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 rosemary (Rosmarinus officinalis) and common sage (Salvia 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 332.435
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 C1CC([C@]2([C@](C1)(C3=C(CC2)C=C(C(=C3O)O)C(C)C)C(=O)O)[H])(C)C
Metabolite of Species Details
Salvia officinalis (NCBI:38868) Found in leaf (BTO:0000713). See: DOI
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): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
food preservative
Substances which are added to food in order to prevent decomposition caused by microbial growth or by undesirable chemical changes.
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.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
food preservative
Substances which are added to food in order to prevent decomposition caused by microbial growth or by undesirable chemical changes.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing carnosic acid (CHEBI:65585) has role angiogenesis modulating agent (CHEBI:50926)
carnosic acid (CHEBI:65585) has role anti-inflammatory agent (CHEBI:67079)
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 apoptosis inducer (CHEBI:68495)
carnosic acid (CHEBI:65585) has role food preservative (CHEBI:65255)
carnosic acid (CHEBI:65585) has role HIV protease inhibitor (CHEBI:35660)
carnosic acid (CHEBI:65585) has role plant metabolite (CHEBI:76924)
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 Links Databases
Carnosic_acid Wikipedia
CPD-18103 MetaCyc
View more database links
Registry Numbers Types Sources
2707918 Reaxys Registry Number Reaxys
3650-09-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
21 November 2017