532
Pathway
D-Alanine Metabolism
L-Alanine is an essential component of protein and peptidoglycan. The latter also contains about three molecules of D-alanine for every L-alanine. Only about 10 percent of the total alanine synthesized flows into peptidoglycan. Please refer to L-alanine metabolism (pathway PW000788 or SMP0000810). In this pathway, D-amino acid dehydrogenase degrades D-alanine to form pyruvate, which the later will serve as source of carbon for central metabolism. D-alanine can be formed by either biosynthetic alanine racemase or catabolic alanine racemase. D-alanine is required for forming the cell wall peptidoglycan (murein). D-alanine is metabolized by ATP driven D-alanine ligase A and B resulting in D-alanyl-D-alanine. This product is incorporated into peptidoglycan biosynthesis.
Metabolic
PW000768
Center
PathwayVisualizationContext1054
1593
1971
#000099
PathwayVisualization516
532
D-Alanine Metabolism
L-Alanine is an essential component of protein and peptidoglycan. The latter also contains about three molecules of D-alanine for every L-alanine. Only about 10 percent of the total alanine synthesized flows into peptidoglycan. Please refer to L-alanine metabolism (pathway PW000788 or SMP0000810). In this pathway, D-amino acid dehydrogenase degrades D-alanine to form pyruvate, which the later will serve as source of carbon for central metabolism. D-alanine can be formed by either biosynthetic alanine racemase or catabolic alanine racemase. D-alanine is required for forming the cell wall peptidoglycan (murein). D-alanine is metabolized by ATP driven D-alanine ligase A and B resulting in D-alanyl-D-alanine. This product is incorporated into peptidoglycan biosynthesis.
Metabolic
3
79947
556
SubPathway
77906
105
Compound
79949
554
SubPathway
77908
105
Compound
79950
553
SubPathway
77909
105
Compound
79951
551
SubPathway
77910
105
Compound
79952
549
SubPathway
77911
164
Compound
79953
671
SubPathway
77912
1900
Compound
3303
13292
Franklin FC, Venables WA: Biochemical, genetic, and regulatory studies of alanine catabolism in Escherichia coli K12. Mol Gen Genet. 1976 Dec 8;149(2):229-37.
532
Pathway
3304
1091641
Kaczorowski G, Shaw L, F-entes M, Walsh C: Coupling of alanine racemase and D-alanine dehydrogenase to active transport of amino acids in Escherichia coli B membrane vesicles. J Biol Chem. 1975 Apr 25;250(8):2855-65.
532
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
6
Myocyte
CL:0000187
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
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
31
Periplasmic Space
GO:0005620
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
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
34
Plant-Type Vacuole
GO:0000325
6
Lysosome
GO:0005764
16
Lysosomal Lumen
GO:0043202
18
Melanosome Membrane
GO:0033162
25
Golgi apparatus
GO:0005794
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
40
Periplasm
GO:0042597
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
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
4
Adrenal Medulla
BTO:0000049
71
8
28
Stomach
BTO:0001307
155
26
11
Heart
BTO:0000562
73
10
107
31
3
PW_BS000107
108
1
3
PW_BS000108
318
31
23
PW_BS000024
315
1
23
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
117
1
3
1
PW_BS000117
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
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
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
322
1
23
1
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
6
1
3
1
PW_BS000006
212
1
7
18
1
PW_BS000024
227
34
4
1
PW_BS000024
241
5
29
PW_BS000024
257
15
29
1
PW_BS000024
17
12
1
1
PW_BS000017
304
1
2
PW_BS000024
293
4
1
PW_BS000024
384
12
5
1
PW_BS000100
391
12
6
1
PW_BS000112
121
12
17
1
PW_BS000121
298
1
7
10
1
PW_BS000024
513
1
7
6
1
PW_BS000115
50
9
5
1
6
PW_BS000050
105
11
3
PW_BS000105
85
24
10
1
1
PW_BS000085
320
11
23
PW_BS000024
346
9
5
12
6
PW_BS000028
327
1
1
12
5
PW_BS000028
326
8
12
PW_BS000028
114
11
12
PW_BS000114
423
9
5
5
6
PW_BS000115
424
1
1
5
5
PW_BS000115
416
8
5
PW_BS000115
409
11
5
PW_BS000115
458
9
5
17
6
PW_BS000115
459
1
1
17
5
PW_BS000115
452
8
17
PW_BS000115
137
11
17
PW_BS000137
9
6
1
1
PW_BS000009
28
1
16
1
1
PW_BS000028
20
4
1
1
1
PW_BS000020
33
18
1
1
PW_BS000033
43
25
1
1
PW_BS000043
24
4
10
1
1
PW_BS000024
60
25
1
PW_BS000060
70
28
5
1
1
PW_BS000070
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
113
6
12
1
PW_BS000113
110
2
3
1
PW_BS000110
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
140
10
3
PW_BS000140
95
1
7
2
1
PW_BS000095
157
2
24
1
PW_BS000157
159
24
PW_BS000159
180
2
21
1
PW_BS000180
152
8
4
PW_BS000152
207
6
6
1
PW_BS000024
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
224
2
4
1
PW_BS000024
162
12
18
1
PW_BS000162
286
36
4
1
PW_BS000024
287
53
4
1
PW_BS000024
249
13
4
1
PW_BS000024
65
11
1
PW_BS000065
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
301
6
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
294
11
4
1
PW_BS000024
337
1
16
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
343
18
12
1
PW_BS000028
347
1
3
12
5
PW_BS000028
352
25
12
PW_BS000028
356
25
12
1
PW_BS000028
360
4
10
12
1
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
232
40
3
PW_BS000024
415
18
5
1
PW_BS000115
414
1
5
5
1
PW_BS000115
425
1
3
5
5
PW_BS000115
419
25
5
1
PW_BS000115
434
4
10
5
1
PW_BS000115
436
25
5
PW_BS000115
443
6
17
1
PW_BS000115
448
1
16
17
1
PW_BS000115
451
18
17
1
PW_BS000115
450
1
5
17
1
PW_BS000115
460
1
3
17
5
PW_BS000115
455
25
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
471
25
17
PW_BS000115
482
4
10
1
PW_BS000115
483
11
10
PW_BS000115
487
18
10
1
PW_BS000115
490
25
10
1
PW_BS000115
480
12
10
1
PW_BS000115
502
4
6
1
PW_BS000115
208
11
6
PW_BS000024
504
18
6
1
PW_BS000115
507
25
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
156
12
24
1
PW_BS000156
177
1
21
1
PW_BS000177
220
1
4
PW_BS000024
367
1
60
1
PW_BS000028
1009
D-Alanine
HMDB0001310
Alanine is a nonessential amino acid made in the body from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (Branched Chain Amino Acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as regulator in glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine and glycine, is an inhibitory neurotransmitter in the brain. http://www.dcnutrition.com/AminoAcids/).
338-69-2
C00133
71080
15570
D-ALANINE
64234
C[C@@H](N)C(O)=O
C3H7NO2
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1
QNAYBMKLOCPYGJ-UWTATZPHSA-N
(2R)-2-aminopropanoic acid
89.0932
89.047678473
0.70
2
D-alanine
0
0
FDB022546
(r)-alanine;D(-)-a -alanine;D(-)-alpha-alanine;D-(-)-alanine;D-2-aminopropionic acid;D-alanine;D-alpha-alanine;Dl-alanine;Delta-(-)-alanine;Delta-2-aminopropionic acid;Delta-alanine;Delta-alpha-alanine;Alanine;(r)-2-aminopropanoic acid;D-ala;D-alanin;D-alpha-aminopropionic acid;(r)-2-aminopropanoate;(2r)-2-aminopropanoate;D-2-aminopropionate;D-a-alanine;D-α-alanine;D-a-aminopropionate;D-a-aminopropionic acid;D-alpha-aminopropionate;D-α-aminopropionate;D-α-aminopropionic acid
PW_C001009
D-Ala
6340
107
6341
108
42436
318
42437
315
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
1900
D-Alanyl-D-alanine
HMDB0003459
The ATP-dependent carboxylate-amine/thiol ligase superfamily is known to contain enzymes catalyzing the formation of various types of peptide, one of which is d-alanyl-d-alanine.(PMID: 16030213). The glycopeptide antibiotic vancomycin acts by binding to the D-alanyl-D-alanine terminus of the cell wall precursor lipid II in the cytoplasmic membrane.(PMID: 17418637). D-alanine-D-alanine ligase from Thermotoga maritima ATCC 43589 (TmDdl) was a useful biocatalyst for synthesizing D-amino acid dipeptides.D-Alanine-D-alanine ligase (Ddl) catalyzes the biosynthesis of an essential bacterial peptidoglycan precursor D-alanyl-D-alanine and it represents an important target for development of new antibacterial drugs. (PMID: 17267218).
923-16-0
C00993
5460362
16576
D-ALA-D-ALA
4573916
C[C@@H](N)C(=O)N[C@H](C)C(O)=O
C6H12N2O3
InChI=1S/C6H12N2O3/c1-3(7)5(9)8-4(2)6(10)11/h3-4H,7H2,1-2H3,(H,8,9)(H,10,11)/t3-,4-/m1/s1
DEFJQIDDEAULHB-QWWZWVQMSA-N
(2R)-2-[(2R)-2-aminopropanamido]propanoic acid
160.1711
160.08479226
-0.36
3
D-ala-D-ala
0
0
FDB006399
Alanyl-d-alanine;(d-ala)2;D-ala-d-ala;H-d-ala-d-ala-oh;(2r)-2-[[(2r)-2-aminopropanoyl]amino]propanoate
PW_C001900
Ala-Ala
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
1104
Phosphate
HMDB0001429
Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.
14265-44-2
C00009
1061
18367
CPD-8587
1032
[O-]P([O-])([O-])=O
O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3
NBIIXXVUZAFLBC-UHFFFAOYSA-K
phosphoric acid
94.9714
94.95342
3
phosphoric acid
0
-2
DBMET00532
FDB022617
Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ion
PW_C001104
Pi
24
4
84
8
814
5
818
18
831
2
980
3
1763
14
1767
49
2500
10
2729
47
2737
46
3129
29
3166
72
3636
61
3851
23
4249
22
4475
31
5031
27
5158
7
5207
97
5216
100
5317
111
5351
112
5381
103
5447
120
5543
129
5573
133
5605
135
5625
108
5693
6
5848
143
5855
146
5911
147
5941
151
6040
155
6100
161
6294
107
6487
178
6691
101
6714
117
6842
188
6889
160
7161
205
7189
206
7212
211
7306
198
7389
210
7402
212
7436
163
7475
222
8196
225
8258
227
10118
241
10134
257
11748
132
11761
115
11773
213
11904
170
11927
164
12014
281
12728
290
13263
223
34819
17
42255
304
42350
315
42435
318
43692
322
77018
253
77194
293
77217
134
77940
336
77966
130
78048
332
78057
329
78245
353
78669
331
80022
368
89279
308
93831
383
94796
384
110558
390
110640
391
113235
94
115845
398
116206
109
119982
406
120069
122
120699
407
121057
124
121216
125
121268
429
121352
121
121409
123
121423
382
121852
405
123304
119
123621
118
123786
136
123838
464
123968
447
123981
399
124405
376
124948
472
125362
479
125446
297
125774
481
125954
299
126221
478
126594
300
126604
298
126723
484
126904
501
127413
388
127783
209
128166
395
128177
513
128315
389
105
L-Alanine
HMDB0000161
Alanine is a non-essential amino acid made in the body from either the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (branched-chain amino acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as a regulator of glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine, and glycine, is an inhibitory neurotransmitter in the brain (http://www.dcnutrition.com/AminoAcids/). L-Alanine has been found to be associated with glucagon deficiency, which is an inborn error of metabolism.
56-41-7
C00041
5950
16977
L-ALPHA-ALANINE
5735
DB00160
C[C@H](N)C(O)=O
C3H7NO2
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
QNAYBMKLOCPYGJ-REOHCLBHSA-N
(2S)-2-aminopropanoic acid
89.0932
89.047678473
0.70
2
L-alanine
0
0
FDB000556
(2s)-2-aminopropanoate;(2s)-2-aminopropanoic acid;(s)-(+)-alanine;(s)-2-aminopropanoate;(s)-2-aminopropanoic acid;(s)-2-amino-propanoate;(s)-2-amino-propanoic acid;(s)-alanine;2-aminopropanoate;2-aminopropanoic acid;2-aminopropionate;2-aminopropionic acid;2-ammoniopropanoate;2-ammoniopropanoic acid;Ala;Alanine;L-(+)-alanine;L-2-aminopropanoate;L-2-aminopropanoic acid;L-2-aminopropionate;L-2-aminopropionic acid;L-a-alanine;L-a-aminopropionate;L-a-aminopropionic acid;L-alpha-alanine;L-alpha-aminopropionate;L-alpha-aminopropionic acid;A-alanine;A-aminopropionate;A-aminopropionic acid;Alpha-alanine;Alpha-aminopropanoate;Alpha-aminopropanoic acid;Alpha-aminopropionate;Alpha-aminopropionic acid;A;L-alanin;L-α-alanine
PW_C000105
Ala
10
2
29
4
316
8
1446
50
1453
51
1454
26
3022
15
3439
3
5407
117
5418
103
5431
118
5452
120
5557
132
5578
133
5637
107
5638
108
5883
105
6529
85
8350
225
12271
151
12620
31
12627
18
15230
222
42452
320
42453
318
42534
315
77969
346
77975
327
77988
326
78008
111
78092
112
79165
114
80693
135
119910
122
120015
124
120026
406
121145
423
121151
424
121164
416
121220
409
122139
407
123717
458
123723
459
123736
452
123790
137
124691
119
125300
297
125393
299
125404
479
126296
481
126850
205
126933
388
126944
501
127860
206
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
22608
Ammonium
HMDB0041827
Ammonium is an important source of nitrogen for many plant species, especially those growing on hypoxic soils. However, it is also toxic to most crop species and is rarely applied as a sole nitrogen source. The ammonium (more obscurely: aminium) cation is a positively charged polyatomic cation with the chemical formula NH4+. It is formed by the protonation of ammonia (NH3). Ammonium is also a general name for positively charged or protonated substituted amines and quaternary ammonium cations (NR4+), where one or more hydrogen atoms are replaced by organic radical groups (indicated by R).
14798-03-9
C01342
16741146
28938
218
[NH4+]
H4N
InChI=1S/H3N/h1H3/p+1
QGZKDVFQNNGYKY-UHFFFAOYSA-O
azanium
18.0385
18.034374133
1
azanium
1
1
Ammonium ion;Ammonia ion;Ammonium;Ammonium chloride;Ammonium(1+);Azanium;Nh4+;[nh4]+;[nh4](+);Nh4(+)
PW_C022608
Ammon
5751
108
5892
95
5969
100
6226
166
8273
151
8367
225
11909
170
12470
249
42627
315
116281
109
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
41508
1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide
1,6-Anhydrous-N-acetylmuramyl-tetrapeptide belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. 1,6-Anhydrous-N-acetylmuramyl-tetrapeptide is considered to be a practically insoluble (in water) and relatively neutral molecule. 1,6-Anhydrous-N-acetylmuramyl-tetrapeptide may be a unique E.coli metabolite. 1,6-Anhydrous-N-acetylmuramyl-tetrapeptide can be converted into D-alanine and 1,6-anhydrous-N-acetylmuramyl-tripeptide; which is mediated by the enzyme murein tetrapeptide carboxypeptidase.
46173341
[H]C(N)(CCC[C@]([H])(N=C(O)[C@@]([H])(CCC(O)=O)N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC[C@]1([H])N=C(C)O)C(O)=NC([H])(C)C(O)=O)C(O)=O
C29H48N6O15
InChI=1S/C29H48N6O15/c1-12(31-25(42)14(3)50-23-19(33-15(4)37)11-49-20(10-36)22(23)40)24(41)34-18(8-9-21(38)39)27(44)35-17(7-5-6-16(30)29(47)48)26(43)32-13(2)28(45)46/h12-14,16-20,22-23,36,40H,5-11,30H2,1-4H3,(H,31,42)(H,32,43)(H,33,37)(H,34,41)(H,35,44)(H,38,39)(H,45,46)(H,47,48)/t12-,13?,14+,16?,17-,18+,19-,20+,22+,23+/m0/s1
OUWAMZWZTFUVMV-NPLPHQDTSA-N
(6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}-6-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]hexanoic acid
720.7226
720.317764896
-3.78
11
(6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}-6-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]hexanoic acid
0
-1
PW_C041508
16ANATe
41509
1,6-Anhydrous-N-Acetylmuramyl-tripeptide
1,6-Anhydrous-N-acetylmuramyl-tripeptide belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. 1,6-Anhydrous-N-acetylmuramyl-tripeptide is considered to be a practically insoluble (in water) and relatively neutral molecule. 1,6-Anhydrous-N-acetylmuramyl-tripeptide may be a unique E.coli metabolite. D-Alanine and 1,6-anhydrous-N-acetylmuramyl-tripeptide can be biosynthesized from 1,6-anhydrous-N-acetylmuramyl-tetrapeptide through the action of the enzyme murein tetrapeptide carboxypeptidase.
46173119
[H]C(N)(CCC[C@]([H])(N=C(O)[C@@]([H])(CCC(O)=O)N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC[C@]1([H])N=C(C)O)C(O)=O)C(O)=O
C26H43N5O14
InChI=1S/C26H43N5O14/c1-11(28-23(38)12(2)45-21-17(29-13(3)33)10-44-18(9-32)20(21)36)22(37)30-15(7-8-19(34)35)24(39)31-16(26(42)43)6-4-5-14(27)25(40)41/h11-12,14-18,20-21,32,36H,4-10,27H2,1-3H3,(H,28,38)(H,29,33)(H,30,37)(H,31,39)(H,34,35)(H,40,41)(H,42,43)/t11-,12+,14?,15+,16-,17-,18+,20+,21+/m0/s1
KGVLFEPQSVUIRC-FYQNUYSYSA-N
(6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}heptanedioic acid
649.6447
649.280651109
-3.71
10
(6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}heptanedioic acid
0
-1
PW_C041509
16ANATr
231
an electron-transfer quinone
Compound
1860
Compound
PW_EC000231
AETQ
232
electron-transfer quinol
Compound
41682
Compound
PW_EC000232
ETQ
5935
D-alanine--D-alanine ligase B
P07862
Involved in ATP binding. Cell wall formation.
ddlB
b0092
AP009048
3
6.3.2.4
8564
101
5997
D-alanine--D-alanine ligase A
P0A6J8
Involved in ATP binding. Cell wall formation.
ddlA
b0381
AP009048
3
6.3.2.4
8565
101
6484
Alanine racemase, catabolic
P29012
Isomerizes L-alanine to D-alanine which is then oxidized to pyruvate by DadA.
dadX
b1190
AP009048
3
5.1.1.1
131200
117
5978
Alanine racemase, biosynthetic
P0A6B4
Catalyzes the interconversion of L-alanine and D-alanine. Provides the D-alanine required for cell wall biosynthesis.
alr
b4053
AP009048
3
5.1.1.1
131201
117
5996
D-amino acid dehydrogenase small subunit
P0A6J5
Involved in D-amino-acid dehydrogenase activity. Oxidative deamination of D-amino acids.
dadA
b1189
AP009048
3
1.4.99.1
5895
95
8566
109
6731
Murein tetrapeptide carboxypeptidase
P76008
Defense mechanisms. Releases the terminal D-alanine residue from the cytoplasmic tetrapeptide recycling product L-Ala-gamma-D-Glu-meso- Dap-D-Ala. To a lesser extent, can also cleave D-Ala from murein derivatives containing the tetrapeptide, i.e. MurNAc-tetrapeptide, UDP-MurNAc-tetrapeptide, GlcNAc-MurNAc-tetrapeptide, and GlcNAc- anhMurNAc-tetrapeptide. Does not act on murein sacculi or cross- linked muropeptides. The tripeptides produced by the lcdA reaction can then be reused as peptidoglycan building blocks; lcdA is thereby involved in murein recycling. Is also essential for viability during stationary phase.
ldcA
b1192
AP009048
3
3.4.17.13
8567
101
1228
D-alanine ligase
3
PW_P001228
1419
5935
1420
5997
1227
L-alanine racemase
3
PW_P001227
1417
6484
1418
5978
1378
D-amino acid dehydrogenase
3
PW_P001378
1607
5996
2
3934
Murein tetrapeptide carboxypeptidase
3
PW_P003934
10913
6731
2513
false
PW_R002513
Right
9748
1009
2
Compound
false
9749
414
1
Compound
false
9750
1900
1
Compound
false
9751
1034
1
Compound
false
9752
1104
1
Compound
false
2480
1228
6.3.2.4
3732
false
PW_R003732
Right
15023
105
1
Compound
false
15024
1009
1
Compound
false
3706
1227
3733
false
PW_R003733
Right
15025
1009
1
Compound
false
15026
1420
1
Compound
false
15027
231
1
ElementCollection
false
15028
22608
1
Compound
false
15029
164
1
Compound
false
15030
232
1
ElementCollection
false
3707
1378
5342
false
PW_R005342
Right
21696
1420
1
Compound
false
21697
41508
1
Compound
false
21698
1009
1
Compound
false
21699
41509
1
Compound
false
5302
3934
3.4.17.13
13076
1009
3
false
1002
668
10
regular
100
100
13077
414
42
false
1117
789
10
regular
50
30
13078
1900
3
false
999
1194
10
regular
100
110
13079
1034
43
false
1099
1094
10
regular
50
30
13080
1104
46
false
1104
1032
10
regular
44
43
24917
105
3
false
1002
349
10
regular
100
100
24961
1420
49
false
868
770
10
regular
78
78
24962
22608
3
false
442
549
10
regular
100
100
24963
164
3
false
302
669
10
regular
100
100
63207
1420
49
false
1523
799
10
regular
78
78
63208
41508
3
false
1572
657
10
regular
100
130
63209
41509
3
false
1197
753
10
regular
100
130
1164
231
37
false
752
528
12
regular
100
90
1165
232
37
false
452
779
12
regular
100
90
6938
5935
101
2
false
974
869
8
subunit
regular
150
70
6939
5997
101
2
false
1054
909
8
subunit
regular
150
70
12016
6484
2
false
1077
519
8
subunit
regular
150
70
12017
5978
2
false
877
519
8
subunit
regular
150
70
12036
5996
109
6
false
592
679
8
subunit
regular
160
80
29301
6731
101
2
false
1327
685
8
subunit
regular
150
70
5633
1228
516
6862
6938
6863
6939
9217
1227
516
11774
12016
11775
12017
9236
1378
516
11794
12036
24645
3934
516
28989
29301
20343
M1052 768 C1052 798 1053 842 1053 872
5
false
18
20344
M1110 803 C1049 800 1055 839 1055 869
5
false
18
false
false
20345
M1049 1194 C1049 1164 1055 982 1055 952
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
20346
M1096 1109 C1066 1110 1055 1071 1055 943
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
20347
M1105 1048 C1071 1051 1057 1031 1057 1001
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
20350
M749 374 C748 537 749 373 749 535
5
false
18
true
M 491.5 164.99038105676658 L 484 152 L 476.5 164.99038105676658
false
true
M 477.0251928578299 286.7202385063009 L 484 300 L 492.0132072386567 287.319759081534
false
37340
M1052 449 C1000 484 1001 486 952 519
5
false
18
37341
M1052 668 C951 590 1051 668 952 589
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
37422
M1002 718 C972 718 782 719 752 719
5
false
18
37423
M906 770 C905 715 782 719 752 719
5
false
18
37424
M492 649 C492 717 493 720 592 719
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
37425
M402 719 C432 719 562 719 592 719
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
37426
M804 651 C803 696 782 719 752 719
5
false
18
37427
M502 779 C501 720 514 720 592 719
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
37429
M1052 449 C1083 472 1114 495 1152 519
5
false
18
37430
M1147.3333333333333 589.3333333333333 C1099.3333333333333 631.3333333333333 1128 602 1052 668
5
false
18
true
M 1767.39773431632 839.9448514274402 L 1782.3333333333333 841.3333333333333 L 1776.067994428025 827.7044842109153
false
90500
M1523 838 C1516 739 1507 720 1477 720
5
false
18
90501
M1572 722 C1542 722 1507 720 1477 720
5
false
18
90502
M1102 718 C1132 718 1297 720 1327 720
5
false
18
true
M 580.0159167793616 528.2915794955691 L 565.0690617351968 527.030023199273 L 571.4499494563826 540.6051575223514
false
90503
M1297 818 C1297 775 1297 720 1327 720
5
false
18
true
M 580.0159167793616 528.2915794955691 L 565.0690617351968 527.030023199273 L 571.4499494563826 540.6051575223514
false
2842169
M1093 449 C1156 450 1281 449 1307 449
5
false
18
true
M 2125.9903810567666 547.5 L 2113 555 L 2125.9903810567666 562.5
false
2842172
M1096 348 C1197 349 1276 348 1307 349
5
false
18
true
M 1870.0096189432334 462.5 L 1883 455 L 1870.0096189432334 447.5
false
2842173
M1002 350 C919 350 854 348 772 349
5
false
18
true
M 1112.2997956372376 576.9815292484632 L 1125 569 L 1111.7376907284013 561.9920650128254
false
2842174
M1006 449 C976 449 807 449 777 449
5
false
18
true
M 1540.9903810567666 512.5 L 1528 520 L 1540.9903810567666 527.5
false
true
M 1685.0096189432334 607.5 L 1698 600 L 1685.0096189432334 592.5
false
2842175
M352 769 C352 799 352 934 352 964
5
false
18
true
M 513.5 981.9903810567666 L 506 969 L 498.5 981.9903810567666
false
2842176
M1099 1249 C1069 1249 1279 1251 1324 1249
5
false
18
true
M 2114.1101286888043 1400.3155563507548 L 2125 1390 L 2110.6215304904786 1385.7268729759385
false
3586
516
2513
11902
13076
20343
Left
11903
13077
20344
Left
11904
13078
20345
Right
11905
13079
20346
Right
11906
13080
20347
Right
3786
2480
5633
6489
516
3732
23311
24917
37340
Left
23312
13076
37341
Right
6690
3706
9217
6508
516
3733
23372
13076
37422
Left
23373
24961
37423
Left
23374
24962
37424
Right
23375
24963
37425
Right
1296
1164
37426
Left
1297
1165
37427
Right
6708
3707
9236
18402
516
5342
71046
63207
90500
Left
71047
63208
90501
Left
71048
13076
90502
Right
71049
63209
90503
Right
18588
5302
24645
79391
79947
516
14
false
1307
414
16
regular
76352
24917
2842169
Right
79393
79949
516
14
false
1307
314
16
regular
76354
24917
2842172
Right
79394
79950
516
14
false
622
314
16
regular
76355
24917
2842173
Right
79396
79951
516
14
false
627
414
16
regular
76356
24917
2842174
Right
79398
79952
516
14
false
277
964
16
regular
76357
24963
2842175
Left
79399
79953
516
14
false
1324
1214
16
regular
76358
13078
2842176
Left
770
37429
771
37430
186241
490
815
1.1
1.1
0
2
92
479
481
890
M227 328 C227 278 277 228 327 228 C720 228 1232 228 1625 228 C1675 228 1725 278 1725 328 C1725 614 1725 986 1725 1272 C1725 1322 1675 1372 1625 1372 C1232 1372 720 1372 327 1372 C277 1372 227 1322 227 1272 C227 986 227 614 227 328
1
true
6
1498.0
1144.0
891
M128 224 C128 174 178 124 228 124 C682 124 1271 124 1725 124 C1775 124 1825 174 1825 224 C1825 573 1825 1027 1825 1376 C1825 1426 1775 1476 1725 1476 C1271 1476 682 1476 228 1476 C178 1476 128 1426 128 1376 C128 1027 128 573 128 224
1
true
6
1697.0
1352.0