3,7-Dihydroxy-12-oxocholanoic acid (CHEM034845)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:16:15 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034845
Identification
Common Name3,7-Dihydroxy-12-oxocholanoic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3alpha,5beta,7alpha)-3,7-Dihydroxy-12-oxocholan-24-Oic acidChEBI
3alpha,7alpha-Dihydroxy-12-oxo-5beta-cholanateChEBI
(3a,5b,7a)-3,7-Dihydroxy-12-oxocholan-24-OateGenerator
(3a,5b,7a)-3,7-Dihydroxy-12-oxocholan-24-Oic acidGenerator
(3alpha,5beta,7alpha)-3,7-Dihydroxy-12-oxocholan-24-OateGenerator
(3Α,5β,7α)-3,7-dihydroxy-12-oxocholan-24-OateGenerator
(3Α,5β,7α)-3,7-dihydroxy-12-oxocholan-24-Oic acidGenerator
3a,7a-Dihydroxy-12-oxo-5b-cholanateGenerator
3a,7a-Dihydroxy-12-oxo-5b-cholanic acidGenerator
3alpha,7alpha-Dihydroxy-12-oxo-5beta-cholanic acidGenerator
3Α,7α-dihydroxy-12-oxo-5β-cholanateGenerator
3Α,7α-dihydroxy-12-oxo-5β-cholanic acidGenerator
3,7-Dihydroxy-12-oxocholanoateGenerator
(3a,5b,7a)-3,7-Dihydroxy-12-oxo-cholan-24-OateHMDB
(3a,5b,7a)-3,7-Dihydroxy-12-oxo-cholan-24-Oic acidHMDB
12-Keto-3a,7a-dihydroxy-5b-cholanateHMDB
12-Keto-3a,7a-dihydroxy-5b-cholanic acidHMDB
12-Keto-chenodeoxycholateHMDB
12-Keto-chenodeoxycholic acidHMDB
12-KetochenodeoxycholateHMDB
12-Ketochenodeoxycholic acidHMDB
12-oxo-3a,7a-Dihydroxy-5b-cholan-24-OateHMDB
12-oxo-3a,7a-Dihydroxy-5b-cholan-24-Oic acidHMDB
12-OxochenodeoxycholateHMDB
12-Oxochenodeoxycholic acidHMDB
3a,7a-Dihydroxy-12-keto-5b-cholanateHMDB
3a,7a-Dihydroxy-12-keto-5b-cholanic acidHMDB
3a,7a-Dihydroxy-12-ketocholanateHMDB
3a,7a-Dihydroxy-12-ketocholanic acidHMDB
3a,7a-Dihydroxy-12-ketocholateHMDB
3a,7a-Dihydroxy-12-ketocholic acidHMDB
3a,7a-Dihydroxy-12-oxo-5b-cholan-24-OateHMDB
3a,7a-Dihydroxy-12-oxo-5b-cholan-24-Oic acidHMDB
3a,7a-Dihydroxy-12-oxo-5b-cholanoateHMDB
3a,7a-Dihydroxy-12-oxo-5b-cholanoic acidHMDB
3a,7a-Dihydroxy-12-oxocholateHMDB
3a,7a-Dihydroxy-12-oxocholic acidHMDB
5b-Cholanic acid-3a,7a-diol-12-oneHMDB
12-MonoketocholateHMDB
12-Monoketocholic acidHMDB
12-oxo-3,7-Dihydroxycholanoic acidHMDB
3 alpha, 7 alpha-Dihydroxy-12-one-5 beta-cholanoic acidHMDB
3 alpha,7 alpha-Dihydroxy-12-keto-5 beta-cholanoic acidHMDB
3alpha,7alpha-Dihydroxy-12-keto-5beta-cholanoic acidHMDB
Sodium monoketocholateHMDB
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
3,7-Dihydroxy-12-oxocholanoic acidChEBI
Chemical FormulaC24H38O5
Average Molecular Mass406.556 g/mol
Monoisotopic Mass406.272 g/mol
CAS Registry Number2458-08-4
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name12-ketochenodeoxycholic acid
SMILES[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)C(=O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C
InChI IdentifierInChI=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/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,22+,23+,24-/m1/s1
InChI KeyMIHNUBCEFJLAGN-DMMBONCOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 12-oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP2.56ALOGPS
logP3.05ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.39ChemAxon
pKa (Strongest Basic)-0.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.97 m³·mol⁻¹ChemAxon
Polarizability46.44 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-0629000000-3135db41ff8b968182b8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-2201198000-bb38056a165602f5feb7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0009100000-bccc650b1cd4508f1aa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0009000000-c0c7d7baa207e3cc0a05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056u-1109000000-e710af896d258d339fefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0008900000-dd8b045786455a7b2b5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1009300000-40bda8fb29d7dc21b644Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-879f42792050e0f3d07aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-042ac9446c06cee5ac0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0009700000-eec83a5cd15c56ccdff9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1039100000-e4f72f94d4744ca5a96cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059i-0009300000-f1bc8868b74d47d136beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-1169100000-6bf02d9105b1f9389f99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9561000000-ee15985d116087cd50ecSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000400
FooDB IDFDB022017
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5389
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID85044
ChEBI ID16312
PubChem Compound ID94235
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Fossati Elena; Polentini Fausto; Carrea Giacomo; Riva Sergio Exploitation of the alcohol dehydrogenase-acetone NADP-regeneration system for the enzymatic preparative-scale production of 12-ketochenodeoxycholic acid. Biotechnology and bioengineering (2006), 93(6), 1216-20.
2. Kuramoto T, Furukawa Y, Nishina T, Sugimoto T, Mahara R, Tohma M, Kihira K, Hoshita T: Identification of short side chain bile acids in urine of patients with cerebrotendinous xanthomatosis. J Lipid Res. 1990 Oct;31(10):1895-902.
3. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86.
4. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21.
5. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56.
6. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43.