Bisnorcholic acid (CHEM035323)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:39:41 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035323
Identification
Common NameBisnorcholic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass380.518 g/mol
Monoisotopic Mass380.256 g/mol
CAS Registry NumberNot Available
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
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 IdentifierInChI=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
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 Solubility0.4 g/LALOGPS
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
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, Positivesplash10-01p9-0529000000-b04e0366cce1376a81edSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0udi-1011089000-50ba701842a02b834059Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0009000000-30d357cb5a415db49136Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-029b-0019000000-f03ae90a61da7c188319Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015i-1139000000-91cdcf707b1d9276f389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-0009000000-33deb05acd6e685f3195Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02vr-0009000000-21482a677813d12f6254Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ap0-4039000000-d9a1001f6fe17a0cbb5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-fa13e281787d8224701bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00p0-0009000000-9d72024d0fcea38513b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0170-0009000000-8aa2382c5e23bf13ff6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ea-0009000000-4ea3187ab548a0d79444Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pt-1459000000-e9a3a589aa47055ddd29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar4-7970000000-84cb6adf135c90098924Spectrum
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 IDHMDB0002082
FooDB IDFDB022836
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID7826644
ChEBI ID145219
PubChem Compound ID9547705
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2079611
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22838635
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=3559381