-PHOSPHATE
648
DB04326
OCC(=O)COP(O)(O)=O
C3H7O6P
InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
GNGACRATGGDKBX-UHFFFAOYSA-N
(3-hydroxy-2-oxopropoxy)phosphonic acid
170.0578
169.998024468
-0.89
3
dihydroxyacetone-phosphate
0
-2
FDB001618
1,3-dihydroxy-2-propanone mono(dihydrogen phosphate);1,3-dihydroxy-2-propanone phosphate;1,3-dihydroxyacetone 1-phosphate;1-hydroxy-3-(phosphonooxy)-2-propanone;1-hydroxy-3-(phosphonooxy)acetone;Dhap;Di-oh-acetone-p;Dihydroxy-acetone-p;Dihydroxy-acetone-phosphate;Dihydroxyacetone 3-phosphate;Dihydroxyacetone monophosphate;Dihydroxyacetone phosphate;Dihydroxyacetone-p;Dihydroxyacetone-phosphate;Glycerone phosphate;Glycerone-phosphate;Phosphoric acid ester with 1,3-dihydroxy-2-propanone;1,3-dihydroxy-2-propanone monodihydrogen phosphate;3-hydroxy-2-oxopropyl phosphate;Glycerone monophosphate;1,3-dihydroxy-2-propanone monodihydrogen phosphoric acid;Glycerone phosphoric acid;1,3-dihydroxy-2-propanone phosphoric acid;1,3-dihydroxyacetone 1-phosphoric acid;3-hydroxy-2-oxopropyl phosphoric acid;Dihydroxyacetone monophosphoric acid;Dihydroxyacetone phosphoric acid;Glycerone monophosphoric acid
PW_C001134
Dhapp
1026
8
1474
2
3305
5
4253
42
5813
108
5908
147
5936
151
6884
160
42660
315
77098
132
77934
111
78374
345
78559
334
93824
124
110551
388
115839
118
120733
122
122564
418
122590
408
123333
135
125137
454
125162
374
125787
297
125950
299
126712
489
126736
482
127242
205
128303
506
128330
502
40962
(S)-lactaldehyde
L-Lactaldehyde, also known as 2-hydroxypropanal, belongs to the class of organic compounds known as alpha-hydroxyaldehydes. These are organic compounds containing an aldehyde substituted with a hydroxyl group on the adjacent carbon. L-Lactaldehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Outside of the human body, L-lactaldehyde can be found in a number of food items such as jicama, cereals and cereal products, wax gourd, and devilfish. This makes L-lactaldehyde a potential biomarker for the consumption of these food products.
18041
CC(O)C=O
C3H6O2
InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3
BSABBBMNWQWLLU-UHFFFAOYSA-N
2-hydroxypropanal
74.079
74.036779433
0.95
1
lactaldehyde
0
0
PW_C040962
S-Lacal
40963
L-fuculose 1-phosphate
L-fuculose 1-phosphate belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. L-fuculose 1-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa).
57846
CC(O)C(O)C(O)C(=O)COP([O-])([O-])=O
C6H11O8P
InChI=1S/C6H13O8P/c1-3(7)5(9)6(10)4(8)2-14-15(11,12)13/h3,5-7,9-10H,2H2,1H3,(H2,11,12,13)/p-2
KNYGWWDTPGSEPD-UHFFFAOYSA-L
3,4,5-trihydroxy-1-(phosphonatooxy)hexan-2-one
242.121
242.020251472
-0.64
3
3,4,5-trihydroxy-1-(phosphonatooxy)hexan-2-one
-2
-2
PW_C040963
LF1P
40964
L-fuculose
L-fuculose belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. L-fuculose is soluble (in water) and a very weakly acidic compound (based on its pKa). L-Fuculose has the chemical formula C6H12O5, and an average molecular weight of 164.157. L-Fuculose is involved in the Fucose and Rhamnose Degradation Pathway.
17617
CC(O)C(O)C(O)C(=O)CO
C6H12O5
InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h3,5-8,10-11H,2H2,1H3
QZNPNKJXABGCRC-UHFFFAOYSA-N
1,3,4,5-tetrahydroxyhexan-2-one
164.157
164.068473486
0.37
4
fuculose
0
0
L-fuculose,l-fuculose,6-deoxy-l-lyxo-hex-2-ulose
PW_C040964
LF
40965
α-L-fucopyranose
Alpha-L-Fucose, also known as alpha-L-fuc or α-L-fuc, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Alpha-L-Fucose is soluble (in water) and a very weakly acidic compound (based on its pKa). Alpha-L-Fucose is also a parent compound for other transformation products, including but not limited to, alpha-L-fucose 1-phosphate, quercetin 3-O-alpha-L-fucopyranoside, and 4-O-acetyl-2,3-di-O-methyl-alpha-L-fucopyranose..
42548
C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O
C6H12O5
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6+/m0/s1
SHZGCJCMOBCMKK-SXUWKVJYSA-N
(2R,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
164.1565
164.068473494
0.70
4
α-L-fucose
0
0
Alpha-l-fucopyranose, alpha-l-fucose
PW_C040965
αLF
40966
β-L-fucopyranose
HMDB0124735
β-L-fucopyranose belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. β-L-fucopyranose is soluble (in water) and a very weakly acidic compound (based on its pKa). β-L-fucopyranose exists in all living organisms, ranging from bacteria to humans.
42589
CC1OC(O)C(O)C(O)C1O
C6H12O5
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3
SHZGCJCMOBCMKK-UHFFFAOYSA-N
6-methyloxane-2,3,4,5-tetrol
164.157
164.068473486
0.70
4
6-methyloxane-2,3,4,5-tetrol
0
0
β-l-fucose, beta-l-fucose
PW_C040966
βLF
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
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
1144
NADH
HMDB0001487
NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, 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). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).
58-68-4
C00004
439153
16908
NADH
388299
DB00157
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O14P2
InChI=1S/C21H29N7O14P2/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/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BOPGDPNILDQYTO-NNYOXOHSSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
665.441
665.124771695
-2.35
8
NADH
0
-2
FDB022649
1,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotide
PW_C001144
NADH
143
4
153
3
490
8
648
10
1115
2
1275
5
1469
54
2230
49
2781
17
2836
29
3109
9
4806
18
4812
18
4821
28
4904
6
4959
31
5169
95
5240
103
5332
111
5358
112
5466
123
5479
125
5593
135
5698
100
5737
108
5829
141
5915
147
5945
151
6027
155
6079
161
6387
1
6472
178
6771
117
6893
160
7011
188
7099
163
7172
205
7195
206
7462
222
8244
226
8360
225
9086
224
11809
198
11821
216
12320
249
13003
298
13015
300
13255
223
42403
322
42618
315
77107
132
77123
133
77208
134
77371
331
77651
336
77668
334
77700
332
77707
130
77917
113
77986
347
80009
368
80691
119
93822
124
110549
388
112854
94
115838
118
119955
406
120172
407
120378
122
120986
408
121162
425
121244
126
121693
429
121818
383
122616
384
122745
120
123127
447
123138
136
123551
374
123734
460
123814
443
124242
464
124371
398
125189
121
125345
479
125531
481
125762
297
125808
299
125926
482
126516
495
126767
480
126888
501
127385
502
128090
390
128362
391
128429
395
122
L-Lactic acid
HMDB0000190
Lactic acid is an organic acid. It is a chiral molecule, consisting of two optical isomers, L-lactic acid and D-lactic acid, with the L-isomer being the most common in living organisms. Lactic acid plays a role in several biochemical processes and is produced in the muscles during intense activity. In animals, L-lactate is constantly produced from pyruvate via the enzyme lactate dehydrogenase (LDH) in a process of fermentation during normal metabolism and exercise. It does not increase in concentration until the rate of lactate production exceeds the rate of lactate removal. This is governed by a number of factors, including monocarboxylate transporters, lactate concentration, the isoform of LDH, and oxidative capacity of tissues. The concentration of blood lactate is usually 1-2 mmol/L at rest, but can rise to over 20 mmol/L during intense exertion. There are some indications that lactate, and not glucose, is preferentially metabolized by neurons in the brain of several mammalian species, including mice, rats, and humans. Glial cells, using the lactate shuttle, are responsible for transforming glucose into lactate, and for providing lactate to the neurons. Lactate measurement in critically ill patients has been traditionally used to stratify patients with poor outcomes. However, plasma lactate levels are the result of a finely tuned interplay of factors that affect the balance between its production and its clearance. When the oxygen supply does not match its consumption, organisms adapt in many different ways, up to the point when energy failure occurs. Lactate, being part of the adaptive response, may then be used to assess the severity of the supply/demand imbalance. In such a scenario, the time to intervention becomes relevant: early and effective treatment may allow tissues and cells to revert to a normal state, as long as the oxygen machinery (i.e. mitochondria) is intact. Conversely, once the mitochondria are deranged, energy failure occurs even in the presence of normoxia. The lactate increase in critically ill patients may, therefore, be viewed as an early marker of a potentially reversible state (PMID: 16356243). When present in sufficiently high levels, lactic acid can act as an oncometabolite, an immunosuppressant, an acidogen, and a metabotoxin. An oncometabolite is a compound that promotes tumor growth and survival. An immunosuppressant reduces or arrests the activity of the immune system. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of lactic acid are associated with at least a dozen inborn errors of metabolism, including 2-methyl-3-hydroxybutyryl CoA dehydrogenase deficiency, biotinidase deficiency, fructose-1,6-diphosphatase deficiency, glycogen storage disease type 1A (GSD1A) or Von Gierke disease, glycogenosis type IB, glycogenosis type IC, glycogenosis type VI, Hers disease, lactic acidemia, Leigh syndrome, methylmalonate semialdehyde dehydrogenase deficiency, pyruvate decarboxylase E1 component deficiency, pyruvate dehydrogenase complex deficiency, pyruvate dehydrogenase deficiency, and short chain acyl CoA dehydrogenase deficiency (SCAD deficiency). Locally high concentrations of lactic acid or lactate are found near many tumors due to the upregulation of lactate dehydrogenase (PMID: 15279558). Lactic acid produced by tumors through aerobic glycolysis acts as an immunosuppressant and tumor promoter (PMID: 23729358). Indeed, lactic acid has been found to be a key player or regulator in the development and malignant progression of a variety of cancers (PMID: 22084445). A number of studies have demonstrated that malignant transformation is associated with an increase in aerobic cellular lactate excretion. Lactate concentrations in various carcinomas (e.g. uterine cervix, head and neck, colorectal region) at first diagnosis of the disease, can be relatively low or extremely high (up to 40 µmol/g) in different individual tumors or within the same lesion (PMID: 15279558). High molar concentrations of lactate are correlated with a high incidence of distant metastasis. Low lactate tumors (< median of approximately 8 µmol/g) are associated with both an overall longer and disease-free survival compared to high lactate lesions (lactate > approximately 8 µmol/g). Lactate-induced secretion of hyaluronan by tumor-associated fibroblasts creates a milieu favourable for cell migration and metastases (PMID: 22084445). An acidic environment (pH 6-6.5), which is common in many tumors, allows tumor cells to evade the immune response, and therefore allows them to grow unchecked. Locally high concentrations of lactic acid are known to markedly impede the function of normal immune cells and will lead to a loss of T-cell function of human tumor-infiltrating lymphocytes (PMID: 22084445). Lactic acid is also an organic acid and acts as a general acidogen. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development.
79-33-4
C00186
107689
422
L-LACTATE
96860
C[C@@H](O)C(O)=O
C3H6O3
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
JVTAAEKCZFNVCJ-UWTATZPHSA-N
(2S)-2-hydroxypropanoic acid
90.0779
90.031694058
0.79
2
(α)-lactate
0
-1
FDB003294
(+)-lactate;(+)-lactic acid;(s)-(+)-2-hydroxypropanoate;(s)-(+)-2-hydroxypropanoic acid;(s)-2-hydroxypropanoate;(s)-2-hydroxypropanoic acid;(s)-2-hydroxypropionate;(s)-2-hydroxypropionic acid;(s)-2-hydroxy-propanoate;(s)-2-hydroxy-propanoic acid;(s)-lactate;(s)-lactic acid;(alpha)-lactate;(alpha)-lactic acid;1-hydroxyethane 1-carboxylate;1-hydroxyethane 1-carboxylic acid;1-hydroxyethanecarboxylate;1-hydroxyethanecarboxylic acid;2-hydroxypropanoate;2-hydroxypropanoic acid;2-hydroxypropionate;L-(+)- lactic acid;L-2-hydroxypropanoate;L-2-hydroxypropanoic acid;Lactate;Lactic acid;Milk acid;Sarcolactic acid;A-hydroxypropanoate;A-hydroxypropanoic acid;A-hydroxypropionate;A-hydroxypropionic acid;Alpha-hydroxypropanoate;Alpha-hydroxypropanoic acid;Alpha-hydroxypropionate;Alpha-hydroxypropionic acid;(s)-(+)-lactic acid;L-(+)-alpha-hydroxypropionic acid;L-(+)-lactic acid;L-lactic acid;L-milchsaeure
PW_C000122
Lactate
1717
8
2399
2
5050
15
77964
132
78764
111
117833
114
121214
124
121438
122
122677
409
123784
118
123996
135
125252
137
126062
297
126788
299
126810
483
127514
205
128385
388
128409
208
40967
(S)-Propane-1,2-diol
CC(CO)O1,2-Propanediol (1,2-PDO) occurs in two stereoisomers - (S)-propane-1,2-diol and (R)-propane-1,2-diol. Both forms are produced by certain organisms. For example, during the catabolism of 6-deoxyhexoses [Suzuki68, Weimer84] or during the fermentation of glucose via methylglyoxal [TranDin85, Cameron86].
1,2-PDO is a bulk industrial chemical with a global demand of around 1.36 million tons/year [Shelley07]. It is widely used in the production of unsaturated polyester resin and as a nontoxic replacement of ethylene glycol in deicer and antifreeze products. Current commercial production of 1,2-PDO is mainly by a synthetic process that results in a racemic mixture.
29002
CC(O)CO
C3H8O2
InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3
DNIAPMSPPWPWGF-UHFFFAOYSA-N
propane-1,2-diol
76.0944
76.0524295
1.10
2
1,2-propanediol
0
0
(s)-propane-1,2-diol, (s)-1,2-propane-diol, (s)-1,2-propanediol, (s)-1,2-dihydroxypropane, l-1,2-propanediol
PW_C040967
Sp12di
164
Pyruvic acid
HMDB0000243
Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).
127-17-3
C00022
1060
32816
PYRUVATE
1031
DB00119
CC(=O)C(O)=O
C3H4O3
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
LCTONWCANYUPML-UHFFFAOYSA-N
2-oxopropanoic acid
88.0621
88.016043994
0.18
1
pyruvic acid
0
-1
FDB008293
2-oxopropanoate;2-oxopropanoic acid;2-oxopropionate;2-oxopropionic acid;Acetylformate;Acetylformic acid;Bts;Pyroracemate;Pyroracemic acid;Pyruvate;A-ketopropionate;A-ketopropionic acid;Alpha-ketopropionate;Alpha-ketopropionic acid;2-ketopropionic acid;2-oxopropansaeure;2-oxopropionsaeure;Acide pyruvique;Alpha-oxopropionsaeure;Brenztraubensaeure;Ch3cocooh;2-ketopropionate;α-ketopropionate;α-ketopropionic acid;A-oxopropionsaeure;α-oxopropionsaeure
PW_C000164
Pyr
17
2
20
4
422
8
1181
3
1449
50
1457
26
5365
103
5405
117
5440
118
5444
120
5566
132
5570
133
5893
95
5920
147
5951
151
6022
155
6067
156
6074
161
6126
160
6383
1
6467
178
6510
177
6532
85
7457
222
7495
220
8200
225
12622
31
15292
249
15349
18
77310
111
77972
346
77978
327
78090
112
80004
368
80042
367
80695
135
112879
94
115683
121
119950
406
120011
124
120175
122
120878
407
121148
423
121154
424
123454
119
123720
458
123726
459
125340
479
125390
299
125534
297
125854
481
126883
501
126931
388
127067
205
127858
206
227
oxidized electron acceptor
Compound
Compound
PW_EC000227
ox-e
40
Reduced acceptor
Compound
PW_EC000040
15022
ChEBI
RA
7394
L-rhamnose-proton symporter
P27125
Involved in rhamnose transmembrane transporter activity. Uptake of L-rhamnose across the boundary membrane with the concomitant transport of protons into the cell (symport system). Can also transport L-mannose and L-xylose, but at reduced rates.
rhaT
b3907
AP009048
3
8607
109
7648
L-rhamnose mutarotase
P32156
Involved in protein binding. Involved in the anomeric conversion of L-rhamnose.
rhaM
U00096
3
5.1.3.32
8716
101
6522
L-rhamnose isomerase
P32170
Involved in L-rhamnose isomerase activity. L-rhamnose = L-rhamnulose.
rhaA
b3903
AP009048
3
5.3.1.14
8717
101
6523
Rhamnulokinase
P32171
Involved in phosphotransferase activity, alcohol group as acceptor. ATP + L-rhamnulose = ADP + L-rhamnulose 1- phosphate.
rhaB
b3904
AP009048
3
2.7.1.5
6521
Rhamnulose-1-phosphate aldolase
P32169
Involved in metal ion binding. Catalyzes the reversible cleavage of L-rhamnulose-1- phosphate to dihydroxyacetone phosphate (DHAP) and L-lactaldehyde.
rhaD
b3902
AP009048
3
4.1.2.19
8718
101
6160
L-fuculose phosphate aldolase
P0AB87
Involved in metal ion binding. L-fuculose 1-phosphate = glycerone phosphate + (S)-lactaldehyde.
fucA
b2800
AP009048
3
4.1.2.17
6315
L-fuculokinase
P11553
Involved in phosphotransferase activity, alcohol group as acceptor. ATP + L-fuculose = ADP + L-fuculose 1- phosphate.
fucK
b2803
AP009048
3
2.7.1.51
6711
L-fucose isomerase
P69922
Involved in L-fucose isomerase activity. Converts the aldose L-fucose into the corresponding ketose L-fuculose. Is also able to convert D-arabinose into D- ribulose, but this isomerase has a higher affinity for fucose and fuculose than for arabinose and ribulose, respectively.
fucI
b2802
AP009048
3
5.3.1.25; 5.3.1.3
8719
101
6245
L-fucose mutarotase
P0AEN8
Involved in racemase and epimerase activity. Involved in the anomeric conversion of L-fucose. It also exhibits a pyranase activity for D-ribose.
fucU
b2804
AP009048
3
5.1.3.29
8720
101
6448
Lactaldehyde dehydrogenase
P25553
Involved in oxidoreductase activity. Acts on lactaldehyde as well as other aldehydes.
aldA
b1415
AP009048
3
1.2.1.22; 1.2.1.21
6139
Lactaldehyde reductase
P0A9S1
Involved in oxidoreductase activity. (R)-propane-1,2-diol + NAD(+) = (R)- lactaldehyde + NADH.
fucO
b2799
AP009048
3
1.1.1.77
6539
L-lactate dehydrogenase [cytochrome]
P33232
Involved in catalytic activity. (S)-lactate + 2 ferricytochrome c = pyruvate + 2 ferrocytochrome c + 2 H(+).
lldD
b3605
AP009048
3
1.1.-.-
8721
109
1569
rhamnose / lyxose:H+ symporter
3
PW_P001569
1852
7394
1570
L-rhamnose mutarotase
3
PW_P001570
1853
7648
2
1571
L-rhamnose isomerase
3
PW_P001571
1854
6522
4
1572
L-rhamnulose kinase
3
PW_P001572
1855
6523
1573
rhamnulose-1-phosphate aldolase
3
PW_P001573
1856
6521
4
1574
L-fuculose-phosphate aldolase
3
PW_P001574
1857
6160
4
1575
L-fuculokinase
3
PW_P001575
1858
6315
1576
L-fucose isomerase
3
PW_P001576
1859
6711
6
1577
L-fucose mutarotase
3
PW_P001577
1860
6245
6
1578
aldehyde dehydrogenase A, NAD-linked
3
PW_P001578
1861
6448
4
1579
L-1,2-propanediol oxidoreductase
3
PW_P001579
1862
6139
2
1580
L-lactate dehydrogenase
3
PW_P001580
1863
6539
2967
false
PW_R002967
Right
11768
40957
1
Compound
false
11769
40958
1
Compound
false
2934
1570
5.1.3.32
2968
false
PW_R002968
Right
11770
40958
1
Compound
false
11771
40959
1
Compound
false
2935
1571
5.3.1.14
2969
true
PW_R002969
Right
11772
40959
1
Compound
false
11773
40960
1
Compound
false
2970
false
PW_R002970
Right
11774
40960
1
Compound
false
11775
414
1
Compound
false
11776
1034
1
Compound
false
11777
40034
1
Compound
false
11778
40961
1
Compound
false
2936
1572
2.7.1.5
2971
false
PW_R002971
Right
11779
40961
1
Compound
false
11780
1134
1
Compound
false
11781
40962
1
Compound
false
2937
1573
4.1.2.19
2972
false
PW_R002972
Right
11782
40963
1
Compound
false
11783
1134
1
Compound
false
11784
40962
1
Compound
false
2938
1574
4.1.2.17
2973
false
PW_R002973
Right
11785
414
1
Compound
false
11786
40964
1
Compound
false
11787
40963
1
Compound
false
11788
1034
1
Compound
false
11789
40034
1
Compound
false
2939
1575
2.7.1.51
2974
false
PW_R002974
Right
11790
40965
1
Compound
false
11791
40964
1
Compound
false
2940
1576
5.3.1.25
2975
false
PW_R002975
Right
11792
40966
1
Compound
false
11793
40965
1
Compound
false
2941
1577
5.1.3.29
2976
false
PW_R002976
Right
11794
721
1
Compound
false
11795
1420
1
Compound
false
11796
40962
1
Compound
false
11797
1144
1
Compound
false
11798
40034
2
Compound
false
11799
122
1
Compound
false
2942
1578
1.2.1.22
2977
false
PW_R002977
Right
11800
40962
1
Compound
false
11801
1144
1
Compound
false
11802
40034
1
Compound
false
11803
721
1
Compound
false
11804
40967
1
Compound
false
2943
1579
1.1.1.77
2978
false
PW_R002978
Right
11805
122
1
Compound
false
11806
227
1
ElementCollection
false
11807
40
1
ElementCollection
false
11808
164
1
Compound
false
2944
1580
1.1.-.-
363
PW_T000363
Active
424
40957
1
Compound
107
108
Right
425
40034
1
Compound
107
108
Right
309
1569
2015-03-27T21:52:11-06:00
2015-03-27T21:52:11-06:00
109
440
PW_T000440
540
40034
1
Compound
107
108
Right
541
40958
1
Compound
107
108
Right
378
1569
2015-06-12T16:27:03-06:00
2015-06-12T16:27:03-06:00
109
15952
40957
107
3
false
655
240
10
regular
100
110
15958
40957
108
3
false
656
675
10
regular
100
110
15959
40034
107
55
false
537
326
10
regular
78
78
15960
40034
108
55
false
536
516
10
regular
78
78
15961
40958
3
false
1101
675
10
regular
100
110
15962
40959
3
false
1496
675
10
regular
100
110
15963
40960
3
false
1701
675
10
regular
100
110
15964
414
42
false
1841
665
10
regular
50
30
15965
1034
43
false
2107
670
10
regular
50
30
15966
40034
55
false
2082
782
10
regular
78
78
15967
40961
3
false
2225
670
10
regular
100
110
15968
1134
3
false
2635
670
10
regular
100
110
15969
40962
3
false
2435
1260
10
regular
100
110
15970
40963
3
false
1960
1260
10
regular
100
110
15971
1134
3
false
2200
1070
10
regular
100
110
15972
414
42
false
1581
1245
10
regular
50
30
15973
40964
3
false
1451
1265
10
regular
100
100
15974
1034
43
false
1872
1365
10
regular
50
30
15975
40034
55
false
1847
1191
10
regular
78
78
15976
40965
3
false
956
1260
10
regular
100
110
15977
40966
108
3
false
511
1260
10
regular
100
110
15978
721
59
false
2542
1435
10
regular
50
30
15979
1420
49
false
2352
1396
10
regular
78
78
15980
1144
60
false
2537
1645
10
regular
50
30
15981
40034
55
false
2352
1636
10
regular
78
78
15982
122
3
false
2440
1720
10
regular
100
100
15987
1144
60
false
2667
1430
10
regular
50
30
15988
40034
55
false
2837
1416
10
regular
78
78
15989
721
59
false
2661
1620
10
regular
50
30
15990
40967
3
false
2731
1675
10
regular
100
110
22021
40034
107
55
false
1224
347
10
regular
78
78
22022
40034
108
55
false
1019
547
10
regular
78
78
22162
164
3
false
2440
2156
10
regular
100
100
2678957
40958
108
3
false
1104
241
10
regular
100
110
626
227
144
false
2245
1840
12
regular
150
70
627
40
144
false
2255
2066
12
regular
150
70
7991
7394
109
76
false
630
435
8
subunit
regular
150
70
7992
7648
101
6
false
846
690
8
subunit
regular
160
80
7993
6522
101
8
false
1281
690
8
subunit
regular
140
85
7994
6523
2
false
1923
692
8
subunit
regular
150
70
7995
6521
101
8
false
2410
687
8
subunit
regular
140
85
7996
6160
8
false
2180
1275
8
subunit
regular
140
85
7997
6315
2
false
1658
1282
8
subunit
regular
150
70
7998
6711
101
17
false
1156
1277
8
subunit
regular
180
85
7999
6245
101
17
false
701
1275
8
subunit
regular
180
85
8000
6448
8
false
2418
1512
8
subunit
regular
140
85
8001
6139
6
false
2698
1520
8
subunit
regular
160
80
10633
6539
109
2
false
2415
1950
8
subunit
regular
150
70
947997
7394
76
false
1078
441
8
subunit
regular
150
70
6419
1569
574
7896
7991
6420
1570
574
7897
7992
6421
1571
574
7898
7993
6422
1572
574
7899
7994
6423
1573
574
7900
7995
6424
1574
574
7901
7996
6425
1575
574
7902
7997
6426
1576
574
7903
7998
6427
1577
574
7904
7999
6428
1578
574
7905
8000
6429
1579
574
7906
8001
8322
1580
574
10455
10633
802872
1569
574
943877
947997
24285
M705 350 C705 380 705 405 705 435
83
false
18
24286
M706 675 C706 645 705 535 705 505
83
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24287
M615 365 C704 365 705 405 705 435
83
false
18
24288
M614 555 C694 554 705 535 705 505
83
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24289
M756 730 C787 731 814 731 846 730
5
false
18
24290
M1101 730 C1075 731 1037 731 1006 730
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24291
M1201 730 C1221 730 1263 730 1281 730
5
false
18
24292
M1496 730 C1476 731 1459 730 1421 730
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24293
M1646 729 C1665 729 1672 729 1691 730
5
false
18
24294
M1701 730 C1681 730 1627 727 1596 730
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24295
M1801 730 C1822 729 1906 727 1923 727
5
false
18
24296
M1866 695 C1867 728 1890 726 1923 727
5
false
18
24297
M2127 695 C2126 716 2109 727 2073 727
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24298
M2121 782 C2122 747 2120 728 2073 727
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24299
M2225 725 C2201 725 2114 728 2073 727
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24300
M2325 725 C2347 726 2387 727 2410 727
5
false
18
24301
M2635 725 C2614 726 2602 726 2550 727
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24302
M2485 1260 C2485 1203 2480 849 2480 772
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24303
M2060 1315 C2106 1314 2137 1317 2180 1315
5
false
18
24304
M2250 1180 C2250 1235 2250 1254 2250 1275
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24305
M2435 1315 C2354 1315 2372 1314 2320 1315
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24306
M1551 1315 C1613 1315 1616 1315 1658 1317
5
false
18
24307
M1606 1275 C1603 1300 1631 1318 1658 1317
5
false
18
24308
M1960 1315 C1929 1316 1860 1316 1808 1317
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24309
M1886 1269 C1886 1292 1849 1317 1808 1317
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24310
M1897 1365 C1898 1330 1846 1318 1808 1317
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24311
M1056 1315 C1082 1315 1112 1318 1156 1317
5
false
18
24312
M1451 1315 C1414 1315 1360 1317 1336 1317
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24313
M611 1315 C632 1315 676 1315 701 1315
5
false
18
24314
M956 1315 C911 1315 910 1317 881 1315
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24315
M2542 1450 C2482 1451 2488 1482 2488 1512
5
false
18
false
false
24316
M2430 1435 C2488 1437 2488 1482 2488 1512
5
false
18
24317
M2485 1370 C2487 1436 2485 1399 2488 1512
5
false
18
24318
M2537 1660 C2483 1663 2488 1627 2488 1597
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24319
M2430 1675 C2488 1673 2488 1627 2488 1597
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24320
M2490 1720 C2490 1690 2488 1627 2488 1597
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24326
M2535 1315 C2607 1314 2698 1315 2776 1317 C2776 1417 2777 1474 2778 1520
5
false
18
24327
M2717 1445 C2783 1446 2778 1490 2778 1520
5
false
18
24328
M2837 1455 C2786 1457 2778 1490 2778 1520
5
false
18
24329
M2711 1635 C2778 1639 2778 1630 2778 1600
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24330
M2781 1675 C2781 1645 2780 1629 2778 1600
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
32889
M2490 1820 C2490 1850 2490 1920 2490 1950
5
false
18
32890
M2490 2156 C2490 2126 2490 2050 2490 2020
5
false
18
true
M 25.946855044164835 2331.5949514418553 L 11 2330.3333951455593 L 17.380887721185843 2343.9085294686374
false
32891
M2395 1875 C2487 1874 2490 1909 2490 1950
5
false
18
32892
M2405 2101 C2483 2100 2490 2050 2490 2020
5
false
18
true
M 25.946855044164835 2331.5949514418553 L 11 2330.3333951455593 L 17.380887721185843 2343.9085294686374
false
3657765
M2685 670 C2685 646 2685 666 2685 623
5
false
18
3659591
M2250 1070 C2249 1053 2250 1027 2250 1012
5
false
18
3659592
M2490 2256 C2490 2286 2490 2276 2490 2306
5
false
18
3659593
M1224 386 C1175 386 1153 411 1153 441
83
false
18
3659594
M1097 586 C1150 584 1153 541 1153 511
83
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3659595
M1154 351 C1154 381 1153 411 1153 441
83
false
18
3659596
M1151 675 C1151 645 1153 541 1153 511
83
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4220
574
2967
14622
15958
24289
Left
14623
15961
24290
Right
4411
2934
6420
4221
574
2968
14624
15961
24291
Left
14625
15962
24292
Right
4412
2935
6421
4222
574
2969
14626
15962
24293
Left
14627
15963
24294
Right
4223
574
2970
14628
15963
24295
Left
14629
15964
24296
Left
14630
15965
24297
Right
14631
15966
24298
Right
14632
15967
24299
Right
4413
2936
6422
4224
574
2971
14633
15967
24300
Left
14634
15968
24301
Right
14635
15969
24302
Right
4414
2937
6423
4225
574
2972
14636
15970
24303
Left
14637
15971
24304
Right
14638
15969
24305
Right
4415
2938
6424
4226
574
2973
14639
15972
24306
Left
14640
15973
24307
Left
14641
15970
24308
Right
14642
15974
24309
Right
14643
15975
24310
Right
4416
2939
6425
4227
574
2974
14644
15976
24311
Left
14645
15973
24312
Right
4417
2940
6426
4228
574
2975
14646
15977
24313
Left
14647
15976
24314
Right
4418
2941
6427
4229
574
2976
14648
15978
24315
Left
14649
15979
24316
Left
14650
15969
24317
Left
14651
15980
24318
Right
14652
15981
24319
Right
14653
15982
24320
Right
4419
2942
6428
4231
574
2977
14659
15969
24326
Left
14660
15987
24327
Left
14661
15988
24328
Left
14662
15989
24329
Right
14663
15990
24330
Right
4420
2943
6429
5709
574
2978
20744
15982
32889
Left
20745
22162
32890
Right
580
626
32891
Left
581
627
32892
Right
5978
2944
8322
630
363
574
1389
15952
24285
Left
1390
15958
24286
Right
1391
15959
24287
Left
1392
15960
24288
Right
417
6419
309
78056
440
574
156877
22021
3659593
Left
156878
22022
3659594
Right
156879
15961
3659595
Left
156880
2678957
3659596
Right
24691
802872
378
109372
109709
574
14
false
2610
553
16
regular
106076
15968
3657765
Left
109459
109709
574
14
false
2175
942
16
regular
106155
15971
3659591
Left
109460
109788
574
14
false
2415
2306
16
regular
106156
22162
3659592
Left
186297
1955
1406
2.2
2.2
90
2
92
479
481
369549
M425 576 C425 526 475 476 525 476 C1237 476 2164 476 2876 476 C2926 476 2976 526 2976 576 C2976 1137 2976 1865 2976 2426 C2976 2476 2926 2526 2876 2526 C2164 2526 1237 2526 525 2526 C475 2526 425 2476 425 2426 C425 1865 425 1137 425 576
1
true
6
2551.0
2050.0
369550
M125 274 C125 224 175 174 225 174 C1120 174 2282 174 3177 174 C3227 174 3277 224 3277 274 C3277 1017 3277 1984 3277 2727 C3277 2777 3227 2827 3177 2827 C2282 2827 1120 2827 225 2827 C175 2827 125 2777 125 2727 C125 1984 125 1017 125 274
1
true
6
3152.0
2653.0
1539
15
Aerobic conditions
2405
2411
20
1.0
1.0
160
15
1540
15
Anaerobic conditions
2695
1773
20
1.0
1.0
160
15