CHEBI:65585 - carnosic acid

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ChEBI Name carnosic acid
ChEBI ID CHEBI:65585
Definition An abietane diterpenoid that is abieta-8,11,13-triene substituted by hydroxy groups at positions 11 and 12 and a carboxy group at position 20. It is isolated from Rosmarinus officinalis and exhibits anti-angiogenic, antineoplastic, antioxidant and anti-HIV activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H28O4
Net Charge 0
Average Mass 332.43390
Monoisotopic Mass 332.199
InChI InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1
InChIKey QRYRORQUOLYVBU-VBKZILBWSA-N
SMILES [H][C@@]12CCc3cc(C(C)C)c(O)c(O)c3[C@]1(CCCC2(C)C)C(O)=O
Metabolite of Species Details
Rosmarinus officinalis (NCBI:39367) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Chemical Role(s): 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 (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
HIV protease inhibitor
An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
Application(s): angiogenesis modulating agent
An agent that modulates the physiologic angiogenesis process. This is accomplished by endogenous angiogenic proteins and a variety of other chemicals and pharmaceutical agents.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing carnosic acid (CHEBI:65585) has role angiogenesis modulating agent (CHEBI:50926)
carnosic acid (CHEBI:65585) has role antineoplastic agent (CHEBI:35610)
carnosic acid (CHEBI:65585) has role antioxidant (CHEBI:22586)
carnosic acid (CHEBI:65585) has role HIV protease inhibitor (CHEBI:35660)
carnosic acid (CHEBI:65585) has role metabolite (CHEBI:25212)
carnosic acid (CHEBI:65585) is a abietane diterpenoid (CHEBI:36762)
carnosic acid (CHEBI:65585) is a carbotricyclic compound (CHEBI:38032)
carnosic acid (CHEBI:65585) is a catechols (CHEBI:33566)
carnosic acid (CHEBI:65585) is a monocarboxylic acid (CHEBI:25384)
carnosic acid (CHEBI:65585) is conjugate acid of carnosate (CHEBI:138943)
Incoming carnosate (CHEBI:138943) is conjugate base of carnosic acid (CHEBI:65585)
IUPAC Name
11,12-dihydroxyabieta-8,11,13-trien-20-oic acid
Synonyms Sources
(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylic acid IUPAC
11,12-dihydroxy-13-isopropylpodocarpa-8,11,13-trien-17-oic acid ChEBI
Salvin ChemIDplus
Database Link Database
Carnosic_acid Wikipedia
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Registry Numbers Types Sources
2707918 Reaxys Registry Number Reaxys
3650-09-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22232247 PubMed citation Europe PMC
22246562 PubMed citation Europe PMC
22687582 PubMed citation Europe PMC
22828666 PubMed citation Europe PMC
8229021 PubMed citation Europe PMC
Last Modified
06 December 2012