Details of the Drug

General Information of Drug (ID: DM2LZ8F)

Drug Name
Taurocholic Acid
Synonyms
Taurocholic acid; TAUROCHOLIC ACID; Taurocholate; Cholyltaurine; Cholaic acid; N-Choloyltaurine; Cholic acid taurine conjugate; 81-24-3; Taurine, N-choloyl-; Acidum cholatauricum; Taurine Cholate; UNII-5E090O0G3Z; HSDB 832; C26H45NO7S; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid 24-taurine; NSC25505; EINECS 201-336-2; NSC 25505; Ethanesulfonic acid, 2-(((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)amino)-; 2-((3-alpha,7-alpha,12-alpha-Trihydroxy-24-oxo-5-be ta-cholan-24-yl)amino)ethanesulfonic acid; [3H]taurocholic acid
Indication
Disease Entry ICD 11 Status REF
Type-2 diabetes 5A11 Phase 1/2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 515.7
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C26H45NO7S
IUPAC Name
2-[[(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]pentanoyl]amino]ethanesulfonic acid
Canonical SMILES
C[C@H](CCC(=O)NCCS(=O)(=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/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1
InChIKey
WBWWGRHZICKQGZ-HZAMXZRMSA-N
Cross-matching ID
PubChem CID
6675
ChEBI ID
CHEMBL224867
CAS Number
81-24-3
UNII
5E090O0G3Z
DrugBank ID
DB04348
TTD ID
D09NTG
VARIDT ID
DR01121
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bile-salt-activated lipase (CEL) TTTRNQW CEL_HUMAN Inhibitor [2]
Ileal sodium/bile acid cotransporter (SLC10A2) TTPI1M5 NTCP2_HUMAN Modulator [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic solute transporter subunit alpha (SLC51A) DTMEQ32 OSTA_HUMAN Substrate [4]
Apical sodium-dependent bile acid transporter (SLC10A2) DT7JELC NTCP2_HUMAN Substrate [5]
Organic solute transporter subunit beta (SLC51B) DT1V9AJ OSTB_HUMAN Substrate [4]
Organic anion transporting polypeptide 4A1 (SLCO4A1) DT8H2IC SO4A1_HUMAN Substrate [6]
Bile salt export pump (ABCB11) DTJ0EW4 ABCBB_HUMAN Substrate [7]
Sodium/taurocholate cotransporting polypeptide (SLC10A1) DT56EKP NTCP_HUMAN Substrate [8]
Multidrug resistance-associated protein 3 (ABCC3) DTQ3ZHF MRP3_HUMAN Substrate [9]
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [10]
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTPFTEQ SO2B1_HUMAN Substrate [11]
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTE2B1D SO1A2_HUMAN Substrate [12]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [13]
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [14]
Organic anion transporting polypeptide 1B3 (SLCO1B3) DT9C1TS SO1B3_HUMAN Substrate [15]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ABC-type organic anion transporter ABCA8 (ABCA8) OTCWLX6N ABCA8_HUMAN Regulation of Drug Effects [16]
ATP-binding cassette sub-family C member 3 (ABCC3) OTC3IJV4 MRP3_HUMAN Regulation of Drug Effects [17]
Bile acid receptor (NR1H4) OTWZLPTB NR1H4_HUMAN Gene/Protein Processing [18]
Caveolin-2 (CAV2) OT1FGRQX CAV2_HUMAN Regulation of Drug Effects [19]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [20]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [21]
Myc proto-oncogene protein (MYC) OTPV5LUK MYC_HUMAN Gene/Protein Processing [21]
Nuclear receptor subfamily 0 group B member 2 (NR0B2) OT7UVICX NR0B2_HUMAN Gene/Protein Processing [18]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [18]
Organic anion transporter 3 (SLC22A8) OT8BY933 S22A8_HUMAN Regulation of Drug Effects [22]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Type-2 diabetes
ICD Disease Classification 5A11
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Ileal sodium/bile acid cotransporter (SLC10A2) DTT SLC10A2 2.54E-01 -0.06 -0.17
Multidrug resistance-associated protein 3 (ABCC3) DTP MRP3 9.87E-01 -1.86E-01 -4.71E-01
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTP OATP2B1 4.61E-01 -7.46E-02 -2.18E-01
Organic solute transporter subunit alpha (SLC51A) DTP OSTalpha 1.79E-01 -1.10E-01 -2.53E-01
Bile salt export pump (ABCB11) DTP BSEP 5.33E-01 -8.86E-02 -2.56E-01
Breast cancer resistance protein (ABCG2) DTP BCRP 1.85E-01 -1.34E-01 -4.20E-01
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTP OATP1A2 1.39E-01 -6.13E-01 -6.63E-01
Multidrug resistance-associated protein 4 (ABCC4) DTP MRP4 6.77E-01 3.03E-02 1.51E-01
Organic anion transporting polypeptide 1B3 (SLCO1B3) DTP OATP1B3 5.85E-01 1.81E-01 6.68E-01
Organic anion transporting polypeptide 4A1 (SLCO4A1) DTP OATP4A1 5.51E-01 -6.63E-03 -5.81E-02
Apical sodium-dependent bile acid transporter (SLC10A2) DTP ASBT 2.54E-01 -6.48E-02 -1.69E-01
Sodium/taurocholate cotransporting polypeptide (SLC10A1) DTP NTCP 2.93E-01 2.87E-02 1.38E-01
Organic anion transporting polypeptide 1B1 (SLCO1B1) DTP OATP1B1 2.81E-01 3.67E-02 2.82E-01
Organic solute transporter subunit beta (SLC51B) DTP OSTbeta 4.32E-01 1.33E-01 1.00E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 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: 4547).
2 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
3 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.
4 Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta. J Biol Chem. 2003 Jul 25;278(30):27473-82.
5 Identification of a region of the ileal-type sodium/bile acid cotransporter interacting with a competitive bile acid transport inhibitor. Biochemistry. 2002 Dec 17;41(50):14916-24.
6 Identification of thyroid hormone transporters in humans: different molecules are involved in a tissue-specific manner. Endocrinology. 2001 May;142(5):2005-12.
7 Inhibition of transport across the hepatocyte canalicular membrane by the antibiotic fusidate. Biochem Pharmacol. 2002 Jul 1;64(1):151-8.
8 Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity. J Pharmacol Exp Ther. 1999 Dec;291(3):1204-9.
9 Characterization of the role of polar amino acid residues within predicted transmembrane helix 17 in determining the substrate specificity of multidrug resistance protein 3. Biochemistry. 2003 Aug 26;42(33):9989-10000.
10 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
11 Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human. J Pharmacol Exp Ther. 2004 Feb;308(2):438-45.
12 Identification of multiple binding sites for substrate transport in bovine organic anion transporting polypeptide 1a2. Drug Metab Dispos. 2013 Mar;41(3):602-7.
13 Characterization of the role of ABCG2 as a bile acid transporter in liver and placenta. Mol Pharmacol. 2012 Feb;81(2):273-83.
14 Identification of a novel gene family encoding human liver-specific organic anion transporter LST-1. J Biol Chem. 1999 Jun 11;274(24):17159-63.
15 Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3. Eur J Pharmacol. 2008 Apr 14;584(1):57-65.
16 Functional analysis of ABCA8, a new drug transporter. Biochem Biophys Res Commun. 2002 Oct 18;298(1):41-5.
17 Uremic solutes modulate hepatic bile acid handling and induce mitochondrial toxicity. Toxicol In Vitro. 2019 Apr;56:52-61. doi: 10.1016/j.tiv.2019.01.003. Epub 2019 Jan 9.
18 Role of vitamin C transporters and biliverdin reductase in the dual pro-oxidant and anti-oxidant effect of biliary compounds on the placental-fetal unit in cholestasis during pregnancy. Toxicol Appl Pharmacol. 2008 Oct 15;232(2):327-36.
19 Hepatic overexpression of caveolins increases bile salt secretion in mice. Hepatology. 2003 Dec;38(6):1477-88. doi: 10.1016/j.hep.2003.09.011.
20 Taurocholate induces cyclooxygenase-2 expression via the sphingosine 1-phosphate receptor 2 in a human cholangiocarcinoma cell line. J Biol Chem. 2015 Dec 25;290(52):30988-1002.
21 Sorafenib triggers antiproliferative and pro-apoptotic signals in human esophageal adenocarcinoma cells. Dig Dis Sci. 2008 Dec;53(12):3055-64. doi: 10.1007/s10620-008-0294-y. Epub 2008 May 30.
22 Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86.