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CHEBI:16433 - trans-caffeic acid
| Formula | C9H8O4 |
| Net Charge | 0 |
| Average Mass | 180.159 |
| Monoisotopic Mass | 180.04226 |
| SMILES | O=C(O)/C=C/c1ccc(O)c(O)c1 |
| InChI | InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+ |
| InChIKey | QAIPRVGONGVQAS-DUXPYHPUSA-N |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Solanum campaniforme (IPNI:818569-1) | leaf (BTO:0000713) | PubMed (21962208) | Dried leaves were extracted with ethyl alcohol. |
| Mus musculus (ncbitaxon:10090) | - | PubMed (19425150) | Source: BioModels - MODEL1507180067 |
| Roles Classification |
|---|
| Chemical Roles: | antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). |
| Biological Roles: | mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor A lipoxygenase inhibitor that interferes with the action of arachidonate 5-lipoxygenase (EC 1.13.11.34). EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor A lipoxygenase inhibitor that interferes with the action of arachidonate 15-lipoxygenase (EC 1.13.11.33). EC 2.5.1.18 (glutathione transferase) inhibitor An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of a glutathione transferase (EC 2.5.1.18). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. EC 3.5.1.98 (histone deacetylase) inhibitor An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98). |
| Application: | geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| trans-caffeic acid (CHEBI:16433) has role geroprotector (CHEBI:176497) |
| trans-caffeic acid (CHEBI:16433) has role mouse metabolite (CHEBI:75771) |
| trans-caffeic acid (CHEBI:16433) is a caffeic acid (CHEBI:36281) |
| trans-caffeic acid (CHEBI:16433) is conjugate acid of trans-caffeate (CHEBI:57770) |
| Incoming Relation(s) |
| (2S,3R)-trans-caftaric acid (CHEBI:76075) has functional parent trans-caffeic acid (CHEBI:16433) |
| Cuscuta propenamide 1 (CHEBI:65700) has functional parent trans-caffeic acid (CHEBI:16433) |
| N-caffeoylspermidine (CHEBI:138030) has functional parent trans-caffeic acid (CHEBI:16433) |
| N1,N5,N10-tris-(E)-caffeoyl spermidine (CHEBI:232324) has functional parent trans-caffeic acid (CHEBI:16433) |
| N1,N8-bis(caffeoyl)spermidine (CHEBI:138028) has functional parent trans-caffeic acid (CHEBI:16433) |
| trans-5-O-caffeoyl-D-quinic acid (CHEBI:16384) has functional parent trans-caffeic acid (CHEBI:16433) |
| trans-caffeoyl-CoA (CHEBI:87449) has functional parent trans-caffeic acid (CHEBI:16433) |
| 1-O-caffeoylquinic acid (CHEBI:136555) has functional parent trans-caffeic acid (CHEBI:16433) |
| 1-caffeoyl-5-feruloylquinic acid (CHEBI:88343) has functional parent trans-caffeic acid (CHEBI:16433) |
| 1-caffeoyl-β-D-glucose (CHEBI:614) has functional parent trans-caffeic acid (CHEBI:16433) |
| 1,3-dicaffeoylquinic acid (CHEBI:520) has functional parent trans-caffeic acid (CHEBI:16433) |
| 1,3,4,5-tetracaffeoylquinic acid (CHEBI:512) has functional parent trans-caffeic acid (CHEBI:16433) |
| 2-O-caffeoyl maslinic acid (CHEBI:65547) has functional parent trans-caffeic acid (CHEBI:16433) |
| 3-O-β-D-glucosyl-trans-caffeic acid (CHEBI:3293) has functional parent trans-caffeic acid (CHEBI:16433) |
| 3,4-dihydroxy-5-prenylcinnamic acid (CHEBI:65784) has functional parent trans-caffeic acid (CHEBI:16433) |
| 3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has functional parent trans-caffeic acid (CHEBI:16433) |
| 4-O-trans-caffeoylquinic acid (CHEBI:75491) has functional parent trans-caffeic acid (CHEBI:16433) |
| 4-O-β-D-glucosyl-trans-caffeic acid (CHEBI:142393) has functional parent trans-caffeic acid (CHEBI:16433) |
| 5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) has functional parent trans-caffeic acid (CHEBI:16433) |
| 7-O-[6-(6-methoxycaffeoyl)glucosyl]isovitexin (CHEBI:75420) has functional parent trans-caffeic acid (CHEBI:16433) |
| acteoside (CHEBI:132853) has functional parent trans-caffeic acid (CHEBI:16433) |
| caffeic acid 3-sulfate (CHEBI:90242) has functional parent trans-caffeic acid (CHEBI:16433) |
| caffeic acid 3-sulfate(2−) (CHEBI:133740) has functional parent trans-caffeic acid (CHEBI:16433) |
| caffeoylglycolic acid methyl ester (CHEBI:65548) has functional parent trans-caffeic acid (CHEBI:16433) |
| calabricoside B (CHEBI:65551) has functional parent trans-caffeic acid (CHEBI:16433) |
| chlorogenic acid (CHEBI:16112) has functional parent trans-caffeic acid (CHEBI:16433) |
| ethyl trans-caffeate (CHEBI:132714) has functional parent trans-caffeic acid (CHEBI:16433) |
| evolvoid A (CHEBI:65890) has functional parent trans-caffeic acid (CHEBI:16433) |
| gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) has functional parent trans-caffeic acid (CHEBI:16433) |
| litseaefoloside C (CHEBI:66582) has functional parent trans-caffeic acid (CHEBI:16433) |
| malvidin 3-O-{6-O-[(E)-caffeoyl]-β-D-glucoside} (CHEBI:131453) has functional parent trans-caffeic acid (CHEBI:16433) |
| methyl 3,4-dicaffeoylquinate (CHEBI:85153) has functional parent trans-caffeic acid (CHEBI:16433) |
| quercetin 3-O-[(6-O-caffeoyl-β-D-glucosyl)-(1→2)-β-D-glucoside] (CHEBI:145787) has functional parent trans-caffeic acid (CHEBI:16433) |
| quercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside) (CHEBI:66284) has functional parent trans-caffeic acid (CHEBI:16433) |
| rosmarinic acid (CHEBI:17226) has functional parent trans-caffeic acid (CHEBI:16433) |
| subulatin (CHEBI:66533) has functional parent trans-caffeic acid (CHEBI:16433) |
| trans-caffeate (CHEBI:57770) is conjugate base of trans-caffeic acid (CHEBI:16433) |
| IUPAC Name |
|---|
| (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid |
| Synonyms | Source |
|---|---|
| 3,4-Dihydroxy-trans-cinnamate | KEGG COMPOUND |
| trans-Caffeate | KEGG COMPOUND |
| 3,4-dihydroxy-trans-cinnamate | ChEBI |
| trans-caffeate | ChEBI |
| CAFFEIC ACID | PDBeChem |
| 3,4-Dihydroxy-trans-cinnamate | KEGG COMPOUND |
| Manual Xrefs | Databases |
|---|---|
| C01197 | KEGG COMPOUND |
| DHC | PDBeChem |
| Caffeic_acid | Wikipedia |
| HMDB0001964 | HMDB |
| C00000615 | KNApSAcK |
| C01481 | KEGG COMPOUND |
| Registry Numbers | Sources |
|---|---|
| Reaxys:1954563 | Reaxys |
| CAS:501-16-6 | KEGG COMPOUND |
| CAS:501-16-6 | ChemIDplus |
| CAS:331-39-5 | KEGG COMPOUND |
| Citations |
|---|