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CHEBI:145550 - peregrinol

ChEBI IDCHEBI:145550
ChEBI Nameperegrinol
Stars
DefinitionA 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.
Last Modified22 August 2023
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC20H36O2
Net Charge0
Average Mass308.506
Monoisotopic Mass308.27153
SMILES[H][C@@]12CC[C@@H](C)[C@](O)(CC/C(C)=C/CO)[C@@]1(C)CCCC2(C)C
InChIInChI=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
InChIKeyXFADQGUJWIMYJI-UEHSRLBXSA-N
Species of MetaboliteComponentSourceComments
Marrubium peregrinum (ncbitaxon:53166) - Article (Khim. Prir. Soedin., 1967,301)
Roles Classification
Biological Role:
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 Relation(s)
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 Relation(s)
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
UniProt Name  Source
peregrinolUniProt
Manual XrefsDatabases
CPD-20438MetaCyc
C00023322KNApSAcK
Registry NumbersSources
CAS:17140-23-7ChemIDplus
Citations