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CHEBI:50371 - (R)-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)O[C@H](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+/t16-/m1/s1 |
| InChIKey | DOUMFZQKYFQNTF-WUTVXBCWSA-N |
| Wikipedia |
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| Roles Classification |
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| 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: | plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. 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). serine proteinase inhibitor An exogenous or endogenous compound which inhibits serine endopeptidases. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| Applications: | geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. 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) |
| (R)-rosmarinic acid (CHEBI:50371) has role geroprotector (CHEBI:176497) |
| (R)-rosmarinic acid (CHEBI:50371) has role plant metabolite (CHEBI:76924) |
| (R)-rosmarinic acid (CHEBI:50371) is a rosmarinic acid (CHEBI:17226) |
| (R)-rosmarinic acid (CHEBI:50371) is conjugate acid of (R)-rosmarinate (CHEBI:71493) |
| (R)-rosmarinic acid (CHEBI:50371) is enantiomer of (S)-rosmarinic acid (CHEBI:50372) |
| Incoming Relation(s) |
| (R)-rosmarinate (CHEBI:71493) is conjugate base of (R)-rosmarinic acid (CHEBI:50371) |
| (S)-rosmarinic acid (CHEBI:50372) is enantiomer of (R)-rosmarinic acid (CHEBI:50371) |
| IUPAC Name |
|---|
| (2R)-3-(3,4-dihydroxyphenyl)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoic acid |
| Synonyms | Source |
|---|---|
| (2R)-O-caffeoyl-3-(3,4-dihydroxyphenyl)lactic acid | ChEBI |
| Rosmarinic acid | KEGG COMPOUND |
| Manual Xrefs | Databases |
|---|---|
| C00002770 | KNApSAcK |
| C01850 | KEGG COMPOUND |
| CPD-6981 | MetaCyc |
| HMDB0003572 | HMDB |
| ROA | PDBeChem |
| Rosmarinic_acid | Wikipedia |
| WO2008032212 | Patent |
| WO2008072941 | Patent |
| WO2010074764 | Patent |
| Registry Numbers | Sources |
|---|---|
| Reaxys:2227587 | Reaxys |
| CAS:20283-92-5 | KEGG COMPOUND |
| CAS:20283-92-5 | ChemIDplus |
| Citations |
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