17215925
ChemSpider
1.3.1.10,1.3.1.38
false
1.3.1.10,1.3.1.38
(2E)-Octadecenoyl-CoA + Hydrogen Ion + NADPH → NADP + Stearoyl-CoA
LEFT_TO_RIGHT
71627315
PubChem-compound
3.1.2.2
false
3.1.2.2
Stearoyl-CoA + Water → Coenzyme A + Hydrogen Ion + Stearic acid
LEFT_TO_RIGHT
1.0
Reaction6394
false
(3R)-3-hydroxy-arachidoyl-CoA → (2E)-eicosenoyl-CoA + Water
LEFT_TO_RIGHT
937
ChemSpider
DEHYDROSPHINGANINE
BioCyc
17220830
ChemSpider
Eicosanoyl-CoA
1.0
PHYTOSPINGOSINE
BioCyc
SMILES
O
C16216
KEGG Compound
2.3.1.199
false
2.3.1.199
Hydrogen Ion + Malonyl-CoA + Palmityl-CoA → 3-Oxooctadecanoyl-CoA + Carbon dioxide + Coenzyme A
LEFT_TO_RIGHT
C16218
KEGG Compound
6.2.1.3
false
6.2.1.3
Adenosine triphosphate + Coenzyme A + Palmitic acid → Adenosine monophosphate + Palmityl-CoA + Pyrophosphate
LEFT_TO_RIGHT
C10H14N5O7P
Adenosine monophosphate
347.06308
Pyrophosphate
1.1.1.100
false
1.1.1.100
3-Oxooctadecanoyl-CoA + Hydrogen Ion + NADPH → (3R)-3-hydroxy-stearoyl-CoA + NADP
LEFT_TO_RIGHT
P41903
UniProt
ReactionCatalysis6338
ACTIVATION
4.2.1.119,1.1.1.n12
false
4.2.1.119,1.1.1.n12
(3R)-3-hydroxy-stearoyl-CoA → (2E)-Octadecenoyl-CoA + Water
LEFT_TO_RIGHT
ReactionCatalysis6337
ACTIVATION
1.0
ReactionCatalysis6336
ACTIVATION
CHEBI:16027
ChEBI
CHEBI:17115
ChEBI
ReactionCatalysis6341
ACTIVATION
C41H70N7O18P3S
(3R)-3-hydroxy-arachidoyl-CoA
1073.3733
ReactionCatalysis6340
ACTIVATION
C39H66N7O18P3S
(3R)-3-hydroxy-stearoyl-CoA
1045.342
5281
PubChem-compound
C42H70N7O18P3S
3-oxoicosanoyl-CoA
1085.3733
HMDB0000538
HMDB
C01530
KEGG Compound
ATP
BioCyc
388366
ChemSpider
3-Dehydrosphinganine
Biosynthesis of Unsaturated Fatty Acids (Icosanoyl-CoA)
HMDB0006529
HMDB
1.0
6816
PubChem-compound
559142
ChemSpider
(2E)-eicosenoyl-CoA
1.0
P39002
UniProt
PALMITYL-COA
BioCyc
C41H68N7O17P3S
(2E)-eicosenoyl-CoA
1055.3627
53-59-8
CAS
5742
ChemSpider
1.0
1038
PubChem-compound
Ceramide synthase subunit LIP1
CHEBI:16474
ChEBI
952
ChemSpider
GO:0005829
GENE ONTOLOGY
439853
PubChem-compound
C39H68N7O17P3S
(2E)-Octadecenoyl-CoA
1031.3605
274
ChemSpider
Adenosine monophosphate
5858
ChemSpider
Peroxisomal hydratase-dehydrogenase-epimerase
2-enoyl thioester reductase
5736
ChemSpider
Peroxisomal acyl-coenzyme A thioester hydrolase 1
dihydrosphingosine C-4 hydroxylase
long chain fatty acyl:CoA synthetase
Long-chain-fatty-acid--CoA ligase 1
Long-chain-fatty-acid--CoA ligase 3
3-oxoacyl-[acyl-carrier-protein] reductase
Very long-chain fatty acid transport protein
NADPH
1010
ChemSpider
SER
BioCyc
Saccharomyces cerevisiae
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS
Palmitic acid
Serine palmitoyltransferase 1
NADP
PPI
BioCyc
C21H30N7O17P3
NADPH
745.0911
Reaction6395
false
(2E)-eicosenoyl-CoA + Hydrogen Ion + NADPH → Eicosanoyl-CoA + NADP
LEFT_TO_RIGHT
C16H32O2
Palmitic acid
256.24023
N-icosanoylphytosphingosine
C21H29N7O17P3
NADP
744.08325
3-ketosphinganine reductase
C38H77NO4
N-icosanoylphytosphingosine
611.58527
1.0
1.0
70678852
PubChem-compound
NADPH
BioCyc
1.0
Hydrogen Ion
CHEBI:15525
ChEBI
Carbon dioxide
Cytosol
CPD-6641
BioCyc
Adenosine triphosphate
SMILES
CCCCCCCCCCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H](C(O)[C@H]1OP(=O)(O)O)N1C=NC2=C1N=CN=C2N
HMDB0001423
HMDB
CHEBI:28842
ChEBI
HMDB0004258
HMDB
Phytosphingosine
HMDB0000217
HMDB
5091
ChemSpider
Oxygen
SMP0002346
SMPDB
124-38-9
CAS
C39H70N7O17P3S
Stearoyl-CoA
1033.3762
3-ketoacyl-CoA synthase ELO1
Long-chain-fatty-acid--CoA ligase 2
CHEBI:15531
ChEBI
53477850
PubChem-compound
C00249
KEGG Compound
C00007
KEGG Compound
C00006
KEGG Compound
CHEBI:18009
ChEBI
Hydrogen Ion
C00001
KEGG Compound
CHEBI:18361
ChEBI
P25045
UniProt
1763-10-6
CAS
C00005
KEGG Compound
C00002
KEGG Compound
SMILES
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
HMDB0000221
HMDB
SMILES
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
SMILES
CCCCCCCCCCCCCCCC(O)=O
CHEBI:15527
ChEBI
1.0
HMDB0000220
HMDB
53-57-6
CAS
(3R)-3-hydroxy-stearoyl-CoA
388895
ChemSpider
3-oxoicosanoyl-CoA
1.0
Coenzyme A
C00011
KEGG Compound
SMILES
O=C=O
C00010
KEGG Compound
C18H37NO2
3-Dehydrosphinganine
299.28244
(3R)-3-hydroxy-arachidoyl-CoA
5951
PubChem-compound
C00013
KEGG Compound
122121
PubChem-compound
O7P2
Pyrophosphate
173.91193
SMILES
CCCCCCCCCCCCCCCC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
554-62-1
CAS
ReactionCatalysis6317
ACTIVATION
C41H74N7O17P3S
Eicosanoyl-CoA
1061.4075
1.0
NAD(P)
BioCyc
Stearoyl-CoA
1.-.-.-
false
1.-.-.-
2 Hydrogen Ion + Oxygen + Sphinganine + ferrocytochrome b5 → Phytosphingosine + Water + ferricytochrome b5
LEFT_TO_RIGHT
1.1.1.102
false
1.1.1.102
3-Dehydrosphinganine + Hydrogen Ion + NADPH → NADP + Sphinganine
LEFT_TO_RIGHT
5957
PubChem-compound
ReactionCatalysis6312
ACTIVATION
ReactionCatalysis6316
ACTIVATION
HMDB0062227
HMDB
ReactionCatalysis6315
ACTIVATION
ReactionCatalysis6314
ACTIVATION
ReactionCatalysis6435
ACTIVATION
ReactionCatalysis6313
ACTIVATION
H
Hydrogen Ion
1.007825
1.0
CHEBI:15756
ChEBI
56-65-5
CAS
15895-27-9
CAS
C00020
KEGG Compound
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O
C37H66N7O17P3S
Palmityl-CoA
1005.34485
Sphinganine
SMILES
N[C@@H](CO)C(O)=O
Reaction6515
false
Eicosanoyl-CoA + Phytosphingosine → Coenzyme A + Hydrogen Ion + N-icosanoylphytosphingosine
LEFT_TO_RIGHT
Palmityl-CoA
HMDB0001338
HMDB
1.0
ReactionCatalysis6321
ACTIVATION
1.0
ReactionCatalysis6320
ACTIVATION
C18H39NO2
Sphinganine
301.29807
CHEBI:17862
ChEBI
P35731
UniProt
1.0
ferricytochrome b5
C00836
KEGG Compound
ferricytochrome b5
1.0
C00154
KEGG Compound
SMILES
CCCCCCCCCCCCCCCC(=O)[C@@H](N)CO
1.0
764-22-7
CAS
CHEBI:1146900
ChEBI
AMP
BioCyc
Water
HMDB0004610
HMDB
SMILES
CCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
STEARIC_ACID
BioCyc
91486
PubChem-compound
HMDB0000250
HMDB
STEAROYL-COA
BioCyc
SMILES
[O-]P([O-])(=O)OP([O-])([O-])=O
14000-31-8
CAS
16061151
PubChem-compound
1.0
CO-A
BioCyc
CPD-8475
BioCyc
5675
ChemSpider
82609
ChemSpider
1.0
Coenzyme A
1.0
SMILES
CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
C21H36N7O16P3S
Coenzyme A
767.11523
1.0
HMDB0001114
HMDB
SMILES
CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO
3-ketoacyl-CoA synthase ELO1
72193813
PubChem-compound
HMDB0000269
HMDB
Long-chain-fatty-acid--CoA ligase 2
C12144
KEGG Compound
SMILES
[H][C@@](O)(CCCCCCCCCCCCCC)[C@@]([H])(O)[C@]([H])(CO)N=C(O)CCCCCCCCCCCCCCCCCCC
Serine palmitoyltransferase 1
2.3.1.50
false
2.3.1.50
Hydrogen Ion + L-Serine + Palmityl-CoA ? 3-Dehydrosphinganine + Carbon dioxide + Coenzyme A
Reaction6412
false
Hydrogen Ion + Malonyl-CoA + Stearoyl-CoA → 3-oxoicosanoyl-CoA + Carbon dioxide + Coenzyme A
LEFT_TO_RIGHT
10213
ChemSpider
Reaction6413
false
3-oxoicosanoyl-CoA + Hydrogen Ion + NADPH → (3R)-3-hydroxy-arachidoyl-CoA + NADP
LEFT_TO_RIGHT
CHEBI:15541
ChEBI
70678676
PubChem-compound
1.0
14902
ChemSpider
CHEBI:15422
ChEBI
6557
ChemSpider
1.0
1.0
P30624
UniProt
524-14-1
CAS
7732-18-5
CAS
16105-69-4
CAS
HMDB0000827
HMDB
ICOSANOYL-COA
BioCyc
61-19-8
CAS
SMILES
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
O2
Oxygen
31.98983
1.0
3-ketosphinganine reductase
dihydrosphingosine C-4 hydroxylase
108921
ChemSpider
HMDB0006498
HMDB
P38225
UniProt
Peroxisomal hydratase-dehydrogenase-epimerase
3-oxoacyl-[acyl-carrier-protein] reductase
Peroxisomal acyl-coenzyme A thioester hydrolase 1
2-enoyl thioester reductase
HMDB0001480
HMDB
long chain fatty acyl:CoA synthetase
57-10-3
CAS
P38342
UniProt
Very long-chain fatty acid transport protein
Long-chain-fatty-acid--CoA ligase 3
Long-chain-fatty-acid--CoA ligase 1
C18H39NO3
Phytosphingosine
317.293
C10H16N5O13P3
Adenosine triphosphate
506.99576
1.0
1.0
Palmityl-CoA
CHEBI:16526
ChEBI
C00065
KEGG Compound
7782-44-7
CAS
HMDB0001377
HMDB
HMDB0000045
HMDB
Stearic acid
C18H36O2
Stearic acid
284.27155
Ceramide synthase subunit LIP1
P39540
UniProt
22833663
PubChem-compound
962
PubChem-compound
1.0
1.0
C02934
KEGG Compound
CO2
Carbon dioxide
43.98983
C00080
KEGG Compound
SMILES
O=O
ferrocytochrome b5
(2E)-Octadecenoyl-CoA
17216373
ChemSpider
C00083
KEGG Compound
C39H68N7O18P3S
3-Oxooctadecanoyl-CoA
1047.3555
1.0
SMILES
CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO
HMDB0002111
HMDB
L-Serine
57-11-4
CAS
PW002434
PathWhiz
CHEBI:15377
ChEBI
C24H38N7O19P3S
Malonyl-CoA
853.1156
CHEBI:15379
ChEBI
CHEBI:15378
ChEBI
SMILES
[H+]
3-Dehydrosphinganine
SMILES
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
56-45-1
CAS
5886
PubChem-compound
Q02207
UniProt
1.0
960
ChemSpider
280
PubChem-compound
P38071
UniProt
SMILES
CCCCCCCCCCCCCCCCCC(O)=O
CHEBI:46961
ChEBI
86370-20-9
CAS
C3H7NO3
L-Serine
105.042595
P38992
UniProt
HMDB0000187
HMDB
439229
PubChem-compound
985
PubChem-compound
362-66-3
CAS
P39518
UniProt
644102
PubChem-compound
4932
TAXONOMY
6083
PubChem-compound
ferrocytochrome b5
3-Oxooctadecanoyl-CoA
C00412
KEGG Compound
Malonyl-CoA
10663
PubChem-compound
22833512
PubChem-compound
C02041
KEGG Compound
1.0
Acyl-CoA synthase
H2O
Water
18.010565
SMILES
CCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
2.0
15667
PubChem-compound
SMILES
CCCCCCCCCCCCCCCCCC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OCC1OC(C)(C(O)C1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N
A6ZN14
UniProt
SMILES
[H][C@@](O)(CCCCCCCCCCCCCCCCC)CC(=O)SCCN=C([O-])CCN=C([O-])[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP([O-])([O-])=O
CHEBI:16566
ChEBI
977
PubChem-compound
HMDB0059597
HMDB
SMILES
CCCCCCCCCCCCCCCC(O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OCC1OC(C(O)C1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N
1.0
Carbon dioxide
HMDB0001967
HMDB
P47912
UniProt
CHEBI:76374
ChEBI
85-61-0
CAS
SMILES
[H]\C(CCCCCCCCCCCCCCCCC)=C(\[H])C(=O)SCCN=C([O-])CCN=C([O-])[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP([O-])([O-])=O
MALONYL-COA
BioCyc
HMDB0001175
HMDB