Structure Database (LMSD)

Common Name
3-Oxocholic acid
Systematic Name
3-oxo-7α,12α-dihydroxy-5β-cholan-24-oic Acid
Synonyms
  • 3-Dehydrocholic acid
  • 3-ketoCA
  • 3-Ketocholic acid
LM ID
LMST04010443
Formula
C24H38O5
Exact Mass
Calculate m/z
406.271925
Sum Composition
ST 24:2;O5
Status
Active
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Bile acids and derivatives [ST04]
C24 bile acids, alcohols, and derivatives [ST0401]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Clostridium perfringens (#1502)
Clostridia (#186801)
Identification of 7alpha-, 12alpha-dihydroxy-3-oxo cholanoic acid as the major degradation product from cholic by C. perfringens,
J Steroid Biochem, 1978
Pubmed ID: 207931

String Representations

InChiKey (Click to copy)
OEKUSRBIIZNLHZ-DJDNIQJZSA-N
InChi (Click to copy)
InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
SMILES (Click to copy)
[C@@]12([H])[C@H](O)C[C@]3([H])CC(=O)CC[C@]3(C)[C@@]1([H])C[C@H](O)[C@]1(C)[C@@]([H])([C@@](C)([H])CCC(=O)O)CC[C@@]21[H]

Other Databases

HMDB ID
HMDB0000502
CHEBI ID
88108
PubChem CID
5283956
SwissLipids ID
SLM:000501380
Cayman ID
28403

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 4
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 412.99
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 4.23
Molar Refractivity 110.06

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Created at
-
Updated at
28th Feb 2024