CHEBI:138224 - (13R)-epi-8,13-epoxylabd-14-ene

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ChEBI Name (13R)-epi-8,13-epoxylabd-14-ene
ChEBI ID CHEBI:138224
ChEBI ASCII Name (13R)-epi-8,13-epoxylabd-14-ene
Definition A tricyclic diterpenoid that is isolated from plants and fungi and exhibits anti-bacterial protperties.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C20H34O
Net Charge 0
Average Mass 290.484
Monoisotopic Mass 290.26097
InChI InChI=1S/C20H34O/c1-7-18(4)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)21-18/h7,15-16H,1,8-14H2,2-6H3/t15-,16+,18+,19-,20+/m1/s1
InChIKey IGGWKHQYMAJOHK-QVHQYWGISA-N
SMILES CC1(CCC[C@]2(C)[C@]1([H])CC[C@@]3(O[C@@](CC[C@@]23[H])(C)C=C)C)C
Metabolite of Species Details
Cistus creticus (NCBI:txid191224) Found in rhizome (BTO:0001181). See: PubMed
Cistus monspeliensis (NCBI:txid335184) Found in leaf (BTO:0000713). See: PubMed
Cistus monspeliensis (NCBI:txid335184) Found in fruit (BTO:0000486). See: PubMed
Cistus incanus subsp. creticus (NCBI:txid393199) Obtained from the essential oil See: DOI
Phaeosphaeria sp. (NCBI:txid65784) of strain L487 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.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (13R)-epi-8,13-epoxylabd-14-ene (CHEBI:138224) has role antibacterial agent (CHEBI:33282)
(13R)-epi-8,13-epoxylabd-14-ene (CHEBI:138224) has role fungal metabolite (CHEBI:76946)
(13R)-epi-8,13-epoxylabd-14-ene (CHEBI:138224) has role plant metabolite (CHEBI:76924)
(13R)-epi-8,13-epoxylabd-14-ene (CHEBI:138224) is a cyclic ether (CHEBI:37407)
(13R)-epi-8,13-epoxylabd-14-ene (CHEBI:138224) is a labdane diterpenoid (CHEBI:36770)
(13R)-epi-8,13-epoxylabd-14-ene (CHEBI:138224) is a organic heterotricyclic compound (CHEBI:26979)
(13R)-epi-8,13-epoxylabd-14-ene (CHEBI:138224) is a tricyclic diterpenoid (CHEBI:79084)
IUPAC Name
(3R,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyldodecahydro-1H-naphtho[2,1-b]pyran
Synonyms Sources
(-)-ent-13-epi-Manoyl oxide KNApSAcK
ent-13-epi-manoyl oxide UniProt
Manual Xrefs Databases
C00043487 KNApSAcK
CPD-20258 MetaCyc
View more database links
Registry Numbers Types Sources
27642-41-7 CAS Registry Number KNApSAcK
7269026 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11301869 PubMed citation Europe PMC
12443786 PubMed citation Europe PMC
15564689 PubMed citation Europe PMC
17236091 PubMed citation Europe PMC
26077765 PubMed citation SUBMITTER
7765688 PubMed citation Europe PMC
IND20393159 Agricola citation Europe PMC
Last Modified
25 October 2017