CHEBI:50372 - (S)-rosmarinic acid

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ChEBI Name (S)-rosmarinic acid
ChEBI ASCII Name (S)-rosmarinic acid
Definition The (S)-stereoisomer of rosmarinic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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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-/m0/s1
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): serine proteinase inhibitor
An exogenous or endogenous compound which inhibits serine endopeptidases.
(via rosmarinic acid )
EC (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
(via rosmarinic acid )
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 )
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 (S)-rosmarinic acid (CHEBI:50372) is a rosmarinic acid (CHEBI:17226)
(S)-rosmarinic acid (CHEBI:50372) is enantiomer of (R)-rosmarinic acid (CHEBI:50371)
Incoming (R)-rosmarinic acid (CHEBI:50371) is enantiomer of (S)-rosmarinic acid (CHEBI:50372)
(2S)-3-(3,4-dihydroxyphenyl)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoic acid
Synonym Source
Registry Numbers Types Sources
4208785 Reaxys Registry Number Reaxys
4208785 Beilstein Registry Number Beilstein
Last Modified
08 January 2016