Glycochenodeoxycholic Acid
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Identification
- Generic Name
- Glycochenodeoxycholic Acid
- DrugBank Accession Number
- DB02123
- Background
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]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 449.6233
Monoisotopic: 449.314123491 - Chemical Formula
- C26H43NO5
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U7-alpha-hydroxysteroid dehydrogenase Not Available Escherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The risk or severity of adverse effects can be increased when Abciximab is combined with Glycochenodeoxycholic Acid. Acenocoumarol The risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Glycochenodeoxycholic Acid. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Glycochenodeoxycholic Acid. Alteplase The risk or severity of bleeding and bruising can be increased when Alteplase is combined with Glycochenodeoxycholic Acid. Aluminium phosphate Aluminium phosphate can cause a decrease in the absorption of Glycochenodeoxycholic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy. - Food Interactions
- Not Available
Categories
- Drug Categories
- Amino Acids
- Amino Acids, Peptides, and Proteins
- Bile Acids and Salts
- BSEP/ABCB11 Inhibitors
- BSEP/ABCB11 Substrates
- Cholanes
- Cholic Acids
- Compounds used in a research, industrial, or household setting
- Detergents
- Fused-Ring Compounds
- Glycodeoxycholic Acid
- Household Products
- N-substituted Glycines
- Steroids
- Surface-Active Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as glycinated bile acids and derivatives. These are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Bile acids, alcohols and derivatives
- Direct Parent
- Glycinated bile acids and derivatives
- Alternative Parents
- Dihydroxy bile acids, alcohols and derivatives / 7-hydroxysteroids / 3-alpha-hydroxysteroids / N-acyl-alpha amino acids / N-acyl amines / Secondary carboxylic acid amides / Secondary alcohols / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids show 5 more
- Substituents
- 3-alpha-hydroxysteroid / 3-hydroxysteroid / 7-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-amino acid or derivatives / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative show 20 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- bile acid glycine conjugate (CHEBI:36274) / C26 bile acids, alcohols, and derivatives (C05466) / Glycine conjugates (LMST05030008)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 451ZNJ667Y
- CAS number
- 640-79-9
- InChI Key
- GHCZAUBVMUEKKP-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-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11aR)-4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-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
References
- General References
- Not Available
- External Links
- KEGG Compound
- C05466
- PubChem Compound
- 12544
- PubChem Substance
- 46506300
- ChemSpider
- 12027
- BindingDB
- 50375590
- ChEBI
- 36274
- ChEMBL
- CHEMBL1552
- ZINC
- ZINC000003914812
- PDBe Ligand
- CHO
- PDB Entries
- 1ahi / 1fmc / 2b04 / 2lba / 2lfo / 2mm3 / 6e47 / 6gvz / 6gw1 / 6gw4 … show 5 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 3.15 mg/L (at 20 °C) RODA,A ET AL. (1990) logP 2.12 RODA,A ET AL. (1990) - Predicted Properties
Property Value Source Water Solubility 0.00793 mg/mL ALOGPS logP 2.4 ALOGPS logP 2.61 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 3.77 Chemaxon pKa (Strongest Basic) -0.49 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 106.86 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 122.08 m3·mol-1 Chemaxon Polarizability 52.05 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 215.4906668 predictedDarkChem Lite v0.1.0 [M-H]- 216.47783 predictedDeepCCS 1.0 (2019) [M+H]+ 217.6606668 predictedDarkChem Lite v0.1.0 [M+H]+ 218.20155 predictedDeepCCS 1.0 (2019) [M+Na]+ 215.1526668 predictedDarkChem Lite v0.1.0 [M+Na]+ 224.53123 predictedDeepCCS 1.0 (2019)
Targets
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1. Details7-alpha-hydroxysteroid dehydrogenase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Identical protein binding
- Specific Function
- 7-alpha-dehydroxylation of cholic acid, yielding deoxycholic acid and lithocholic acid, respectively. Highest affinity with taurochenodeoxycholic acid.
- Gene Name
- hdhA
- Uniprot ID
- P0AET8
- Uniprot Name
- 7-alpha-hydroxysteroid dehydrogenase
- Molecular Weight
- 26778.32 Da
References
Transporters
1. DetailsBile salt export pump
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Transporter activity
- Specific Function
- Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
- Gene Name
- ABCB11
- Uniprot ID
- O95342
- Uniprot Name
- Bile salt export pump
- Molecular Weight
- 146405.83 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- 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. [Article]
- 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. [Article]
3. DetailsIleal sodium/bile acid cotransporter
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Bile acid:sodium symporter activity
- Specific Function
- Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism.
- Gene Name
- SLC10A2
- Uniprot ID
- Q12908
- Uniprot Name
- Ileal sodium/bile acid cotransporter
- Molecular Weight
- 37713.405 Da
References
- 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. [Article]
- 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. [Article]
4. DetailsSodium/bile acid cotransporter
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Virus receptor activity
- Specific Function
- The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
- Gene Name
- SLC10A1
- Uniprot ID
- Q14973
- Uniprot Name
- Sodium/bile acid cotransporter
- Molecular Weight
- 38118.64 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52