CHEBI:50371 - (R)-rosmarinic acid

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ChEBI Name (R)-rosmarinic acid
ChEBI ID CHEBI:50371
ChEBI ASCII Name (R)-rosmarinic acid
Definition A stereoisomer of rosmarinic acid having (R)-configuration.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H16O8
Net Charge 0
Average Mass 360.31480
Monoisotopic Mass 360.08452
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
SMILES OC(=O)[C@@H](Cc1ccc(O)c(O)c1)OC(=O)\C=C\c1ccc(O)c(O)c1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
(via rosmarinic acid )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via rosmarinic acid )
serine proteinase inhibitor
An exogenous or endogenous compound which inhibits serine endopeptidases.
(via rosmarinic acid )
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).
(via rosmarinic acid )
Application(s): 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.
(via rosmarinic acid )
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.
(via rosmarinic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (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 (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 Sources
(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
View more database links
Registry Numbers Types Sources
20283-92-5 CAS Registry Number ChemIDplus
2227587 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
22169194 PubMed citation Europe PMC
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22718679 PubMed citation Europe PMC
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Last Modified
08 January 2016