indicanone (CHEBI:66072)

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ChEBI Name	indicanone

ChEBI ID	CHEBI:66072

Definition	A guaiane sesquiterpenoid that is 4,5,6,7-tetrahydroazulen-2(1H)-one substituted by a hydroxymethyl group at position 8, a methyl group at position 3 and an isopropenyl group at position 5. Isolated from the roots of Wikstroemia indica, it exhibits antiinflammatory activity.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C15H20O2

Net Charge

Average Mass

232.31810

Monoisotopic Mass

232.14633

InChI

InChI=1S/C15H20O2/c1-9(2)11-4-5-12(8-16)14-7-15(17)10(3)13(14)6-11/h11,16H,1,4-8H2,2-3H3/t11-/m1/s1

InChIKey

BIWBNAFBKLFTGT-LLVKDONJSA-N

SMILES

CC(=C)[C@@H]1CCC(CO)=C2CC(=O)C(C)=C2C1

Metabolite of Species	Details
Wikstroemia indica (NCBI:txid714517)	Found in root (BTO:0001188). See: PubMed

Roles Classification
Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. EC 1.14.13.39 (nitric oxide synthase) inhibitor An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).

Application(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	indicanone (CHEBI:66072) has role anti-inflammatory agent (CHEBI:67079) indicanone (CHEBI:66072) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908) indicanone (CHEBI:66072) has role metabolite (CHEBI:25212) indicanone (CHEBI:66072) is a guaiane sesquiterpenoid (CHEBI:36744) indicanone (CHEBI:66072) is a primary alcohol (CHEBI:15734)

IUPAC Name

(5R)-8-(hydroxymethyl)-3-methyl-5-(prop-1-en-2-yl)-4,5,6,7-tetrahydroazulen-2(1H)-one

Synonym	Source
(+)-indicanone	ChEBI

Registry Number	Type	Source
22726878	Reaxys Registry Number	Reaxys

Last Modified

28 February 2013