Details of the Drug

General Information of Drug (ID: DMFKRQE)

Drug Name
tauroursodeoxycholic acid
Synonyms tauroursodeoxycholate; TUDCA
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 499.7
Logarithm of the Partition Coefficient (xlogp) 3.6
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C26H45NO6S
IUPAC Name
2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
InChI
InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1
InChIKey
BHTRKEVKTKCXOH-LBSADWJPSA-N
Cross-matching ID
PubChem CID
9848818
ChEBI ID
CHEBI:80774
CAS Number
14605-22-2
DrugBank ID
DB08834
TTD ID
D03RKW
VARIDT ID
DR00519

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [2]
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTE2B1D SO1A2_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cyclic AMP-dependent transcription factor ATF-4 (ATF4) OTRFV19J ATF4_HUMAN Gene/Protein Processing [4]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Biotransformations [5]
Endothelin-1 (EDN1) OTZCACEG EDN1_HUMAN Gene/Protein Processing [6]
Fatty acid-binding protein, adipocyte (FABP4) OT3DKFOU FABP4_HUMAN Gene/Protein Processing [4]
G-protein coupled bile acid receptor 1 (GPBAR1) OT4BKEJ9 GPBAR_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction 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: 4746).
2 Human multidrug resistance protein 2 transports the therapeutic bile salt tauroursodeoxycholate. J Pharmacol Exp Ther. 2007 Feb;320(2):893-9.
3 Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver. Gastroenterology. 1995 Oct;109(4):1274-82.
4 Ursodeoxycholic acid but not tauroursodeoxycholic acid inhibits proliferation and differentiation of human subcutaneous adipocytes. PLoS One. 2013 Dec 3;8(12):e82086. doi: 10.1371/journal.pone.0082086. eCollection 2013.
5 Novel insights into bile acid detoxification via CYP, UGT and SULT enzymes. Toxicol In Vitro. 2023 Mar;87:105533. doi: 10.1016/j.tiv.2022.105533. Epub 2022 Dec 5.
6 Ursodeoxycholic acid inhibits endothelin-1 production in human vascular endothelial cells. Eur J Pharmacol. 2004 Nov 28;505(1-3):67-74. doi: 10.1016/j.ejphar.2004.10.042.