114413
Pathway
Cyclopropane Fatty Acid (CFA) Biosynthesis
Cyclopropane fatty acids (CFA) are synthesized by the modification of an unsaturated bond of acyl chains of phospholipid bilayers by methylenation via cyclopropane fatty acyl phospholipid synthase. CFA phospholipid synthase is a unique enzyme in that it acts on the nonpolar part of the phospholipids. The bond that is modified is about nine to eleven carbon atoms from the glycerol backbone. S-adenosyl-L-methionine donates a methylene group to the cis double bond of the unsaturated fatty acid. CFA synthase acts on phosphatidylethanolamine, phosphatidylglycerol and phosphatidylcholine. Cyclopropane fatty acids in the cytoplasmic membrane protect cells from ethanol, high osmotic pressure and other environmental stressors.
Metabolic
PW123573
Center
PathwayVisualizationContext123849
1102
1251
#000099
PathwayVisualization114276
114413
Cyclopropane Fatty Acid (CFA) Biosynthesis
Cyclopropane fatty acids (CFA) are synthesized by the modification of an unsaturated bond of acyl chains of phospholipid bilayers by methylenation via cyclopropane fatty acyl phospholipid synthase. CFA phospholipid synthase is a unique enzyme in that it acts on the nonpolar part of the phospholipids. The bond that is modified is about nine to eleven carbon atoms from the glycerol backbone. S-adenosyl-L-methionine donates a methylene group to the cis double bond of the unsaturated fatty acid. CFA synthase acts on phosphatidylethanolamine, phosphatidylglycerol and phosphatidylcholine. Cyclopropane fatty acids in the cytoplasmic membrane protect cells from ethanol, high osmotic pressure and other environmental stressors.
Metabolic
23
112351
S-Adenosyl-L-Methionine Biosynthesis
SubPathway
111946
921
Compound
112352
S-Adenosyl-L-Methionine Cycle
SubPathway
111947
749
Compound
1
Cell
CL:0000000
6
Myocyte
CL:0000187
5
Hepatocyte
CL:0000182
1
Homo sapiens
9606
Eukaryote
Human
17
Rattus norvegicus
10116
Eukaryote
Rat
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
3
Escherichia coli
562
Prokaryote
2
Bacteria
2
Prokaryote
Bacteria
24
Solanum lycopersicum
4081
Eukaryote
Tomato
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
5
Cytoplasm
GO:0005737
17
Nucleoplasm
GO:0005654
1
Cytosol
GO:0005829
2
Mitochondrion
GO:0005739
15
Nucleus
GO:0005634
7
Endoplasmic Reticulum Membrane
GO:0005789
13
Endoplasmic Reticulum
GO:0005783
3
Mitochondrial Matrix
GO:0005759
35
Chloroplast
GO:0009507
39
Mitochondrial membrane
GO:0031966
14
Mitochondrial Outer Membrane
GO:0005741
11
Extracellular Space
GO:0005615
12
Mitochondrial Inner Membrane
GO:0005743
24
Mitochondrial Intermembrane Space
GO:0005758
31
Periplasmic Space
GO:0005620
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
4
Adrenal Medulla
BTO:0000049
71
8
1
Liver
BTO:0000759
72
9
9
Muscle
BTO:0000887
141
18
28
Stomach
BTO:0001307
155
26
8
Blood Vessel
BTO:0001102
74
11
8
5
1
1
PW_BS000008
30
17
1
1
PW_BS000030
20
4
1
1
1
PW_BS000020
3
2
1
1
PW_BS000003
27
15
1
PW_BS000027
2
1
1
1
PW_BS000002
10
1
7
1
1
PW_BS000010
50
9
5
1
6
PW_BS000050
135
5
17
1
PW_BS000135
163
2
18
1
PW_BS000163
210
13
18
1
PW_BS000024
213
7
18
1
PW_BS000024
160
1
18
1
PW_BS000160
151
1
4
1
PW_BS000151
195
13
18
PW_BS000024
198
5
18
1
PW_BS000024
222
3
4
1
PW_BS000024
225
35
4
1
PW_BS000024
249
13
4
1
PW_BS000024
18
13
1
1
PW_BS000018
309
39
1
1
PW_BS000024
293
4
1
PW_BS000024
164
4
PW_BS000164
224
2
4
1
PW_BS000024
111
5
12
1
PW_BS000111
338
17
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
132
1
12
1
PW_BS000132
351
15
12
PW_BS000028
346
9
5
12
6
PW_BS000028
112
2
12
1
PW_BS000112
361
39
12
1
PW_BS000028
22
14
1
1
PW_BS000022
382
14
5
1
PW_BS000100
386
39
5
1
PW_BS000100
389
14
6
1
PW_BS000112
397
39
6
1
PW_BS000113
399
14
17
1
PW_BS000113
401
39
17
1
PW_BS000113
122
5
5
1
PW_BS000122
413
17
5
1
PW_BS000115
407
2
5
1
PW_BS000115
124
1
5
1
PW_BS000124
435
15
5
PW_BS000115
449
17
17
1
PW_BS000115
119
2
17
1
PW_BS000119
118
1
17
1
PW_BS000118
470
15
17
PW_BS000115
297
5
10
1
PW_BS000024
481
2
10
1
PW_BS000115
299
1
10
1
PW_BS000024
499
15
10
PW_BS000115
205
5
6
1
PW_BS000024
206
2
6
1
PW_BS000024
388
1
6
1
PW_BS000112
517
15
6
PW_BS000115
136
13
17
1
PW_BS000136
130
13
12
1
PW_BS000130
125
13
5
1
PW_BS000125
4
3
1
1
PW_BS000004
15
11
1
PW_BS000015
31
1
5
1
1
PW_BS000031
26
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
42
24
1
1
PW_BS000042
70
28
5
1
1
PW_BS000070
103
3
3
1
PW_BS000103
108
1
3
PW_BS000108
107
31
3
PW_BS000107
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
219
31
4
PW_BS000024
220
1
4
PW_BS000024
212
1
7
18
1
PW_BS000024
170
18
PW_BS000170
226
4
4
1
PW_BS000024
162
12
18
1
PW_BS000162
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
315
1
23
PW_BS000024
318
31
23
PW_BS000024
322
1
23
1
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
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
327
1
1
12
5
PW_BS000028
347
1
3
12
5
PW_BS000028
345
24
12
1
PW_BS000028
368
3
60
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
383
7
5
1
PW_BS000100
94
3
PW_BS000094
390
7
6
1
PW_BS000112
398
7
17
1
PW_BS000113
336
1
12
1
PW_BS000028
109
32
3
PW_BS000109
406
3
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
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
479
3
10
1
PW_BS000115
483
11
10
PW_BS000115
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
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
749
S-Adenosylhomocysteine
HMDB0000939
S-Adenosyl-L-homocysteine (SAH) is formed by the demethylation of S-adenosyl-L-methionine. S-Adenosylhomocysteine (AdoHcy or SAH) is also the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of SAH. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, SAH is the product of all methylation reactions that involve S-adenosylmethionine (SAM) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these SAM-mediated processes by SAH is a proven mechanism for metabolic alteration. Because the conversion of SAH to homocysteine is reversible, with the equilibrium favoring the formation of SAH, increases in plasma homocysteine are accompanied by an elevation of SAH in most cases. Disturbances in the transmethylation pathway indicated by abnormal SAH, SAM, or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression, and Parkinson's disease (PMID: 18065573, 17892439). Therefore, when present in sufficiently high levels, S-adenosylhomocysteine 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 S-adenosylhomocysteine are associated with S-adenosylhomocysteine (SAH) hydrolase deficiency and adenosine deaminase deficiency. S-Adenosylhomocysteine forms when there are elevated levels of homocysteine and adenosine. S-Adenosyl-L-homocysteine is a potent inhibitor of S-adenosyl-L-methionine-dependent methylation reactions. It is toxic to immature lymphocytes and can lead to immunosuppression (PMID: 221926).
979-92-0
C00021
25246222
16680
ADENOSYL-HOMO-CYS
388301
N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O
C14H20N6O5S
InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1
ZJUKTBDSGOFHSH-WFMPWKQPSA-N
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid
384.411
384.12158847
-1.97
5
S-adenosyl-L-homocysteine
0
0
DBMET00514
FDB022327
(s)-5'-(s)-(3-amino-3-carboxypropyl)-5'-thioadenosine;2-s-adenosyl-l-homocysteine;5'-deoxy-s-adenosyl-l-homocysteine;5'-s-(3-amino-3-carboxypropyl)-5'-thio-l-adenosine;Adenosyl-l-homocysteine;Adenosyl-homo-cys;Adenosylhomo-cys;Adenosylhomocysteine;Adohcy;Formycinylhomocysteine;L-5'-s-(3-amino-3-carboxypropyl)-5'-thior-adenosine;L-s-adenosyl-homocysteine;L-s-adenosylhomocysteine;S-(5'-adenosyl)-l-homocysteine;S-(5'-deoxyadenosin-5'-yl)-l-homocysteine;S-(5'-deoxyadenosine-5')-l-homocysteine;S-adenosyl-l-homocysteine;S-adenosyl-homocysteine;Sah;(2s)-2-amino-4-({[(2s,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid;S-[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl]-l-homocysteine;S-adenosylhomocysteine
PW_C000749
SAH
520
8
575
18
635
30
705
20
1221
3
1882
27
2067
2
4683
10
5025
50
5607
136
7137
163
7542
210
7546
213
7634
160
8268
151
9237
195
11875
198
12359
225
15294
249
15364
309
77489
111
77611
130
77733
338
77773
341
78098
132
78305
351
78337
346
79156
112
79962
361
80863
22
94831
382
94834
386
113287
389
113289
397
115544
399
115547
401
120394
122
120486
125
120539
413
120940
407
121053
124
122284
435
123037
135
123173
449
123506
119
123617
118
124838
470
125880
481
126303
299
126449
499
127341
206
127596
388
128019
517
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
257
a [phospholipid] olefinic fatty acid
Compound
Compound
PW_EC000257
C01229
KEGG Compound
APOFA
258
a [phospholipid] cyclopropane fatty acid
Compound
Compound
PW_EC000258
C04340
KEGG Compound
APCFA
18719
Methyltransferase domain protein
A0A2R3J082
CSB93_3682
23
137724
312
11860
Unknown
Unknown
23
42305
312
42313
314
42315
316
42316
317
42321
319
42334
321
42345
315
42500
323
42594
324
42624
322
43762
325
131600
313
136981
198
136982
211
6560
cyclopropane fatty acyl phospholipid synthase
23
PW_P006560
14288
11860
2
187078
false
PW_R187078
Right
709029
257
1
ElementCollection
false
709030
921
1
Compound
false
709031
258
1
ElementCollection
false
709032
749
1
Compound
false
709033
40034
1
Compound
false
176932
6560
2.1.1.79
2755499
921
3
false
300
568
10
regular
100
110
2755500
749
3
false
850
569
10
regular
100
110
2755501
40034
55
false
761
484
10
regular
78
78
22929
257
37
false
420
678
12
regular
100
90
22930
258
37
false
735
692
12
regular
100
90
979000
18719
312
6
false
540
583
8
subunit
regular
160
80
828734
6560
114276
974765
979000
3775072
M400 623 C430 623 510 623 540 623
5
false
18
3775073
M850 624 C788 624 730 623 700 623
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3775074
M800 562 C799 632 730 623 700 623
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3775075
M470 678 C472 632 474 623 540 623
5
false
18
3775076
M785 692 C783 609 735 623 700 623
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3775077
M350 568 C350 538 350 435 350 405
5
false
18
true
M 392.5 606.0096189432334 L 400 619 L 407.5 606.0096189432334
false
3775078
M900 569 C901 524 901 465 900 404
5
false
18
true
M 1177.0096189432334 682.5 L 1190 675 L 1177.0096189432334 667.5
false
822419
114276
187078
3321836
2755499
3775072
Left
3321837
2755500
3775073
Right
3321838
2755501
3775074
Right
22057
22929
3775075
Left
22058
22930
3775076
Right
777865
176932
828734
112064
112351
114276
217
false
275
335
16
regular
108707
2755499
3775077
Right
112065
112352
114276
217
false
825
334
16
regular
108708
2755500
3775078
Left
189202
470
269
0.6
0.6
0
2
92
479
481
373846
M125 225 C125 175 175 125 225 125 C468 125 783 125 1026 125 C1076 125 1126 175 1126 225 C1126 423 1126 679 1126 877 C1126 927 1076 977 1026 977 C783 977 468 977 225 977 C175 977 125 927 125 877 C125 679 125 423 125 225
1
true
6
1001.0
852.0
373847
M225 323 C225 273 275 223 325 223 C507 223 744 223 926 223 C976 223 1026 273 1026 323 C1026 459 1026 636 1026 772 C1026 822 976 872 926 872 C744 872 507 872 325 872 C275 872 225 822 225 772 C225 636 225 459 225 323
1
true
6
801.0
649.0