peregrinol (CHEBI:145550)

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ChEBI Name	peregrinol

ChEBI ID	CHEBI:145550

Definition	A labdane diterpenoid that is labdane which has been hydroxylated at position 5 of the decalin ring and in which the 3-methylpentyl substituent (also at position 5 of the decalin ring) has been dehydrogenated to introduce a trans double bond at the 3-4 position and hydroxylated at position 5.

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

Submitter	Kristian Axelsen

Supplier Information

Download	Molfile XML SDF

Formula

C20H36O2

Net Charge

Average Mass

308.506

Monoisotopic Mass

308.27153

InChI

InChI=1S/C20H36O2/c1-15(10-14-21)9-13-20(22)16(2)7-8-17-18(3,4)11-6-12-19(17,20)5/h10,16-17,21-22H,6-9,11-14H2,1-5H3/b15-10+/t16-,17+,19+,20-/m1/s1

InChIKey

XFADQGUJWIMYJI-UEHSRLBXSA-N

SMILES

[C@@]1(CC/C(/C)=C/CO)([C@@H](CC[C@@]2([C@]1(C)CCCC2(C)C)[H])C)O

Metabolite of Species	Details
Marrubium peregrinum (NCBI:txid53166)	See: Khim. Prir. Soedin., 1967,301

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.

ChEBI Ontology
Outgoing	peregrinol (CHEBI:145550) has parent hydride labdane (CHEBI:36505) peregrinol (CHEBI:145550) has role plant metabolite (CHEBI:76924) peregrinol (CHEBI:145550) is a carbobicyclic compound (CHEBI:36785) peregrinol (CHEBI:145550) is a labdane diterpenoid (CHEBI:36770) peregrinol (CHEBI:145550) is a primary allylic alcohol (CHEBI:134394) peregrinol (CHEBI:145550) is a tertiary alcohol (CHEBI:26878)

Incoming	labd-13Z-ene-9,15,16-triol (CHEBI:145552) has functional parent peregrinol (CHEBI:145550) peregrinol diphosphate (CHEBI:138890) has functional parent peregrinol (CHEBI:145550)

IUPAC Name

(1R,2R,4aS,8aS)-1-[(3E)-5-hydroxy-3-methylpent-3-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-1-ol

Synonym	Source
peregrinol	UniProt

Registry Number	Type	Source
17140-23-7	CAS Registry Number	ChemIDplus

Citation	Type	Source
29315936	PubMed citation	SUBMITTER

Last Modified

22 August 2023