bicyclosesquiphellandrene (CHEBI:192811)

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ChEBI Name	bicyclosesquiphellandrene

ChEBI ID	CHEBI:192811

Definition	An octahydronaphthalene that is 1,2,3,4,4a,5,6,7-octahydronaphthalene substituted by isopropyl, methyl, and methylidene groups at positions 1, 4 and 7, respectively (the (1S,4R,4aR)-stereoisomer).

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

Submitter	Tereza Calounova

Supplier Information

Download	Molfile XML SDF

Formula

C15H24

Net Charge

Average Mass

204.357

Monoisotopic Mass

204.18780

InChI

InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,12-14H,3,5-8H2,1-2,4H3/t12-,13+,14-/m1/s1

InChIKey

RNDFUOKDULDZPR-HZSPNIEDSA-N

SMILES

[H][C@]12CCC(=C)C=C1[C@@H](CC[C@H]2C)C(C)C

Metabolite of Species	Details
Helichrysum gymnocephalum (NCBI:txid1442664)	Found in leaf (BTO:0000713). See: PubMed
Lipotriche scandens (NCBI:txid1670799)	Found in leaf (BTO:0000713). Species also known as Melanthera scandens. See: Florence, Affia & Félix, Tonzibo & Muriel, Koffi & Figueredo, Gilles. (2011). Chemical composition of essential oil of Melanthera scandens (Shum. et Thonn) Roberty. World Applied Sciences Journal.
Clinopodium alpinum (NCBI:txid224743)	Found in aerial part (BTO:0001658). Species also known as Acinos alpinus. See: DOI
Dictyota dichotoma (NCBI:txid2876)	Found in HAP-1 (EFO:0007598). See: PubMed
Lippia alba (NCBI:txid320345)	See: PubMed
Piper cubeba (NCBI:txid405322)	See: DOI
Citrus depressa (NCBI:txid697036)	Found in Pooled sample (NCIT:C45910). Isolated from pulp essential oil.. See: PubMed

Roles Classification
Biological Role(s):	volatile oil component Any plant metabolite that is found naturally as a component of a volatile oil. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.

ChEBI Ontology
Outgoing	bicyclosesquiphellandrene (CHEBI:192811) has role algal metabolite (CHEBI:84735) bicyclosesquiphellandrene (CHEBI:192811) has role plant metabolite (CHEBI:76924) bicyclosesquiphellandrene (CHEBI:192811) has role volatile oil component (CHEBI:27311) bicyclosesquiphellandrene (CHEBI:192811) is a octahydronaphthalenes (CHEBI:138397) bicyclosesquiphellandrene (CHEBI:192811) is a sesquiterpene (CHEBI:35189)

IUPAC Name

(1S,4R,4aR)-4-methyl-7-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene

Synonym	Source
(1S,4R,4aR)-1-isopropyl-4-methyl-7-methylene-1,2,3,4,4a,5,6,7-octahydronaphthalene	ChEBI

Registry Number	Type	Source
54324-03-7	CAS Registry Number	NIST Chemistry WebBook

Last Modified

12 August 2022