JN3

CHENODEOXYCHOLIC ACID

Created: 2007-01-02
Last modified:  2021-03-13

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Chemical Details

Formal Charge0
Atom Count68
Chiral Atom Count10
Bond Count71
Aromatic Bond Count0
2D diagram of JN3
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Chemical Component Summary

NameCHENODEOXYCHOLIC ACID
Synonyms(3ALPHA,5ALPHA,7BETA,8ALPHA,17ALPHA)-3,7-DIHYDROXYCHOLAN-24-OIC ACID
Systematic Name (OpenEye OEToolkits)(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 O4
Molecular Weight392.572
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(O)CCC(C4C3(C(C1C(C2(C(CC1O)CC(O)CC2)C)CC3)CC4)C)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]3CC[C]12C
SMILESOpenEye OEToolkits1.5.0CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)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]3CC[C@]12C
Canonical SMILESOpenEye OEToolkits1.5.0 C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
InChIInChI1.03 InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
InChIKeyInChI1.03 RUDATBOHQWOJDD-BSWAIDMHSA-N

Drug Info: DrugBank

DrugBank IDDB06777 
NameChenodeoxycholic acid
Groups approved
DescriptionChenodeoxycholic acid (or Chenodiol) is an epimer of ursodeoxycholic acid (DB01586). Chenodeoxycholic acid is a bile acid naturally found in the body. It works by dissolving the cholesterol that makes gallstones and inhibiting production of cholesterol in the liver and absorption in the intestines, which helps to decrease the formation of gallstones. It can also reduce the amount of other bile acids that can be harmful to liver cells when levels are elevated.
Synonyms
  • 3alpha,7alpha-Dihydroxy-5beta-cholanic acid
  • Chenodesoxycholic acid
  • Chenocholic acid
  • Anthropodeoxycholic acid
  • Chenodiol
Brand Names
  • Chenodeoxycholic Acid Leadiant
  • Chenodiol
  • Chenodal
IndicationChenodiol is indicated for patients with radiolucent stones in well-opacifying gallbladders, in whom selective surgery would be undertaken except for the presence of increased surgical risk due to systemic disease or age. Chenodiol will not dissolve calcified (radiopaque) or radiolucent bile pigment stones.
Categories
  • Alimentary Tract and Metabolism
  • Bile Acid Preparations
  • Bile acids and derivatives
  • Bile Acids and Salts
  • Bile and Liver Therapy
ATC-CodeA05AA01
CAS number474-25-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Bile acid receptorMVMQFQGLENPIQISPHCSCTPSGFFMEMMSMKPAKGVLTEQVAGPLGQN...unknownother
Nuclear receptor subfamily 1 group I member 2MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...unknown
G-protein coupled bile acid receptor 1MTPNSTGEVPSPIPKGALGLSLALASLIITANLLLALGIAWDRRLRSPPA...unknown
Aldo-keto reductase family 1 member C2MDSKYQCVKLNDGHFMPVLGFGTYAPAEVPKSKALEAVKLAIEAGFHHID...unknownsubstrate
Sterol 26-hydroxylase, mitochondrialMAALGCARLRWALRGAGRGLCPHGARAKAAIPAALPSDKATGAPGAGPGV...unknownsubstrate
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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
Pharos CHEMBL240597
PubChem 10133
ChEMBL CHEMBL240597
ChEBI CHEBI:16755
CCDC/CSD SIFGOD