Details of the Drug

General Information of Drug (ID: DMUGQIV)

Drug Name
2-chloro-5-nitro-N-phenylbenzamide
Synonyms
2-Chloro-5-nitro-N-phenylbenzamide; GW9662; 22978-25-2; GW 9662; 2-Chloro-5-nitrobenzanilide; GW-9662; MLS001056751; CHEBI:79993; 2-Chloro-5-nitro-N-phenyl-benzamide; 2-Chloro-5-nitro-N-4-phenylbenzamide; benzamide, 2-chloro-5-nitro-N-phenyl-; SMR000326735; (2-chloro-5-nitrophenyl)-N-benzamide; SR-01000075999; Tocris-1508; Spectrum5_001989; Lopac-M-6191; AC1LD8S0; DSSTox_RID_79570; DSSTox_CID_20723; DSSTox_GSID_40723; Lopac0_000798; KBioGR_000361; KBioSS_000361; BSPBio_001021; SCHEMBL420231; CHEMBL375270; GTPL3442; cid_644213
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) 276.67
Logarithm of the Partition Coefficient (xlogp) 3.3
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C13H9ClN2O3
IUPAC Name
2-chloro-5-nitro-N-phenylbenzamide
Canonical SMILES
C1=CC=C(C=C1)NC(=O)C2=C(C=CC(=C2)[N+](=O)[O-])Cl
InChI
InChI=1S/C13H9ClN2O3/c14-12-7-6-10(16(18)19)8-11(12)13(17)15-9-4-2-1-3-5-9/h1-8H,(H,15,17)
InChIKey
DNTSIBUQMRRYIU-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
644213
ChEBI ID
CHEBI:79993
CAS Number
22978-25-2
DrugBank ID
DB07863
TTD ID
D00ACX
INTEDE ID
DR2165

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Peroxisome proliferator-activated receptor gamma (PPAR-gamma) TTZMAO3 PPARG_HUMAN Inhibitor [1]
PPAR-gamma messenger RNA (PPARG mRNA) TTT2SVW PPARG_HUMAN Inhibitor [2]
Retinoic acid receptor RXR-alpha (RXRA) TT6PEUO RXRA_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Oxygen-insensitive NADPH nitroreductase A (nfsA) DEX5D46 NFSA_SALTY Substrate [3]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DEOWDK1 NFSB_SALTY Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [4]
Cytochrome P450 4F2 (CYP4F2) OTKILAER CP4F2_HUMAN Gene/Protein Processing [5]
Cytochrome P450 4V2 (CYP4V2) OTQKNK0D CP4V2_HUMAN Gene/Protein Processing [6]
Glutamate--cysteine ligase catalytic subunit (GCLC) OTESDI4D GSH1_HUMAN Gene/Protein Processing [7]
Glutamate--cysteine ligase regulatory subunit (GCLM) OT6CP234 GSH0_HUMAN Gene/Protein Processing [7]
NAD(P)H dehydrogenase 1 (NQO1) OTZGGIVK NQO1_HUMAN Gene/Protein Processing [7]
Phospholipid-transporting ATPase ABCA1 (ABCA1) OT94G6BQ ABCA1_HUMAN Gene/Protein Processing [8]
Proliferation marker protein Ki-67 (MKI67) OTA8N1QI KI67_HUMAN Gene/Protein Processing [9]
Sterol 26-hydroxylase, mitochondrial (CYP27A1) OT649C01 CP27A_HUMAN Gene/Protein Processing [8]
T-lymphocyte activation antigen CD80 (CD80) OTJBLUQE CD80_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Peroxisome proliferator-activated receptor gamma (PPAR-gamma) DTT PPARG 2.41E-01 -0.06 -0.25
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
2 Tryptophan-containing dipeptide derivatives as potent PPARgamma antagonists: design, synthesis, biological evaluation, and molecular modeling. Eur J Med Chem. 2008 Dec;43(12):2699-716.
3 Effects of bacterial and presystemic nitroreductase metabolism of 2-chloro-5-nitro-N-phenylbenzamide on its mutagenicity and bioavailability. Chem Biol Interact. 2012 Apr 15;197(1):16-22.
4 Concentration-dependent effects of chlorpyrifos oxon on peroxisome proliferator-activated receptor signaling in MCF-7 cells. Toxicol In Vitro. 2022 Feb;78:105268. doi: 10.1016/j.tiv.2021.105268. Epub 2021 Oct 29.
5 CYP4F2 repression and a modified alpha-tocopherol (vitamin E) metabolism are two independent consequences of ethanol toxicity in human hepatocytes. Toxicol In Vitro. 2017 Apr;40:124-133.
6 Expression of CYP4V2 in human THP1 macrophages and its transcriptional regulation by peroxisome proliferator-activated receptor gamma. Toxicol Appl Pharmacol. 2017 Sep 1;330:100-106. doi: 10.1016/j.taap.2017.07.009. Epub 2017 Jul 17.
7 Identification of UV-protective activators of nuclear factor erythroid-derived 2-related factor 2 (Nrf2) by combining a chemical library screen with computer-based virtual screening. J Biol Chem. 2012 Sep 21;287(39):33001-13.
8 Resveratrol mediates anti-atherogenic effects on cholesterol flux in human macrophages and endothelium via PPARgama and adenosine. Eur J Pharmacol. 2013 Jan 5;698(1-3):299-309.
9 Involvement of peroxisome proliferator-activated receptor gamma (PPAR) and autophagic pathways in the mechanism of action of the tris(2,3-dibromopropyl) isocyanurate (TDBP-TAZTO or TBC) flame retardant in the lung adenocarcinoma (A549) cells in vitro. J Appl Toxicol. 2023 Sep;43(9):1358-1367. doi: 10.1002/jat.4470. Epub 2023 Mar 31.
10 9-cis-Retinoic acid (9cRA), a retinoid X receptor (RXR) ligand, exerts immunosuppressive effects on dendritic cells by RXR-dependent activation: inhibition of peroxisome proliferator-activated receptor gamma blocks some of the 9cRA activities, and precludes them to mature phenotype development. J Immunol. 2007 May 15;178(10):6130-9. doi: 10.4049/jimmunol.178.10.6130.