Details of the Drug

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]
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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)

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Repurposed Drugs (RPD)

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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]

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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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Sulfotransferase 1A1 (SULT1A1)_{Main DME}	DEYWLRK	ST1A1_HUMAN	Substrate	[10]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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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
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Cholic Acid 50mg capsule	50mg	Capsule	Oral
Cholic Acid 250mg capsule	250mg	Capsule	Oral

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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.