General Information of Drug (ID: DM7OKQV)

Drug Name
Cholic Acid
Synonyms
cholic acid; 81-25-4; Cholalic acid; cholate; Cholalin; Colalin; Cholsaeure; NSC-6135; Cholic acid, 5beta-; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic acid; UNII-G1JO7801AE; HSDB 982; (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid; Cholic acid [USAN]; 3,7,12-Trihydroxycholanic acid; G1JO7801AE; CHEMBL205596; CHEBI:16359; NSC6135; BHQCQFFYRZLCQQ-OELDTZBJSA-N
Indication
Disease Entry ICD 11 Status REF
Cholelithiasis DC11 Approved [1]
Peroxisomal disorder 5C57 Approved [2]
Synthesis disorder 5C52-5C59 Approved [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 408.6
Logarithm of the Partition Coefficient (xlogp) 3.6
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C24H40O5
IUPAC Name
(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
Canonical SMILES
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
InChI
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
InChIKey
BHQCQFFYRZLCQQ-OELDTZBJSA-N
Cross-matching ID
PubChem CID
221493
ChEBI ID
CHEBI:16359
CAS Number
81-25-4
DrugBank ID
DB02659
TTD ID
D0OR2L
VARIDT ID
DR00657
INTEDE ID
DR0314
ACDINA ID
D00943
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Ferrochelatase (FECH) TTQ6VF4 HEMH_HUMAN Inhibitor [3]
Liver carboxylesterase (CES1) TTMF541 EST1_HUMAN Inhibitor [3]
Phospholipase A2 (PLA2G1B) TT9V5JH PA21B_HUMAN Inhibitor [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Apical sodium-dependent bile acid transporter (SLC10A2) DT7JELC NTCP2_HUMAN Substrate [4]
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [5]
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [6]
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTE2B1D SO1A2_HUMAN Substrate [7]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [8]
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Sulfotransferase 1A1 (SULT1A1)
Main DME
DEYWLRK ST1A1_HUMAN Substrate [10]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase (CYP8B1) OTRI4UR1 CP8B1_HUMAN Gene/Protein Processing [11]
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Gene/Protein Processing [11]
ATP-binding cassette sub-family C member 3 (ABCC3) OTC3IJV4 MRP3_HUMAN Gene/Protein Processing [11]
ATP-binding cassette sub-family G member 5 (ABCG5) OT1OMY93 ABCG5_HUMAN Gene/Protein Processing [11]
Bile acid receptor (NR1H4) OTWZLPTB NR1H4_HUMAN Gene/Protein Processing [11]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [12]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [13]
Cytochrome P450 7A1 (CYP7A1) OT8Z5KLD CP7A1_HUMAN Gene/Protein Processing [12]
Fibroblast growth factor 19 (FGF19) OT2DVJWY FGF19_HUMAN Gene/Protein Processing [11]
G-protein coupled bile acid receptor 1 (GPBAR1) OT4BKEJ9 GPBAR_HUMAN Gene/Protein Processing [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Cholelithiasis
ICD Disease Classification DC11
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Liver carboxylesterase (CES1) DTT CES1 3.82E-08 1.86 1.9
Breast cancer resistance protein (ABCG2) DTP BCRP 2.28E-08 -3.66E-01 -8.07E-01
Multidrug resistance-associated protein 2 (ABCC2) DTP MRP2 4.30E-02 -2.29E-01 -9.10E-01
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTP OATP1A2 7.28E-02 -7.13E-02 -4.55E-01
Multidrug resistance-associated protein 4 (ABCC4) DTP MRP4 1.52E-01 4.56E-01 8.84E-01
Apical sodium-dependent bile acid transporter (SLC10A2) DTP ASBT 4.03E-01 -2.62E-02 -1.26E-01
Organic anion transporting polypeptide 1B1 (SLCO1B1) DTP OATP1B1 3.27E-01 -5.78E-02 -3.84E-01
Sulfotransferase 1A1 (SULT1A1) DME SULT1A1 1.61E-12 1.01E+00 1.51E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Gelatin E00630 Not Available Other agent
Magnesium stearate E00208 11177 lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Haematite red E00236 14833 Colorant
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Cholic Acid 50mg capsule 50mg Capsule Oral
Cholic Acid 250mg capsule 250mg Capsule Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Cholic acid FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 609).
3 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
4 Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am J Physiol. 1998 Jan;274(1):G157-69.
5 Multiple pathways for fluoroquinolone secretion by human intestinal epithelial (Caco-2) cells. Br J Pharmacol. 2002 Mar;135(5):1263-75.
6 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
7 Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver. Gastroenterology. 1995 Oct;109(4):1274-82.
8 Characterization of the role of ABCG2 as a bile acid transporter in liver and placenta. Mol Pharmacol. 2012 Feb;81(2):273-83.
9 Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
10 Kinetic analysis of bile acid sulfation by stably expressed human sulfotransferase 2A1 (SULT2A1). Xenobiotica. 2010 Mar;40(3):184-94.
11 Potency of individual bile acids to regulate bile acid synthesis and transport genes in primary human hepatocyte cultures. Toxicol Sci. 2014 Oct;141(2):538-46. doi: 10.1093/toxsci/kfu151. Epub 2014 Jul 23.
12 The farnesoid X receptor controls gene expression in a ligand- and promoter-selective fashion. J Biol Chem. 2004 Mar 5;279(10):8856-61. doi: 10.1074/jbc.M306422200. Epub 2003 Dec 18.
13 Acetylated deoxycholic (DCA) and cholic (CA) acids are potent ligands of pregnane X (PXR) receptor. Toxicol Lett. 2017 Jan 4;265:86-96.