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Triacylglycerols BioCyc DIACYLGLYCEROL BioCyc 1.0 Reaction81133 false DG(22:1(13Z)/19:2(10Z,13Z)/0:0) + Docosahexaenoyl-CoA → Coenzyme A + TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) LEFT_TO_RIGHT Reaction81132 false PA(22:1(13Z)/19:2(10Z,13Z)) + Water → DG(22:1(13Z)/19:2(10Z,13Z)/0:0) + Phosphate LEFT_TO_RIGHT (10Z,13Z)-Nonadecadienoyl-CoA 937 ChemSpider SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O CPD-8587 BioCyc 439162 PubChem-compound SMILES CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O 5682 ChemSpider SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O Glycerol-3-phosphate acyltransferase 1, mitochondrial Dihydroxyacetone phosphate SubPathwayOutput Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic NADH CHEBI:1146900 ChEBI LPA(22:1(13Z)/0:0) Water PW037753 PathWhiz P21695 UniProt 439153 PubChem-compound SMILES O Reaction81131 false (10Z,13Z)-Nonadecadienoyl-CoA + LPA(22:1(13Z)/0:0) → Coenzyme A + PA(22:1(13Z)/19:2(10Z,13Z)) LEFT_TO_RIGHT 1.0 C43H66N7O17P3S Docosahexaenoyl-CoA 1077.3448 CO-A BioCyc SMILES [H][C@@](COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCC\C=C/C\C=C/CCCCC NAD Reaction64129 false Erucoyl-CoA + Glycerol 3-phosphate → Coenzyme A + LPA(22:1(13Z)/0:0) LEFT_TO_RIGHT C00165 KEGG Compound C00681 KEGG Compound 648 ChemSpider SMILES CCCCCCCC\C=C/CCCCCCCCCCCC(=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 1.0 Coenzyme A Dihydroxyacetone phosphate Phosphatidate phosphatase LPIN1 C21H36N7O16P3S Coenzyme A 767.11523 6816 PubChem-compound C3H7O6P Dihydroxyacetone phosphate 169.99803 Reaction55814 false Dihydroxyacetone phosphate + Hydrogen Ion + NADH → Glycerol 3-phosphate + NAD LEFT_TO_RIGHT CHEBI:15846 ChEBI C44H80O5 DG(22:1(13Z)/19:2(10Z,13Z)/0:0) 688.6006 HMDB0062217 HMDB Diacylglycerol O-acyltransferase 1 HMDB0001473 HMDB 1.0 6557 ChemSpider 668 PubChem-compound PA(22:1(13Z)/19:2(10Z,13Z)) 1038 PubChem-compound 388299 ChemSpider 7732-18-5 CAS SubPathwayInteraction29115 SubPathway29115Reaction SubPathwayReaction Erucoyl-CoA HMDB0001487 HMDB C43H76N7O17P3S Erucoyl-CoA 1087.4231 GO:0005829 GENE ONTOLOGY 1.0 C44H81O8P PA(22:1(13Z)/19:2(10Z,13Z)) 768.5669 CHEBI:16908 ChEBI DIHYDROXY-ACETONE-PHOSPHATE BioCyc 1.0 1.0 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha SMILES CCCCC\C=C/C\C=C/CCCCCCCCC(=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 O4P Phosphate 94.95342 70678705 PubChem-compound 1.0 http://identifiers.org/smpdb/SMP36851 SMPDB 1010 ChemSpider 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)NCCS C25H49O7P LPA(22:1(13Z)/0:0) 492.3216 HMDB0112237 HMDB 1.0 SMILES OCC(=O)COP(O)(O)=O O75907 UniProt ACYL-SN-GLYCEROL-3P BioCyc 962 PubChem-compound SMILES [H][C@](COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCC\C=C/C\C=C/CCCCC ReactionCatalysis45943 ACTIVATION CHEBI:16975 ChEBI CHEBI:16337 ChEBI Hydrogen Ion ReactionCatalysis45941 ACTIVATION ReactionCatalysis45942 ACTIVATION C00111 KEGG Compound Cytosol 2.0 Phosphate 5893 PubChem-compound 1.0 58-68-4 CAS C00080 KEGG Compound Glycerol-3-phosphate acyltransferase 1, mitochondrial HMDB0001423 HMDB SMILES [O-]P([O-])([O-])=O CPD-17312 BioCyc Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic C40H68N7O17P3S (10Z,13Z)-Nonadecadienoyl-CoA 1043.3605 C16531 KEGG Compound HMDB0002111 HMDB CHEBI:15377 ChEBI C00009 KEGG Compound 1.0 DG(22:1(13Z)/19:2(10Z,13Z)/0:0) CHEBI:15378 ChEBI SMILES [H+] 14265-44-2 CAS CHEBI:16108 ChEBI 17989-41-2 CAS Q14693 UniProt C00001 KEGG Compound HMDB0001429 HMDB Diacylglycerol O-acyltransferase 1 C00004 KEGG Compound CHEBI:18367 ChEBI C00003 KEGG Compound 1032 ChemSpider Q9HCL2 UniProt 1.0 Phosphatidate phosphatase LPIN1 C3H9O6P Glycerol 3-phosphate 172.01367 1.0 GLYCEROL-3P BioCyc Q99943 UniProt C00093 KEGG Compound 57-04-5 CAS Glycerol 3-phosphate C00416 KEGG Compound SMILES [H][C@](CO)(COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCC\C=C/C\C=C/CCCCC HMDB0062235 HMDB C66H110O6 TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 998.83026 Docosahexaenoyl-CoA C21H28N7O14P2 NAD 664.11694 C00010 KEGG Compound HMDB0000902 HMDB 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha L-PHOSPHATIDATE BioCyc Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic C21H29N7O14P2 NADH 665.12476 H2O Water 18.010565 CHEBI:15978 ChEBI Glycolysis SubPathway NADH BioCyc NAD BioCyc H Hydrogen Ion 1.007825 1061 PubChem-compound CHEBI:65132 ChEBI HMDB0059597 HMDB 388308 ChemSpider 1.0 TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=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 CHEBI:74106 ChEBI 53-84-9 CAS 1.0 C00422 KEGG Compound ReactionCatalysis45939 ACTIVATION De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) HMDB0000126 HMDB ReactionCatalysis45940 ACTIVATION 85-61-0 CAS 71448925 PubChem-compound C16169 KEGG Compound SMILES OC[C@@H](O)COP(O)(O)=O Glycerol-3- phosphate dehydrogenase [NAD(+)], cytoplasmic glycerol-3- phosphate acyltransferase 1-acyl-sn- glycerol-3- phosphate acyltransferase phosphatidate phosphatase diacylglycerol O- acyltransferase Dihydroxyacetone phosphate NADH H + NAD Glycerol 3-phosphate Erucoyl-CoA CoA LPA(22:1(13Z)/0:0) LPA(22:1(13Z)/0:0) (10Z,13Z)- Nonadecadienoyl- CoA CoA PA(22:1(13Z)/19:2(10Z,13Z)) H 2 O DG(22:1(13Z)/19:2(10Z,13Z)/0:0) P i Docosahexaenoyl- CoA TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) CoA Glycolysis Mitochondria Outer Membrane Endoplasmic Reticulum Membrane Cytosol
Triacylglycerols BioCyc DIACYLGLYCEROL BioCyc 1.0 Reaction81133 false DG(22:1(13Z)/19:2(10Z,13Z)/0:0) + Docosahexaenoyl-CoA → Coenzyme A + TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) LEFT_TO_RIGHT Reaction81132 false PA(22:1(13Z)/19:2(10Z,13Z)) + Water → DG(22:1(13Z)/19:2(10Z,13Z)/0:0) + Phosphate LEFT_TO_RIGHT (10Z,13Z)-Nonadecadienoyl-CoA 937 ChemSpider SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O CPD-8587 BioCyc 439162 PubChem-compound SMILES CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O 5682 ChemSpider SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O Glycerol-3-phosphate acyltransferase 1, mitochondrial Dihydroxyacetone phosphate SubPathwayOutput Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic NADH CHEBI:1146900 ChEBI LPA(22:1(13Z)/0:0) Water PW037753 PathWhiz P21695 UniProt 439153 PubChem-compound SMILES O Reaction81131 false (10Z,13Z)-Nonadecadienoyl-CoA + LPA(22:1(13Z)/0:0) → Coenzyme A + PA(22:1(13Z)/19:2(10Z,13Z)) LEFT_TO_RIGHT 1.0 C43H66N7O17P3S Docosahexaenoyl-CoA 1077.3448 CO-A BioCyc SMILES [H][C@@](COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCC\C=C/C\C=C/CCCCC NAD Reaction64129 false Erucoyl-CoA + Glycerol 3-phosphate → Coenzyme A + LPA(22:1(13Z)/0:0) LEFT_TO_RIGHT C00165 KEGG Compound C00681 KEGG Compound 648 ChemSpider SMILES CCCCCCCC\C=C/CCCCCCCCCCCC(=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 1.0 Coenzyme A Dihydroxyacetone phosphate Phosphatidate phosphatase LPIN1 C21H36N7O16P3S Coenzyme A 767.11523 6816 PubChem-compound C3H7O6P Dihydroxyacetone phosphate 169.99803 Reaction55814 false Dihydroxyacetone phosphate + Hydrogen Ion + NADH → Glycerol 3-phosphate + NAD LEFT_TO_RIGHT CHEBI:15846 ChEBI C44H80O5 DG(22:1(13Z)/19:2(10Z,13Z)/0:0) 688.6006 HMDB0062217 HMDB Diacylglycerol O-acyltransferase 1 HMDB0001473 HMDB 1.0 6557 ChemSpider 668 PubChem-compound PA(22:1(13Z)/19:2(10Z,13Z)) 1038 PubChem-compound 388299 ChemSpider 7732-18-5 CAS SubPathwayInteraction29115 SubPathway29115Reaction SubPathwayReaction Erucoyl-CoA HMDB0001487 HMDB C43H76N7O17P3S Erucoyl-CoA 1087.4231 GO:0005829 GENE ONTOLOGY 1.0 C44H81O8P PA(22:1(13Z)/19:2(10Z,13Z)) 768.5669 CHEBI:16908 ChEBI DIHYDROXY-ACETONE-PHOSPHATE BioCyc 1.0 1.0 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha SMILES CCCCC\C=C/C\C=C/CCCCCCCCC(=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 O4P Phosphate 94.95342 70678705 PubChem-compound 1.0 http://identifiers.org/smpdb/SMP36851 SMPDB 1010 ChemSpider 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)NCCS C25H49O7P LPA(22:1(13Z)/0:0) 492.3216 HMDB0112237 HMDB 1.0 SMILES OCC(=O)COP(O)(O)=O O75907 UniProt ACYL-SN-GLYCEROL-3P BioCyc 962 PubChem-compound SMILES [H][C@](COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCC\C=C/C\C=C/CCCCC ReactionCatalysis45943 ACTIVATION CHEBI:16975 ChEBI CHEBI:16337 ChEBI Hydrogen Ion ReactionCatalysis45941 ACTIVATION ReactionCatalysis45942 ACTIVATION C00111 KEGG Compound Cytosol 2.0 Phosphate 5893 PubChem-compound 1.0 58-68-4 CAS C00080 KEGG Compound Glycerol-3-phosphate acyltransferase 1, mitochondrial HMDB0001423 HMDB SMILES [O-]P([O-])([O-])=O CPD-17312 BioCyc Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic C40H68N7O17P3S (10Z,13Z)-Nonadecadienoyl-CoA 1043.3605 C16531 KEGG Compound HMDB0002111 HMDB CHEBI:15377 ChEBI C00009 KEGG Compound 1.0 DG(22:1(13Z)/19:2(10Z,13Z)/0:0) CHEBI:15378 ChEBI SMILES [H+] 14265-44-2 CAS CHEBI:16108 ChEBI 17989-41-2 CAS Q14693 UniProt C00001 KEGG Compound HMDB0001429 HMDB Diacylglycerol O-acyltransferase 1 C00004 KEGG Compound CHEBI:18367 ChEBI C00003 KEGG Compound 1032 ChemSpider Q9HCL2 UniProt 1.0 Phosphatidate phosphatase LPIN1 C3H9O6P Glycerol 3-phosphate 172.01367 1.0 GLYCEROL-3P BioCyc Q99943 UniProt C00093 KEGG Compound 57-04-5 CAS Glycerol 3-phosphate C00416 KEGG Compound SMILES [H][C@](CO)(COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCC\C=C/C\C=C/CCCCC HMDB0062235 HMDB C66H110O6 TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 998.83026 Docosahexaenoyl-CoA C21H28N7O14P2 NAD 664.11694 C00010 KEGG Compound HMDB0000902 HMDB 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha L-PHOSPHATIDATE BioCyc Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic C21H29N7O14P2 NADH 665.12476 H2O Water 18.010565 CHEBI:15978 ChEBI Glycolysis SubPathway NADH BioCyc NAD BioCyc H Hydrogen Ion 1.007825 1061 PubChem-compound CHEBI:65132 ChEBI HMDB0059597 HMDB 388308 ChemSpider 1.0 TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) SMILES CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=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 CHEBI:74106 ChEBI 53-84-9 CAS 1.0 C00422 KEGG Compound ReactionCatalysis45939 ACTIVATION De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) HMDB0000126 HMDB ReactionCatalysis45940 ACTIVATION 85-61-0 CAS 71448925 PubChem-compound C16169 KEGG Compound SMILES OC[C@@H](O)COP(O)(O)=O Mitochondria Endoplasmic Reticulum GPD1 GPAM AGPAT1 LPIN1 DGAT1 Dihydroxyacetone phosphate NADH Hydrogen Ion NAD Glycerol 3-phosphate Erucoyl-CoA Coenzyme A LPA(22:1(13Z)/0:0) LPA(22:1(13Z)/0:0) (10Z,13Z)- Nonadecadienoyl- CoA Coenzyme A PA(22:1(13Z)/19:2(10Z,13Z)) Water DG(22:1(13Z)/19:2(10Z,13Z)/0:0) Phosphate Docosahexaenoyl- CoA TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) Coenzyme A Glycolysis