Allocholic acid (CHEM027731)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:56:31 UTC
Update Date2016-11-09 01:18:31 UTC
Accession NumberCHEM027731
Identification
Common NameAllocholic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass408.571 g/mol
Monoisotopic Mass408.288 g/mol
CAS Registry Number2464-18-8
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
SMILESCC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C
InChI IdentifierInChI=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)
InChI KeyBHQCQFFYRZLCQQ-UHFFFAOYSA-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
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 Solubility0.074 g/LALOGPS
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
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, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-1fb995e2a2a10479ff54Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0009000000-814238696e6fb3e11648Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0bta-1983000000-7ec50e0786625a29b904Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-a764d2a5e3d1918ae5faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0007900000-d1ed92b278bc96ae6ebdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1019600000-c907470476ed433e714eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0abc-0019500000-627bd12690a4dc559a07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-4379100000-2566436d8a667838d682Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-8930000000-8acc72953d3f45da3f73Spectrum
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 IDHMDB0000505
FooDB IDFDB011602
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-16581
METLIN ID5491
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID141151
ChEBI ID81308
PubChem Compound ID160636
Kegg Compound IDC17737
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Mitra, 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.
2. Kihira K, Shimazu K, Kuwabara M, Yoshii M, Takeuchi H, Nakano I, Ozawa S, Onuki M, Hatta Y, Hoshita T: Bile acid profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis. Steroids. 1986 Jul-Aug;48(1-2):109-19.
3. 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.
4. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30.
5. Amuro Y, Hayashi E, Endo T, Higashino K, Kishimoto S: Unusual trihydroxylated bile acids in urine of patients with liver cirrhosis. Clin Chim Acta. 1983 Jan 7;127(1):61-7.
6. Clayton PT, Muller DP, Lawson AM: The bile acid composition of gastric contents from neonates with high intestinal obstruction. Biochem J. 1982 Sep 15;206(3):489-98.
7. Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9.
8. Salen G, Tint GS, Eliav B, Deering N, Mosbach EH: Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid. J Clin Invest. 1974 Feb;53(2):612-21.
9. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86.
10. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21.
11. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56.
12. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43.
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=11041240
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=12460600
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=1255017
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=12810826
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=14012853
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=14285492
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=14689221
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=15666352
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=15672658
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=16132221
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=19464381
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=23646473
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=24940599
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=28538412
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=4644219
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=4673765
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=5073332
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=5541504
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=5542000
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=5634890
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=5797529
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=5965294