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CHEBI:17226 - rosmarinic acid
| Formula | C18H16O8 |
| Net Charge | 0 |
| Average Mass | 360.318 |
| Monoisotopic Mass | 360.08452 |
| SMILES | O=C(/C=C/c1ccc(O)c(O)c1)OC(Cc1ccc(O)c(O)c1)C(=O)O |
| InChI | InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+ |
| InChIKey | DOUMFZQKYFQNTF-ZZXKWVIFSA-N |
| 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). |
| Biological Roles: | serine proteinase inhibitor An exogenous or endogenous compound which inhibits serine endopeptidases. EC 1.1.1.21 (aldehyde reductase) inhibitor An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| Applications: | peripheral nervous system drug A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system. non-steroidal anti-inflammatory drug An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| rosmarinic acid (CHEBI:17226) has functional parent trans-caffeic acid (CHEBI:16433) |
| rosmarinic acid (CHEBI:17226) has role antioxidant (CHEBI:22586) |
| rosmarinic acid (CHEBI:17226) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550) |
| rosmarinic acid (CHEBI:17226) has role non-steroidal anti-inflammatory drug (CHEBI:35475) |
| rosmarinic acid (CHEBI:17226) has role peripheral nervous system drug (CHEBI:49110) |
| rosmarinic acid (CHEBI:17226) has role plant metabolite (CHEBI:76924) |
| rosmarinic acid (CHEBI:17226) has role serine proteinase inhibitor (CHEBI:48353) |
| rosmarinic acid (CHEBI:17226) is a carboxylic ester (CHEBI:33308) |
| rosmarinic acid (CHEBI:17226) is a monocarboxylic acid (CHEBI:25384) |
| rosmarinic acid (CHEBI:17226) is a phenylpropanoid (CHEBI:26004) |
| rosmarinic acid (CHEBI:17226) is a polyphenol (CHEBI:26195) |
| rosmarinic acid (CHEBI:17226) is conjugate acid of rosmarinate (CHEBI:58062) |
| Incoming Relation(s) |
| (R)-rosmarinic acid (CHEBI:50371) is a rosmarinic acid (CHEBI:17226) |
| (S)-rosmarinic acid (CHEBI:50372) is a rosmarinic acid (CHEBI:17226) |
| rosmarinate (CHEBI:58062) is conjugate base of rosmarinic acid (CHEBI:17226) |
| IUPAC Name |
|---|
| 3-(3,4-dihydroxyphenyl)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoic acid |
| Synonyms | Source |
|---|---|
| R-(+)-2-(3,4-Dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionic acid | ChemIDplus |
| alpha-(((3,4-Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy- benzenepropanoic acid | ChemIDplus |
| Registry Numbers | Sources |
|---|---|
| CAS:537-15-5 | ChemIDplus |
| Citations |
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