1874
Pathway
L-Lyxose Degradation
L-lyxose is a sugar and a monosaccharide containing five carbon atoms and aldehyde group. Wild-type E.coli can't utilize L-lyxose as its source of carbon and energy. In mutated E.coli, it can metabolize l-lyxose through utilization of enzymes of the rhamnose, arabinose and 2,3-diketo-L-gulonate systems. β-L-lyxopyranose enter cell by L-rhamnose-proton symporter, then convert to l-xylulose by L-rhamnose isomerase. L-xylulose is further metabolized to L-xylulose-5-phosphate with energy ATP. Putative L-ribulose-5-phosphate 3-epimerase can convert L-xylulose -5-phosphate to L-ribulose 5-phosphate, and L-ribulose 5-phosphate 4-epimerase can catalyze L-ribulose 5-phosphate to xylulose 5-phosphate for further pentose phosphate.
Metabolic
PW002100
Center
PathwayVisualizationContext2387
1850
1948
#000099
PathwayVisualization1858
1874
L-Lyxose Degradation
L-lyxose is a sugar and a monosaccharide containing five carbon atoms and aldehyde group. Wild-type E.coli can't utilize L-lyxose as its source of carbon and energy. In mutated E.coli, it can metabolize l-lyxose through utilization of enzymes of the rhamnose, arabinose and 2,3-diketo-L-gulonate systems. β-L-lyxopyranose enter cell by L-rhamnose-proton symporter, then convert to l-xylulose by L-rhamnose isomerase. L-xylulose is further metabolized to L-xylulose-5-phosphate with energy ATP. Putative L-ribulose-5-phosphate 3-epimerase can convert L-xylulose -5-phosphate to L-ribulose 5-phosphate, and L-ribulose 5-phosphate 4-epimerase can catalyze L-ribulose 5-phosphate to xylulose 5-phosphate for further pentose phosphate.
Metabolic
3
109889
113174
SubPathway
109420
691
Compound
3945
1650346
Badia J, Gimenez R, Baldoma L, Barnes E, Fessner WD, Aguilar J: L-lyxose metabolism employs the L-rhamnose pathway in mutant cells of Escherichia coli adapted to grow on L-lyxose. J Bacteriol. 1991 Aug;173(16):5144-50.
1874
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
44531
β-L-lyxopyranose
β-L-lyxopyranose, also known as β-L-lyxose, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. β-L-lyxopyranose is very soluble (in water) and a very weakly acidic compound (based on its pKa). An L-lyxose in cyclic pyranose form.
1949-78-6
642638
557832
[H][C@]1(O)CO[C@]([H])(O)[C@]([H])(O)[C@]1([H])O
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-RSJOWCBRSA-N
(2S,3R,4R,5S)-oxane-2,3,4,5-tetrol
150.13
150.052823422
0.91
4
(2S,3R,4R,5S)-oxane-2,3,4,5-tetrol
0
0
β-l-lyxose
PW_C044531
βLL
6811
117
43766
322
42615
L-xylulose
L-Threo-2-pentulose, also known as L-lyxulose or L-xul, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. L-Threo-2-pentulose is soluble (in water) and a very weakly acidic compound (based on its pKa). L-Threo-2-pentulose has been detected in multiple biofluids, such as urine, blood, and cerebrospinal fluid. Within the cell, L-threo-2-pentulose is primarily located in the cytoplasm. L-Threo-2-pentulose exists in all living organisms, ranging from bacteria to humans. L-Threo-2-pentulose has been found to be associated with the diseases known as leukoencephalopathy; l-threo-2-pentulose has also been linked to the inborn metabolic disorders including ribose-5-phosphate isomerase deficiency.
OC[C@H](O)[C@@H](O)C(=O)CO
C5H10O5
InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m0/s1
ZAQJHHRNXZUBTE-WVZVXSGGSA-N
(3R,4S)-1,3,4,5-tetrahydroxypentan-2-one
150.1299
150.05282343
0.65
4
xylulose
0
0
PW_C042615
LX
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
40863
L-xylulose -5-phosphate
L-Xylulose 5-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). L-Xylulose 5-phosphate may be a unique E.coli metabolite. L-Xylulose -5-phosphate has the chemical formula C7H13O6P, and an average molecular weight of 224.15. L-Xylulose -5-phosphate is involved in a couple of pathways, which are Ascorbate Metabolism Pathway and L-Lyxose Degradation Pathway.
23615403
57829
CC(COP([O-])([O-])=O)C(C)C(=O)CO
C7H13O6P
InChI=1S/C7H15O6P/c1-5(4-13-14(10,11)12)6(2)7(9)3-8/h5-6,8H,3-4H2,1-2H3,(H2,10,11,12)/p-2
GOBYCGYLQSIFMQ-UHFFFAOYSA-L
1-hydroxy-3,4-dimethyl-5-(phosphonatooxy)pentan-2-one
224.15
224.046072296
-0.83
1
1-hydroxy-3,4-dimethyl-5-(phosphonatooxy)pentan-2-one
-2
-2
L-xylulose-5-p, l-xylulose 5-phosphate dianion, 5-o-phosphonato-l-xylulose, 5-o-phosphonato-l-threo-pentos-2-ulose
PW_C040863
LX5P
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
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
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
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
6581
L-xylulose/3-keto-L-gulonate kinase
P37677
Involved in phosphotransferase activity, alcohol group as acceptor. Catalyzes the phosphorylation of L-xylulose and 3-keto- L-gulonate. Is involved in L-lyxose utilization via xylulose, and may also be involved in the utilization of 2,3-diketo-L-gulonate.
lyx
b3580
AP009048
3
2.7.1.-; 2.7.1.53
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
7539
predicted L-xylulose 5-phosphate 3-epimerase
P37679
yiaR
b3582
3
5.1.3.22
6603
L-ribulose-5-phosphate 4-epimerase ulaF
P39306
Involved in metal ion binding. Catalyzes the isomerization of L-ribulose 5-phosphate to D-xylulose 5-phosphate. Is involved in the anaerobic L-ascorbate utilization.
ulaF
b4198
AP009048
3
5.1.3.4
6602
L-ribulose-5-phosphate 3-epimerase ulaE
P39305
Involved in intramolecular oxidoreductase activity, interconverting aldoses and ketoses. Catalyzes the isomerization of L-xylulose-5-phosphate to L-ribulose-5-phosphate. Is involved in the anaerobic L-ascorbate utilization.
ulaE
b4197
AP009048
3
5.1.3.22
1571
L-rhamnose isomerase
3
PW_P001571
1854
6522
4
1404
L-xylulose kinase
3
PW_P001404
1636
6581
2
1569
rhamnose / lyxose:H+ symporter
3
PW_P001569
1852
7394
1411
predicted L-xylulose 5-phosphate 3-epimerase
3
PW_P001411
1643
7539
1410
L-ribulose 5-phosphate 4-epimerase
3
PW_P001410
1642
6603
1409
L-xylulose 5-phosphate 3-epimerase
3
PW_P001409
1641
6602
6124
false
PW_R006124
Both
25063
44531
1
Compound
false
25064
42615
1
Compound
false
6085
1571
6125
false
PW_R006125
Right
25065
42615
1
Compound
false
25066
414
1
Compound
false
25067
40863
1
Compound
false
25068
1034
1
Compound
false
25069
40034
1
Compound
false
6086
1404
6126
false
PW_R006126
Right
25070
40863
1
Compound
false
25071
40862
1
Compound
false
6087
1411
6088
1409
6127
false
PW_R006127
Both
25072
40862
1
Compound
false
25073
691
1
Compound
false
6089
1410
513
PW_T000513
Active
652
40034
1
Compound
107
117
Right
653
44531
1
Compound
107
117
Right
442
1569
2015-10-14T10:10:53-06:00
2015-10-14T10:10:53-06:00
109
71656
44531
3
false
578
600
10
regular
100
110
71657
42615
3
false
578
960
10
regular
100
100
71658
414
42
false
533
1090
10
regular
50
30
71659
40863
3
false
941
1135
10
regular
100
110
71660
1034
43
false
761
1125
10
regular
50
30
71661
40034
55
false
816
1286
10
regular
78
78
71667
40034
107
55
false
500
506
10
regular
78
78
71668
40034
117
55
false
500
301
10
regular
78
78
71669
44531
117
3
false
578
185
10
regular
100
110
71670
40862
3
false
1346
1135
10
regular
100
110
71683
691
3
false
1346
730
10
regular
100
110
32829
6522
101
8
false
558
795
8
subunit
regular
140
85
32830
6581
6
false
550
1152
8
subunit
regular
160
80
32833
7394
109
76
false
553
390
8
subunit
regular
150
70
32834
7539
2
false
1131
1155
8
subunit
regular
150
70
32837
6603
2
false
1321
925
8
subunit
regular
150
70
27565
1571
1858
32510
32829
27566
1404
1858
32511
32830
27569
1569
1858
32514
32833
27570
1411
1858
32515
32834
27573
1410
1858
32518
32837
101711
M628 710 C628 740 628 765 628 795
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101712
M628 960 C628 930 628 910 628 880
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101713
M628 1060 C628 1090 630 1122 630 1152
5
false
18
101714
M583 1105 C633 1106 630 1122 630 1152
5
false
18
101715
M941 1190 C883 1192 756 1192 710 1192
5
false
18
true
M 219.65556106314202 544.8080957992291 L 204.70870601897718 543.5465395029331 L 211.08959374016302 557.1216738260115
false
101716
M786 1155 C776 1191 764 1192 710 1192
5
false
18
true
M 219.65556106314202 544.8080957992291 L 204.70870601897718 543.5465395029331 L 211.08959374016302 557.1216738260115
false
101717
M855 1286 C856 1222 808 1190 710 1192
5
false
18
true
M 219.65556106314202 544.8080957992291 L 204.70870601897718 543.5465395029331 L 211.08959374016302 557.1216738260115
false
101724
M578 545 C628 544 628 490 628 460
83
false
18
true
M 798.5 363.0096189432334 L 806 376 L 813.5 363.0096189432334
false
101725
M578 340 C625 342 628 360 628 390
83
false
18
false
false
101726
M628 600 C628 570 628 490 628 460
83
false
18
true
M 922.5 392.0096189432334 L 930 405 L 937.5 392.0096189432334
false
101727
M628 290 C628 320 628 355 628 385
83
false
18
false
false
101728
M1041 1190 C1089 1190 1091 1190 1131 1190
5
false
18
true
M 3285.0096189432334 1707.5 L 3298 1700 L 3285.0096189432334 1692.5
false
101729
M1346 1190 C1309 1189 1306 1190 1281 1190
5
false
18
true
M 71.00691433020143 989.2525345158999 L 56.0600592860366 987.9909782196039 L 62.440947007222434 1001.5661125426823
false
101744
M1396 1135 C1396 1103 1398 1029 1396 995
5
false
18
true
M 631.0669671724928 1241.5047835172536 L 616.120112128328 1240.2432272209576 L 622.5009998495137 1253.818361544036
false
101745
M1396 840 C1398 885 1395 895 1396 925
5
false
18
true
M 631.0669671724928 1241.5047835172536 L 616.120112128328 1240.2432272209576 L 622.5009998495137 1253.818361544036
false
3660985
M1396 730 C1396 700 1397 637 1397 607
5
false
18
true
M 1526.5 600.9903810567666 L 1519 588 L 1511.5 600.9903810567666
false
20780
1858
6124
80747
71656
101711
Left
80748
71657
101712
Right
20955
6085
27565
20781
1858
6125
80749
71657
101713
Left
80750
71658
101714
Left
80751
71659
101715
Right
80752
71660
101716
Right
80753
71661
101717
Right
20956
6086
27566
20782
1858
6126
80754
71659
101728
Left
80755
71670
101729
Right
20957
6087
27570
20787
1858
6127
80769
71670
101744
Left
80770
71683
101745
Right
20960
6089
27573
968
513
1858
2369
71667
101724
Left
2370
71668
101725
Right
2371
71656
101726
Left
2372
71669
101727
Right
720
27569
442
109561
109889
1858
14
false
1322
537
16
regular
106254
71683
3660985
Left
186486
767
574
1.0
1.0
0
2
92
479
481
3619
M125 225 C125 175 175 125 225 125 C679 125 1269 125 1723 125 C1773 125 1823 175 1823 225 C1823 649 1823 1201 1823 1625 C1823 1675 1773 1725 1723 1725 C1269 1725 679 1725 225 1725 C175 1725 125 1675 125 1625 C125 1201 125 649 125 225
1
true
6
1698.0
1600.0
3620
M423 524 C423 474 473 424 523 424 C796 424 1152 424 1425 424 C1475 424 1525 474 1525 524 C1525 766 1525 1082 1525 1324 C1525 1374 1475 1424 1425 1424 C1152 1424 796 1424 523 1424 C473 1424 423 1374 423 1324 C423 1082 423 766 423 524
1
true
6
1102.0
1000.0