CHEBI:65847 - epi-cochlioquinone A

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ChEBI Name epi-cochlioquinone A
ChEBI ID CHEBI:65847
ChEBI ASCII Name epi-cochlioquinone A
Definition An organic heterotetracyclic that is 1,2,3,4a,5,6,6a,12,12a,12b-decahydropyrano[3,2-a]xanthene-8,11-dione substituted by a 2-hydroxypropan-2-yl group at position 3, hydroxy group at position 12, methyl groups at positions 6a and 12b and a 3-(acetyloxy)-4-methylhexan-2-yl moiety at position 9. Isolated from the fermentation broth of Stachybotrys bisbyi SANK 17777, it acts as an inhibitor of acyl-CoA:cholesterol acyltransferase.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H44O8
Net Charge 0
Average Mass 532.66560
Monoisotopic Mass 532.30362
InChI InChI=1S/C30H44O8/c1-9-15(2)25(36-17(4)31)16(3)18-14-19(32)22-24(34)27-29(7)12-10-20(28(5,6)35)37-21(29)11-13-30(27,8)38-26(22)23(18)33/h14-16,20-21,24-25,27,34-35H,9-13H2,1-8H3/t15-,16-,20+,21+,24+,25+,27+,29-,30-/m0/s1
InChIKey UWSYUCZPPVXEKW-UDLMDNSSSA-N
SMILES [H][C@@]12CC[C@]3(C)OC4=C([C@@H](O)[C@]3([H])[C@@]1(C)CC[C@@H](O2)C(C)(C)O)C(=O)C=C([C@H](C)[C@H](OC(C)=O)[C@@H](C)CC)C4=O
Metabolite of Species Details
Stachybotrys bisbyi (NCBI:txid80385) of strain SANK17777 See: PubMed
Roles Classification
Biological Role(s): EC 2.3.1.26 (sterol O-acyltransferase) inhibitor
An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of acyl-CoA:cholesterol acyltransferase (EC 2.3.1.26).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing epi-cochlioquinone A (CHEBI:65847) has role EC 2.3.1.26 (sterol O-acyltransferase) inhibitor (CHEBI:64696)
epi-cochlioquinone A (CHEBI:65847) has role metabolite (CHEBI:25212)
epi-cochlioquinone A (CHEBI:65847) is a p-quinones (CHEBI:25830)
epi-cochlioquinone A (CHEBI:65847) is a acetate ester (CHEBI:47622)
epi-cochlioquinone A (CHEBI:65847) is a cyclic ether (CHEBI:37407)
epi-cochlioquinone A (CHEBI:65847) is a organic heterotetracyclic compound (CHEBI:38163)
epi-cochlioquinone A (CHEBI:65847) is a secondary alcohol (CHEBI:35681)
epi-cochlioquinone A (CHEBI:65847) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(2S,3R,4S)-2-[(3R,4aR,6aS,12S,12aS,12bR)-12-hydroxy-3-(2-hydroxypropan-2-yl)-6a,12b-dimethyl-8,11-dioxo-1,2,3,4a,5,6,6a,8,11,12,12a,12b-dodecahydropyrano[3,2-a]xanthen-9-yl]-4-methylhexan-3-yl acetate
Registry Number Type Source
7609731 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
8682715 PubMed citation Europe PMC
Last Modified
03 June 2016