Dehydrocholic acid (CHEM016655)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:39:34 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016655
Identification
Common NameDehydrocholic acid
ClassSmall Molecule
DescriptionAn oxo-5beta-cholanic acid in which three oxo substituents are located at positions 3, 7 and 12 on the cholanic acid skeleton.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,7,12-Triketo-5beta-cholanoic acidChEBI
3,7,12-Triketocholanic acidChEBI
3,7,12-Trioxocholanic acidChEBI
DecholinChEBI
Purified dehydrocholic acidKegg
3,7,12-Triketo-5b-cholanoateGenerator
3,7,12-Triketo-5b-cholanoic acidGenerator
3,7,12-Triketo-5beta-cholanoateGenerator
3,7,12-Triketo-5β-cholanoateGenerator
3,7,12-Triketo-5β-cholanoic acidGenerator
3,7,12-TriketocholanateGenerator
3,7,12-TrioxocholanateGenerator
Purified dehydrocholateGenerator
DehydrocholateGenerator
Dehydrocholic acidChEBI
(4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoateGenerator
Ciba vision brand OF dehydrocholic acidMeSH
Dehydrocholate, sodiumMeSH
Ketocholanic acidMeSH
Sodium dehydrocholateMeSH
Dehydrocholic acid, magnesium saltMeSH
AtrocholinMeSH
TrioxocholateMeSH
Bayer brand OF dehydrocholic acidMeSH
Dehydrocholic acid, potassium saltMeSH
Dehydrocholic acid, sodium saltMeSH
Cholan-HMBMeSH
Dehydrocholic acid, lithium saltMeSH
Triketocholanic acidMeSH
(5beta)-3,7,12-Trioxocholan-24-Oic acidMeSH
ChologonMeSH
glaxo Wellcome brand OF dehydrocholic acidMeSH
Cholan HMBMeSH
CholanHMBMeSH
Chemical FormulaC24H34O5
Average Molecular Mass402.531 g/mol
Monoisotopic Mass402.241 g/mol
CAS Registry Number81-23-2
IUPAC Name(4R)-4-[(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-5,9,16-trioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-5,9,16-trioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
SMILES[H][C@@](C)(CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C(=O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C
InChI IdentifierInChI=1S/C24H34O5/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/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1
InChI KeyOHXPGWPVLFPUSM-KLRNGDHRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentBile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Bile acid, alcohol, or derivatives
  • 3-oxosteroid
  • 3-oxo-5-beta-steroid
  • 7-oxosteroid
  • Oxosteroid
  • 12-oxosteroid
  • Ketone
  • Cyclic ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.007 g/LALOGPS
logP3.37ALOGPS
logP3.64ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area88.51 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.01 m³·mol⁻¹ChemAxon
Polarizability44.99 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 (TMS_4_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kr-0459000000-435f87bc1a58a855a0ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-3962000000-2dfafa7266e72ac813b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0019100000-fa5bf60a4d1599fa3b77Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0029000000-f9c226fc3f0811dc78efSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0029000000-3dfad07549f72814be6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0009000000-eb22bdb679d22824f879Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00kr-0459000000-435f87bc1a58a855a0ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-3962000000-2dfafa7266e72ac813b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fri-0009300000-adf69cbd7c3392fe2497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0550-0109000000-6a0f619762c4dac4b7d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ox-2509000000-1e083a89b113cea0660bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003900000-7dac494f613914063076Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2009800000-226eb3c31ffc7948fdffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9205000000-47490b3d85ab485a4567Spectrum
MSMass Spectrum (Electron Ionization)Not 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 IDDB11622
HMDB IDHMDB0240357
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDehydrocholic acid
Chemspider IDNot Available
ChEBI ID31459
PubChem Compound IDNot Available
Kegg Compound IDC13154
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17604970
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18507070
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18613358
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19102397
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19734023
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21181147
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22153852
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22237952
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22581067
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22806613
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22899496
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23130230
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23315150
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25641915
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=26849336
16.
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=PMC3716435