CHD

CHOLIC ACID

Created:2000-02-08
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count69
Chiral Atom Count11
Bond Count72
Aromatic Bond Count0
2D diagram of CHD
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Chemical Component Summary

NameCHOLIC ACID
Systematic Name (OpenEye OEToolkits)(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
FormulaC24 H40 O5
Molecular Weight408.571
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04O=C(O)CCC(C3CCC2C1C(O)CC4CC(O)CCC4(C)C1CC(O)C23C)C
SMILESCACTVS3.341C[CH](CCC(O)=O)[CH]1CC[CH]2[CH]3[CH](O)C[CH]4C[CH](O)CC[C]4(C)[CH]3C[CH](O)[C]12C
SMILESOpenEye OEToolkits1.5.0CC(CCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
Canonical SMILESCACTVS3.341 C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
Canonical SMILESOpenEye OEToolkits1.5.0 C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
InChIInChI1.03 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
InChIKeyInChI1.03 BHQCQFFYRZLCQQ-OELDTZBJSA-N

Drug Info: DrugBank

DrugBank IDDB02659 
NameCholic Acid
Groups approved
DescriptionA major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. [PubChem] Cholic acid, formulated as Cholbam capsules, is approved by the United States Food and Drug Administration as a treatment for children and adults with bile acid synthesis disorders due to single enzyme defects, and for peroxisomal disorders (such as Zellweger syndrome).
SynonymsCholic Acid
Brand Names
  • Orphacol
  • Kolbam
  • Cholbam
IndicationOral cholic acid is indicated for: treatment of bile acid synthesis disorders due to single enzyme defects; and as adjunctive treatment of peroxisomal disorders including Zellweger spectrum disorders in patients who exhibit manifestations of liver disease, steatorrhea or complications from decreased fat soluble vitamin absorption.
Categories
  • Alimentary Tract and Metabolism
  • Bile Acid Preparations
  • Bile acids and derivatives
  • Bile Acids and Salts
  • Bile and Liver Therapy
ATC-CodeA05AA03
CAS number81-25-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Phospholipase A2MKLLVLAVLLTVAAADSGISPRAVWQFRKMIKCVIPGSDPFLEYNNYGCY...unknowninhibitor
Ferrochelatase, mitochondrialMRSLGANMAAALRAAGVLLRDPLASSSWRVCQPWRWKSGAAAAAVTTETA...unknowninhibitor
Liver carboxylesterase 1MWLRAFILATLSASAAWGHPSSPPVVDTVHGKVLGKFVSLEGFAQPVAIF...unknowninhibitor
Alcohol dehydrogenase 1CMSTAGKVIKCKAAVLWELKKPFSIEEVEVAPPKAHEVRIKMVAAGICRSD...unknown
Estrogen-related receptor gammaMDSVELCLPESFSLHYEEELLCRMSNKDRHIDSSCSSFIKTEPSSPASLT...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 221493
ChEMBL CHEMBL205596
ChEBI CHEBI:16359
CCDC/CSD APUTIP01, GEKKEP, BIFQAI01, LEVTAH, JEYDEW01, JOQHEC, GEKKIT, GUNPOU, PAZYOG, GUNNAE, GUNMIL, APUTIP, ECARAB, NUMVEW, BUGJES01, GUNLEG, JEYDEW, GUNLIK, PAZYIA, GUNKUV, GUNKOP, DUYBEF, GUNPUA, LAFCAW, LAFCEA, GUNMEH, PEHYOR, GUNNEI, GUNLUW, HURNUD, JOLFIZ, GUNMOR, GUNMUX, HURPEP, GUNLAC, GUNNOS, GUNPIO, ERIPUQ, ERIPEA, GUNNUY, GUNMAD
COD 4116788, 4511132, 4116789, 1507695, 4503333, 2007477, 1507694, 4503332, 7203349, 7216028, 7212033, 7203342, 7216021, 4503337, 7203339, 7216018, 7212790, 4503335, 7203345, 7216024, 4503338, 7203348, 7216027, 2018089, 7203341, 7216020, 7203347, 7216026, 4503331, 4503334, 7203340, 7216019, 7203344, 7216023, 4503336