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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. 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: | 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 |
|---|---|
| Rosmarinic acid | KEGG COMPOUND |
| (2R)-O-caffeoyl-3-(3,4-dihydroxyphenyl)lactic acid | ChEBI |
| Manual Xrefs | Databases |
|---|---|
| ROA | PDBeChem |
| C01850 | KEGG COMPOUND |
| CPD-6981 | MetaCyc |
| WO2010074764 | Patent |
| WO2008072941 | Patent |
| WO2008032212 | Patent |
| HMDB0003572 | HMDB |
| Rosmarinic_acid | Wikipedia |
| C00002770 | KNApSAcK |
| Registry Numbers | Sources |
|---|---|
| Reaxys:2227587 | Reaxys |
| CAS:20283-92-5 | KEGG COMPOUND |
| CAS:20283-92-5 | ChemIDplus |
| Citations |
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