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Fatty Acid Biosynthesis C23H38N7O17P3S Acetyl-CoA 809.1258 142-62-1 CAS 1871-67-6 CAS trans-Dodec-2-enoic acid 1.0 Dodecanoic acid 1.0 C01771 KEGG Compound 552744 ChemSpider CHEBI:30794 ChEBI 3-OXODODECANOATE BioCyc Reaction1248 false Acetyl-CoA → Malonyl-CoA LEFT_TO_RIGHT PW000167 PathWhiz HMDB00357 HMDB HMDB01568 HMDB HMDB01206 HMDB 3-Hydroxybutyric acid Caproic acid CPD-195 BioCyc CHEBI:30776 ChEBI ReactionCatalysis962 ACTIVATION 3-Oxohexadecanoic acid CHEBI:37162 ChEBI 5312804 PubChem-compound CHEBI:30772 ChEBI HMDB00482 HMDB 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 SMP00051 SMPDB SMP00057 SMPDB trans-Tetra-dec-2-enoic acid CHEBI:41131 ChEBI 4445841 ChemSpider HMDB01423 HMDB ReactionCatalysis2050 ACTIVATION Cytosol HMDB00691 HMDB 1.0 1.0 ReactionCatalysis2053 ACTIVATION ReactionCatalysis2052 ACTIVATION ReactionCatalysis2055 ACTIVATION ReactionCatalysis2054 ACTIVATION ReactionCatalysis2057 ACTIVATION 94 ChemSpider ReactionCatalysis2056 ACTIVATION Fatty acid synthase C00249 KEGG Compound 1.0 C01571 KEGG Compound 11005 PubChem-compound C00246 KEGG Compound But-2-enoic acid HMDB00220 HMDB 1.0 Myristic acid 4445834 ChemSpider CHEBI:37099 ChEBI 1.0 Coenzyme A C02679 KEGG Compound C01585 KEGG Compound C00010 KEGG Compound 1.0 4472286 ChemSpider 334-48-5 CAS 1.0 8892 PubChem-compound CHEBI:42539 ChEBI 1.0 C00383 KEGG Compound 388783 ChemSpider C00024 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 1.0 ACET BioCyc 1.0 3-Oxohexanoic acid 1.0 4472229 ChemSpider 4472223 ChemSpider HMDB00535 HMDB C3H4O4 Malonic acid 104.010956 Reaction2191 false Caprylic acid + Malonic acid → 3-Oxodecanoic acid LEFT_TO_RIGHT CL:0000000 CELL TYPE ONTOLOGY C00033 KEGG Compound Reaction2192 false 3-Oxodecanoic acid → (R)-3-Hydroxydecanoic acid LEFT_TO_RIGHT Reaction2190 false trans-2-Octenoic acid → Caprylic acid LEFT_TO_RIGHT CHEBI:18037 ChEBI Reaction2188 false 3-Oxooctanoic acid → (R)-3-Hydroxyoctanoic acid LEFT_TO_RIGHT Reaction2189 false (R)-3-Hydroxyoctanoic acid → trans-2-Octenoic acid LEFT_TO_RIGHT Reaction2186 false trans-Hex-2-enoic acid → Caproic acid LEFT_TO_RIGHT Reaction2187 false Caproic acid + Malonic acid → 3-Oxooctanoic acid LEFT_TO_RIGHT Reaction2184 false 3-Oxohexanoic acid → (R)-3-Hydroxyhexanoic acid LEFT_TO_RIGHT Reaction2185 false (R)-3-Hydroxyhexanoic acid → trans-Hex-2-enoic acid LEFT_TO_RIGHT 5312798 PubChem-compound Reaction2182 false But-2-enoic acid → Butyric acid LEFT_TO_RIGHT Reaction2183 false Butyric acid + Malonic acid → 3-Oxohexanoic acid LEFT_TO_RIGHT 334-49-6 CAS (R)-3-Hydroxy-hexadecanoic acid Reaction2180 false Acetoacetic acid → 3-Hydroxybutyric acid LEFT_TO_RIGHT Reaction2181 false 3-Hydroxybutyric acid → But-2-enoic acid LEFT_TO_RIGHT C00164 KEGG Compound Reaction2177 false Acetic acid + Malonic acid → Acetoacetic acid LEFT_TO_RIGHT Reaction2178 false Acetyl-CoA → Acetic acid + Coenzyme A LEFT_TO_RIGHT SMILES CCCC(=O)CC(O)=O 1.0 Reaction2179 false Malonyl-CoA → Coenzyme A + Malonic acid LEFT_TO_RIGHT MALONATE BioCyc HMDB00511 HMDB C14H28O2 Myristic acid 228.20892 (R)-3-Hydroxydodecanoic acid SMILES CC(O)=O 4380-91-0 CAS SMILES CCCC(O)=O P49327 UniProt 57-10-3 CAS SMILES CCCCCCCCCC(O)=O SMP00456 SMPDB C6H12O2 Caproic acid 116.08373 2863 ChemSpider C02367 KEGG Compound 428 ChemSpider C02122 KEGG Compound 21865352 ChemSpider SMILES CC(=O)CC(O)=O Reaction2197 false (R)-3-Hydroxydodecanoic acid → trans-Dodec-2-enoic acid LEFT_TO_RIGHT Reaction2198 false trans-Dodec-2-enoic acid → Dodecanoic acid LEFT_TO_RIGHT Reaction2195 false Capric acid + Malonic acid → 3-Oxododecanoic acid LEFT_TO_RIGHT Reaction2196 false 3-Oxododecanoic acid → (R)-3-Hydroxydodecanoic acid LEFT_TO_RIGHT Reaction2193 false (R)-3-Hydroxydecanoic acid → trans-Dec-2-enoic acid LEFT_TO_RIGHT Reaction2194 false trans-Dec-2-enoic acid → Capric acid LEFT_TO_RIGHT HMDB00638 HMDB 143-07-7 CAS (R)-3-Hydroxyoctanoic acid C00083 KEGG Compound BiologicalState2 SubPathwayInteraction740 SubPathway740Reaction SubPathwayReaction C8H14O2 trans-2-Octenoic acid 142.09938 4450466 ChemSpider 844 ChemSpider 5312861 PubChem-compound 960 ChemSpider 388729 ChemSpider C8H16O2 Caprylic acid 144.11504 96 PubChem-compound Acetic acid 985 PubChem-compound Acetoacetic acid 444493 PubChem-compound 1OXO2YLIDENE BioCyc 399829 ChemSpider SMILES CCC\C=C\C(O)=O SMILES [H][C@@](O)(CCC)CC(O)=O SMILES CCCCCC(=O)CC(O)=O 10663 PubChem-compound SMILES C\C=C\C(O)=O SMILES CCCCCCCCCC(=O)CC(O)=O SMILES CCCCCCC\C=C\C(O)=O 2969 PubChem-compound SMILES CCCCCCCCC\C=C\C(O)=O ACETYL-COA BioCyc SMILES [H][C@@](O)(CCCCCCCCC)CC(O)=O SMILES [H][C@@](O)(CCCCC)CC(O)=O 1.0 SMILES [H][C@@](O)(CCCCCCC)CC(O)=O SMILES CCCCCCCC(=O)CC(O)=O 3756 ChemSpider 454064 PubChem-compound 3-Oxooctanoic acid SMILES [H][C@@](O)(CCCCCCCCCCC)CC(O)=O SMILES CCCCCCCCCCCC(=O)CC(O)=O SMILES CCCCCCCCCCC\C=C\C(O)=O SMILES [H][C@@](O)(CCCCCCCCCCCCC)CC(O)=O SMILES CCCCCCCCCCCCCC(=O)CC(O)=O SMILES CCCCCCCCCCCCC\C=C\C(O)=O CHEBI:44680 ChEBI Trans-Hexa-dec-2-enoic acid C2H4O2 Acetic acid 60.02113 C4H8O2 Butyric acid 88.05243 HMDB10735 HMDB HMDB10734 HMDB C01089 KEGG Compound 8552 ChemSpider 259 ChemSpider C10H20O2 Capric acid 172.14633 64-19-7 CAS 370 ChemSpider Acetyl-CoA SubPathwayOutput 439717 PubChem-compound HMDB00806 HMDB HMDB10729 HMDB HMDB10728 HMDB HMDB10727 HMDB HMDB10726 HMDB 13283-91-5 CAS HMDB10725 HMDB HMDB10724 HMDB C06424 KEGG Compound C06423 KEGG Compound 6816 PubChem-compound HMDB10733 HMDB HMDB10732 HMDB HMDB10731 HMDB HMDB10730 HMDB 141-82-2 CAS C4H6O3 Acetoacetic acid 102.03169 HMDB10719 HMDB HMDB10718 HMDB HMDB10717 HMDB Malonyl-CoA 3-Oxodecanoic acid SubPathwayInteraction739 SubPathwayReaction SubPathway739Reaction 264 PubChem-compound 8373213 ChemSpider GO:0005829 GENE ONTOLOGY trans-2-Octenoic acid CHEBI:20067 ChEBI HMDB10722 HMDB HMDB10721 HMDB C12H24O2 Dodecanoic acid 200.17763 HMDB10720 HMDB 379 PubChem-compound 1.0 trans-Hex-2-enoic acid C4H8O3 3-Hydroxybutyric acid 104.04734 1.0 3724-65-0 CAS 107-92-6 CAS C16H32O2 Palmitic acid 256.24023 114191 ChemSpider Butyric acid 1.0 CPD-335 BioCyc C6H10O2 trans-Hex-2-enoic acid 114.06808 CHEBI:28837 ChEBI C4H6O2 But-2-enoic acid 86.03678 C6H10O3 3-Oxohexanoic acid 130.06299 C6H12O3 (R)-3-Hydroxyhexanoic acid 132.07864 441 PubChem-compound C8H14O3 3-Oxooctanoic acid 158.0943 1.0 C8H16O3 (R)-3-Hydroxyoctanoic acid 160.10994 C10H18O3 3-Oxodecanoic acid 186.1256 1.0 5282743 PubChem-compound C12H22O3 3-Oxododecanoic acid 214.15689 C12H24O3 (R)-3-Hydroxydodecanoic acid 216.17255 5282982 PubChem-compound C10H20O3 (R)-3-Hydroxydecanoic acid 188.14125 SMILES CCCCCCCCCCCC(O)=O C10H18O2 trans-Dec-2-enoic acid 170.13068 3-Oxododecanoic acid CHEBI:15531 ChEBI 1.0 1.0 Q13085 UniProt 544-63-8 CAS 4446124 ChemSpider 10539 ChemSpider C14H28O3 (R)-3-Hydroxy-tetradecanoic acid 244.20384 C14H26O2 trans-Tetra-dec-2-enoic acid 226.19328 C12H22O2 trans-Dodec-2-enoic acid 198.16199 SMILES CC(O)CC(O)=O C14H26O3 3-Oxotetradecanoic acid 242.1882 C16H32O3 (R)-3-Hydroxy-hexadecanoic acid 272.23514 C16H30O2 Trans-Hexa-dec-2-enoic acid 254.22458 C16H30O3 3-Oxohexadecanoic acid 270.21948 SMILES CCCCCCCCCCCCCCCC(O)=O 1.0 5282738 PubChem-compound 1.0 Fatty acid Metabolism SubPathway 637090 PubChem-compound Capric acid 3893 PubChem-compound 1.0 10197713 PubChem-compound 439658 PubChem-compound CHEBI:15756 ChEBI SMILES CCCCC\C=C\C(O)=O 3-Oxotetradecanoic acid 5282997 PubChem-compound SMILES CCCCCCCC(O)=O CHEBI:43197 ChEBI Citric Acid Cycle SubPathway 1.0 4446109 ChemSpider Acetyl-CoA carboxylase 1 (R)-3-Hydroxydecanoic acid 3-KETOBUTYRATE BioCyc Caprylic acid 23511544 PubChem-compound CHEBI:1146900 ChEBI 1.0 5282707 PubChem-compound (R)-3-Hydroxyhexanoic acid 4445870 ChemSpider CO-A BioCyc CPD-8475 BioCyc 72-89-9 CAS 1.0 ReactionCatalysis2028 ACTIVATION ReactionCatalysis2027 ACTIVATION CHEBI:28875 ChEBI C21H36N7O16P3S Coenzyme A 767.11523 ReactionCatalysis2029 ACTIVATION ReactionCatalysis2026 ACTIVATION Cell 10213 ChemSpider 5288266 PubChem-compound Acetyl-CoA carboxylase 1 4445865 ChemSpider 6557 ChemSpider SMILES CC(=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 524-14-1 CAS CHEBI:50467 ChEBI ReactionCatalysis2039 ACTIVATION 5282724 PubChem-compound ReactionCatalysis2038 ACTIVATION Fatty acid synthase CHEBI:30813 ChEBI Malonic acid 300-85-6 CAS ReactionCatalysis2031 ACTIVATION ReactionCatalysis2030 ACTIVATION ReactionCatalysis2033 ACTIVATION ReactionCatalysis2032 ACTIVATION 5282729 PubChem-compound ReactionCatalysis2035 ACTIVATION ReactionCatalysis2034 ACTIVATION ReactionCatalysis2037 ACTIVATION ReactionCatalysis2036 ACTIVATION 4445851 ChemSpider ReactionCatalysis2040 ACTIVATION HMDB01175 HMDB ReactionCatalysis2049 ACTIVATION Palmitic acid SubPathwayInput 1.0 ReactionCatalysis2042 ACTIVATION ReactionCatalysis2041 ACTIVATION CHEBI:30805 ChEBI ReactionCatalysis2044 ACTIVATION ReactionCatalysis2043 ACTIVATION ReactionCatalysis2046 ACTIVATION 1.0 ReactionCatalysis2045 ACTIVATION 4445856 ChemSpider 5282714 PubChem-compound ReactionCatalysis2047 ACTIVATION 9606 TAXONOMY CHEBI:15366 ChEBI PW000023 PathWhiz CHEBI:37271 ChEBI 392413 ChemSpider CHEBI:37270 ChEBI SMILES CCCCCCCCCCCCCC(O)=O CHEBI:38247 ChEBI 1.0 CHEBI:37157 ChEBI 171 ChemSpider C24H38N7O19P3S Malonyl-CoA 853.1156 HMDB00060 HMDB SMILES CCCCCC(O)=O SMILES OC(=O)CC(O)=O 124-07-2 CAS (R)-3-Hydroxy-tetradecanoic acid 128859 PubChem-compound 1.0 CHEBI:15344 ChEBI trans-Dec-2-enoic acid CHEBI:37251 ChEBI CHEBI:37252 ChEBI HMDB00039 HMDB PW000005 PathWhiz CHEBI:28422 ChEBI Reaction2200 false Dodecanoic acid + Malonic acid → 3-Oxotetradecanoic acid LEFT_TO_RIGHT 1.0 Reaction2207 false (R)-3-Hydroxy-hexadecanoic acid → Trans-Hexa-dec-2-enoic acid LEFT_TO_RIGHT Reaction2208 false Trans-Hexa-dec-2-enoic acid → Palmitic acid LEFT_TO_RIGHT Reaction2205 false Malonic acid + Myristic acid → 3-Oxohexadecanoic acid LEFT_TO_RIGHT 541-50-4 CAS Reaction2206 false 3-Oxohexadecanoic acid → (R)-3-Hydroxy-hexadecanoic acid LEFT_TO_RIGHT Reaction2203 false (R)-3-Hydroxy-tetradecanoic acid → trans-Tetra-dec-2-enoic acid LEFT_TO_RIGHT Reaction2204 false trans-Tetra-dec-2-enoic acid → Myristic acid LEFT_TO_RIGHT Reaction2201 false 3-Oxotetradecanoic acid → (R)-3-Hydroxy-tetradecanoic acid LEFT_TO_RIGHT CHEBI:15351 ChEBI HMDB00042 HMDB 176 PubChem-compound 15569776 PubChem-compound 85-61-0 CAS MALONYL-COA BioCyc Acetyl-CoA carboxylase 1 Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Malonyl/Acetyl Transferase domain Fatty acid synthase. Malonyl/Acetyl Transferase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Dyhydrase Domain Fatty acid synthase. Enoyl Reductase Domain Fatty acid synthase Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Dyhydrase Domain Fatty acid synthase. Enoyl Reductase Domain Fatty acid synthase. Malonyl/Acetyl Transferase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Dyhydrase Domain Fatty acid synthase. Enoyl Reductase Domain Fatty acid synthase. Malonyl/Acetyl Transferase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase Fatty acid synthase. Dyhydrase Domain Fatty acid synthase Fatty acid synthase. Malonyl/Acetyl Transferase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Dyhydrase Domain Fatty acid synthase. Enoyl Reductase Domain Fatty acid synthase. Malonyl/Acetyl Transferase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Dyhydrase Domain Fatty acid synthase. Enoyl Reductase Domain Fatty acid synthase. Malonyl/Acetyl Transferase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Beta ketoacyl synthase domain Fatty acid synthase. Dyhydrase Domain Fatty acid synthase. Enoyl Reductase Domain Palmitic acid Acetyl-CoA Malonyl-CoA Malonic acid Acetic acid Acetoacetic acid Coenzyme A Coenzyme A 3- Hydroxybutyric acid But-2-enoic acid Butyric acid Malonyl-CoA Malonic acid Coenzyme A 3-Oxohexanoic acid (R)-3- Hydroxyhexanoic acid trans-Hex-2- enoic acid Caproic acid Malonyl-CoA Malonic acid Coenzyme A 3-Oxooctanoic acid (R)-3- Hydroxyoctanoic acid trans-2- Octenoic acid Caprylic acid Malonyl-CoA Malonic acid Coenzyme A 3-Oxodecanoic acid (R)-3- Hydroxydecanoic acid trans-Dec-2- enoic acid Capric acid Malonyl-CoA Malonic acid Coenzyme A 3-Oxododecanoic acid (R)-3- Hydroxydodecanoic acid trans-Dodec- 2-enoic acid Dodecanoic acid Malonyl-CoA Malonic acid Coenzyme A 3-Oxotetradecanoic acid (R)-3-Hydroxy-tetradecanoic acid trans-Tetra-dec-2-enoic acid Myristic acid Malonyl-CoA Malonic acid Coenzyme A 3-Oxohexadecanoic acid (R)-3-Hydroxy-hexadecanoic acid Trans-Hexa-dec-2-enoic acid Biotin Manganese Fatty acid Metabolism Citric Acid Cycle Intracellular Space
Fatty Acid Biosynthesis C23H38N7O17P3S Acetyl-CoA 809.1258 142-62-1 CAS 1871-67-6 CAS trans-Dodec-2-enoic acid 1.0 Dodecanoic acid 1.0 C01771 KEGG Compound 552744 ChemSpider CHEBI:30794 ChEBI 3-OXODODECANOATE BioCyc Reaction1248 false Acetyl-CoA → Malonyl-CoA LEFT_TO_RIGHT PW000167 PathWhiz HMDB00357 HMDB HMDB01568 HMDB HMDB01206 HMDB 3-Hydroxybutyric acid Caproic acid CPD-195 BioCyc CHEBI:30776 ChEBI ReactionCatalysis962 ACTIVATION 3-Oxohexadecanoic acid CHEBI:37162 ChEBI 5312804 PubChem-compound CHEBI:30772 ChEBI HMDB00482 HMDB 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 SMP00051 SMPDB SMP00057 SMPDB trans-Tetra-dec-2-enoic acid CHEBI:41131 ChEBI 4445841 ChemSpider HMDB01423 HMDB ReactionCatalysis2050 ACTIVATION Cytosol HMDB00691 HMDB 1.0 1.0 ReactionCatalysis2053 ACTIVATION ReactionCatalysis2052 ACTIVATION ReactionCatalysis2055 ACTIVATION ReactionCatalysis2054 ACTIVATION ReactionCatalysis2057 ACTIVATION 94 ChemSpider ReactionCatalysis2056 ACTIVATION Fatty acid synthase C00249 KEGG Compound 1.0 C01571 KEGG Compound 11005 PubChem-compound C00246 KEGG Compound But-2-enoic acid HMDB00220 HMDB 1.0 Myristic acid 4445834 ChemSpider CHEBI:37099 ChEBI 1.0 Coenzyme A C02679 KEGG Compound C01585 KEGG Compound C00010 KEGG Compound 1.0 4472286 ChemSpider 334-48-5 CAS 1.0 8892 PubChem-compound CHEBI:42539 ChEBI 1.0 C00383 KEGG Compound 388783 ChemSpider C00024 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 1.0 ACET BioCyc 1.0 3-Oxohexanoic acid 1.0 4472229 ChemSpider 4472223 ChemSpider HMDB00535 HMDB C3H4O4 Malonic acid 104.010956 Reaction2191 false Caprylic acid + Malonic acid → 3-Oxodecanoic acid LEFT_TO_RIGHT CL:0000000 CELL TYPE ONTOLOGY C00033 KEGG Compound Reaction2192 false 3-Oxodecanoic acid → (R)-3-Hydroxydecanoic acid LEFT_TO_RIGHT Reaction2190 false trans-2-Octenoic acid → Caprylic acid LEFT_TO_RIGHT CHEBI:18037 ChEBI Reaction2188 false 3-Oxooctanoic acid → (R)-3-Hydroxyoctanoic acid LEFT_TO_RIGHT Reaction2189 false (R)-3-Hydroxyoctanoic acid → trans-2-Octenoic acid LEFT_TO_RIGHT Reaction2186 false trans-Hex-2-enoic acid → Caproic acid LEFT_TO_RIGHT Reaction2187 false Caproic acid + Malonic acid → 3-Oxooctanoic acid LEFT_TO_RIGHT Reaction2184 false 3-Oxohexanoic acid → (R)-3-Hydroxyhexanoic acid LEFT_TO_RIGHT Reaction2185 false (R)-3-Hydroxyhexanoic acid → trans-Hex-2-enoic acid LEFT_TO_RIGHT 5312798 PubChem-compound Reaction2182 false But-2-enoic acid → Butyric acid LEFT_TO_RIGHT Reaction2183 false Butyric acid + Malonic acid → 3-Oxohexanoic acid LEFT_TO_RIGHT 334-49-6 CAS (R)-3-Hydroxy-hexadecanoic acid Reaction2180 false Acetoacetic acid → 3-Hydroxybutyric acid LEFT_TO_RIGHT Reaction2181 false 3-Hydroxybutyric acid → But-2-enoic acid LEFT_TO_RIGHT C00164 KEGG Compound Reaction2177 false Acetic acid + Malonic acid → Acetoacetic acid LEFT_TO_RIGHT Reaction2178 false Acetyl-CoA → Acetic acid + Coenzyme A LEFT_TO_RIGHT SMILES CCCC(=O)CC(O)=O 1.0 Reaction2179 false Malonyl-CoA → Coenzyme A + Malonic acid LEFT_TO_RIGHT MALONATE BioCyc HMDB00511 HMDB C14H28O2 Myristic acid 228.20892 (R)-3-Hydroxydodecanoic acid SMILES CC(O)=O 4380-91-0 CAS SMILES CCCC(O)=O P49327 UniProt 57-10-3 CAS SMILES CCCCCCCCCC(O)=O SMP00456 SMPDB C6H12O2 Caproic acid 116.08373 2863 ChemSpider C02367 KEGG Compound 428 ChemSpider C02122 KEGG Compound 21865352 ChemSpider SMILES CC(=O)CC(O)=O Reaction2197 false (R)-3-Hydroxydodecanoic acid → trans-Dodec-2-enoic acid LEFT_TO_RIGHT Reaction2198 false trans-Dodec-2-enoic acid → Dodecanoic acid LEFT_TO_RIGHT Reaction2195 false Capric acid + Malonic acid → 3-Oxododecanoic acid LEFT_TO_RIGHT Reaction2196 false 3-Oxododecanoic acid → (R)-3-Hydroxydodecanoic acid LEFT_TO_RIGHT Reaction2193 false (R)-3-Hydroxydecanoic acid → trans-Dec-2-enoic acid LEFT_TO_RIGHT Reaction2194 false trans-Dec-2-enoic acid → Capric acid LEFT_TO_RIGHT HMDB00638 HMDB 143-07-7 CAS (R)-3-Hydroxyoctanoic acid C00083 KEGG Compound BiologicalState2 SubPathwayInteraction740 SubPathway740Reaction SubPathwayReaction C8H14O2 trans-2-Octenoic acid 142.09938 4450466 ChemSpider 844 ChemSpider 5312861 PubChem-compound 960 ChemSpider 388729 ChemSpider C8H16O2 Caprylic acid 144.11504 96 PubChem-compound Acetic acid 985 PubChem-compound Acetoacetic acid 444493 PubChem-compound 1OXO2YLIDENE BioCyc 399829 ChemSpider SMILES CCC\C=C\C(O)=O SMILES [H][C@@](O)(CCC)CC(O)=O SMILES CCCCCC(=O)CC(O)=O 10663 PubChem-compound SMILES C\C=C\C(O)=O SMILES CCCCCCCCCC(=O)CC(O)=O SMILES CCCCCCC\C=C\C(O)=O 2969 PubChem-compound SMILES CCCCCCCCC\C=C\C(O)=O ACETYL-COA BioCyc SMILES [H][C@@](O)(CCCCCCCCC)CC(O)=O SMILES [H][C@@](O)(CCCCC)CC(O)=O 1.0 SMILES [H][C@@](O)(CCCCCCC)CC(O)=O SMILES CCCCCCCC(=O)CC(O)=O 3756 ChemSpider 454064 PubChem-compound 3-Oxooctanoic acid SMILES [H][C@@](O)(CCCCCCCCCCC)CC(O)=O SMILES CCCCCCCCCCCC(=O)CC(O)=O SMILES CCCCCCCCCCC\C=C\C(O)=O SMILES [H][C@@](O)(CCCCCCCCCCCCC)CC(O)=O SMILES CCCCCCCCCCCCCC(=O)CC(O)=O SMILES CCCCCCCCCCCCC\C=C\C(O)=O CHEBI:44680 ChEBI Trans-Hexa-dec-2-enoic acid C2H4O2 Acetic acid 60.02113 C4H8O2 Butyric acid 88.05243 HMDB10735 HMDB HMDB10734 HMDB C01089 KEGG Compound 8552 ChemSpider 259 ChemSpider C10H20O2 Capric acid 172.14633 64-19-7 CAS 370 ChemSpider Acetyl-CoA SubPathwayOutput 439717 PubChem-compound HMDB00806 HMDB HMDB10729 HMDB HMDB10728 HMDB HMDB10727 HMDB HMDB10726 HMDB 13283-91-5 CAS HMDB10725 HMDB HMDB10724 HMDB C06424 KEGG Compound C06423 KEGG Compound 6816 PubChem-compound HMDB10733 HMDB HMDB10732 HMDB HMDB10731 HMDB HMDB10730 HMDB 141-82-2 CAS C4H6O3 Acetoacetic acid 102.03169 HMDB10719 HMDB HMDB10718 HMDB HMDB10717 HMDB Malonyl-CoA 3-Oxodecanoic acid SubPathwayInteraction739 SubPathwayReaction SubPathway739Reaction 264 PubChem-compound 8373213 ChemSpider GO:0005829 GENE ONTOLOGY trans-2-Octenoic acid CHEBI:20067 ChEBI HMDB10722 HMDB HMDB10721 HMDB C12H24O2 Dodecanoic acid 200.17763 HMDB10720 HMDB 379 PubChem-compound 1.0 trans-Hex-2-enoic acid C4H8O3 3-Hydroxybutyric acid 104.04734 1.0 3724-65-0 CAS 107-92-6 CAS C16H32O2 Palmitic acid 256.24023 114191 ChemSpider Butyric acid 1.0 CPD-335 BioCyc C6H10O2 trans-Hex-2-enoic acid 114.06808 CHEBI:28837 ChEBI C4H6O2 But-2-enoic acid 86.03678 C6H10O3 3-Oxohexanoic acid 130.06299 C6H12O3 (R)-3-Hydroxyhexanoic acid 132.07864 441 PubChem-compound C8H14O3 3-Oxooctanoic acid 158.0943 1.0 C8H16O3 (R)-3-Hydroxyoctanoic acid 160.10994 C10H18O3 3-Oxodecanoic acid 186.1256 1.0 5282743 PubChem-compound C12H22O3 3-Oxododecanoic acid 214.15689 C12H24O3 (R)-3-Hydroxydodecanoic acid 216.17255 5282982 PubChem-compound C10H20O3 (R)-3-Hydroxydecanoic acid 188.14125 SMILES CCCCCCCCCCCC(O)=O C10H18O2 trans-Dec-2-enoic acid 170.13068 3-Oxododecanoic acid CHEBI:15531 ChEBI 1.0 1.0 Q13085 UniProt 544-63-8 CAS 4446124 ChemSpider 10539 ChemSpider C14H28O3 (R)-3-Hydroxy-tetradecanoic acid 244.20384 C14H26O2 trans-Tetra-dec-2-enoic acid 226.19328 C12H22O2 trans-Dodec-2-enoic acid 198.16199 SMILES CC(O)CC(O)=O C14H26O3 3-Oxotetradecanoic acid 242.1882 C16H32O3 (R)-3-Hydroxy-hexadecanoic acid 272.23514 C16H30O2 Trans-Hexa-dec-2-enoic acid 254.22458 C16H30O3 3-Oxohexadecanoic acid 270.21948 SMILES CCCCCCCCCCCCCCCC(O)=O 1.0 5282738 PubChem-compound 1.0 Fatty acid Metabolism SubPathway 637090 PubChem-compound Capric acid 3893 PubChem-compound 1.0 10197713 PubChem-compound 439658 PubChem-compound CHEBI:15756 ChEBI SMILES CCCCC\C=C\C(O)=O 3-Oxotetradecanoic acid 5282997 PubChem-compound SMILES CCCCCCCC(O)=O CHEBI:43197 ChEBI Citric Acid Cycle SubPathway 1.0 4446109 ChemSpider Acetyl-CoA carboxylase 1 (R)-3-Hydroxydecanoic acid 3-KETOBUTYRATE BioCyc Caprylic acid 23511544 PubChem-compound CHEBI:1146900 ChEBI 1.0 5282707 PubChem-compound (R)-3-Hydroxyhexanoic acid 4445870 ChemSpider CO-A BioCyc CPD-8475 BioCyc 72-89-9 CAS 1.0 ReactionCatalysis2028 ACTIVATION ReactionCatalysis2027 ACTIVATION CHEBI:28875 ChEBI C21H36N7O16P3S Coenzyme A 767.11523 ReactionCatalysis2029 ACTIVATION ReactionCatalysis2026 ACTIVATION Cell 10213 ChemSpider 5288266 PubChem-compound Acetyl-CoA carboxylase 1 4445865 ChemSpider 6557 ChemSpider SMILES CC(=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 524-14-1 CAS CHEBI:50467 ChEBI ReactionCatalysis2039 ACTIVATION 5282724 PubChem-compound ReactionCatalysis2038 ACTIVATION Fatty acid synthase CHEBI:30813 ChEBI Malonic acid 300-85-6 CAS ReactionCatalysis2031 ACTIVATION ReactionCatalysis2030 ACTIVATION ReactionCatalysis2033 ACTIVATION ReactionCatalysis2032 ACTIVATION 5282729 PubChem-compound ReactionCatalysis2035 ACTIVATION ReactionCatalysis2034 ACTIVATION ReactionCatalysis2037 ACTIVATION ReactionCatalysis2036 ACTIVATION 4445851 ChemSpider ReactionCatalysis2040 ACTIVATION HMDB01175 HMDB ReactionCatalysis2049 ACTIVATION Palmitic acid SubPathwayInput 1.0 ReactionCatalysis2042 ACTIVATION ReactionCatalysis2041 ACTIVATION CHEBI:30805 ChEBI ReactionCatalysis2044 ACTIVATION ReactionCatalysis2043 ACTIVATION ReactionCatalysis2046 ACTIVATION 1.0 ReactionCatalysis2045 ACTIVATION 4445856 ChemSpider 5282714 PubChem-compound ReactionCatalysis2047 ACTIVATION 9606 TAXONOMY CHEBI:15366 ChEBI PW000023 PathWhiz CHEBI:37271 ChEBI 392413 ChemSpider CHEBI:37270 ChEBI SMILES CCCCCCCCCCCCCC(O)=O CHEBI:38247 ChEBI 1.0 CHEBI:37157 ChEBI 171 ChemSpider C24H38N7O19P3S Malonyl-CoA 853.1156 HMDB00060 HMDB SMILES CCCCCC(O)=O SMILES OC(=O)CC(O)=O 124-07-2 CAS (R)-3-Hydroxy-tetradecanoic acid 128859 PubChem-compound 1.0 CHEBI:15344 ChEBI trans-Dec-2-enoic acid CHEBI:37251 ChEBI CHEBI:37252 ChEBI HMDB00039 HMDB PW000005 PathWhiz CHEBI:28422 ChEBI Reaction2200 false Dodecanoic acid + Malonic acid → 3-Oxotetradecanoic acid LEFT_TO_RIGHT 1.0 Reaction2207 false (R)-3-Hydroxy-hexadecanoic acid → Trans-Hexa-dec-2-enoic acid LEFT_TO_RIGHT Reaction2208 false Trans-Hexa-dec-2-enoic acid → Palmitic acid LEFT_TO_RIGHT Reaction2205 false Malonic acid + Myristic acid → 3-Oxohexadecanoic acid LEFT_TO_RIGHT 541-50-4 CAS Reaction2206 false 3-Oxohexadecanoic acid → (R)-3-Hydroxy-hexadecanoic acid LEFT_TO_RIGHT Reaction2203 false (R)-3-Hydroxy-tetradecanoic acid → trans-Tetra-dec-2-enoic acid LEFT_TO_RIGHT Reaction2204 false trans-Tetra-dec-2-enoic acid → Myristic acid LEFT_TO_RIGHT Reaction2201 false 3-Oxotetradecanoic acid → (R)-3-Hydroxy-tetradecanoic acid LEFT_TO_RIGHT CHEBI:15351 ChEBI HMDB00042 HMDB 176 PubChem-compound 15569776 PubChem-compound 85-61-0 CAS MALONYL-COA BioCyc