1658
Pathway
Selenium Metabolism
The selenium metabolism begins with the introduction of selenate and selenite to the cytosol through a sulphate permease system. Once in the cell, selenate can be reduced to selenite through nitrate reductases A and Z. Selenite then interacts with glutathione and 2 hydrogen ions resulting in the release of 2 water molecules, a hydroxide molecule, a glutathione disulfide and a selenodiglutathione. The latter compound then reacts with NADPH+H resulting in the release of a NADP, a glutathione and a glutathioselenol.
Glutathiolselenol can then be oxidize resulting in a a glutathiolselenol ion which can then interact with a water molecule resulting in a release of glutathion and selenium
Glutathiolselenol can also react with NADPH and hydrogen ion resulting in a release of glutathione, NADP, a hydroxide molecule and a hydrogen selenide. This compound can react in a reversible reaction by being oxidized resulting in a hydrogen selenide ion . This compound can then be phosphorylated by interacting with an ATP and releasing a AMP, a phosphate and a selenophosphate.
Metabolic
PW001894
Center
PathwayVisualizationContext2181
2152
2304
#000099
PathwayVisualization1642
1658
Selenium Metabolism
The selenium metabolism begins with the introduction of selenate and selenite to the cytosol through a sulphate permease system. Once in the cell, selenate can be reduced to selenite through nitrate reductases A and Z. Selenite then interacts with glutathione and 2 hydrogen ions resulting in the release of 2 water molecules, a hydroxide molecule, a glutathione disulfide and a selenodiglutathione. The latter compound then reacts with NADPH+H resulting in the release of a NADP, a glutathione and a glutathioselenol.
Glutathiolselenol can then be oxidize resulting in a a glutathiolselenol ion which can then interact with a water molecule resulting in a release of glutathion and selenium
Glutathiolselenol can also react with NADPH and hydrogen ion resulting in a release of glutathione, NADP, a hydroxide molecule and a hydrogen selenide. This compound can react in a reversible reaction by being oxidized resulting in a hydrogen selenide ion . This compound can then be phosphorylated by interacting with an ATP and releasing a AMP, a phosphate and a selenophosphate.
Metabolic
3
112375
Endocytosis
SubPathway
111965
40445
Compound
3595
9850565
Turner RJ, Weiner JH, Taylor DE: Selenium metabolism in Escherichia coli. Biometals. 1998 Sep;11(3):223-7.
1658
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
2
Platelet
CL:0000233
8
Beta cell
CL:0000639
1
Homo sapiens
9606
Eukaryote
Human
3
Escherichia coli
562
Prokaryote
23
Pseudomonas aeruginosa
287
Prokaryote
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
2
Bacteria
2
Prokaryote
Bacteria
24
Solanum lycopersicum
4081
Eukaryote
Tomato
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
19
Schizosaccharomyces pombe
4896
Eukaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
5
Cytoplasm
GO:0005737
11
Extracellular Space
GO:0005615
31
Periplasmic Space
GO:0005620
1
Cytosol
GO:0005829
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
12
Mitochondrial Inner Membrane
GO:0005743
14
Mitochondrial Outer Membrane
GO:0005741
24
Mitochondrial Intermembrane Space
GO:0005758
13
Endoplasmic Reticulum
GO:0005783
35
Chloroplast
GO:0009507
4
Peroxisome
GO:0005777
10
Cell Membrane
GO:0005886
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
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
15
Nucleus
GO:0005634
40
Periplasm
GO:0042597
19
sarcoplasmic reticulum
GO:0016529
27
Peroxisome Membrane
GO:0005778
1
Liver
BTO:0000759
72
9
28
Stomach
BTO:0001307
155
26
8
Blood Vessel
BTO:0001102
74
11
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
7
Nervous System
BTO:0001484
11
Heart
BTO:0000562
73
10
5
cardiocyte
BTO:0001539
2
Endothelium
BTO:0000393
18
Pancreas
BTO:0000988
8
5
1
1
PW_BS000008
15
11
1
PW_BS000015
107
31
3
PW_BS000107
108
1
3
PW_BS000108
318
31
23
PW_BS000024
315
1
23
PW_BS000024
111
5
12
1
PW_BS000111
122
5
5
1
PW_BS000122
135
5
17
1
PW_BS000135
297
5
10
1
PW_BS000024
205
5
6
1
PW_BS000024
4
3
1
1
PW_BS000004
31
1
5
1
1
PW_BS000031
3
2
1
1
PW_BS000003
2
1
1
1
PW_BS000002
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1
1
1
5
PW_BS000026
54
1
3
1
5
PW_BS000054
49
7
1
1
PW_BS000049
17
12
1
1
PW_BS000017
22
14
1
1
PW_BS000022
42
24
1
1
PW_BS000042
10
1
7
1
1
PW_BS000010
18
13
1
1
PW_BS000018
70
28
5
1
1
PW_BS000070
103
3
3
1
PW_BS000103
112
2
12
1
PW_BS000112
100
5
2
1
PW_BS000100
105
11
3
PW_BS000105
117
1
3
1
PW_BS000117
147
1
24
1
PW_BS000147
155
3
24
1
PW_BS000155
157
2
24
1
PW_BS000157
161
3
18
1
PW_BS000161
159
24
PW_BS000159
166
1
1
PW_BS000166
178
3
21
1
PW_BS000178
152
8
4
PW_BS000152
101
5
3
1
PW_BS000101
188
1
18
PW_BS000024
187
31
18
PW_BS000024
163
2
18
1
PW_BS000163
206
2
6
1
PW_BS000024
219
31
4
PW_BS000024
220
1
4
PW_BS000024
222
3
4
1
PW_BS000024
213
7
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
160
1
18
1
PW_BS000160
170
18
PW_BS000170
225
35
4
1
PW_BS000024
151
1
4
1
PW_BS000151
226
4
4
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
164
4
PW_BS000164
281
1
25
1
PW_BS000024
285
10
4
1
PW_BS000024
286
36
4
1
PW_BS000024
287
53
4
1
PW_BS000024
227
34
4
1
PW_BS000024
223
12
4
1
PW_BS000024
294
11
4
1
PW_BS000024
308
10
1
1
PW_BS000024
322
1
23
1
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
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4
1
PW_BS000024
133
3
12
1
PW_BS000133
134
12
12
1
PW_BS000134
331
7
12
1
PW_BS000028
114
11
12
PW_BS000114
132
1
12
1
PW_BS000132
327
1
1
12
5
PW_BS000028
347
1
3
12
5
PW_BS000028
345
24
12
1
PW_BS000028
130
13
12
1
PW_BS000130
368
3
60
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
119
2
17
1
PW_BS000119
124
1
5
1
PW_BS000124
383
7
5
1
PW_BS000100
388
1
6
1
PW_BS000112
94
3
PW_BS000094
390
7
6
1
PW_BS000112
398
7
17
1
PW_BS000113
118
1
17
1
PW_BS000118
336
1
12
1
PW_BS000028
109
32
3
PW_BS000109
406
3
5
1
PW_BS000115
407
2
5
1
PW_BS000115
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
125
13
5
1
PW_BS000125
120
3
17
1
PW_BS000120
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
136
13
17
1
PW_BS000136
479
3
10
1
PW_BS000115
481
2
10
1
PW_BS000115
483
11
10
PW_BS000115
299
1
10
1
PW_BS000024
495
7
10
1
PW_BS000115
489
24
10
1
PW_BS000115
480
12
10
1
PW_BS000115
300
13
10
1
PW_BS000024
501
3
6
1
PW_BS000115
208
11
6
PW_BS000024
506
24
6
1
PW_BS000115
391
12
6
1
PW_BS000112
395
13
6
1
PW_BS000113
317
32
23
PW_BS000024
9
6
1
1
PW_BS000009
5
4
1
1
PW_BS000005
14
10
1
PW_BS000014
13
1
2
1
PW_BS000013
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
46
1
1
4
PW_BS000046
29
1
1
1
PW_BS000029
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
113
6
12
1
PW_BS000113
110
2
3
1
PW_BS000110
123
1
7
5
1
PW_BS000123
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
129
1
5
12
1
PW_BS000129
6
1
3
1
PW_BS000006
140
10
3
PW_BS000140
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
95
1
7
2
1
PW_BS000095
1
1
PW_BS000001
180
2
21
1
PW_BS000180
207
6
6
1
PW_BS000024
211
10
18
PW_BS000024
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
198
5
18
1
PW_BS000024
216
4
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
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
298
1
7
10
1
PW_BS000024
301
6
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
253
5
4
1
PW_BS000024
332
1
7
12
1
PW_BS000028
333
1
2
12
PW_BS000028
115
10
12
PW_BS000115
334
4
12
1
PW_BS000028
337
1
16
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
343
18
12
1
PW_BS000028
329
14
12
1
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
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
408
4
5
1
PW_BS000115
412
1
2
5
PW_BS000115
405
10
5
PW_BS000115
415
18
5
1
PW_BS000115
414
1
5
5
1
PW_BS000115
429
1
5
1
PW_BS000115
419
25
5
1
PW_BS000115
434
4
10
5
1
PW_BS000115
382
14
5
1
PW_BS000100
436
25
5
PW_BS000115
374
4
17
1
PW_BS000053
443
6
17
1
PW_BS000115
446
1
2
17
PW_BS000115
376
10
17
PW_BS000053
447
1
7
17
1
PW_BS000115
448
1
16
17
1
PW_BS000115
451
18
17
1
PW_BS000115
450
1
5
17
1
PW_BS000115
464
1
17
1
PW_BS000115
455
25
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
399
14
17
1
PW_BS000113
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
482
4
10
1
PW_BS000115
478
10
10
PW_BS000115
487
18
10
1
PW_BS000115
490
25
10
1
PW_BS000115
484
14
10
1
PW_BS000115
502
4
6
1
PW_BS000115
209
10
6
PW_BS000024
504
18
6
1
PW_BS000115
507
25
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
389
14
6
1
PW_BS000112
513
1
7
6
1
PW_BS000115
35
5
19
1
4
PW_BS000035
16
2
1
2
PW_BS000016
32
1
15
1
5
PW_BS000032
39
7
1
1
3
PW_BS000039
58
1
14
1
1
PW_BS000058
59
27
1
1
PW_BS000059
66
18
5
1
8
PW_BS000066
51
8
1
PW_BS000051
23
15
1
1
PW_BS000023
91
8
5
1
1
PW_BS000091
89
2
PW_BS000089
104
14
3
1
PW_BS000104
199
14
18
1
PW_BS000024
217
15
18
PW_BS000024
218
15
18
1
PW_BS000024
350
1
14
12
1
PW_BS000028
128
15
12
1
PW_BS000128
351
15
12
PW_BS000028
335
27
12
1
PW_BS000028
184
1
2
1
PW_BS000024
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1
14
5
1
PW_BS000115
410
15
5
1
PW_BS000115
422
27
5
1
PW_BS000115
435
15
5
PW_BS000115
468
1
14
17
1
PW_BS000115
444
15
17
1
PW_BS000115
375
27
17
1
PW_BS000053
470
15
17
PW_BS000115
485
15
10
1
PW_BS000115
491
27
10
1
PW_BS000115
499
15
10
PW_BS000115
516
15
6
1
PW_BS000115
508
27
6
1
PW_BS000115
517
15
6
PW_BS000115
47
19
1
4
PW_BS000047
241
5
29
PW_BS000024
257
15
29
1
PW_BS000024
6761
Selenite
HMDB0011119
The selenite anion is a selenium oxoanion with the chemical formula SeO32−. A selenite (compound) is a compound that contains this ion. In slightly acid conditions, the hydrogenselenite ion, HSeO3−, is formed; in more acidic conditions selenous acid, H2SeO3, exists. Most selenite salts can be formed by heating the relevant metal oxide with selenium dioxide, e.g.:Na2O + SeO2 → Na2SeO3. Selenite is an inorganic form of selenium which may also be useful in cancer chemotherapy.(Wikipedia).
14124-67-5
C05684
1090
18212
1059
[O-][Se]([O-])=O
O3Se
InChI=1S/H2O3Se/c1-4(2)3/h(H2,1,2,3)/p-2
MCAHWIHFGHIESP-UHFFFAOYSA-L
selenous acid
126.96
127.901265694
2
selenious acid
0
-2
C05684
Selenite (seo32-);Selenite ion (seo32-);Selenite ion(2-);Selenite(2-);[seo3](2-);Selenit
PW_C006761
Selenit
367
8
374
15
6650
107
6651
108
42487
318
42488
315
78834
111
119948
122
122739
135
125338
297
126881
205
40445
Selenic acid
HMDB0060694
Selenate, also known as sodium selenate or [seo2(OH)2], belongs to the class of inorganic compounds known as non-metal selenates. These are inorganic non-metallic compounds containing a selenate as its largest oxoanion. Selenate has been primarily detected in urine. Selenate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, selenate can be found in a number of food items such as turmeric, roman camomile, savoy cabbage, and other soy product. This makes selenate a potential biomarker for the consumption of these food products. Selenate is a potentially toxic compound.
7783-08-6
C05697
1089
18170
1058
O[Se](O)(=O)=O
H2O4Se
InChI=1S/H2O4Se/c1-5(2,3)4/h(H2,1,2,3,4)
QYHFIVBSNOWOCQ-UHFFFAOYSA-N
selenic acid
144.97
145.91183038
2
selenic acid
0
-2
[seo2(oh)2];H2seo4;Selenate
PW_C040445
Selenic
368
8
6652
107
6653
108
42489
318
42490
315
78828
111
119940
122
122732
135
125330
297
126874
205
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
41100
Electron
An electron is a stable subatomic particle that is negatively charged. Electrons can be either free (not attached to any atom), or bound to atoms. Electrons exist in spherical shells of various radii representing energy levels. Electrons act as the primary carrier of electricity in solids.
PW_C041100
Electro
6627
108
6629
109
12840
225
13258
223
15252
249
43512
315
43520
317
77211
134
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
80
Glutathione
HMDB0000125
Glutathione is a compound synthesized from cysteine, perhaps the most important member of the body's toxic waste disposal team. Like cysteine, glutathione contains the crucial thiol (-SH) group that makes it an effective antioxidant. There are virtually no living organisms on this planet-animal or plant whose cells don't contain some glutathione. Scientists have speculated that glutathione was essential to the very development of life on earth. glutathione has many roles; in none does it act alone. It is a coenzyme in various enzymatic reactions. The most important of these are redox reactions, in which the thiol grouping on the cysteine portion of cell membranes protects against peroxidation; and conjugation reactions, in which glutathione (especially in the liver) binds with toxic chemicals in order to detoxify them. glutathione is also important in red and white blood cell formation and throughout the immune system. glutathione's clinical uses include the prevention of oxygen toxicity in hyperbaric oxygen therapy, treatment of lead and other heavy metal poisoning, lowering of the toxicity of chemotherapy and radiation in cancer treatments, and reversal of cataracts. (http://www.dcnutrition.com/AminoAcids/) glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate. GSH is known as a substrate in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in cytosol, microsomes, and mitochondria. However, it is also capable of participating in non-enzymatic conjugation with some chemicals, as in the case of n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450-reactive metabolite formed by acetaminophen, that becomes toxic when GSH is depleted by an overdose (of acetaminophen). glutathione in this capacity binds to NAPQI as a suicide substrate and in the process detoxifies it, taking the place of cellular protein thiol groups which would otherwise be covalently modified; when all GSH has been spent, NAPQI begins to react with the cellular proteins, killing the cells in the process. The preferred treatment for an overdose of this painkiller is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and renew the usable GSH pool. (http://en.wikipedia.org/wiki/glutathione).
70-18-8
C00051
124886
16856
OXIDIZED-GLUTATHIONE
111188
DB00143
N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O
C10H17N3O6S
InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1
RWSXRVCMGQZWBV-WDSKDSINSA-N
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid
307.323
307.083805981
-2.54
6
glutathione
0
-1
DBMET00487
FDB001498
5-l-glutamyl-l-cysteinylglycine;Agifutol s;Bakezyme rx;Copren;Deltathione;Gsh;Glutathion;Glutathione;Glutathione red;Glutathione reduced;Glutathione-sh;Glutatiol;Glutatione;Glutide;Glutinal;Isethion;L-glutamyl-l-cysteinylglycine;L-glutathione;L-glutathione reduce;L-g-glutamyl-l-cysteinyl-glycine;L-gamma-glutamyl-l-cysteinyl-glycine;L-gamma-glutamyl-l-cysteinylglycine;Ledac;Neuthion;Red. glutathione;Reduced glutathione;Tathion;Tathione;Triptide;Gamma-glutamylcysteinylglycine;Gamma-l-glutamyl-l-cysteinyl-glycine;Gamma-l-glutamyl-l-cysteinylglycine;N-(n-gamma-l-glutamyl-l-cysteinyl)glycine;G-l-glutamyl-l-cysteinyl-glycine;γ-l-glutamyl-l-cysteinyl-glycine;N-(n-g-l-glutamyl-l-cysteinyl)glycine;N-(n-γ-l-glutamyl-l-cysteinyl)glycine
PW_C000080
GSH
161
14
199
8
614
2
1337
10
1362
49
4889
31
5193
97
5839
143
8426
151
77403
332
77408
111
77424
331
78015
115
78761
132
80709
135
120098
405
120187
122
120880
124
121067
123
121093
383
122838
376
123456
118
123632
447
123658
398
125467
478
125544
297
125856
299
127004
209
127077
205
819
Hydroxide
HMDB0001039
In chemistry, hydroxide is the most common name for the diatomic anion OH, consisting of oxygen and hydrogen atoms, usually derived from the dissociation of a base. It is one of the simplest diatomic ions known. Hydroxide ion is a kind of ligand. It donates one pair of electrons, behaving as a Lewis base. Examples include the aluminate ion [Al(OH)4]- and aurate ion [Au(OH)4]-.
14280-30-9
C01328
961
16234
NH4OH
936
[OH-]
HO
InChI=1S/H2O/h1H2/p-1
XLYOFNOQVPJJNP-UHFFFAOYSA-M
hydroxide
17.0073
17.002739654
1
hydroxide
-1
0
FDB022386
Hydridooxygenate(1-);Hydrogen oxide;Hydroxide anion;Hydroxide ion;Hydroxide ion(1-);Hydroxide(1-);Hydroxy;Hydroxy anion;Hydroxy ion;Hydroxyl;Hydroxyl anion;Hydroxyl ion;Hydroxyl ion (oh1-);Hydroxyl radical;Hydroxyl radicals;Oh;Oxidanide;Oxygen ion (o1-);Water ion(1-);Oh(-)
PW_C000819
OH
1847
Oxidized glutathione
HMDB0003337
Oxidized glutathione is a glutathione dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized. glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate.
27025-41-8
C00127
5255796
17858
OXIDIZED-GLUTATHIONE
950
NC(CCC(=O)NC(CSSCC(NC(=O)CCC(N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
C20H32N6O12S2
InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)
YPZRWBKMTBYPTK-UHFFFAOYSA-N
2-amino-4-[(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl)carbamoyl]butanoic acid
612.631
612.151961898
-3.18
10
oxiglutatione
0
-2
FDB023147
Gssg;Glutathione disulfide;L(-)-glutathione(oxidized);Oxiglutatione;(2s)-2-azaniumyl-4-{[(1r)-2-{[(2r)-2-[(4s)-4-azaniumyl-4-carboxylatobutanamido]-2-[(carboxylatomethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxylatomethyl)carbamoyl]ethyl]carbamoyl}butanoate
PW_C001847
GSSG
184
8
4878
3
77410
111
78012
112
80711
119
120103
122
120188
407
122840
135
125470
297
125545
481
127007
205
127078
206
41604
Selenodiglutathione
Selenodiglutathione, also known as gssesg, 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. Selenodiglutathione is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Selenodiglutathione may be a unique E.coli metabolite. Outside of the human body, selenodiglutathione can be found in a number of food items such as malabar plum, oriental wheat, red raspberry, and spirulina. This makes selenodiglutathione a potential biomarker for the consumption of these food products.
108069
N[C@@H](CCC(=O)N[C@@H](CS[Se]SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
C20H32N6O12S2Se
InChI=1S/C20H32N6O12S2Se/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-41-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1
GJEZZQVPWMCGSB-BJDJZHNGSA-N
(2S)-2-amino-4-{[(1R)-2-[({[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}selanyl)sulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
691.59
692.068483726
-2.75
10
(2S)-2-amino-4-{[(1R)-2-[({[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}selanyl)sulfanyl]-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid
0
-1
Gssesg
PW_C041604
Selenod
98224
8
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1
ACFIXJIJDZMPPO-NCHANQSKSA-N
{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
745.4209
745.091102105
-2.14
9
[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
0
-4
FDB021909
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reduced
PW_C000146
NADPH
185
8
190
3
778
10
796
5
821
18
837
2
1609
29
1615
49
4687
31
4793
14
4797
14
5310
111
5789
108
5972
147
6128
159
6271
35
6779
117
7068
188
7103
163
7154
205
7205
160
7315
213
7345
210
7559
212
7591
170
8194
225
8219
151
8421
224
11812
198
11893
211
12006
222
12150
164
12245
286
12596
226
12648
249
42343
315
43746
322
76911
293
77166
132
77385
331
77394
332
77460
130
77504
112
77511
115
77623
336
80712
119
113164
94
120105
407
120425
405
120452
122
120616
123
121141
125
121275
429
121402
124
121483
383
123059
376
123086
135
123241
447
123712
136
123846
464
123961
118
124041
398
125472
481
125696
297
126214
299
126529
495
127009
206
127572
388
128101
390
143
NADP
HMDB0000217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O17P3
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
744.4129
744.083277073
-2.27
9
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-3
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
43848
glutathioselenol
Glutathioselenol belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions. Glutathioselenol is soluble (in water) and a weakly acidic compound (based on its pKa). A glutathione derivative that is glutathione in which the hydrogen attached to the sulfur is replaced by a selenol group.
64729
[H]\C(=C(\[H])C1=CC=C[C@@]([H])(O)[C@@]1([H])O)C([O-])=O
C9H9O4
InChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,7,9-10,13H,(H,11,12)/p-1/b5-4+/t7-,9+/m1/s1
AEUBLTTWYCDTGM-HZMPTLLJSA-M
(2E)-3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoate
181.168
181.05063235
-0.47
2
(2E)-3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoate
-1
-1
PW_C043847
glutath
98229
8
6752
Hydrogen selenide
HMDB0011110
Hydrogen selenide is a metabolite of selenium which could have potential antiangiogenic effect in the chemoprevention of cancer. The hydrogen selenide is a key intermediate in the selenium methylation metabolism of inorganic and organic selenium compounds. Accumulation of the hydrogen selenide resulting from inhibition of the selenium methylation metabolism, detoxification metabolic pathway of selenium, is found in animals following repeated administration of a toxic dose of selenocystine. The excess of the hydrogen selenide produced by inhibition of the selenium methylation metabolism contributes to the hepatotoxicity caused by selenocystine. (PMID: 9414580, 11799926).
7783-07-5
C01528
533
16503
518
[SeH2]
H2Se
InChI=1S/H2Se/h1H2
SPVXKVOXSXTJOY-UHFFFAOYSA-N
hydrogen selenide
80.98
81.932171892
1
hydrogen selenide
0
-1
C01528
Dihydrogen monoselenide;Dihydrogen selenide;Hydrogen selenide;Selane;Selenium dihydride;Selenium hydride;Selenium hydride (seh2);[seh2];H2se;Hydroselenic acid;Hydroselenate
PW_C006752
HygSlnd
317
8
12635
31
78814
111
119911
122
122711
135
125301
297
126851
205
43849
glutathioselenium
Glutathioselenol, also known as gsseh or selenoglutathione, 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. Glutathioselenol is slightly soluble (in water) and a moderately acidic compound (based on its pKa).
N[C@@H](CCC(=O)N[C@@H](CS[Se-])C(=O)NCC(O)=O)C(O)=O
C10H16N3O6SSe
InChI=1S/C10H17N3O6SSe/c11-5(10(18)19)1-2-7(14)13-6(4-20-21)9(17)12-3-8(15)16/h5-6,21H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/p-1/t5-,6-/m0/s1
UUYVRXVWXDDDGX-WDSKDSINSA-M
{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}selanide
385.28
385.993052
-1.71
5
{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}selanide
-1
-2
PW_C043849
glutium
1041
Selenium
HMDB0001349
Selenium-dependent enzymes and selenoprotein P regulate immune and endothelial cell function. (PMID: 16607122). Thyroid hormone synthesis, metabolism and action require adequate availability of the essential trace elements iodine and selenium, which affect homeostasis of thyroid hormone-dependent metabolic pathways. The three selenocysteine-containing iodothyronine deiodinases constitute a novel gene family. Selenium is retained and deiodinase expression is maintained at almost normal levels in the thyroid gland, the brain and several other endocrine tissues during selenium deficiency, thus guaranteeing adequate local and systemic levels of the active thyroid hormone T(3). (PMID: 16131327). The trace element nutrient selenium (Se) discharges its well-known nutritional antioxidant activity through the Se-dependent glutathione peroxidases. It also regulates nuclear factor activities by redox mechanisms through the selenoprotein thioredoxin reductases. Converging data from epidemiological, ecological, and clinical studies have shown that Se can decrease the risk for some types of human cancers, especially those of the prostate, lung, and colon. Mechanistic studies have indicated that the methylselenol metabolite pool has many desirable attributes of chemoprevention, targeting both cancer cells and vascular endothelial cells, whereas the hydrogen selenide pool in excess of selenoprotein synthesis can lead to DNA single strand breaks, which may be mediated by some reactive oxygen species. (PMID: 16356132). SePP (selenoprotein P) is the major transporter of Se in the serum. Moreover, in the sanctuary area of the brain, SePP was shown to play a hitherto unexpected role as a local Se storage and recycling protein that directly maintains brain Se levels. Physiologically, it exists as an ion in the body. The function of Se is important in normal brain metabolism, redox regulation, antioxidant defenses, thyroid hormone metabolism and the development of neurodegenerative conditions. (PMID: 15720294). In areas where soils are low in bioavailable selenium (Se), potential Se deficiencies cause health risks for humans. (PMID: 16028492) Dietary selenium comes from cereals, meat, fish, and eggs. The recommended dietary allowance for adults is 55 micrograms per day.
7782-49-2
C01529
60871
27471292
[Se++]
Se
InChI=1S/Se/q+2
MFSBVGSNNPNWMD-UHFFFAOYSA-N
selandiylium
78.96
79.916521828
0
selandiylium
2
2
FDB013400
Selanediide;Selenide;Selenide(2-);Selenium;Selenium ion (se2+);Se(2+);Se2+;Selenium dication
PW_C001041
Se2+
43850
hydrogen selenide ion
Selanide, also known as hydrogenselenide, belongs to the class of inorganic compounds known as other non-metal hydrides. These are inorganic compounds in which the heaviest atom bonded to a hydrogen atom is belongs to the class of 'other non-metals'.
[SeH-]
HSe
InChI=1S/H2Se/h1H2/p-1
SPVXKVOXSXTJOY-UHFFFAOYSA-M
selanide
79.98
80.924896
1
selanide
-1
-1
PW_C043850
HSI
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
32
Adenosine monophosphate
HMDB0000045
Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable.
61-19-8
C00020
6083
16027
AMP
5858
DB00131
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
C10H14N5O7P
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
UDMBCSSLTHHNCD-KQYNXXCUSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
347.2212
347.063084339
-2.02
5
adenylate
0
-2
DBMET00485
FDB021806
5'-amp;5'-adenosine monophosphate;5'-adenylate;5'-adenylic acid;Amp;Adenosine 5'-monophosphate;Adenosine 5'-phosphate;Adenosine 5'-phosphorate;Adenosine 5'-phosphoric acid;Adenosine phosphate;Adenosine-5'-monophosphorate;Adenosine-5'-monophosphoric acid;Adenosine-5-monophosphorate;Adenosine-5-monophosphoric acid;Adenosine-monophosphate;Adenosine-phosphate;Adenovite;Adenylate;Adenylic acid;Cardiomone;Lycedan;Muscle adenylate;Muscle adenylic acid;My-b-den;My-beta-den;Phosaden;Phosphaden;Phosphentaside;5'-o-phosphonoadenosine;Adenosine 5'-(dihydrogen phosphate);Adenosine monophosphate;Adenosine-5'p;Adenosini phosphas;Ado5'p;Fosfato de adenosina;Pa;Pado;Phosphate d'adenosine;5'-adenosine monophosphoric acid;Adenosine phosphoric acid;Adenosine 5'-(dihydrogen phosphoric acid);Adenosine 5'-monophosphoric acid;Adenosine monophosphoric acid;Adenosine-5'-monophosphate;Phosphoric acid d'adenosine
PW_C000032
AMP
11
2
34
4
62
8
270
16
734
32
881
22
1189
14
4572
5
4867
54
5033
89
5251
104
5408
117
5423
103
5432
118
5457
120
5558
132
5583
133
5779
101
5795
108
6977
199
7072
188
11789
198
11868
161
11988
151
12003
222
12580
226
12636
31
12694
290
13331
225
42266
3
42646
315
77234
329
77325
111
78392
334
78809
115
79320
112
80399
1
80684
135
80900
7
119916
122
120016
124
120031
406
120246
382
120888
405
121954
408
122920
399
123464
376
124507
374
125306
297
125394
299
125409
479
125596
484
126853
205
126934
388
126949
501
127124
389
127311
209
127711
502
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
2744
Selenophosphate
HMDB0006407
Selenophosphate is the universal selenium donor that is required for the formation of selenium dependent enzymes and selenium tRNAs (i.e.: selenocysteyl-tRNA). Selenophosphate is also the selenium donor used to synthesize selenocysteine, which is co-translationally incorporated into selenoproteins at in-frame UGA codons. Selenophosphate synthetase (EC 2.7.9.3, human SPS1, product of the selD gene) produces monoselenophosphate from selenide and ATP. The SPS1-encoded enzyme depends on a selenium salvage system that recycles L-selenocysteine. Selenophosphate synthetase genes play a role in cancer cell's response to ionizing radiation and its reaction product, selenophosphate, might be involved in cancer prevention in a p53-dependent manner and could be applied to development of a novel cancer therapy. (PMID: 8986768, 10609888, 16786570).
289702-60-9
C05172
9543205
16144
SEPO3
7822178
OP(O)([O-])=[Se]
H2O3PSe
InChI=1S/H3O3PSe/c1-4(2,3)5/h(H3,1,2,3,5)/p-1
JRPHGDYSKGJTKZ-UHFFFAOYSA-M
hydroxy(selanylidene)phosphonous acid
159.95
160.89067727
3
selenophosphoric acid
0
-3
FDB023912
Dihydroxy-oxido-selanylidenephosphorane;Phosphorus monoselenide;Phosphorus selenide (pse);Selenoxo-phosphino
PW_C002744
SelP
7093
Sulfate transport system permease protein cysT
P16701
Involved in transporter activity. Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. Probably responsible for the translocation of the substrate across the membrane.
cysU
b2424
AP009048
3
6347
109
6357
Sulfate/thiosulfate import ATP-binding protein cysA
P16676
Part of the ABC transporter complex CysAWTP involved in sulfate/thiosulfate import. Responsible for energy coupling to the transport system.
cysA
b2422
AP009048
3
3.6.3.25
6348
109
7042
Sulfate transport system permease protein cysW
P0AEB0
Involved in transporter activity. Part of the ABC transporter complex cysAWTP (TC 3.A.1.6.1) involved in sulfate/thiosulfate import. Probably responsible for the translocation of the substrate across the membrane.
cysW
b2423
AP009048
3
6346
109
5966
Respiratory nitrate reductase 1 alpha chain
P09152
Involved in oxidoreductase activity. The nitrate reductase enzyme complex allows E.coli to use nitrate as an electron acceptor during anaerobic growth. The alpha chain is the actual site of nitrate reduction.
narG
b1224
AP009048
3
1.7.99.4
6792
109
8533
140
113397
94
6308
Respiratory nitrate reductase 1 beta chain
P11349
Involved in iron-sulfur cluster binding. The nitrate reductase enzyme complex allows E.coli to use nitrate as an electron acceptor during anaerobic growth. The beta chain is an electron transfer unit containing four cysteine clusters involved in the formation of iron-sulfur centers. Electrons are transferred from the gamma chain to the molybdenum cofactor of the alpha subunit.
narH
b1225
AP009048
3
1.7.99.4
6793
109
8534
140
113398
94
7523
Nitrate reductase molybdenum cofactor assembly chaperone NarJ
P0AF26
Involved in unfolded protein binding. Chaperone required for proper molybdenum cofactor insertion and final assembly of the membrane-bound respiratory nitrate reductase 1. Required for the insertion of the molybdenum into the apo-NarG subunit, maybe by keeping NarG in an appropriate competent-open conformation for the molybdenum cofactor insertion to occur. NarJ maintains the apoNarGH complex in a soluble state. Upon insertion of the molybdenum cofactor, NarJ seems to dissociate from the activated soluble NarGH complex, before its association with the NarI subunit on the membrane.
narJ
b1226
AP009048
3
6794
109
8535
101
113399
94
6309
Respiratory nitrate reductase 1 gamma chain
P11350
Involved in nitrate reductase activity. The nitrate reductase enzyme complex allows E.coli to use nitrate as an electron acceptor during anaerobic growth. The gamma chain is a membrane-embedded heme-iron unit resembling cytochrome b, which transfers electrons from quinones to the beta subunit.
narI
b1227
AP009048
3
1.7.99.4
6795
109
113400
94
6261
Respiratory nitrate reductase 2 gamma chain
P0AF32
Involved in nitrate reductase activity. This is a second nitrate reductase enzyme which can substitute for the NRA enzyme and allows E.coli to use nitrate as an electron acceptor during anaerobic growth. The gamma chain is a membrane-embedded heme-iron unit resembling cytochrome b, which transfers electrons from quinones to the beta subunit.
narV
b1465
AP009048
3
1.7.99.4
6796
109
113401
94
6377
Probable nitrate reductase molybdenum cofactor assembly chaperone NarW
P19317
Involved in unfolded protein binding. Chaperone required for proper molybdenum cofactor insertion and final assembly of the membrane-bound respiratory nitrate reductase 2.
narW
b1466
AP009048
3
6797
109
8536
101
113402
94
6378
Respiratory nitrate reductase 2 beta chain
P19318
Involved in iron-sulfur cluster binding. This is a second nitrate reductase enzyme which can substitute for the NRA enzyme and allows E.coli to use nitrate as an electron acceptor during anaerobic growth. The beta chain is an electron transfer unit containing four cysteine clusters involved in the formation of iron-sulfur centers. Electrons are transferred from the gamma chain to the molybdenum cofactor of the alpha subunit.
narY
b1467
AP009048
3
1.7.99.4
6798
109
8537
140
113403
94
6379
Respiratory nitrate reductase 2 alpha chain
P19319
Involved in oxidoreductase activity. The alpha chain is the actual site of nitrate reduction.
narZ
b1468
AP009048
3
1.7.99.4
6799
109
8538
140
113404
94
6547
Periplasmic nitrate reductase
P33937
Involved in oxidoreductase activity. Catalytic subunit of the periplasmic nitrate reductase (NAP). Only expressed at high levels during aerobic growth. NapAB complex receives electrons from the membrane-anchored tetraheme protein napC, thus allowing electron flow between membrane and periplasm. Essential function for nitrate assimilation and may have a role in anaerobic metabolism.
napA
b2206
AP009048
3
1.7.99.4
6800
109
8539
232
113405
94
7718
cytochrom c550 subunit nitrate reductase
P0ABL3
napB
3
6801
109
8540
232
113406
94
3911
Selenite/selenate symporter
3
PW_P003911
10879
7093
10880
6357
10881
7042
1166
Nitrate Reductase
3
PW_P001166
1339
5966
1340
6308
1341
7523
1342
6309
1343
6261
1344
6377
1345
6378
1346
6379
1347
6547
1348
7718
5188
PW_R005188
Right
21002
6761
1
Compound
false
21003
40034
2
Compound
false
21004
80
4
Compound
false
21005
1420
2
Compound
false
21006
819
1
Compound
false
21007
1847
1
Compound
false
21008
41604
1
Compound
false
5189
PW_R005189
Right
21009
41604
1
Compound
false
21010
146
1
Compound
false
21011
40034
1
Compound
false
21012
143
1
Compound
false
21013
80
1
Compound
false
21014
43848
1
Compound
false
5190
PW_R005190
Both
21015
43848
1
Compound
false
21016
146
1
Compound
false
21017
40034
1
Compound
false
21018
1420
1
Compound
false
21019
80
1
Compound
false
21020
143
1
Compound
false
21021
819
1
Compound
false
21022
6752
1
Compound
false
5191
PW_R005191
Right
21023
43848
1
Compound
false
21024
40034
1
Compound
false
21025
43849
1
Compound
false
5192
PW_R005192
Right
21026
43849
1
Compound
false
21027
1420
1
Compound
false
21028
80
1
Compound
false
21029
1041
1
Compound
false
5201
PW_R005201
Both
21069
6752
1
Compound
false
21070
43850
1
Compound
false
21071
40034
1
Compound
false
5202
PW_R005202
Right
21072
43850
1
Compound
false
21073
414
1
Compound
false
21074
32
1
Compound
false
21075
1104
1
Compound
false
21076
2744
1
Compound
false
5187
false
PW_R005187
Right
20997
40445
1
Compound
false
20998
40034
2
Compound
false
20999
41100
2
Compound
false
21000
6761
1
Compound
false
21001
1420
1
Compound
false
5155
1166
484
PW_T000484
604
6761
1
Compound
107
108
Right
605
40445
1
Compound
107
108
Right
416
3911
2015-09-10T12:43:12-06:00
2015-09-10T12:43:12-06:00
109
61736
6761
107
3
false
661
179
10
regular
100
100
61737
6761
108
3
false
1046
704
10
regular
100
100
61738
40445
107
3
false
861
179
10
regular
100
100
61739
40445
108
3
false
496
704
10
regular
100
100
61741
40034
55
false
617
800
10
regular
78
78
61742
41100
9
false
591
673
10
regular
100
25
61743
1420
49
false
972
831
10
regular
78
78
61744
40034
55
false
1172
806
10
regular
78
78
61745
80
3
false
1166
604
10
regular
100
100
61746
1420
49
false
1482
616
10
regular
78
78
61747
819
3
false
1346
604
10
regular
100
100
61748
1847
3
false
1356
809
10
regular
100
110
61749
41604
3
false
1596
704
10
regular
100
100
61750
146
62
false
1553
854
10
regular
50
30
61751
40034
55
false
1708
850
10
regular
78
78
61752
143
61
false
1552
1034
10
regular
50
30
61753
80
3
false
1717
999
10
regular
100
100
61754
43848
3
false
1599
1136
10
regular
100
100
61755
146
62
false
1710
1341
10
regular
50
30
61756
40034
55
false
1699
1242
10
regular
78
78
61757
1420
49
false
1532
1252
10
regular
78
78
61758
80
3
false
1487
1456
10
regular
100
100
61759
143
61
false
1702
1461
10
regular
50
30
61760
819
3
false
1727
1506
10
regular
100
100
61761
6752
3
false
1592
1586
10
regular
100
110
61762
40034
3
false
1429
1016
10
regular
100
100
61763
43849
3
false
1339
1136
10
regular
100
100
61764
1420
49
false
1250
1068
10
regular
78
78
61765
80
3
false
1064
1051
10
regular
100
100
61766
1041
3
false
939
1136
10
regular
100
100
61802
43850
3
false
1222
1584
10
regular
100
110
61803
40034
55
false
1373
1519
10
regular
78
78
61804
414
42
false
1132
1564
10
regular
50
30
61805
32
44
false
982
1560
10
regular
50
30
61806
1104
46
false
890
1570
10
regular
44
43
61807
2744
3
false
762
1588
10
regular
100
100
28742
7093
109
76
false
671
349
8
subunit
regular
150
70
28743
6357
109
76
false
816
349
8
subunit
regular
150
70
28744
7042
109
76
false
736
349
8
subunit
regular
150
70
28745
5966
140
2
false
816
744
8
subunit
regular
150
70
28746
6308
140
2
false
731
769
8
subunit
regular
150
70
28747
7523
101
2
false
836
699
8
subunit
regular
150
70
28748
6309
109
2
false
686
724
8
subunit
regular
150
70
28749
6261
109
2
false
836
659
8
subunit
regular
150
70
28750
6377
101
2
false
761
669
8
subunit
regular
150
70
28751
6378
140
2
false
691
674
8
subunit
regular
150
70
28752
6379
140
2
false
801
619
8
subunit
regular
150
70
28753
6547
232
2
false
711
624
8
subunit
regular
150
70
28754
7718
232
2
false
746
719
8
subunit
regular
150
70
24173
3911
1642
28430
28742
28431
28743
28432
28744
24174
1166
1642
28433
28745
28434
28746
28435
28747
28436
28748
28437
28749
28438
28750
28439
28751
28440
28752
28441
28753
28442
28754
88590
M711.3333333333334 279 C807.3333333333334 283 810.3333333333334 285 811.3333333333334 349
83
false
18
88591
M1096.3333333333335 704 C1096.3333333333335 623 1097.3333333333335 461 1096.3333333333335 383 C1060.3333333333335 383 982.3333333333334 383 886.3333333333334 384
83
false
7
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
88592
M911.3333333333334 279 C830.3333333333334 284 809.3333333333334 284 811.3333333333334 349
83
false
18
88593
M546.3333333333334 704 C546.3333333333334 570 543.3333333333334 438 544.3333333333334 385 C611.3333333333334 384 658.3333333333334 385 736.3333333333334 384
83
false
7
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
88599
M1146.3333333333335 754 C1176.3333333333335 754 1566.3333333333335 754 1596.3333333333335 754
5
false
18
88600
M1211.3333333333335 806 C1213.3333333333335 774 1206.3333333333335 756.5 1309.3333333333335 754.5
5
false
18
88601
M1216.3333333333335 704 C1217.3333333333335 739 1245.3333333333335 752.5 1311.3333333333335 753.5
5
false
18
88602
M1521.3333333333335 694 C1520.3333333333335 772 1417.3333333333335 754.5 1305.3333333333335 753.5
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
88603
M1396.3333333333335 704 C1396.3333333333335 731 1392.3333333333335 753.5 1311.3333333333335 753.5
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
88604
M1406.3333333333335 809 C1406.3333333333335 750 1373.3333333333335 754.5 1311.3333333333335 754.5
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
88605
M1596.3333333333335 754 C1566.3333333333335 754 1176.3333333333335 754 1146.3333333333335 754
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
88606
M1646.3333333333335 804 C1646.3333333333335 834 1602.8333333333335 905 1602.8333333333335 935
5
true
18
88607
M1607.3333333333335 869 C1645.3333333333335 869 1644.8333333333335 923 1649.8333333333335 989
5
false
18
88608
M1708.3333333333335 889 C1666.3333333333335 892 1646.8333333333335 907 1649.8333333333335 989
5
false
18
88609
M1606.3333333333335 1049 C1629.3333333333335 1049 1645.8333333333335 1026 1649.8333333333335 989
5
false
18
true
M 153.6135217108315 264.9282229629627 L 138.66666666666666 263.6666666666667 L 145.0475543878525 277.241800989745
false
88610
M1717.3333333333335 1049 C1685.3333333333335 1050 1648.8333333333335 1044 1649.8333333333335 989
5
false
18
true
M 153.6135217108315 264.9282229629627 L 138.66666666666666 263.6666666666667 L 145.0475543878525 277.241800989745
false
88611
M1649.3333333333335 1136 C1649.3333333333335 1106 1646.3333333333335 834 1646.3333333333335 804
5
false
18
true
M 153.6135217108315 264.9282229629627 L 138.66666666666666 263.6666666666667 L 145.0475543878525 277.241800989745
false
88612
M1614.3333333333335 1180 C1614.3333333333335 1210 1614.8333333333335 1276.5 1614.8333333333335 1306.5
5
true
18
false
false
88613
M1710.3333333333335 1356 C1642.3333333333335 1354 1646.3333333333335 1370 1642.3333333333335 1586
5
false
18
false
false
88614
M1699.3333333333335 1281 C1631.3333333333335 1281 1646.3333333333335 1389 1642.3333333333335 1586
5
false
18
false
false
88615
M1610.3333333333335 1291 C1667.3333333333335 1297 1644.3333333333335 1495 1642.3333333333335 1586
5
false
18
false
false
88616
M1587.3333333333335 1506 C1650.3333333333335 1507 1644.3333333333335 1477 1649.3333333333335 1236
5
false
18
true
M 153.6135217108315 531.5948896296294 L 138.66666666666666 530.3333333333334 L 145.0475543878525 543.9084676564117
false
88617
M1702.3333333333335 1476 C1640.3333333333335 1471 1645.3333333333335 1427 1649.3333333333335 1236
5
false
18
true
M 153.6135217108315 531.5948896296294 L 138.66666666666666 530.3333333333334 L 145.0475543878525 543.9084676564117
false
88618
M1727.3333333333335 1556 C1629.3333333333335 1553 1644.3333333333335 1471 1649.3333333333335 1236
5
false
18
true
M 153.6135217108315 531.5948896296294 L 138.66666666666666 530.3333333333334 L 145.0475543878525 543.9084676564117
false
88619
M1642.3333333333335 1586 C1642.3333333333335 1556 1649.3333333333335 1284 1649.3333333333335 1236
5
false
18
true
M 153.6135217108315 531.5948896296294 L 138.66666666666666 530.3333333333334 L 145.0475543878525 543.9084676564117
false
88620
M1554.3333333333335 1126 C1524.3333333333335 1126 1514.3333333333335 1131 1484.3333333333335 1131
5
true
18
88621
M1479.3333333333335 1116 C1484.3333333333335 1186 1569.3333333333335 1186 1599.3333333333335 1186
5
false
18
true
M 153.6135217108315 564.9282229629626 L 138.66666666666666 563.6666666666666 L 145.0475543878525 577.241800989745
false
88622
M1439.3333333333335 1186 C1469.3333333333335 1186 1569.3333333333335 1186 1599.3333333333335 1186
5
false
18
true
M 153.6135217108315 564.9282229629626 L 138.66666666666666 563.6666666666666 L 145.0475543878525 577.241800989745
false
88623
M1339.3333333333335 1186 C1309.3333333333335 1186 929.3333333333334 1131.5 899.3333333333334 1131.5
5
true
18
88624
M1289.3333333333335 1146 C1273.3333333333335 1197 1254.3333333333335 1186 1039.3333333333335 1186
5
false
18
88625
M1114.3333333333335 1151 C1114.3333333333335 1189 1204.3333333333335 1187 1339.3333333333335 1186
5
false
18
true
M 153.6135217108315 564.9282229629626 L 138.66666666666666 563.6666666666666 L 145.0475543878525 577.241800989745
false
88626
M1039.3333333333335 1186 C1069.3333333333335 1186 1309.3333333333335 1186 1339.3333333333335 1186
5
false
18
true
M 153.6135217108315 564.9282229629626 L 138.66666666666666 563.6666666666666 L 145.0475543878525 577.241800989745
false
88669
M1592.3333333333335 1641 C1562.3333333333335 1641 1527.3333333333335 1616 1497.3333333333335 1616
5
true
18
true
M 153.6135217108315 564.9282229629626 L 138.66666666666666 563.6666666666666 L 145.0475543878525 577.241800989745
false
88670
M1322.3333333333335 1639 C1352.3333333333335 1639 1562.3333333333335 1641 1592.3333333333335 1641
5
false
18
true
M 153.6135217108315 564.9282229629626 L 138.66666666666666 563.6666666666666 L 145.0475543878525 577.241800989745
false
88671
M1412.3333333333335 1597 C1413.3333333333335 1646 1515.3333333333335 1640 1592.3333333333335 1641
5
false
18
true
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