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CHEBI:71676 - esculeogenin A

ChEBI IDCHEBI:71676
ChEBI Nameesculeogenin A
Stars
DefinitionA sapogenin that is spirosolane substituted by hydroxy groups at positions 3, 23 and 27 (the 3β,5α,22α,23S,25S stereoisomer).
Last Modified24 April 2013
Submitternamrata
DownloadsMolfile
FormulaC27H45NO4
Net Charge0
Average Mass447.660
Monoisotopic Mass447.33486
SMILES[H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@@]4(C)[C@@]3([H])C[C@]3([H])O[C@@]5(NC[C@@H](CO)C[C@@H]5O)[C@@H](C)[C@]43[H])[C@@]1(C)CC[C@H](O)C2
InChIInChI=1S/C27H45NO4/c1-15-24-22(32-27(15)23(31)10-16(14-29)13-28-27)12-21-19-5-4-17-11-18(30)6-8-25(17,2)20(19)7-9-26(21,24)3/h15-24,28-31H,4-14H2,1-3H3/t15-,16-,17-,18-,19+,20-,21-,22-,23-,24-,25-,26-,27-/m0/s1
InChIKeyFBKQAVWTYDQPAB-HBDLFPIVSA-N
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
esculeogenin A (CHEBI:71676) has role EC 2.3.1.26 (sterol O-acyltransferase) inhibitor (CHEBI:64696)
esculeogenin A (CHEBI:71676) has role metabolite (CHEBI:25212)
esculeogenin A (CHEBI:71676) is a 3β-hydroxy steroid (CHEBI:36836)
esculeogenin A (CHEBI:71676) is a azaspiro compound (CHEBI:35624)
esculeogenin A (CHEBI:71676) is a oxaspiro compound (CHEBI:37948)
esculeogenin A (CHEBI:71676) is a sapogenin (CHEBI:26606)
IUPAC Name 
(3β,5α,22α,23S,25S)-spirosolane-3,23,27-triol
Registry NumbersSources
Reaxys:9826338Reaxys
Citations