515
Pathway
2,3-Dihydroxybenzoate Biosynthesis
2,3-Dihydroxybenzoate is synthesized from chorismate via isochorismate and 2,3-dihydroxy-2,3-dihydrobenzoate. Chorismate is a key intermediate and branch point in the biosynthesis of many aromatic compounds. The biosynthesis of 2,3-dihydroxybenzoate from chorismate is catalyzed by three enzymes: EntC, EntB, and EntA. EntC catalyzes the conversion of chorismate to isochorismate. The N-terminal isochorismate lyase domain of EntB hydrolyzes the pyruvate group of isochorismate to produce 2,3-dihydro-2,3-dihydroxybenzoate. The conversion of this latter compound to 2,3-dihydroxybenzoate is catalyzed by the EntA dehydrogenase.
Metabolic
PW000751
Center
PathwayVisualizationContext1037
1350
1850
#000099
PathwayVisualization499
515
2,3-Dihydroxybenzoate Biosynthesis
2,3-Dihydroxybenzoate is synthesized from chorismate via isochorismate and 2,3-dihydroxy-2,3-dihydrobenzoate. Chorismate is a key intermediate and branch point in the biosynthesis of many aromatic compounds. The biosynthesis of 2,3-dihydroxybenzoate from chorismate is catalyzed by three enzymes: EntC, EntB, and EntA. EntC catalyzes the conversion of chorismate to isochorismate. The N-terminal isochorismate lyase domain of EntB hydrolyzes the pyruvate group of isochorismate to produce 2,3-dihydro-2,3-dihydroxybenzoate. The conversion of this latter compound to 2,3-dihydroxybenzoate is catalyzed by the EntA dehydrogenase.
Metabolic
3
77589
580
SubPathway
75549
7748
Compound
94
2075
26443780
Yamashita S, Buchanan SK: Solute and Ion Transport: Outer Membrane Pores and Receptors. EcoSal Plus. 2010 Sep;4(1). doi: 10.1128/ecosalplus.3.3.1.
515
Pathway
1
Cell
CL:0000000
2
Platelet
CL:0000233
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
6
Myocyte
CL:0000187
3
Escherichia coli
562
Prokaryote
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
23
Pseudomonas aeruginosa
287
Prokaryote
1
Homo sapiens
9606
Eukaryote
Human
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
24
Solanum lycopersicum
4081
Eukaryote
Tomato
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
2
Bacteria
2
Prokaryote
Bacteria
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
19
Schizosaccharomyces pombe
4896
Eukaryote
35
Chloroplast
GO:0009507
1
Cytosol
GO:0005829
5
Cytoplasm
GO:0005737
2
Mitochondrion
GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
6
Lysosome
GO:0005764
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
10
Cell Membrane
GO:0005886
16
Lysosomal Lumen
GO:0043202
11
Extracellular Space
GO:0005615
3
Mitochondrial Matrix
GO:0005759
18
Melanosome Membrane
GO:0033162
14
Mitochondrial Outer Membrane
GO:0005741
24
Mitochondrial Intermembrane Space
GO:0005758
36
Membrane
GO:0016020
12
Mitochondrial Inner Membrane
GO:0005743
31
Periplasmic Space
GO:0005620
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
25
Golgi apparatus
GO:0005794
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
40
Periplasm
GO:0042597
28
Stomach
BTO:0001307
155
26
1
Liver
BTO:0000759
72
9
2
Endothelium
BTO:0000393
4
Adrenal Medulla
BTO:0000049
71
8
8
Blood Vessel
BTO:0001102
74
11
25
Intestine
BTO:0000648
7
Nervous System
BTO:0001484
11
Heart
BTO:0000562
73
10
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
94
3
PW_BS000094
225
35
4
1
PW_BS000024
151
1
4
1
PW_BS000151
313
23
PW_BS000024
8
5
1
1
PW_BS000008
2
1
1
1
PW_BS000002
3
2
1
1
PW_BS000003
70
28
5
1
1
PW_BS000070
10
1
7
1
1
PW_BS000010
163
2
18
1
PW_BS000163
160
1
18
1
PW_BS000160
112
2
12
1
PW_BS000112
132
1
12
1
PW_BS000132
111
5
12
1
PW_BS000111
122
5
5
1
PW_BS000122
407
2
5
1
PW_BS000115
124
1
5
1
PW_BS000124
135
5
17
1
PW_BS000135
119
2
17
1
PW_BS000119
118
1
17
1
PW_BS000118
297
5
10
1
PW_BS000024
481
2
10
1
PW_BS000115
299
1
10
1
PW_BS000024
205
5
6
1
PW_BS000024
388
1
6
1
PW_BS000112
206
2
6
1
PW_BS000024
9
6
1
1
PW_BS000009
5
4
1
1
PW_BS000005
16
2
1
2
PW_BS000016
18
13
1
1
PW_BS000018
14
10
1
PW_BS000014
28
1
16
1
1
PW_BS000028
31
1
5
1
1
PW_BS000031
20
4
1
1
1
PW_BS000020
15
11
1
PW_BS000015
4
3
1
1
PW_BS000004
33
18
1
1
PW_BS000033
49
7
1
1
PW_BS000049
24
4
10
1
1
PW_BS000024
22
14
1
1
PW_BS000022
29
1
1
1
PW_BS000029
42
24
1
1
PW_BS000042
13
1
2
1
PW_BS000013
123
1
7
5
1
PW_BS000123
125
13
5
1
PW_BS000125
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
108
1
3
PW_BS000108
147
1
24
1
PW_BS000147
159
24
PW_BS000159
188
1
18
PW_BS000024
213
7
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
216
4
18
1
PW_BS000024
198
5
18
1
PW_BS000024
215
6
18
1
PW_BS000024
211
10
18
PW_BS000024
164
4
PW_BS000164
286
36
4
1
PW_BS000024
226
4
4
1
PW_BS000024
249
13
4
1
PW_BS000024
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
298
1
7
10
1
PW_BS000024
300
13
10
1
PW_BS000024
301
6
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
223
12
4
1
PW_BS000024
17
12
1
1
PW_BS000017
315
1
23
PW_BS000024
293
4
1
PW_BS000024
294
11
4
1
PW_BS000024
134
12
12
1
PW_BS000134
130
13
12
1
PW_BS000130
331
7
12
1
PW_BS000028
332
1
7
12
1
PW_BS000028
113
6
12
1
PW_BS000113
115
10
12
PW_BS000115
334
4
12
1
PW_BS000028
336
1
12
1
PW_BS000028
337
1
16
12
1
PW_BS000028
129
1
5
12
1
PW_BS000129
341
4
1
12
1
PW_BS000028
114
11
12
PW_BS000114
133
3
12
1
PW_BS000133
329
14
12
1
PW_BS000028
345
24
12
1
PW_BS000028
343
18
12
1
PW_BS000028
360
4
10
12
1
PW_BS000028
408
4
5
1
PW_BS000115
405
10
5
PW_BS000115
414
1
5
5
1
PW_BS000115
409
11
5
PW_BS000115
406
3
5
1
PW_BS000115
415
18
5
1
PW_BS000115
383
7
5
1
PW_BS000100
434
4
10
5
1
PW_BS000115
429
1
5
1
PW_BS000115
382
14
5
1
PW_BS000100
418
24
5
1
PW_BS000115
384
12
5
1
PW_BS000100
374
4
17
1
PW_BS000053
443
6
17
1
PW_BS000115
376
10
17
PW_BS000053
447
1
7
17
1
PW_BS000115
136
13
17
1
PW_BS000136
448
1
16
17
1
PW_BS000115
450
1
5
17
1
PW_BS000115
137
11
17
PW_BS000137
120
3
17
1
PW_BS000120
451
18
17
1
PW_BS000115
398
7
17
1
PW_BS000113
469
4
10
17
1
PW_BS000115
464
1
17
1
PW_BS000115
399
14
17
1
PW_BS000113
454
24
17
1
PW_BS000115
121
12
17
1
PW_BS000121
482
4
10
1
PW_BS000115
478
10
10
PW_BS000115
483
11
10
PW_BS000115
479
3
10
1
PW_BS000115
484
14
10
1
PW_BS000115
495
7
10
1
PW_BS000115
489
24
10
1
PW_BS000115
480
12
10
1
PW_BS000115
502
4
6
1
PW_BS000115
207
6
6
1
PW_BS000024
209
10
6
PW_BS000024
208
11
6
PW_BS000024
501
3
6
1
PW_BS000115
504
18
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
389
14
6
1
PW_BS000112
395
13
6
1
PW_BS000113
390
7
6
1
PW_BS000112
506
24
6
1
PW_BS000115
391
12
6
1
PW_BS000112
26
1
1
1
5
PW_BS000026
54
1
3
1
5
PW_BS000054
103
3
3
1
PW_BS000103
107
31
3
PW_BS000107
100
5
2
1
PW_BS000100
105
11
3
PW_BS000105
117
1
3
1
PW_BS000117
155
3
24
1
PW_BS000155
157
2
24
1
PW_BS000157
161
3
18
1
PW_BS000161
166
1
1
PW_BS000166
178
3
21
1
PW_BS000178
152
8
4
PW_BS000152
101
5
3
1
PW_BS000101
187
31
18
PW_BS000024
219
31
4
PW_BS000024
220
1
4
PW_BS000024
222
3
4
1
PW_BS000024
170
18
PW_BS000170
162
12
18
1
PW_BS000162
224
2
4
1
PW_BS000024
195
13
18
PW_BS000024
281
1
25
1
PW_BS000024
285
10
4
1
PW_BS000024
287
53
4
1
PW_BS000024
227
34
4
1
PW_BS000024
308
10
1
1
PW_BS000024
318
31
23
PW_BS000024
322
1
23
1
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
327
1
1
12
5
PW_BS000028
347
1
3
12
5
PW_BS000028
368
3
60
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
109
32
3
PW_BS000109
424
1
1
5
5
PW_BS000115
425
1
3
5
5
PW_BS000115
459
1
1
17
5
PW_BS000115
460
1
3
17
5
PW_BS000115
43
25
1
1
PW_BS000043
6
1
3
1
PW_BS000006
95
1
7
2
1
PW_BS000095
141
1
7
19
1
PW_BS000141
1
1
PW_BS000001
356
25
12
1
PW_BS000028
419
25
5
1
PW_BS000115
455
25
17
1
PW_BS000115
490
25
10
1
PW_BS000115
507
25
6
1
PW_BS000115
60
25
1
PW_BS000060
46
1
1
4
PW_BS000046
72
5
1
3
PW_BS000072
61
25
1
7
PW_BS000061
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
27
15
1
PW_BS000027
7
1
1
PW_BS000007
97
1
5
2
1
PW_BS000097
110
2
3
1
PW_BS000110
140
10
3
PW_BS000140
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
180
2
21
1
PW_BS000180
214
25
18
1
PW_BS000024
190
11
18
PW_BS000024
277
1
2
18
PW_BS000024
65
11
1
PW_BS000065
290
5
49
1
PW_BS000024
253
5
4
1
PW_BS000024
333
1
2
12
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
232
40
3
PW_BS000024
412
1
2
5
PW_BS000115
436
25
5
PW_BS000115
446
1
2
17
PW_BS000115
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
487
18
10
1
PW_BS000115
513
1
7
6
1
PW_BS000115
50
9
5
1
6
PW_BS000050
156
12
24
1
PW_BS000156
177
1
21
1
PW_BS000177
85
24
10
1
1
PW_BS000085
346
9
5
12
6
PW_BS000028
367
1
60
1
PW_BS000028
423
9
5
5
6
PW_BS000115
458
9
5
17
6
PW_BS000115
7748
Chorismate
HMDB0012199
Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for the aromatic amino acids phenylalanine and tyrosine,indole, indole derivatives and tryptophan,2,3-dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis,the plant hormone salicylic acid and many alkaloids and other aromatic metabolites. -- Wikipedia.
617-12-9
C00251
12039
17333
CPD-9517
11542
O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O
C10H10O6
InChI=1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1
WTFXTQVDAKGDEY-HTQZYQBOSA-N
(3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
226.1828
226.047738052
-1.41
3
chorismic acid
0
-2
C00251
Chorismic acid;(3r,4r)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid;(3r-trans)-3-((1-carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid;(3r,4r)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate;(3r-trans)-3-((1-carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylate
PW_C007748
Chorism
5164
94
8325
225
8329
151
42309
313
40741
isochorismate
Isochorismic acid, also known as isochorismate, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Isochorismic acid is soluble (in water) and a weakly acidic compound (based on its pKa).
C00885
29780
[H][C@]1(O)C(=CC=C[C@]1([H])OC(=C)C([O-])=O)C([O-])=O
C10H8O6
InChI=1S/C10H10O6/c1-5(9(12)13)16-7-4-2-3-6(8(7)11)10(14)15/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/p-2/t7-,8-/m0/s1
NTGWPRCCOQCMGE-YUMQZZPRSA-L
(5S,6S)-5-[(1-carboxylatoeth-1-en-1-yl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylate
224.169
224.033185137
-1.27
1
isochorismate
-2
-2
PW_C040741
isochor
5165
94
42310
313
40770
(2S,3S)-2,3-dihydroxy-2,3-dihydrobenzoate
5,6-Dihydroxycyclohexa-1,3-diene-1-carboxylic acid belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. 5,6-Dihydroxycyclohexa-1,3-diene-1-carboxylic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 5,6-Dihydroxycyclohexa-1,3-diene-1-carboxylic acid can be converted into 2,3-dihydroxy-2,3-dihydrobenzoyl-CoA..
C04171
15941
OC1C=CC=C(C1O)C(O)=O
C7H8O4
InChI=1S/C7H8O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,5-6,8-9H,(H,10,11)
INCSWYKICIYAHB-UHFFFAOYSA-N
5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acid
156.136
156.042258744
-0.23
3
5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acid
0
-1
(2s,3s)-2,3-dihydro-2,3-dihydroxybenzoic acid;2,3-dihydro-2,3-dihydroxybenzoate;2,3-dihydro-2,3-dihydroxybenzoic acid;2,3-dihydroxy-2,3-dihydrobenzoate;2,3-dihydroxy-2,3-dihydrobenzoic acid;5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate;5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acid;Dihydro-dioh-benzoate;Dihydro-dioh-benzoic acid
PW_C040770
223D3D
5220
94
42311
313
296
2-Pyrocatechuic acid
HMDB0000397
2-Pyrocatechuic acid is a normal human benzoic acid metabolite found in plasma (PMID 16351159), and is normally found with increased levels after consumption of many nutrients and drugs, i.e.: cranberry juice (PMID 14733499), aspirin ingestion. (PMID 3342084) It has been found associated with idiopathic oro-facial pain due to stress (oxidative stress might enhance the production of free radicals); it has been suggested that OH radicals are responsible for the production of many systemic and local tissue injury diseases which may initially manifest as pain syndrome, and 2-Pyrocatechuic acid is a biological marker for the detection and quantification of OH radicals, and patients had significantly increased circulating levels of 2-Pyrocatechuic acid after aspirin ingestion than control subjects. (PMID 7748148).
303-38-8
C00196
19
18026
18
DB01672
OC(=O)C1=C(O)C(O)=CC=C1
C7H6O4
InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)
GLDQAMYCGOIJDV-UHFFFAOYSA-N
2,3-dihydroxybenzoic acid
154.121
154.026608673
-1.35
3
2,3-dihydroxy-benzoic acid
0
-1
FDB012200
2,3-dihydroxybenzoate;2,3-dihydroxybenzoic acid;2-pyrocatechuate;2-pyrocatechuic acid;3-hydroxysalicylate;3-hydroxysalicylic acid;Catecholcarboxylate;Catecholcarboxylic acid;Dhba;Dobk;O-pyrocatechuate;O-pyrocatechuic acid;Pyrocatechuate;Pyrocatechuic acid
PW_C000296
DHBA
5221
94
42312
313
1051
Hydrogen
HMDB0001362
Hydrogen is a colorless, odorless, nonmetallic, tasteless, highly flammable diatomic gas with the molecular formula H2. With an atomic weight of 1.00794, hydrogen is the lightest element. Besides the common H1 isotope, hydrogen exists as the stable isotope Deuterium and the unstable, radioactive isotope Tritium. Hydrogen is the most abundant of the chemical elements, constituting roughly 75% of the universe's elemental mass. Hydrogen can form compounds with most elements and is present in water and most organic compounds. It plays a particularly important role in acid-base chemistry, in which many reactions involve the exchange of protons between soluble molecules. Oxidation of hydrogen, in the sense of removing its electron, formally gives H+, containing no electrons and a nucleus which is usually composed of one proton. That is why H+ is often called a proton. This species is central to discussion of acids. Under the Bronsted-Lowry theory, acids are proton donors, while bases are proton acceptors. A bare proton H+ cannot exist in solution because of its strong tendency to attach itself to atoms or molecules with electrons. However, the term 'proton' is used loosely to refer to positively charged or cationic hydrogen, denoted H+. H2 is a product of some types of anaerobic metabolism and is produced by several microorganisms, usually via reactions catalyzed by iron- or nickel-containing enzymes called hydrogenases. These enzymes catalyze the reversible redox reaction between H2 and its component two protons and two electrons. Creation of hydrogen gas occurs in the transfer of reducing equivalents produced during pyruvate fermentation to water.
1333-74-0
C00282
58838673
18276
ALPHA-GLUCOSE-16-BISPHOSPHATE
762
[H][H]
H2
InChI=1S/H2/h1H
UFHFLCQGNIYNRP-UHFFFAOYSA-N
2.0159
2.015650064
0
0
0
FDB016247
Dihydrogen;Hydrogen;Hydrogen cation;Hydrogen gas;Hydrogen ion;Hydronium;Proton;E 949;E-949;E949;H2;Molecular hydrogen
PW_C001051
H2
1756
8
2388
2
2696
3
3146
70
4952
10
7033
163
7045
160
12774
151
13270
225
78594
112
78603
132
78772
111
113163
94
121448
122
122032
407
122037
124
124006
135
124586
119
124591
118
126073
297
126182
481
126188
299
127529
205
128005
388
128323
206
1065
Oxygen
HMDB0001377
Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).
7782-44-7
C00007
977
15379
CPD-6641
952
O=O
O2
InChI=1S/O2/c1-2
MYMOFIZGZYHOMD-UHFFFAOYSA-N
oxidanone
31.9988
31.989829244
0
singlet oxygen
0
0
FDB022589
Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948
PW_C001065
O2
95
9
110
5
245
16
500
18
505
8
549
14
625
28
638
3
649
10
674
31
688
20
754
15
763
4
769
33
836
2
1375
49
2016
24
2531
22
2803
29
4260
42
4747
13
5467
123
5480
125
5493
126
5508
127
5809
108
5973
147
6129
159
7006
188
7032
163
7050
160
7319
213
7533
210
7560
212
8395
151
11816
216
11864
198
11883
215
11894
211
12057
225
12063
164
12247
286
12279
226
12325
249
12706
291
12716
292
13004
298
13016
300
13026
301
13038
302
13260
223
42276
17
42657
315
76910
293
77044
294
77214
134
77350
111
77363
130
77377
331
77395
332
77497
113
77512
115
77537
334
77626
336
77723
337
77736
112
77747
129
77756
341
77805
114
77812
133
78070
329
78151
132
78381
345
78805
343
79111
360
120047
408
120383
122
120426
405
120542
407
120553
414
120594
409
120601
406
120883
415
121045
124
121104
383
121605
434
121656
429
122117
382
122573
418
122689
384
122798
374
122822
443
123027
135
123060
376
123128
447
123139
136
123163
448
123176
119
123187
450
123219
137
123226
120
123459
451
123609
118
123669
398
124163
469
124214
464
124669
399
125145
454
125275
121
125425
482
125706
478
125731
483
125737
297
125740
479
125884
481
126100
299
126272
484
126522
495
126721
489
126825
480
126964
502
126986
207
127198
209
127214
208
127219
205
127222
501
127305
504
127345
206
127557
388
127574
515
127835
389
128081
395
128095
390
128312
506
128432
391
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
41249
2-Carboxymuconate
2-Carboxymuconate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-Carboxymuconate may be a unique E.coli metabolite. 2-Carboxymuconate can be biosynthesized from 2-pyrocatechuic acid; which is mediated by the enzyme blue copper oxidase cueo.
25200400
[O-]C(=O)C=CC=C(C([O-])=O)C([O-])=O
C7H3O6
InChI=1S/C7H6O6/c8-5(9)3-1-2-4(6(10)11)7(12)13/h1-3H,(H,8,9)(H,10,11)(H,12,13)/p-3
SLUDRBHRUDRZJZ-UHFFFAOYSA-K
buta-1,3-diene-1,1,4-tricarboxylate
183.0951
182.992962828
-1.61
0
buta-1,3-diene-1,1,4-tricarboxylate
-3
-3
2-carboxy-cis,cis-muconate;2-carboxy-cis,cis-muconic acid;2-carboxymuconic acid
PW_C041249
2Cxym
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
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
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
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
6238
Isochorismate synthase entC
P0AEJ2
Involved in biosynthetic process. Chorismate = isochorismate.
entC
b0593
AP009048
3
5.4.4.2
112893
94
6224
Isochorismatase
P0ADI4
Involved in isochorismatase activity. Required for production of 2,3-DHB. Also serves as an aryl carrier protein and plays a role in enterobactin assembly.
entB
b0595
AP009048
3
6.3.2.14; 3.3.2.1
8525
101
112880
94
6553
Blue copper oxidase cueO
P36649
Involved in oxidoreductase activity. Probably involved in periplasmic detoxification of copper by oxidizing Cu(+) to Cu(2+) and thus preventing its uptake into the cytoplasm. Possesses phenoloxidase and ferroxidase activities and might be involved in the production of polyphenolic compounds and the prevention of oxidative damage in the periplasm.
cueO
b0123
AP009048
3
8526
232
6341
2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase
P15047
Involved in oxidoreductase activity. 2,3-dihydro-2,3-dihydroxybenzoate + NAD(+) = 2,3-dihydroxybenzoate + NADH.
entA
b0596
AP009048
3
1.3.1.28
112856
94
3957
Blue copper oxidase cueO
3
PW_P003957
10937
6553
4015
2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase
25
PW_P004015
11014
6341
8
6717
117
1189
isochorismatase
3
PW_P001189
1378
6224
1143
Isochorismate synthase
3
PW_P001143
1305
6238
5866
false
PW_R005866
Right
23932
296
1
Compound
false
23933
1065
1
Compound
false
23934
40034
1
Compound
false
23935
41249
1
Compound
false
5832
3957
2423
false
PW_R002423
Right
9402
40770
1
Compound
false
9511
721
1
Compound
false
9403
296
1
Compound
false
9512
1144
1
Compound
false
9513
40034
1
Compound
false
2394
4015
1.3.1.28
2453
false
PW_R002453
Right
9502
1420
1
Compound
false
9503
40741
1
Compound
false
9504
164
1
Compound
false
9505
40770
1
Compound
false
2392
1189
2452
false
PW_R002452
Right
9500
7748
1
Compound
false
9501
40741
1
Compound
false
2391
1143
5.4.4.2
12694
7748
94
3
false
818
299
10
regular
100
100
12695
40741
94
3
false
1268
299
10
regular
100
100
12697
40770
94
3
false
1268
764
10
regular
100
130
12699
296
94
3
false
793
779
10
regular
100
110
12706
1051
3
false
1310
235
10
regular
100
100
69129
1065
65
false
739
926
10
regular
78
78
69130
40034
55
false
414
926
10
regular
78
78
69131
41249
3
false
343
779
10
regular
100
110
2040331
721
94
59
false
1243
929
10
regular
50
30
2040332
1144
94
60
false
893
931
10
regular
50
30
2040333
40034
94
55
false
864
981
10
regular
78
78
2040744
1420
94
49
false
1435
410
10
regular
78
78
2040745
164
94
3
false
1433
739
10
regular
100
100
6796
6238
2
false
325
180
8
subunit
regular
150
70
6799
6224
101
2
false
820
720
8
subunit
regular
150
70
31823
6553
232
2
false
543
797
8
subunit
regular
150
70
725903
6341
94
7
false
993
792
8
subunit
regular
190
85
726024
6224
94
2
false
1243
584
8
subunit
regular
150
70
726075
6238
94
2
false
1015
314
8
subunit
regular
150
70
26809
3957
499
31507
31823
612958
4015
499
94
724388
725903
613079
1189
499
94
724509
726024
613130
1143
499
94
724560
726075
98394
M793 834 C763 834 723 832 693 832
5
false
18
98395
M739 965 C740 894 731 831 693 832
5
false
18
98396
M492 965 C490 917 499 833 543 832
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
98397
M443 834 C473 834 513 832 543 832
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
2773178
M1263 834 C1233 834 1213 832 1183 832
5
false
18
2773179
M1243 944 C1244 908 1218 833 1183 832
5
false
18
2773180
M893 834 C923 834 963 832 993 832
5
false
18
true
M 202.94685504416483 478.261556296296 L 188 477 L 194.38088772118584 490.5751343230783
false
2773181
M918 931 C917 898 939 833 993 832
5
false
18
true
M 202.94685504416483 478.261556296296 L 188 477 L 194.38088772118584 490.5751343230783
false
2773182
M942 1020 C942 966 949 832 993 832
5
false
18
true
M 202.94685504416483 478.261556296296 L 188 477 L 194.38088772118584 490.5751343230783
false
2773729
M1474 488 C1432 486 1317 537 1318 584
5
false
18
2773730
M1318 399 C1318 429 1318 554 1318 584
5
false
18
2773731
M1483 739 C1449 742 1320 702 1318 654
5
false
18
true
M 523.9468550441649 219.26155629629605 L 509 218 L 515.3808877211858 231.57513432307834
false
2773732
M1318 764 C1318 734 1318 684 1318 654
5
false
18
true
M 523.9468550441649 219.26155629629605 L 509 218 L 515.3808877211858 231.57513432307834
false
2774108
M818 349 C788 349 768 351 738 351
5
false
18
true
M 814.0096189432334 362.5 L 827 355 L 814.0096189432334 347.5
false
2774459
M918 349 C948 349 985 349 1015 349
5
false
18
2774460
M1268 349 C1238 349 1195 349 1165 349
5
false
18
true
M 470.94685504416486 133.26155629629605 L 456 132 L 462.38088772118584 145.57513432307834
false
20162
499
5866
78292
12699
98394
Left
78293
69129
98395
Left
78294
69130
98396
Right
78295
69131
98397
Right
20343
5832
26809
617944
499
2423
94
2494331
12697
2773178
Left
2494332
2040331
2773179
Left
2494333
12699
2773180
Right
2494334
2040332
2773181
Right
2494335
2040333
2773182
Right
576000
2394
612958
618065
499
2453
94
2494831
2040744
2773729
Left
2494832
12695
2773730
Left
2494833
2040745
2773731
Right
2494834
12697
2773732
Right
576121
2392
613079
618223
499
2452
94
2495485
12694
2774459
Left
2495486
12695
2774460
Right
576279
2391
613130
77035
77589
499
14
false
588
316
17
regular
73999
12694
2774108
Right
186235
301
355
0.9
0.9
0
2
92
479
481
869
M125 225 C125 175 175 125 225 125 C649 125 1201 125 1625 125 C1675 125 1725 175 1725 225 C1725 498 1725 852 1725 1125 C1725 1175 1675 1225 1625 1225 C1201 1225 649 1225 225 1225 C175 1225 125 1175 125 1125 C125 852 125 498 125 225
1
true
6
1600.0
1100.0
1020
M223 324 C223 274 273 224 323 224 C687 224 1160 224 1524 224 C1574 224 1624 274 1624 324 C1624 536 1624 813 1624 1025 C1624 1075 1574 1125 1524 1125 C1160 1125 687 1125 323 1125 C273 1125 223 1075 223 1025 C223 813 223 536 223 324
1
true
6
1401.0
901.0