Glycocholic acid

Identification

Generic Name
Glycocholic acid
DrugBank Accession Number
DB02691
Background

The glycine conjugate of cholic acid. It acts as a detergent to solubilize fats for absorption and is itself absorbed.

Type
Small Molecule
Groups
Experimental, Investigational
Structure
Thumb
Weight
Average: 464.624
Monoisotopic: 464.301761656
Chemical Formula
C26H42NO6
Synonyms
  • N-choloylglycine

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGastrotropinNot AvailableHumans
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
Medicalerrors
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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.
DrugInteraction
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Glycocholic acid.
AcenocoumarolThe risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Glycocholic acid.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Glycocholic acid.
AlteplaseThe risk or severity of bleeding and bruising can be increased when Alteplase is combined with Glycocholic acid.
Aluminium phosphateThe serum concentration of Glycocholic acid can be decreased when it is combined with Aluminium phosphate.
Aluminum chlorideAluminum chloride can cause a decrease in the absorption of Glycocholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum chlorohydrateAluminum chlorohydrate can cause a decrease in the absorption of Glycocholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum hydroxideThe serum concentration of Glycocholic acid can be decreased when it is combined with Aluminum hydroxide.
Aluminum sulfateThe serum concentration of Glycocholic acid can be decreased when it is combined with Aluminum sulfate.
AnagrelideThe risk or severity of adverse effects can be increased when Anagrelide is combined with Glycocholic acid.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
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
Trihydroxy bile acids, alcohols and derivatives / 12-hydroxysteroids / 3-alpha-hydroxysteroids / 7-hydroxysteroids / N-acyl-alpha amino acids / N-acyl amines / Secondary carboxylic acid amides / Secondary alcohols / Cyclic alcohols and derivatives / Polyols
show 8 more
Substituents
12-hydroxysteroid / 3-alpha-hydroxysteroid / 3-hydroxysteroid / 7-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-amino acid or derivatives / Carbonyl group / Carboxamide group / Carboxylic acid
show 23 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
N-acylglycinate (CHEBI:29746)
Affected organisms
Not Available

Chemical Identifiers

UNII
G59NX3I3RT
CAS number
475-31-0
InChI Key
RFDAIACWWDREDC-FRVQLJSFSA-M
InChI
InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/p-1/t14-,15+,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,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetate
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCC([O-])=O

References

General References
Not Available
KEGG Compound
C01921
PubChem Compound
5460316
PubChem Substance
46507924
ChemSpider
4573891
BindingDB
50420252
RxNav
1426482
ChEBI
29746
PDBe Ligand
GCH
Wikipedia
Glycocholic_acid

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Enrolling by InvitationTreatmentBile Acid Synthesis Defect / Inborn Error of Bile Acid Conjugation / Inborn Error of Bile Acid Metabolism1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)166.5 °CPhysProp
water solubility3.3 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.65RODA,A ET AL. (1990)
logS-5.15ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0214 mg/mLALOGPS
logP2.07ALOGPS
logP1.38ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-0.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.92 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity134.43 m3·mol-1ChemAxon
Polarizability52.37 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9543
Blood Brain Barrier+0.8437
Caco-2 permeable-0.8855
P-glycoprotein substrateSubstrate0.7178
P-glycoprotein inhibitor INon-inhibitor0.767
P-glycoprotein inhibitor IINon-inhibitor0.5333
Renal organic cation transporterNon-inhibitor0.8654
CYP450 2C9 substrateNon-substrate0.7788
CYP450 2D6 substrateNon-substrate0.773
CYP450 3A4 substrateSubstrate0.7391
CYP450 1A2 substrateNon-inhibitor0.9382
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8426
Ames testNon AMES toxic0.9154
CarcinogenicityNon-carcinogens0.9478
BiodegradationNot ready biodegradable0.9798
Rat acute toxicity2.5186 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9826
hERG inhibition (predictor II)Non-inhibitor0.7952
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile ac...
Gene Name
FABP6
Uniprot ID
P51161
Uniprot Name
Gastrotropin
Molecular Weight
14371.245 Da
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. [Article]
  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. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [Article]

Drug created on June 13, 2005 13:24 / Updated on August 01, 2020 13:45