Showing metabocard for Isodeoxycholic acid (BMDB0002536)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:00:46 UTC
Update Date2020-04-22 15:11:08 UTC
BMDB IDBMDB0002536
Secondary Accession Numbers
  • BMDB02536
Metabolite Identification
Common NameIsodeoxycholic acid
DescriptionIsodeoxycholic acid, also known as isodeoxycholate, 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. Based on a literature review a significant number of articles have been published on Isodeoxycholic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7alpha,12alpha-Dihydroxy-5beta-cholanic acidKegg
7alpha,12alpha-Dihydroxycholanoic acidKegg
7a,12a-Dihydroxy-5b-cholanateGenerator
7a,12a-Dihydroxy-5b-cholanic acidGenerator
7alpha,12alpha-Dihydroxy-5beta-cholanateGenerator
7Α,12α-dihydroxy-5β-cholanateGenerator
7Α,12α-dihydroxy-5β-cholanic acidGenerator
7a,12a-DihydroxycholanoateGenerator
7a,12a-Dihydroxycholanoic acidGenerator
7alpha,12alpha-DihydroxycholanoateGenerator
7Α,12α-dihydroxycholanoateGenerator
7Α,12α-dihydroxycholanoic acidGenerator
IsodeoxycholateGenerator
3-Deoxycholic acidHMDB
7a,12a-Dihydroxy-5b-cholan-24-OateHMDB
7a,12a-Dihydroxy-5b-cholan-24-Oic acidHMDB
7a,12a-Dihydroxy-5b-cholanoateHMDB
7a,12a-Dihydroxy-5b-cholanoic acidHMDB
7alpha,12alpha-Dihydroxy-5beta-cholan-24-OateHMDB
7alpha,12alpha-Dihydroxy-5beta-cholan-24-Oic acidHMDB
Isodeoxycholic acidKEGG
(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateGenerator, HMDB
Chemical FormulaC24H40O4
Average Molecular Weight392.572
Monoisotopic Molecular Weight392.292659768
IUPAC Name(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
CAS Registry Number566-17-6
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CCCC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O
InChI Identifier
InChI=1S/C24H40O4/c1-14(7-10-21(27)28)16-8-9-17-22-18(13-20(26)24(16,17)3)23(2)11-5-4-6-15(23)12-19(22)25/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
InChI KeyZHCAAZIHTDCFJX-QLEQUTGBSA-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
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.16ALOGPS
logP3.87ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.12 m³·mol⁻¹ChemAxon
Polarizability46.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r2-1349000000-c20944bdb515b39b1d8bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1110190000-4fbd3514c97db8f97c4dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-875537fa9339c3a3bbecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1009000000-20a7c31d6177cdac7eccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02vj-7009000000-e32583ec8a96a2d6796dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-a7e668c25bb4e322f429View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1009000000-af1365631dc58c1b7979View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-33d068d8853add57effaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-e572c29938091d5ba610View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05bf-5297000000-e9bd316f7bfb3538706aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9530000000-343097ad815cfbd487e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7eba834115ee2c679208View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0009000000-03834bc03b5a1c28e5f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1039000000-b5eba12dd80348c13a4dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002536
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023024
KNApSAcK IDNot Available
Chemspider ID144358
KEGG Compound IDC17661
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound164672
PDB IDNot Available
ChEBI ID81256
References
Synthesis ReferenceGrand, R.; Reichstein, T. Bile acids and related compounds. XXXIII. Derivatives of cholic acid. Helvetica Chimica Acta (1945), 28 344-9.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available