Showing metabocard for Murocholic acid (BMDB0000811)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:57 UTC
Update Date2020-05-11 20:21:40 UTC
BMDB IDBMDB0000811
Secondary Accession Numbers
  • BMDB00811
Metabolite Identification
Common NameMurocholic acid
DescriptionMurocholic acid, also known as murideoxycholate or nahdc compound, 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 Murocholic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3alpha,6beta-Dihydroxy-5beta-cholanic acidChEBI
6beta-HydroxylithocholateChEBI
6beta-Hydroxylithocholic acidChEBI
MurideoxycholateChEBI
3a,6b-Dihydroxy-5b-cholanateGenerator
3a,6b-Dihydroxy-5b-cholanic acidGenerator
3alpha,6beta-Dihydroxy-5beta-cholanateGenerator
3Α,6β-dihydroxy-5β-cholanateGenerator
3Α,6β-dihydroxy-5β-cholanic acidGenerator
6b-HydroxylithocholateGenerator
6b-Hydroxylithocholic acidGenerator
6Β-hydroxylithocholateGenerator
6Β-hydroxylithocholic acidGenerator
Murideoxycholic acidGenerator
MurocholateGenerator
3a,6b-Dihydroxy-5b-cholan-24-OateHMDB
3a,6b-Dihydroxy-5b-cholan-24-Oic acidHMDB
3a,6b-Dihydroxy-5b-cholanoateHMDB
3a,6b-Dihydroxy-5b-cholanoic acidHMDB
3a,6b-DihydroxycholanoateHMDB
3a,6b-Dihydroxycholanoic acidHMDB
3,6-Dihydroxy-5alpha-cholanoic acidHMDB
NaHDC compoundHMDB
Hyodeoxycholic acidHMDB
Hyodeoxycholic acid, (3alpha,5beta,6beta)-isomerHMDB
Hyodeoxycholic acid, (3alpha,6beta)-isomerHMDB
Hyodeoxycholic acid, sodium saltHMDB
Hyodesoxycholic acidHMDB
Sodium hyodeoxycholateHMDB
Murocholic acidChEBI
Chemical FormulaC24H40O4
Average Molecular Weight392.572
Monoisotopic Molecular Weight392.292659768
IUPAC Name(4R)-4-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number668-49-5
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20+,21-,23-,24-/m1/s1
InChI KeyDGABKXLVXPYZII-PLYQRAMGSA-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
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 6-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • 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
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
LogP3.08RODA,A ET AL. (1990)
Predicted Properties
PropertyValueSource
logP2.98ALOGPS
logP3.71ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.79ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.27 m³·mol⁻¹ChemAxon
Polarizability46.58 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, Positivesplash10-004m-0329000000-58d5a781e1d72501a6fcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1100290000-3298b2503a68dd31087eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-0009000000-c3986d5f0fc5c79bd19dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-035fbc6f30c118171a30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-b6392133bd5f96611dceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-581fe3701cfd4409cf1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0009000000-9218797d27b939f6059aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02vl-1219000000-acd8de6ea11917fdc1bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-0009000000-f969293bf286459bff3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-0009000000-c32f7dbb58c16bc8f793View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-a8bee4058c100d760c3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054o-0009000000-79e7c3afd290f34646cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3159000000-20e08d1a7b218eb91ebdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9681000000-7db68edc57414ccf438eView 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-0009000000-375fefa884fafe6b05bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000g-2009000000-f58a3057b3e321a1006cView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Gallbladder
  • Intestine
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
GallbladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000811
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022259
KNApSAcK IDNot Available
Chemspider ID4446909
KEGG Compound IDC15515
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5775
PubChem Compound5283821
PDB IDNot Available
ChEBI ID52030
References
Synthesis ReferenceMitropoulos, K. A.; Myant, Nicolas B. Formation of lithocholic acid, chenodeoxycholic acid and other bile acids from 3b-hydroxychol-5-enoic acid in vitro and in vivo. Biochimica et Biophysica Acta, Lipids and Lipid Metabolism (1967), 144(2), 430-9.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available