2273
Pathway
Lipoic Acid Metabolism
The lipoic acid metabolism involves the metabolism of octanoyl-acp by reacting with a sulfur donor and a S-adenosylmethionine through a lipoic acid synthetase resulting in the release of L-methionine, deoxyadenosine and lipoyl-ACP. Lipoyl-ACP reacts with an apoprotein through a through a lipoyl(octanoyl) transferase resulting in the release of an ACP and a protein N6-(lypoyl)lysine.
Octanoyl-acp can also interact with a apoprotein through a lipoyl(octanoyl) transferase resulting in the release of an ACP and a protein N6-(octanoyl)lysine. Protein N6-(octanoyl) lysine reacts with sulfur donor and a S-adenosylmethionine through a lipoic acid synthetase resulting in the release of L-methionine, deoxyadenosine and Protein N6(lipoyl) lysine.
Metabolic
PW002499
Center
PathwayVisualizationContext2785
2050
1963
#000099
PathwayVisualization2256
2273
Lipoic Acid Metabolism
The lipoic acid metabolism involves the metabolism of octanoyl-acp by reacting with a sulfur donor and a S-adenosylmethionine through a lipoic acid synthetase resulting in the release of L-methionine, deoxyadenosine and lipoyl-ACP. Lipoyl-ACP reacts with an apoprotein through a through a lipoyl(octanoyl) transferase resulting in the release of an ACP and a protein N6-(lypoyl)lysine.
Octanoyl-acp can also interact with a apoprotein through a lipoyl(octanoyl) transferase resulting in the release of an ACP and a protein N6-(octanoyl)lysine. Protein N6-(octanoyl) lysine reacts with sulfur donor and a S-adenosylmethionine through a lipoic acid synthetase resulting in the release of L-methionine, deoxyadenosine and Protein N6(lipoyl) lysine.
Metabolic
18
5318
26476454
Kanehisa M, Sato Y, Kawashima M, Furumichi M, Tanabe M: KEGG as a reference resource for gene and protein annotation. Nucleic Acids Res. 2016 Jan 4;44(D1):D457-62. doi: 10.1093/nar/gkv1070. Epub 2015 Oct 17.
2273
Pathway
5319
10592173
Kanehisa M, Goto S: KEGG: kyoto encyclopedia of genes and genomes. Nucleic Acids Res. 2000 Jan 1;28(1):27-30.
2273
Pathway
1
Cell
CL:0000000
2
Platelet
CL:0000233
5
Hepatocyte
CL:0000182
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
7
Epithelial Cell
CL:0000066
6
Myocyte
CL:0000187
1
Homo sapiens
9606
Eukaryote
Human
2
Bacteria
2
Prokaryote
Bacteria
3
Escherichia coli
562
Prokaryote
12
Mus musculus
10090
Eukaryote
Mouse
17
Rattus norvegicus
10116
Eukaryote
Rat
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
5
Bos taurus
9913
Eukaryote
Cattle
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
1
Cytosol
GO:0005829
3
Mitochondrial Matrix
GO:0005759
5
Cytoplasm
GO:0005737
14
Mitochondrial Outer Membrane
GO:0005741
2
Mitochondrion
GO:0005739
15
Nucleus
GO:0005634
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
7
Endoplasmic Reticulum Membrane
GO:0005789
10
Cell Membrane
GO:0005886
27
Peroxisome Membrane
GO:0005778
31
Periplasmic Space
GO:0005620
11
Extracellular Space
GO:0005615
35
Chloroplast
GO:0009507
12
Mitochondrial Inner Membrane
GO:0005743
32
Inner Membrane
GO:0070258
17
Nucleoplasm
GO:0005654
39
Mitochondrial membrane
GO:0031966
2
Endothelium
BTO:0000393
1
Liver
BTO:0000759
72
9
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
25
Intestine
BTO:0000648
8
Blood Vessel
BTO:0001102
74
11
4
Adrenal Medulla
BTO:0000049
71
8
9
Muscle
BTO:0000887
141
18
2
1
1
1
PW_BS000002
4
3
1
1
PW_BS000004
8
5
1
1
PW_BS000008
16
2
1
2
PW_BS000016
22
14
1
1
PW_BS000022
13
1
2
1
PW_BS000013
32
1
15
1
5
PW_BS000032
5
4
1
1
PW_BS000005
39
7
1
1
3
PW_BS000039
3
2
1
1
PW_BS000003
18
13
1
1
PW_BS000018
10
1
7
1
1
PW_BS000010
49
7
1
1
PW_BS000049
14
10
1
PW_BS000014
58
1
14
1
1
PW_BS000058
59
27
1
1
PW_BS000059
27
15
1
PW_BS000027
46
1
1
4
PW_BS000046
29
1
1
1
PW_BS000029
66
18
5
1
8
PW_BS000066
72
5
1
3
PW_BS000072
61
25
1
7
PW_BS000061
51
8
1
PW_BS000051
23
15
1
1
PW_BS000023
31
1
5
1
1
PW_BS000031
91
8
5
1
1
PW_BS000091
54
1
3
1
5
PW_BS000054
89
2
PW_BS000089
26
1
1
1
5
PW_BS000026
7
1
1
PW_BS000007
97
1
5
2
1
PW_BS000097
100
5
2
1
PW_BS000100
104
14
3
1
PW_BS000104
101
5
3
1
PW_BS000101
111
5
12
1
PW_BS000111
112
2
12
1
PW_BS000112
103
3
3
1
PW_BS000103
117
1
3
1
PW_BS000117
118
1
17
1
PW_BS000118
120
3
17
1
PW_BS000120
129
1
5
12
1
PW_BS000129
132
1
12
1
PW_BS000132
133
3
12
1
PW_BS000133
135
5
17
1
PW_BS000135
108
1
3
PW_BS000108
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
107
31
3
PW_BS000107
147
1
24
1
PW_BS000147
151
1
4
1
PW_BS000151
155
3
24
1
PW_BS000155
161
3
18
1
PW_BS000161
166
1
1
PW_BS000166
178
3
21
1
PW_BS000178
188
1
18
PW_BS000024
160
1
18
1
PW_BS000160
199
14
18
1
PW_BS000024
205
5
6
1
PW_BS000024
206
2
6
1
PW_BS000024
210
13
18
1
PW_BS000024
213
7
18
1
PW_BS000024
211
10
18
PW_BS000024
198
5
18
1
PW_BS000024
216
4
18
1
PW_BS000024
217
15
18
PW_BS000024
218
15
18
1
PW_BS000024
163
2
18
1
PW_BS000163
222
3
4
1
PW_BS000024
190
11
18
PW_BS000024
225
35
4
1
PW_BS000024
277
1
2
18
PW_BS000024
170
18
PW_BS000170
281
1
25
1
PW_BS000024
164
4
PW_BS000164
285
10
4
1
PW_BS000024
226
4
4
1
PW_BS000024
290
5
49
1
PW_BS000024
223
12
4
1
PW_BS000024
308
10
1
1
PW_BS000024
315
1
23
PW_BS000024
322
1
23
1
PW_BS000024
318
31
23
PW_BS000024
253
5
4
1
PW_BS000024
134
12
12
1
PW_BS000134
329
14
12
1
PW_BS000028
333
1
2
12
PW_BS000028
336
1
12
1
PW_BS000028
332
1
7
12
1
PW_BS000028
350
1
14
12
1
PW_BS000028
128
15
12
1
PW_BS000128
351
15
12
PW_BS000028
353
25
12
7
PW_BS000028
335
27
12
1
PW_BS000028
115
10
12
PW_BS000115
130
13
12
1
PW_BS000130
331
7
12
1
PW_BS000028
334
4
12
1
PW_BS000028
368
3
60
1
PW_BS000028
184
1
2
1
PW_BS000024
119
2
17
1
PW_BS000119
1
1
PW_BS000001
124
1
5
1
PW_BS000124
94
3
PW_BS000094
388
1
6
1
PW_BS000112
109
32
3
PW_BS000109
122
5
5
1
PW_BS000122
406
3
5
1
PW_BS000115
407
2
5
1
PW_BS000115
382
14
5
1
PW_BS000100
412
1
2
5
PW_BS000115
429
1
5
1
PW_BS000115
123
1
7
5
1
PW_BS000123
433
1
14
5
1
PW_BS000115
408
4
5
1
PW_BS000115
410
15
5
1
PW_BS000115
125
13
5
1
PW_BS000125
383
7
5
1
PW_BS000100
405
10
5
PW_BS000115
422
27
5
1
PW_BS000115
435
15
5
PW_BS000115
399
14
17
1
PW_BS000113
446
1
2
17
PW_BS000115
464
1
17
1
PW_BS000115
447
1
7
17
1
PW_BS000115
468
1
14
17
1
PW_BS000115
374
4
17
1
PW_BS000053
444
15
17
1
PW_BS000115
136
13
17
1
PW_BS000136
398
7
17
1
PW_BS000113
376
10
17
PW_BS000053
472
25
17
7
PW_BS000115
375
27
17
1
PW_BS000053
470
15
17
PW_BS000115
297
5
10
1
PW_BS000024
479
3
10
1
PW_BS000115
299
1
10
1
PW_BS000024
481
2
10
1
PW_BS000115
484
14
10
1
PW_BS000115
485
15
10
1
PW_BS000115
300
13
10
1
PW_BS000024
495
7
10
1
PW_BS000115
478
10
10
PW_BS000115
491
27
10
1
PW_BS000115
499
15
10
PW_BS000115
501
3
6
1
PW_BS000115
389
14
6
1
PW_BS000112
516
15
6
1
PW_BS000115
395
13
6
1
PW_BS000113
390
7
6
1
PW_BS000112
209
10
6
PW_BS000024
508
27
6
1
PW_BS000115
517
15
6
PW_BS000115
249
13
4
1
PW_BS000024
288
14
4
1
PW_BS000024
306
35
51
1
PW_BS000024
17
12
1
1
PW_BS000017
372
10
2
PW_BS000028
384
12
5
1
PW_BS000100
391
12
6
1
PW_BS000112
121
12
17
1
PW_BS000121
502
4
6
1
PW_BS000115
30
17
1
1
PW_BS000030
20
4
1
1
1
PW_BS000020
50
9
5
1
6
PW_BS000050
195
13
18
PW_BS000024
309
39
1
1
PW_BS000024
293
4
1
PW_BS000024
224
2
4
1
PW_BS000024
338
17
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
346
9
5
12
6
PW_BS000028
361
39
12
1
PW_BS000028
386
39
5
1
PW_BS000100
397
39
6
1
PW_BS000113
401
39
17
1
PW_BS000113
413
17
5
1
PW_BS000115
449
17
17
1
PW_BS000115
105
11
3
PW_BS000105
320
11
23
PW_BS000024
42563
lipoate
(R)-Lipoic acid, also known as thioctic acid or alpha-lipoate, belongs to the class of organic compounds known as lipoic acids and derivatives. Lipoic acids and derivatives are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring (R)-Lipoic acid exists as a solid and is considered to be practically insoluble (in water) and relatively neutral (R)-Lipoic acid may be a unique E.coli metabolite (R)-Lipoic acid and hydrogen ion can be converted into lipoyl-AMP through its interaction with the enzyme lipoate---protein ligase. Outside of the human body, (R)-lipoic acid can be found in broccoli and spinach. This makes (R)-lipoic acid a potential biomarker for the consumption of these food products (R)-Lipoic acid is a potentially toxic compound.
864
16494
OC(=O)CCCCC1CCSS1
C8H14O2S2
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
AGBQKNBQESQNJD-UHFFFAOYSA-N
5-(1,2-dithiolan-3-yl)pentanoic acid
206.326
206.043521072
-2.96
1
6,8-thioctic acid
0
-1
PW_C042563
Lipoate
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
170
Pyrophosphate
HMDB0000250
The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.
14000-31-8
C00013
644102
18361
PPI
559142
DB04160
[O-]P([O-])(=O)OP([O-])([O-])=O
O7P2
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4
XPPKVPWEQAFLFU-UHFFFAOYSA-J
(phosphonooxy)phosphonic acid
173.9433
173.911925378
4
pyrophosphoric acid
0
-3
FDB021918
(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ion
PW_C000170
Ppi
12
2
35
4
63
8
429
23
735
32
882
22
1217
3
1620
49
2410
59
2815
29
4175
14
4868
54
5034
89
5252
104
5294
101
5409
117
5424
103
5433
118
5458
120
5548
111
5559
132
5584
133
5606
135
5655
108
5879
107
6239
166
6978
199
7073
188
7134
163
7272
160
7312
198
7318
213
8275
151
8283
210
11869
161
12002
222
12041
164
12315
225
12323
249
12512
288
12579
226
12695
290
15219
306
15375
18
34760
17
42561
315
42697
318
77235
329
77317
128
77635
336
78416
335
78928
331
79153
112
79950
134
79958
130
80047
372
80417
170
85630
1
94786
384
94814
125
94819
382
98678
223
110634
391
113270
395
113275
389
115527
136
115532
399
119934
122
120017
124
120032
406
120330
410
120936
407
121261
429
121341
121
121486
383
122407
422
122985
444
123502
119
123831
464
124044
398
124977
375
125324
297
125395
299
125410
479
125597
484
125656
485
125876
481
126552
491
126869
205
126935
388
126950
501
127337
206
128124
508
40072
Lipoyl-AMP
HMDB0059635
Lipoyl-AMP belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated. Lipoyl-AMP is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Lipoyl-AMP exists in all living organisms, ranging from bacteria to humans. Lipoyl-AMP can be biosynthesized from (R)-lipoic acid and hydrogen ion; which is catalyzed by the enzyme lipoate---protein ligase. Lipoyl-amp is part of the Protein modification, and Lipoic acid metabolism pathways. It is a substrate for: Lipoyltransferase 1, mitochondrial.
C16238
23724672
55451
26330628
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O
C18H26N5O8PS2
InChI=1S/C18H26N5O8PS2/c19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)11(30-18)7-29-32(27,28)31-12(24)4-2-1-3-10-5-6-33-34-10/h8-11,14-15,18,25-26H,1-7H2,(H,27,28)(H2,19,20,21)/t10?,11-,14-,15-,18-/m1/s1
QWEGOCJRZOKSOE-NLJBGGCZSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[5-(1,2-dithiolan-3-yl)pentanoyl]oxy})phosphinic acid
535.532
535.096040725
-2.68
4
Lipoyl-AMP
0
-1
PW_C040072
L-AMP
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
921
S-Adenosylmethionine
HMDB0001185
S-Adenosylmethionine (CAS: 29908-03-0), also known as SAM or AdoMet, is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in the treatment of chronic liver disease (From Merck, 11th ed). S-Adenosylmethionine is a natural substance present in the cells of the body. It plays a crucial biochemical role by donating a one-carbon methyl group in a process called transmethylation. S-Adenosylmethionine, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine, and other molecules.
485-80-3
C00019
24762165
15414
S-ADENOSYLMETHIONINE
31983
DB00118
C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
C15H23N6O5S
InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1
MEFKEPWMEQBLKI-AIRLBKTGSA-O
[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
399.445
399.145063566
-2.56
5
SAMe
1
1
FDB022473
(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine;2-s-adenosyl-l-methionine;5'-deoxyadenosine-5'-l-methionine disulfate ditosylate;Active methionine;Ademetionine;Adenosylmethionine;Adomet;Donamet;L-s-adenosylmethionine;S-(5'-adenosyl)-l-methionine;S-(5'-deoxyadenosin-5'-yl)-l-methionine;S-adenosyl methionine;S-adenosyl-l-methionine disulfate tosylate;S-adenosyl-l-methionine;S-adenosyl-methionine;S-adenosylmethionine;5'-deoxyadenosine-5'-l-methionine disulphate ditosylate;S-adenosyl-l-methionine disulphate tosylate;(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt;[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl][(3s)-3-amino-3-carboxypropyl](methyl)sulfonium;Acylcarnitine;Sam;Same
PW_C000921
SAMe
519
8
633
30
704
20
1220
3
1880
27
2066
2
4681
10
5023
50
5604
135
7136
163
7540
210
7544
213
7632
160
8266
151
9235
195
11874
198
12031
222
12358
225
15293
249
15345
18
15363
309
76897
293
76899
164
76984
224
77488
111
77731
338
77772
341
78099
132
78303
351
78335
346
79155
112
79961
361
80861
22
94830
382
94833
386
113286
389
113288
397
115543
399
115546
401
120393
122
120537
413
120939
407
121052
124
122282
435
123171
449
123505
119
123616
118
124836
470
125859
297
125879
481
126304
299
126447
499
127321
205
127340
206
127595
388
128017
517
548
L-Methionine
HMDB0000696
Methionine is an essential amino acid (there are 9 essential amino acids) required for normal growth and development of humans, other mammals, and avian species. In addition to being a substrate for protein synthesis, it is an intermediate in transmethylation reactions, serving as the major methyl group donor in vivo, including the methyl groups for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyltransferase (methionine synthase), the only reaction that allows for the recycling of this form of folate, and is also a methyl acceptor for the catabolism of betaine. Methionine is the metabolic precursor for cysteine. Only the sulfur atom from methionine is transferred to cysteine; the carbon skeleton of cysteine is donated by serine (PMID: 16702340). There is a general consensus concerning normal sulfur amino acid (SAA) requirements. WHO recommendations amount to 13 mg/kg per 24 h in healthy adults. This amount is roughly doubled in artificial nutrition regimens. In disease or after trauma, requirements may be altered for methionine, cysteine, and taurine. Although in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function, hypermethioninemia or hyperhomocysteinemia may occur, SAA supplementation can be considered safe in amounts exceeding 2-3 times the minimum recommended daily intake. Apart from some very specific indications (e.g. acetaminophen poisoning) the usefulness of SAA supplementation is not yet established (PMID: 16702341). Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, but there is no evidence of similar effects in healthy subjects. The role of methionine as a precursor of homocysteine is the most notable cause for concern. Acute doses of methionine can lead to acute increases in plasma homocysteine, which can be used as an index of the susceptibility to cardiovascular disease. Sufficiently high doses of methionine can actually result in death. Longer-term studies in adults have indicated no adverse consequences of moderate fluctuations in dietary methionine intake, but intakes higher than 5 times the normal amount resulted in elevated homocysteine levels. These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid (PMID: 16702346). When present in sufficiently high levels, methionine can act as an atherogen and a metabotoxin. An atherogen is a compound that when present at chronically high levels causes atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of methionine are associated with at least ten inborn errors of metabolism, including cystathionine beta-synthase deficiency, glycine N-methyltransferase deficiency, homocystinuria, tyrosinemia, galactosemia, homocystinuria-megaloblastic anemia due to defects in cobalamin metabolism, methionine adenosyltransferase deficiency, methylenetetrahydrofolate reductase deficiency, and S-adenosylhomocysteine (SAH) hydrolase deficiency. Chronically elevated levels of methionine in infants can lead to intellectual disability and other neurological problems, delays in motor skills, sluggishness, muscle weakness, and liver problems. Many individuals with these metabolic disorders tend to develop cardiovascular disease later in life. Studies on feeding rodents high levels of methionine have shown that methionine promotes atherosclerotic plaques independently of homocysteine levels (PMID: 26647293). A similar study in Finnish men showed the same effect (PMID: 16487911).
63-68-3
C00073
6137
16643
MET
5907
DB00134
CSCC[C@H](N)C(O)=O
C5H11NO2S
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
FFEARJCKVFRZRR-BYPYZUCNSA-N
(2S)-2-amino-4-(methylsulfanyl)butanoic acid
149.211
149.051049291
-0.80
2
L-methionine
0
0
DBMET00506
FDB012683
(2s)-2-amino-4-(methylsulfanyl)butanoate;(2s)-2-amino-4-(methylsulfanyl)butanoic acid;(l)-methionine;(s)-(+)-methionine;(s)-2-amino-4-(methylthio)butanoate;(s)-2-amino-4-(methylthio)butanoic acid;(s)-2-amino-4-(methylthio)-butanoate;(s)-2-amino-4-(methylthio)-butanoic acid;(s)-2-amino-4-(methylthio)butyric acid;(s)-methionine;2-amino-4-(methylthio)butyrate;2-amino-4-(methylthio)butyric acid;2-amino-4-methylthiobutanoate;2-amino-4-methylthiobutanoic acid;A-amino-g-methylmercaptobutyrate;A-amino-g-methylmercaptobutyric acid;Acimethin;Cymethion;G-methylthio-a-aminobutyrate;G-methylthio-a-aminobutyric acid;H-met-h;H-met-oh;L(-)-amino-alpha-amino-alpha-aminobutyric acid;L(-)-amino-gamma-methylthiobutyric acid;L-(-)-methionine;L-2-amino-4-(methylthio)butyric acid;L-2-amino-4-methylthiobutyric acid;L-methionin;L-methionine;L-methioninum;L-a-amino-g-methylthiobutyrate;L-a-amino-g-methylthiobutyric acid;L-alpha-amino-gamma-methylmercaptobutyric acid;L-alpha-amino-gamma-methylthiobutyrate;L-alpha-amino-gamma-methylthiobutyric acid;L-gamma-methylthio-alpha-aminobutyric acid;Liquimeth;Met;Mepron;Methilanin;Methionine;Methioninum;Metionina;Neo-methidin;Poly-l-methionine;Polymethionine;S-methionine;S-methyl-l-homocysteine;Toxin war;Alpha-amino-alpha-aminobutyric acid;Alpha-amino-gamma-methylmercaptobutyrate;Alpha-amino-gamma-methylmercaptobutyric acid;Gamma-methylthio-alpha-aminobutyrate;Gamma-methylthio-alpha-aminobutyric acid;M;(2s)-2-amino-4-(methylsulphanyl)butanoate;(2s)-2-amino-4-(methylsulphanyl)butanoic acid;(s)-2-amino-4-(methylthio)butyrate;L-a-amino-g-methylmercaptobutyrate;L-a-amino-g-methylmercaptobutyric acid;L-alpha-amino-gamma-methylmercaptobutyrate;L-α-amino-γ-methylmercaptobutyrate;L-α-amino-γ-methylmercaptobutyric acid
PW_C000548
Met
568
8
1825
2
5597
135
5680
107
5681
108
5875
105
8267
151
12033
222
42550
315
42565
318
42693
320
76985
224
77609
111
78106
132
120478
122
122152
124
124704
118
125858
297
126311
299
127320
205
127873
388
68
Deoxyadenosine
HMDB0000101
Deoxyadenosine is a derivative of the nucleoside adenosine. It is composed of adenine attached to a deoxyribose moiety via a N9-glycosidic bond. Deoxyribose differs from ribose by the absence of oxygen in the 3' position of its ribose ring. Deoxyadenosine is a critical component of DNA. When present in sufficiently high levels, deoxyadensoine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of deoxyadenosine are associated with adenosine deaminase (ADA) deficiency, an inborn error of metabolism. ADA deficiency damages the immune system and causes severe combined immunodeficiency (SCID). People with SCID lack virtually all immune protection from bacteria, viruses, and fungi. They are prone to repeated and persistent infections that can be very serious or life-threatening. These infections are often caused by "opportunistic" organisms that ordinarily do not cause illness in people with a normal immune system. The main symptoms of ADA deficiency are pneumonia, chronic diarrhea, and widespread skin rashes. The mechanism by which dATP functions as an immunotoxin is as follows: because deoxyadenosine is a precursor to dATP, a buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes.
958-09-8
C00559
13730
17256
13135
NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1
C10H13N5O3
InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1
OLXZPDWKRNYJJZ-RRKCRQDMSA-N
(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
251.2419
251.101839307
-1.37
3
2-deoxyadenosine
0
0
FDB021894
1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-b-d-ribofuranose;1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-beta-d-ribofuranose;1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-beta-delta-ribofuranose;2'-deoxyadenosine;2-deoxyadenosine;9-(2-deoxy-b-d-erythro-pentofuranosyl)-9h-purin-6-amine;9-(2-deoxy-b-d-erythro-pentofuranosyl)adenine;9-(2-deoxy-b-d-ribofuranosyl)-9h-purin-6-amine;9-(2-deoxy-beta-d-erythro-pentofuranosyl)-9h-purin-6-amine;9-(2-deoxy-beta-d-erythro-pentofuranosyl)adenine;9-(2-deoxy-beta-d-ribofuranosyl)-9h-purin-6-amine;9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-9h-purin-6-amine;9-(2-deoxy-beta-delta-erythro-pentofuranosyl)adenine;9-(2-deoxy-beta-delta-ribofuranosyl)-9h-purin-6-amine;Adenine deoxyribonucleoside;Adenine deoxyribose;Adenine-9 2-deoxy-b-d-erythro-pentofuranoside;Adenine-9 2-deoxy-beta-d-erythro-pentofuranoside;Adenine-9 2-deoxy-beta-delta-erythro-pentofuranoside;Adenyldeoxyriboside;Da;Deoxyadenosine;Desoxyadenosine;(2r,3s,5r)-5-(6-amino-9h-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol;5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol;9-(2-deoxy-β-d-erythro-pentofuranosyl)adenine;9-(2-deoxy-β-d-ribofuranosyl)-9h-purin-6-amine
PW_C000068
DA
1895
8
11827
198
78704
111
121898
122
124451
135
164
apoprotein
ProteinComplex
ProteinComplex
PW_EC000164
Apoprot
201
Protein N6-(lipoyl)lysine
ProteinComplex
ProteinComplex
PW_EC000201
PNLL
182
Lipoyl-ACP
ProteinComplex
ProteinComplex
PW_EC000182
LA
184
[ACP]
ProteinComplex
ProteinComplex
PW_EC000184
[ACP]
187
Octanoyl-[acyl-carrier protein]
ProteinComplex
ProteinComplex
PW_EC000187
OACP
199
a sulfur donor
ProteinComplex
1375
ProteinComplex
PW_EC000199
ASD
200
Protein N6-(octanoyl)lysine
ProteinComplex
ProteinComplex
PW_EC000200
PNOL
10977
putative lipoate--protein ligase
P47051
Catalyzes both the ATP-dependent activation of exogenously supplied lipoate to lipoyl-AMP and the transfer of the activated lipoyl onto the lipoyl domains of lipoate-dependent enzymes.
AIM22, LIP3, RRG3
29
2.7.7.63
7850
160
10978
lipoyl(octanoyl) transferase
Q06005
Catalyzes the transfer of endogenously produced octanoic acid from octanoyl-acyl-carrier-protein onto the lipoyl domains of lipoate-dependent enzymes. Lipoyl-ACP can also act as a substrate although octanoyl-ACP is likely to be the physiological substrate (By similarity).
LIP2
29
2.3.1.181
7852
160
10979
lipoic acid synthetase
P32875
Catalyzes the radical-mediated insertion of two sulfur atoms into the C-6 and C-8 positions of the octanoyl moiety bound to the lipoyl domains of lipoate-dependent enzymes, thereby converting the octanoylated domains into lipoylated derivatives.
LIP5
29
2.8.1.8
7851
160
4753
lipoate-protein ligase A
18
PW_P004753
11941
10977
4754
lipoyl(octanoyl) transferase
18
PW_P004754
11942
10978
4755
lipoic acid synthetase
18
PW_P004755
11943
10979
7050
false
PW_R007050
Right
29043
42563
1
Compound
false
29044
414
1
Compound
false
29045
170
1
Compound
false
29046
40072
1
Compound
false
7028
4753
2.7.7.63
7051
false
PW_R007051
Right
29047
40072
1
Compound
false
29048
164
1
ElementCollection
false
29049
201
1
ElementCollection
false
29050
32
1
Compound
false
7029
4753
7052
false
PW_R007052
Right
29051
182
1
ElementCollection
false
29052
164
1
ElementCollection
false
29053
201
1
ElementCollection
false
29054
184
1
ElementCollection
false
7030
4754
2.3.1.181
7053
false
PW_R007053
Right
29055
187
1
ElementCollection
false
29056
921
1
Compound
false
29057
199
1
ElementCollection
false
29058
182
1
ElementCollection
false
29059
548
1
Compound
false
29060
68
1
Compound
false
7031
4755
2.8.1.8
7054
false
PW_R007054
Right
29061
199
2
ElementCollection
false
29062
200
1
ElementCollection
false
29063
921
2
Compound
false
29064
548
2
Compound
false
29065
201
1
ElementCollection
false
29066
68
2
Compound
false
7032
4755
7055
false
PW_R007055
Right
29067
187
1
ElementCollection
false
29068
164
1
ElementCollection
false
29069
200
1
ElementCollection
false
29070
184
1
ElementCollection
false
7033
4754
81654
42563
3
false
588
808
10
regular
100
100
81655
414
42
false
487
943
10
regular
50
30
81656
170
45
false
473
1161
10
regular
63
43
81657
40072
3
false
591
1198
10
regular
100
100
81658
32
44
false
433
1593
10
regular
50
30
81659
921
3
false
1097
393
10
regular
100
110
81660
548
3
false
790
848
10
regular
100
100
81661
68
3
false
1065
843
10
regular
100
100
81663
921
3
false
1465
1003
10
regular
100
110
81664
548
3
false
1483
1493
10
regular
100
100
81665
68
3
false
1328
1608
10
regular
100
100
1641
164
144
false
396
1303
12
regular
150
70
1642
201
144
false
893
1598
12
regular
150
70
1643
182
144
false
895
988
12
regular
150
70
1644
164
144
false
990
1123
12
regular
150
70
1645
184
144
false
998
1413
12
regular
150
70
1646
187
144
false
897
348
12
regular
150
70
1647
199
144
false
1077
533
12
regular
150
70
1648
199
144
false
1165
1038
12
regular
150
70
1649
200
144
false
1300
883
12
regular
150
70
1650
187
144
false
1297
353
12
regular
150
70
1651
164
144
false
1442
418
12
regular
150
70
1652
184
144
false
1435
748
12
regular
150
70
38782
10977
160
2
false
565
1023
8
subunit
regular
150
70
38783
10977
160
2
false
566
1445
8
subunit
regular
150
70
38784
10978
160
2
false
895
1278
8
subunit
regular
150
70
38785
10979
160
2
false
897
688
8
subunit
regular
150
70
38787
10979
160
2
false
1300
1295
8
subunit
regular
150
70
38788
10978
160
2
false
1297
598
8
subunit
regular
150
70
31562
4753
2256
38104
38782
31563
4753
2256
38105
38783
31564
4754
2256
38106
38784
31565
4755
2256
38107
38785
31566
4755
2256
38108
38787
31567
4754
2256
38109
38788
117193
M638 908 C638 938 640 988 640 1018
5
false
18
117194
M512 973 C616 976 640 988 640 1018
5
false
18
117195
M504.5 1161 C636.5 1162 640 1118 640 1088
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false
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true
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117196
M641 1198 C641 1168 640 1123 640 1093
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true
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117197
M641 1298 C641 1328 641 1415 641 1445
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117198
M458 1593 C647 1586 641 1545 641 1515
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true
M 25.946855044164835 397.261556296296 L 11 396 L 17.380887721185843 409.5751343230783
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117199
M471 1373 C640 1374 641 1415 641 1445
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117200
M893 1633 C811 1634 689 1637 642 1635 C642 1610 643 1557 641 1515
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true
M 25.946855044164835 397.261556296296 L 11 396 L 17.380887721185843 409.5751343230783
false
117201
M970 1058 C970 1088 970 1248 970 1278
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false
18
117202
M1065 1193 C959 1192 970 1248 970 1278
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18
117203
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117204
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M 372.94685504416486 531.261556296296 L 358 530 L 364.38088772118584 543.5751343230784
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117205
M1147 503 C948 505 972 658 972 688
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false
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117206
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true
M 586.9468550441649 327.261556296296 L 572 326 L 578.3808877211858 339.5751343230783
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117207
M1115 843 C975 840 972 788 972 758
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M 586.9468550441649 327.261556296296 L 572 326 L 578.3808877211858 339.5751343230783
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117208
M972 418 C972 448 972 658 972 688
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false
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117209
M1152 603 C1016 604 972 658 972 688
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117210
M970 988 C970 958 972 788 972 758
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true
M 586.9468550441649 327.261556296296 L 572 326 L 578.3808877211858 339.5751343230783
false
117211
M1515 1113 C1379 1113 1375 1265 1375 1295
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18
117212
M1533 1493 C1363 1487 1375 1395 1375 1365
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false
18
true
M 472.94685504416486 826.261556296296 L 458 825 L 464.38088772118584 838.5751343230784
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117213
M1378 1608 C1378 1578 1375 1395 1375 1365
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false
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true
M 472.94685504416486 826.261556296296 L 458 825 L 464.38088772118584 838.5751343230784
false
117214
M1315 1073 C1380 1077 1375 1265 1375 1295
5
false
18
117215
M1375 953 C1375 983 1375 1265 1375 1295
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117216
M1043 1638 C1367 1643 1376 1444 1375 1365
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M 472.94685504416486 826.261556296296 L 458 825 L 464.38088772118584 838.5751343230784
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117217
M1372 423 C1372 453 1372 568 1372 598
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18
117218
M1517 488 C1373 488 1372 568 1372 598
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18
117219
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117220
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117193
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117194
Left
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Right
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117196
Right
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117197
Left
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Right
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Left
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1642
117200
Right
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117201
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Left
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Right
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117205
Left
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Right
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117207
Right
1900
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117208
Left
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Left
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117210
Right
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117211
Left
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Right
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117213
Right
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Left
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Left
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Right
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117217
Left
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117218
Left
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Right
1909
1652
117220
Right
23860
7033
31567
186785
780
890
1.0
1.0
200
2
90
484
497
4395
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true
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1402.0
1528.0
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