Details of the Drug

General Information of Drug (ID: DM2KEW6)

Drug Name
3R14S-OCHRATOXIN A
Synonyms
Ochratoxin A; OCHRATOXIN A; Antibiotic 9663; 303-47-9; Phenylalanine - ochratoxin A; NCI-C56586; C20H18ClNO6; CHEBI:7719; RWQKHEORZBHNRI-BMIGLBTASA-N; Ochratoxin A, aspergillus ochraceus; Ochratoxin A-BSA conjugate from Aspergillus ochraceus; N-(((3R)-5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenyl-L-alanine; (-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine; NSC 201422; UNII-1779SX6LUY; OTA; ochratoxin A
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 403.8
Logarithm of the Partition Coefficient (xlogp) 4.7
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C20H18ClNO6
IUPAC Name
(2S)-2-[[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoic acid
Canonical SMILES
C[C@@H]1CC2=C(C=C(C(=C2C(=O)O1)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O)Cl
InChI
InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1
InChIKey
RWQKHEORZBHNRI-BMIGLBTASA-N
Cross-matching ID
PubChem CID
442530
ChEBI ID
CHEMBL589366
CAS Number
303-47-9
TTD ID
D0KN6Q
VARIDT ID
DR00229
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
Solute carrier family 22 member 8 (SLC22A8) TTTQR47 S22A8_HUMAN Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
ATP-binding cassette sub-family A member 8 (ABCA8) DT9NXMV ABCA8_HUMAN Substrate [3]
Organic anion transporter 4 (SLC22A11) DT06JWZ S22AB_HUMAN Substrate [4]
Organic anion transporter 1 (SLC22A6) DTQ23VB S22A6_HUMAN Substrate [5]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1 (PLCG1) OTSBQR6D PLCG1_HUMAN Gene/Protein Processing [6]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2 (PLCG2) OTGVC9MY PLCG2_HUMAN Gene/Protein Processing [6]
14-3-3 protein sigma (SFN) OTLJCZ1U 1433S_HUMAN Gene/Protein Processing [7]
2-oxoglutarate dehydrogenase complex component E1 (OGDH) OTHGTQWF ODO1_HUMAN Gene/Protein Processing [8]
24-hydroxycholesterol 7-alpha-hydroxylase (CYP39A1) OTBAJT4I CP39A_HUMAN Gene/Protein Processing [9]
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 (HSD3B1) OTNAZVKB 3BHS1_HUMAN Gene/Protein Processing [10]
3-ketoacyl-CoA thiolase, peroxisomal (ACAA1) OTVKRET0 THIK_HUMAN Gene/Protein Processing [11]
4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6 (FUT6) OTBZUQ7F FUT6_HUMAN Gene/Protein Processing [11]
5-azacytidine-induced protein 2 (AZI2) OT61Q7Q8 AZI2_HUMAN Gene/Protein Processing [9]
5-demethoxyubiquinone hydroxylase, mitochondrial (COQ7) OTSLAEUP COQ7_HUMAN Gene/Protein Processing [11]
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: 4672).
2 Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members. J Biol Chem. 2007 Aug 17;282(33):23841-53.
3 Functional analysis of ABCA8, a new drug transporter. Biochem Biophys Res Commun. 2002 Oct 18;298(1):41-5.
4 Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75.
5 Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35.
6 Inhibition of CXCL12-mediated chemotaxis of Jurkat cells by direct immunotoxicants. Arch Toxicol. 2016 Jul;90(7):1685-94. doi: 10.1007/s00204-015-1585-7. Epub 2015 Aug 28.
7 Comparison of base-line and chemical-induced transcriptomic responses in HepaRG and RPTEC/TERT1 cells using TempO-Seq. Arch Toxicol. 2018 Aug;92(8):2517-2531.
8 Ochratoxin A induces reprogramming of glucose metabolism by switching energy metabolism from oxidative phosphorylation to glycolysis in human gastric epithelium GES-1 cells in vitro. Toxicol Lett. 2020 Oct 15;333:232-241. doi: 10.1016/j.toxlet.2020.08.008. Epub 2020 Aug 22.
9 Persistence of epigenomic effects after recovery from repeated treatment with two nephrocarcinogens. Front Genet. 2018 Dec 3;9:558.
10 Potential endocrine disrupting effect of ochratoxin A on human placental 3beta-hydroxysteroid dehydrogenase/isomerase in JEG-3 cells at levels relevant to human exposure. Reprod Toxicol. 2013 Jul;38:47-52.
11 Ochratoxin a lowers mRNA levels of genes encoding for key proteins of liver cell metabolism. Cancer Genomics Proteomics. 2008 Nov-Dec;5(6):319-32.