EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:65847 - epi-cochlioquinone A

ChEBI IDCHEBI:65847
ChEBI Nameepi-cochlioquinone A
Stars
ASCII Nameepi-cochlioquinone A
DefinitionAn 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.
Last Modified3 June 2016
DownloadsMolfile
FormulaC30H44O8
Net Charge0
Average Mass532.674
Monoisotopic Mass532.30362
SMILES[H][C@]12[C@H](O)C3=C(O[C@@]1(C)CC[C@@]1([H])O[C@@H](C(C)(C)O)CC[C@]21C)C(=O)C([C@H](C)[C@H](OC(C)=O)[C@@H](C)CC)=CC3=O
InChIInChI=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
InChIKeyUWSYUCZPPVXEKW-UDLMDNSSSA-N
Species of MetaboliteComponentSourceComments
Stachybotrys bisbyi (ncbitaxon:80385) - PubMed (8682715) Strain: SANK17777
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:7609731Reaxys
Citations