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Identification
NameGlycochenodeoxycholic Acid
Accession NumberDB02123  (EXPT00909)
Typesmall molecule
Groupsexperimental
Description

A bile salt formed in the liver from chenodeoxycholate and glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number640-79-9
WeightAverage: 449.6233
Monoisotopic: 449.314123491
Chemical FormulaC26H43NO5
InChI KeyGHCZAUBVMUEKKP-GYPHWSFCSA-N
InChI
InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-/m1/s1
IUPAC Name
2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
SMILES
C[C@H](CCC(=O)NCC(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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassBile Acids, Alcohols and Derivatives
Direct parentDihydroxy Bile Acids, Alcohols and Derivatives
Alternative parentsHydroxysteroids; N-acyl-alpha Amino Acids; Cyclohexanols; Secondary Carboxylic Acid Amides; Cyclic Alcohols and Derivatives; Polyamines; Enolates; Carboxylic Acids
Substituents7-hydroxy-steroid; 3-hydroxy-steroid; n-acyl-alpha amino acid or derivative; n-acyl-alpha-amino acid; alpha-amino acid or derivative; cyclohexanol; cyclic alcohol; secondary alcohol; carboxamide group; secondary carboxylic acid amide; carboxylic acid derivative; enolate; carboxylic acid; polyamine; organonitrogen compound; amine; alcohol
Classification descriptionThis compound belongs to the dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9543
Blood Brain Barrier + 0.8437
Caco-2 permeable - 0.8855
P-glycoprotein substrate Substrate 0.7178
P-glycoprotein inhibitor I Non-inhibitor 0.767
P-glycoprotein inhibitor II Non-inhibitor 0.5333
Renal organic cation transporter Non-inhibitor 0.8654
CYP450 2C9 substrate Non-substrate 0.7788
CYP450 2D6 substrate Non-substrate 0.773
CYP450 3A4 substrate Substrate 0.7391
CYP450 1A2 substrate Non-inhibitor 0.9382
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8426
Ames test Non AMES toxic 0.9154
Carcinogenicity Non-carcinogens 0.9478
Biodegradation Not ready biodegradable 0.9798
Rat acute toxicity 2.5186 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9826
hERG inhibition (predictor II) Non-inhibitor 0.7952
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubility3.15 mg/L (at 20 °C)RODA,A ET AL. (1990)
logP2.12RODA,A ET AL. (1990)
Predicted Properties
PropertyValueSource
water solubility7.93e-03 g/lALOGPS
logP2.4ALOGPS
logP2.61ChemAxon
logS-4.8ALOGPS
pKa (strongest acidic)3.77ChemAxon
pKa (strongest basic)-0.29ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count4ChemAxon
polar surface area106.86ChemAxon
rotatable bond count6ChemAxon
refractivity122.08ChemAxon
polarizability52.08ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC05466
PubChem Compound12544
PubChem Substance46506300
ChemSpider25982
ChEBI36274
ChEMBL
HETCHO
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 7-alpha-hydroxysteroid dehydrogenase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
7-alpha-hydroxysteroid dehydrogenase P0AET8 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Transporters

1. Bile salt export pump

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Bile salt export pump O95342 Details

References:

  1. Byrne JA, Strautnieks SS, Mieli-Vergani G, Higgins CF, Linton KJ, Thompson RJ: The human bile salt export pump: characterization of substrate specificity and identification of inhibitors. Gastroenterology. 2002 Nov;123(5):1649-58. Pubmed
  2. Stieger B, Fattinger K, Madon J, Kullak-Ublick GA, Meier PJ: Drug- and estrogen-induced cholestasis through inhibition of the hepatocellular bile salt export pump (Bsep) of rat liver. Gastroenterology. 2000 Feb;118(2):422-30. Pubmed
  3. Mita S, Suzuki H, Akita H, Stieger B, Meier PJ, Hofmann AF, Sugiyama Y: Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G159-67. Epub 2004 Aug 5. Pubmed

2. Solute carrier organic anion transporter family member 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 1A2 P46721 Details

References:

  1. Kullak-Ublick GA, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ: Functional characterization of the basolateral rat liver organic anion transporting polypeptide. Hepatology. 1994 Aug;20(2):411-6. Pubmed
  2. Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. Pubmed

3. Ileal sodium/bile acid cotransporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Ileal sodium/bile acid cotransporter Q12908 Details

References:

  1. Craddock AL, Love MW, Daniel RW, Kirby LC, Walters HC, Wong MH, Dawson PA: Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am J Physiol. 1998 Jan;274(1 Pt 1):G157-69. Pubmed
  2. Walters HC, Craddock AL, Fusegawa H, Willingham MC, Dawson PA: Expression, transport properties, and chromosomal location of organic anion transporter subtype 3. Am J Physiol Gastrointest Liver Physiol. 2000 Dec;279(6):G1188-200. Pubmed

4. Sodium/bile acid cotransporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Sodium/bile acid cotransporter Q14973 Details

References:

  1. Mita S, Suzuki H, Akita H, Stieger B, Meier PJ, Hofmann AF, Sugiyama Y: Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G159-67. Epub 2004 Aug 5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17