CHEBI:82799 - (R)-nephthenol

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ChEBI Name (R)-nephthenol
ChEBI ID CHEBI:82799
ChEBI ASCII Name (R)-nephthenol
Definition A cembrane diterpenoid obtained by regio- and stereoselective hydration of the exocyclic double bond of cembrene C.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
Download Molfile XML SDF
Formula C20H34O
Net Charge 0
Average Mass 290.48340
Monoisotopic Mass 290.26097
InChI InChI=1S/C20H34O/c1-16-8-6-10-17(2)12-14-19(20(4,5)21)15-13-18(3)11-7-9-16/h8,11-12,19,21H,6-7,9-10,13-15H2,1-5H3/b16-8+,17-12+,18-11+/t19-/m0/s1
InChIKey ZJWQYSDAWSDJRA-QPHFJTKNSA-N
SMILES C\C1=C/CC\C(C)=C\C[C@@H](CC\C(C)=C\CC1)C(C)(C)O
Roles Classification
Biological Role(s): coral metabolite
Any animal metabolite produced during a metabolic reaction in corals (marine invertebrates).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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ChEBI Ontology
Outgoing (R)-nephthenol (CHEBI:82799) has functional parent cembrene C (CHEBI:82798)
(R)-nephthenol (CHEBI:82799) has role bacterial metabolite (CHEBI:76969)
(R)-nephthenol (CHEBI:82799) has role coral metabolite (CHEBI:76498)
(R)-nephthenol (CHEBI:82799) is a cembrane diterpenoid (CHEBI:60687)
(R)-nephthenol (CHEBI:82799) is a macrocycle (CHEBI:51026)
(R)-nephthenol (CHEBI:82799) is a olefinic compound (CHEBI:78840)
(R)-nephthenol (CHEBI:82799) is a tertiary alcohol (CHEBI:26878)
(R)-nephthenol (CHEBI:82799) is enantiomer of (S)-nephthenol (CHEBI:193073)
Incoming (S)-nephthenol (CHEBI:193073) is enantiomer of (R)-nephthenol (CHEBI:82799)
IUPAC Name
2-[(1R,3E,7E,11E)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]propan-2-ol
Synonyms Sources
(-)-Nephthenol KNApSAcK
(R)-nephthenol UniProt
Nephthenol ChemIDplus
Manual Xrefs Databases
C00049734 KNApSAcK
CPD-16929 MetaCyc
View more database links
Registry Numbers Types Sources
4189963 Reaxys Registry Number Reaxys
53915-41-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10579864 PubMed citation Europe PMC
17007411 PubMed citation Europe PMC
23386483 PubMed citation SUBMITTER
9677266 PubMed citation Europe PMC
Last Modified
31 August 2022
General Comment
2014-11-04 An erratum has been published for citation MED:23386483 in which the structure is depicted with incorrect stereochemistry. For details see: http://onlinelibrary.wiley.com/doi/10.1002/cbic.201402114/pdf.