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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:7719
CAS Number: 303-47-9
TTD ID: D0KN6Q
VARIDT ID: DR00229

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]

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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]

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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-aminomuconic semialdehyde dehydrogenase (ALDH8A1)	OTINY3MW	AL8A1_HUMAN	Gene/Protein Processing	[8]
2-oxoglutarate dehydrogenase complex component E1 (OGDH)	OTHGTQWF	ODO1_HUMAN	Gene/Protein Processing	[9]
24-hydroxycholesterol 7-alpha-hydroxylase (CYP39A1)	OTBAJT4I	CP39A_HUMAN	Gene/Protein Processing	[10]
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 (HSD3B1)	OTNAZVKB	3BHS1_HUMAN	Gene/Protein Processing	[11]
3-ketoacyl-CoA thiolase, peroxisomal (ACAA1)	OTVKRET0	THIK_HUMAN	Gene/Protein Processing	[12]
4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT6 (FUT6)	OTBZUQ7F	FUT6_HUMAN	Gene/Protein Processing	[12]
5-azacytidine-induced protein 2 (AZI2)	OT61Q7Q8	AZI2_HUMAN	Gene/Protein Processing	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

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	Transcriptome-based functional classifiers for direct immunotoxicity. Arch Toxicol. 2014 Mar;88(3):673-89.
9	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.
10	Persistence of epigenomic effects after recovery from repeated treatment with two nephrocarcinogens. Front Genet. 2018 Dec 3;9:558.
11	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.
12	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.