7-Ketodeoxycholic acid (CHEM034840)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:16:00 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034840
Identification
Common Name7-Ketodeoxycholic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-Oic acidChEBI
3alpha,12alpha-Dihydroxy-7-keto-5beta-cholanoic acidChEBI
3alpha,12alpha-Dihydroxy-7-oxo-5beta-cholanateChEBI
3alpha,12alpha-Diol-7-one-5beta-cholanoic acidChEBI
7-Oxodeoxycholic acidChEBI
(3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-OateGenerator
(3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-Oic acidGenerator
(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-OateGenerator
(3Α,5β,12α)-3,12-dihydroxy-7-oxocholan-24-OateGenerator
(3Α,5β,12α)-3,12-dihydroxy-7-oxocholan-24-Oic acidGenerator
3a,12a-Dihydroxy-7-keto-5b-cholanoateGenerator
3a,12a-Dihydroxy-7-keto-5b-cholanoic acidGenerator
3alpha,12alpha-Dihydroxy-7-keto-5beta-cholanoateGenerator
3Α,12α-dihydroxy-7-keto-5β-cholanoateGenerator
3Α,12α-dihydroxy-7-keto-5β-cholanoic acidGenerator
3a,12a-Dihydroxy-7-oxo-5b-cholanateGenerator
3a,12a-Dihydroxy-7-oxo-5b-cholanic acidGenerator
3alpha,12alpha-Dihydroxy-7-oxo-5beta-cholanic acidGenerator
3Α,12α-dihydroxy-7-oxo-5β-cholanateGenerator
3Α,12α-dihydroxy-7-oxo-5β-cholanic acidGenerator
3a,12a-Diol-7-one-5b-cholanoateGenerator
3a,12a-Diol-7-one-5b-cholanoic acidGenerator
3alpha,12alpha-Diol-7-one-5beta-cholanoateGenerator
3Α,12α-diol-7-one-5β-cholanoateGenerator
3Α,12α-diol-7-one-5β-cholanoic acidGenerator
7-OxodeoxycholateGenerator
7-KetodeoxycholateGenerator
(3a,5b,12a)-3,12-Dihydroxy-7-oxo-cholan-24-OateHMDB
(3a,5b,12a)-3,12-Dihydroxy-7-oxo-cholan-24-Oic acidHMDB
3 alpha,12 alpha-Diol-7-one-5 beta-cholanoateHMDB
3 alpha,12 alpha-Diol-7-one-5 beta-cholanoic acidHMDB
3 alpha,7 alpha-Dihydroxy-7-keto-5 beta-cholanoateHMDB
3 alpha,7 alpha-Dihydroxy-7-keto-5 beta-cholanoic acidHMDB
3a,12a-Dihydroxy-7-oxo-5b-cholan-24-OateHMDB
3a,12a-Dihydroxy-7-oxo-5b-cholan-24-Oic acidHMDB
7-Ketodeoxycholic acid, (3alpha,12alpha)-isomerHMDB
(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,16-Dihydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
7-Ketodeoxycholic acidChEBI
Chemical FormulaC24H38O5
Average Molecular Mass406.556 g/mol
Monoisotopic Mass406.272 g/mol
CAS Registry Number911-40-0
IUPAC Name(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name7-ketodeoxycholic acid
SMILES[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])C(=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/h13-18,20,22,25,27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,20+,22+,23+,24-/m1/s1
InChI KeyRHCPKKNRWFXMAT-RRWYKFPJSA-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-oxosteroid
  • 3-alpha-hydroxysteroid
  • 12-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • 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 Solubility0.041 g/LALOGPS
logP2.61ALOGPS
logP2.87ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.44ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.86 m³·mol⁻¹ChemAxon
Polarizability46.22 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, Positivesplash10-03di-0229000000-f4573054b1373ba25c43Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-1200097000-a328d301b9f2734f7a3fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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_1_5) - 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_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 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 (TMS_3_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-052r-0009300000-ca7ded990dc45187bf33Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0019000000-8ae130c589121cdfb070Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-2793000000-011c0c178df6b144dfe2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-2793000000-e7a868da91e004e56a7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0009100000-e53168576c29dec4ba1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00du-0009000000-f85ab4860a22a24d931dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056v-0109000000-fa17bdbd4a2e5abdc658Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0008900000-88fb88b08cd50a69ab8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1009300000-b632dccfee47dc4f5e6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9207000000-316b16e5098a68abb1d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-074c6bb08c4c08acb7c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0009700000-3e7500c867ff6bbdf776Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0039000000-2dcd29515d1454079783Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059i-0009400000-1677f5d16dbb699fffc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-1179100000-2e7695e0d4a36f0d2b25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9461000000-5853807a64c3c0ca1121Spectrum
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 IDHMDB0000391
FooDB IDFDB022009
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5380
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID163659
ChEBI ID16390
PubChem Compound ID188292
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bortolini, Olga; Cova, Umberto; Fantin, Giancarlo; Medici, Alessandro. A new non-enzymic route to chenodeoxycholic acid. Chemistry Letters (1996), (5), 335-336
2. Kihira K, Shimazu K, Kuwabara M, Yoshii M, Takeuchi H, Nakano I, Ozawa S, Onuki M, Hatta Y, Hoshita T: Bile acid profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis. Steroids. 1986 Jul-Aug;48(1-2):109-19.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.