Structure database (LMSD)

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LM IDLMST04050017
Common NameBendigole D
Systematic Name24-dinor-3-oxo,7α,12α-dihydroxy-chola-1,4-dien-22-oic acid
Synonyms-
Exact Mass
374.2093 (neutral)    Calculate m/z:
FormulaC22H30O5
CategorySterol Lipids [ST]
Main ClassBile acids and derivatives [ST04]
Sub ClassC22 bile acids, alcohols, and derivatives [ST0405]
AbbrevST 22:4;O5
PubChem CID54764154
InChIKeyRIPUUOOMDLZCBV-QYVBNZPWSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C22H30O5/c1-11(20(26)27)14-4-5-15-19-16(10-18(25)22(14,15)3)21(2)7-6-13(23)8-12(21)9-17(19)24/h6-8,11,14-19,24-25H,4-5,9-10H2,1-3H3,(H,26,27)/t11-,14+,15-,16-,17+,18-,19-,21-,22+/m0/s1
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SMILES
C1=CC(=O)C=C2C[C@@H](O)[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)C(=O)O)[C@@]4(C)[C@@H](O)C[C@]3([H])[C@@]12C
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StatusActive
ReferencesBendigoles D-F, bioactive sterols from the marine sponge-derived Actinomadura sp. SBMs009.
Bioorg Med Chem, 2011
DOI: 10.1016/j.bmc.2011.05.044
PMID: 21684166
Calculated physicochemical properties (?):
 Heavy Atoms27Rings4Aromatic Rings0Rotatable Bonds2
 van der Waals
Molecular Volume
373.11Topological Polar
Surface Area
94.83Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
5
 logP3.15Molar
Refractivity
100.71