Showing metabocard for Bisnorcholic acid (BMDB0002082)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:50:58 UTC
Update Date2020-04-22 15:09:41 UTC
BMDB IDBMDB0002082
Secondary Accession Numbers
  • BMDB02082
Metabolite Identification
Common NameBisnorcholic acid
DescriptionBisnorcholic acid, also known as dinorcholate, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Bisnorcholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
24-Dinor-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-22-Oic acidChEBI
Dinorcholic acidChEBI
24-Dinor-3a,7a,12a-trihydroxy-5b-cholan-22-OateGenerator
24-Dinor-3a,7a,12a-trihydroxy-5b-cholan-22-Oic acidGenerator
24-Dinor-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-22-OateGenerator
24-Dinor-3α,7α,12α-trihydroxy-5β-cholan-22-OateGenerator
24-Dinor-3α,7α,12α-trihydroxy-5β-cholan-22-Oic acidGenerator
DinorcholateGenerator
BisnorcholateGenerator
Chemical FormulaC22H36O5
Average Molecular Weight380.5182
Monoisotopic Molecular Weight380.256274262
IUPAC Name(2S)-2-[(1S,2S,5R,7S,9R,10R,11S,14R,15S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]propanoic acid
Traditional Namebisnorcholic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)C(O)=O
InChI Identifier
InChI=1S/C22H36O5/c1-11(20(26)27)14-4-5-15-19-16(10-18(25)22(14,15)3)21(2)7-6-13(23)8-12(21)9-17(19)24/h11-19,23-25H,4-10H2,1-3H3,(H,26,27)/t11-,12-,13+,14+,15-,16-,17+,18-,19-,21-,22+/m0/s1
InChI KeyBBSJMECOWBMUCF-XPCRKILGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • Steroid acid
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • 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
logP1.71ALOGPS
logP1.85ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.51ChemAxon
pKa (Strongest Basic)-0.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity101.61 m³·mol⁻¹ChemAxon
Polarizability42.75 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, Positivesplash10-01p9-0529000000-b04e0366cce1376a81edView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0udi-1011089000-50ba701842a02b834059View 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, Positivesplash10-03dj-0009000000-30d357cb5a415db49136View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-029b-0019000000-f03ae90a61da7c188319View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015i-1139000000-91cdcf707b1d9276f389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-0009000000-33deb05acd6e685f3195View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02vr-0009000000-21482a677813d12f6254View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ap0-4039000000-d9a1001f6fe17a0cbb5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-fa13e281787d8224701bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00p0-0009000000-9d72024d0fcea38513b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0170-0009000000-8aa2382c5e23bf13ff6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ea-0009000000-4ea3187ab548a0d79444View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pt-1459000000-e9a3a589aa47055ddd29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar4-7970000000-84cb6adf135c90098924View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002082
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022836
KNApSAcK IDNot Available
Chemspider ID7826644
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547705
PDB IDNot Available
ChEBI ID145219
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available