Showing metabocard for Allocholic acid (BMDB0000505)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:31:48 UTC
Update Date2020-05-11 20:21:01 UTC
BMDB IDBMDB0000505
Secondary Accession Numbers
  • BMDB00505
Metabolite Identification
Common NameAllocholic acid
DescriptionAllocholic acid, also known as allocholate or 5alpha-cholate, 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. Based on a literature review a significant number of articles have been published on Allocholic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholanoic acidChEBI
5alpha-Cholic acidChEBI
AllocholateKegg
(3a,5a,7a,12a)-3,7,12-Trihydroxycholan-24-OateGenerator
(3a,5a,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acidGenerator
(3alpha,5alpha,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-OateGenerator
(3Α,5α,7α,12α)-3,7,12-trihydroxycholan-24-OateGenerator
(3Α,5α,7α,12α)-3,7,12-trihydroxycholan-24-Oic acidGenerator
3a,7a,12a-Trihydroxy-5a-cholanoateGenerator
3a,7a,12a-Trihydroxy-5a-cholanoic acidGenerator
3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholanoateGenerator
5a-CholateGenerator
5a-Cholic acidGenerator
5alpha-CholateGenerator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acidHMDB
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-OateHMDB
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acidHMDB
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-OateHMDB
(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-OateHMDB
(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acidHMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-OateHMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-Oic acidHMDB
3a,7a,12a-TrihydroxycholanateHMDB
3a,7a,12a-Trihydroxycholanic acidHMDB
5alpha-Allocholic acidHMDB
5Α-allocholic acidHMDB
Allocholic acidHMDB
Chemical FormulaC24H40O5
Average Molecular Weight408.579
Monoisotopic Molecular Weight408.287574388
IUPAC Name(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic 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)CCC(O)=O
InChI Identifier
InChI=1S/C24H40O5/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/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
InChI KeyBHQCQFFYRZLCQQ-PGHAKIONSA-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
  • 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
logP2.26ALOGPS
logP2.48ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.79 m³·mol⁻¹ChemAxon
Polarizability47.2 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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 IDHMDB0000505
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011602
KNApSAcK IDC00054052
Chemspider ID141151
KEGG Compound IDC17737
BioCyc IDCPD-16581
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5491
PubChem Compound160636
PDB IDNot Available
ChEBI ID81308
References
Synthesis ReferenceMitra, Manindra N.; Elliott, William Hueckel. Bile acids. XXIII. New direct synthesis of allocholic acid and its 3b isomer. Journal of Organic Chemistry (1968), 33(1), 175-81.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available