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Showing Compound 7-Ketodeoxycholic acid (FDB022009)

Record Information
Version1.0
Creation date2011-09-21 00:06:56 UTC
Update date2015-07-21 06:56:56 UTC
Primary IDFDB022009
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7-Ketodeoxycholic acid
Description7-Ketodeoxycholic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB]
CAS Number911-40-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(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
(3a,5b,12a)-3,12-dihydroxy-7-oxo-Cholan-24-oatehmdb
(3a,5b,12a)-3,12-dihydroxy-7-oxo-Cholan-24-oic acidhmdb
(3α,5β,12α)-3,12-dihydroxy-7-oxocholan-24-OateGenerator
(3α,5β,12α)-3,12-dihydroxy-7-oxocholan-24-Oic acidGenerator
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
3α,12α-dihydroxy-7-keto-5β-cholanoateGenerator
3α,12α-dihydroxy-7-keto-5β-cholanoic acidGenerator
3α,12α-dihydroxy-7-oxo-5β-cholanateGenerator
3α,12α-dihydroxy-7-oxo-5β-cholanic acidGenerator
3α,12α-diol-7-one-5β-cholanoateGenerator
3α,12α-diol-7-one-5β-cholanoic acidGenerator
7-ketodeoxycholatehmdb
7-ketodeoxycholic acidhmdb
7-oxodeoxycholatehmdb
7-oxodeoxycholic acidhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H38O5
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
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
Isomeric 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
Average Molecular Weight406.5555
Monoisotopic Molecular Weight406.271924326
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS7-Ketodeoxycholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-0229000000-f4573054b1373ba25c43Spectrum
Predicted GC-MS7-Ketodeoxycholic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1200097000-a328d301b9f2734f7a3fSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7-Ketodeoxycholic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-052r-0009300000-ca7ded990dc45187bf332021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0019000000-8ae130c589121cdfb0702021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-2793000000-011c0c178df6b144dfe22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-2793000000-e7a868da91e004e56a7b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0009100000-e53168576c29dec4ba1b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00du-0009000000-f85ab4860a22a24d931d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056v-0109000000-fa17bdbd4a2e5abdc6582017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0008900000-88fb88b08cd50a69ab8d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1009300000-b632dccfee47dc4f5e6c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9207000000-316b16e5098a68abb1d22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-074c6bb08c4c08acb7c92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0009700000-3e7500c867ff6bbdf7762021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0039000000-2dcd29515d14540797832021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059i-0009400000-1677f5d16dbb699fffc42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-1179100000-2e7695e0d4a36f0d2b252021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9461000000-5853807a64c3c0ca11212021-09-24View Spectrum
NMRNot Available
ChemSpider ID163659
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID188292
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00391
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference