CHEBI:78370 - cyclooctatin

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ChEBI Name cyclooctatin
Definition A diterpenoid characterized by a 5-8-5 dodecahydrodicyclopenta[a,d]cyclooctene fused-ring system, with a single double bond and one isopropyl, two hydroxy, one hydroxymethyl and two methyl substituents.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H34O3
Net Charge 0
Average Mass 322.489
Monoisotopic Mass 322.25079
InChI InChI=1S/C20H34O3/c1-12(2)14-5-7-19(3)10-15-13(11-21)9-17(22)18(15)20(4,23)8-6-16(14)19/h6,12-15,17-18,21-23H,5,7-11H2,1-4H3/b16-6-/t13-,14+,15+,17+,18-,19+,20-/m0/s1
SMILES [H][C@@]1(CO)C[C@@H](O)[C@]2([H])[C@]1([H])C[C@@]1(C)CC[C@H](C(C)C)\C1=C\C[C@]2(C)O
Metabolite of Species Details
Streptomyces melanosporofaciens (NCBI:txid67327) of strain MI614-43F2 See: PubMed
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC (lysophospholipase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of the enzyme lysophospholipase (EC, which catalyses the release of fatty acids from lysophospholipids.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cyclooctatin (CHEBI:78370) has role bacterial metabolite (CHEBI:76969)
cyclooctatin (CHEBI:78370) has role EC (lysophospholipase) inhibitor (CHEBI:78372)
cyclooctatin (CHEBI:78370) is a carbotricyclic compound (CHEBI:38032)
cyclooctatin (CHEBI:78370) is a diterpenoid (CHEBI:23849)
cyclooctatin (CHEBI:78370) is a primary alcohol (CHEBI:15734)
cyclooctatin (CHEBI:78370) is a secondary alcohol (CHEBI:35681)
cyclooctatin (CHEBI:78370) is a tertiary alcohol (CHEBI:26878)
Incoming cyclooctat-9-en-5,7-diol (CHEBI:141020) has functional parent cyclooctatin (CHEBI:78370)
cyclooctat-9-en-7-ol (CHEBI:78352) has functional parent cyclooctatin (CHEBI:78370)
Synonyms Sources
(1R,3R,3aS,4S,6Z,7R,9aR,10aR)-1-(hydroxymethyl)-7-isopropyl-4,9a-dimethyl-1,2,3,3a,4,5,7,8,9,9a,10,10a-dodecahydrodicyclopenta[a,d][8]annulene-3,4-diol IUPAC
(1R,3R,3aS,4S,6Z,7R,9aR,10aR)-1-(hydroxymethyl)-7-isopropyl-4,9a-dimethyl-1,2,3,3a,4,5,7,8,9,9a,10,10a-dodecahydrodicyclopenta[a,d]cyclooctene-3,4-diol IUPAC
cyclooctatin UniProt
Manual Xref Database
CPD-16666 MetaCyc
View more database links
Registry Number Type Source
31158120 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1335449 PubMed citation Europe PMC
1474002 PubMed citation Europe PMC
19635410 PubMed citation Europe PMC
25689152 PubMed citation Europe PMC
26371548 PubMed citation Europe PMC
26526514 PubMed citation Europe PMC
26681256 PubMed citation Europe PMC
28463490 PubMed citation Europe PMC
Last Modified
03 August 2020
General Comment
2018-02-22 For determination of absolute stereochemistry, see Angew. Chem. Int. Ed., 2015, 54, 4353-4356 and associated supplementary information.