capsidiol (CHEBI:28283)

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ChEBI Name	capsidiol

ChEBI ID	CHEBI:28283

Definition	An eremophilane sesquiterpenoid that is (+)-5-epi-aristolochene bearing additional 1β- and 3α-hydroxy substituents. It is a phytoalexin produced in Nicotiana and Capsicum plant species in response to pathogen attack.

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

Secondary ChEBI IDs	CHEBI:3377, CHEBI:23001

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Formula

C15H24O2

Net Charge

Average Mass

236.34986

Monoisotopic Mass

236.17763

InChI

InChI=1S/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h6,10-11,13-14,16-17H,1,5,7-8H2,2-4H3/t10-,11-,13-,14-,15-/m1/s1

InChIKey

BXXSHQYDJWZXPB-OKNSCYNVSA-N

SMILES

C[C@@H]1[C@H](O)C[C@@H](O)C2=CC[C@H](C[C@]12C)C(C)=C

Metabolite of Species	Details
Nicotiana silvestris (IPNI:817067-1)	See: PubMed
Capsicum annuum (NCBI:txid4072)	Found in Root (BTO:0001188). See: PubMed
Nicotiana benthamiana (NCBI:txid4100)	Found in leaf (BTO:0000713). See: PubMed

Roles Classification
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. antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. phytoalexin A toxin made by a plant that acts against an organism attacking it. (via terpenoid phytoalexin )

ChEBI Ontology
Outgoing	capsidiol (CHEBI:28283) has functional parent (+)-5-epi-aristolochene (CHEBI:23925) capsidiol (CHEBI:28283) has role antifungal agent (CHEBI:35718) capsidiol (CHEBI:28283) has role plant metabolite (CHEBI:76924) capsidiol (CHEBI:28283) is a eremophilane sesquiterpenoid (CHEBI:36753) capsidiol (CHEBI:28283) is a octahydronaphthalenes (CHEBI:138397) capsidiol (CHEBI:28283) is a sesquiterpene phytoalexin (CHEBI:142279)

Incoming	capsidiol 3-acetate (CHEBI:183320) has functional parent capsidiol (CHEBI:28283)

IUPAC Names

(1R,3R,4S,4aR,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol

1β,3α,4βH-eremophila-9,11-diene-1,3-diol

Synonyms	Sources
(1R,3R,4S,4aR,6R)-6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol	IUPAC
Capsidiol	KEGG COMPOUND
capsidiol	UniProt

Last Modified

05 November 2021