Details of the Drug

General Information of Drug (ID: DMNBA0G)

Drug Name
BENZOQUINONE
Synonyms
p-benzoquinone; Benzoquinone; 1,4-BENZOQUINONE; Quinone; 106-51-4; p-Quinone; Chinone; 2,5-Cyclohexadiene-1,4-dione; para-Benzoquinone; cyclohexa-2,5-diene-1,4-dione; Cyclohexadienedione; para-Quinone; 1,4-Benzoquine; Steara pbq; 1,4-Dioxybenzene; p-Chinon; 1,4-Cyclohexadienedione; Benzo-chinon; Benzo-1,4-quinone; 1,4-Diossibenzene; Chinon; 1,4-Dioxy-benzol; 1,4-Cyclohexadiene dioxide; Semiquinone anion; semiquinone radicals; RCRA waste number U197; p-Chinon [German]; NCI-C55845; Caswell No. 719C; Benzo-chinon [German]; USAF P-220
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
ATC Code
P01AX04: BENZOQUINONE
P01AX: Other agents against amoebiasis and other protozoal diseases
P01A: AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
P01: ANTIPROTOZOALS
P: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 108.09
Logarithm of the Partition Coefficient (xlogp) 0.2
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C6H4O2
IUPAC Name
cyclohexa-2,5-diene-1,4-dione
Canonical SMILES
C1=CC(=O)C=CC1=O
InChI
InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
InChIKey
AZQWKYJCGOJGHM-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4650
ChEBI ID
CHEMBL8320
CAS Number
106-51-4
TTD ID
D0M2EM
INTEDE ID
DR2205
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA 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
Acetylcholinesterase (AChE) TT1RS9F ACES_HUMAN Inhibitor [2]
Cholinesterase (BCHE) TTEB0GD CHLE_HUMAN Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Nitroreductase (NTR) DEAN5EW NFSB_ENTCL Substrate [3]
Retro-nitroreductase (rNR) DEKVGPX A0A0H3CM55_ENTCC Substrate [4]
Sulfide-quinone reductase (SQR) DEGLTNR SQRD_ACIF2 Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3 (PFKFB3) OT25JBA3 F263_HUMAN Gene/Protein Processing [6]
Albumin (ALB) OTVMM513 ALBU_HUMAN Drug Response [7]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [8]
ATP-dependent 6-phosphofructokinase, liver type (PFKL) OTVHGAT7 PFKAL_HUMAN Gene/Protein Processing [6]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [9]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Gene/Protein Processing [9]
C-C motif chemokine 4 (CCL4) OT6B8P25 CCL4_HUMAN Gene/Protein Processing [9]
C-C motif chemokine 5 (CCL5) OTSCA5CK CCL5_HUMAN Gene/Protein Processing [9]
Carnitine O-palmitoyltransferase 1, liver isoform (CPT1A) OTI862QH CPT1A_HUMAN Gene/Protein Processing [10]
Carnitine O-palmitoyltransferase 2, mitochondrial (CPT2) OTIN6G20 CPT2_HUMAN Gene/Protein Processing [10]
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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
Acetylcholinesterase (AChE) DTT ACHE 6.39E-02 -1.07 -1.15
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: 6307).
2 Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15.
3 Overexpression, isotopic labeling, and spectral characterization of Enterobacter cloacae nitroreductase. Protein Expr Purif. 1998 Jun;13(1):53-60.
4 Retro-nitroreductase, a putative evolutionary precursor to Enterobacter cloacae strain 96-3 nitroreductase. Antioxid Redox Signal. 2001 Oct;3(5):747-55.
5 The quinone-binding site of Acidithiobacillus ferrooxidans sulfide: quinone oxidoreductase controls both sulfide oxidation and quinone reduction. Biochem Cell Biol. 2016 Apr;94(2):159-66.
6 Overexpression of HIF-1a could partially protect K562 cells from 1,4-benzoquinone induced toxicity by inhibiting ROS, apoptosis and enhancing glycolysis. Toxicol In Vitro. 2019 Mar;55:18-23. doi: 10.1016/j.tiv.2018.11.005. Epub 2018 Nov 15.
7 A new assay for albumin and hemoglobin adducts of 1,2- and 1,4-benzoquinones. Chem Biol Interact. 1998 Sep 4;115(2):117-39. doi: 10.1016/s0009-2797(98)00067-2.
8 A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells. Cutan Ocul Toxicol. 2010 Sep;29(3):171-92.
9 Identification of human cell responses to benzene and benzene metabolites. Genomics. 2007 Sep;90(3):324-33.
10 l-Carnitine protects against 1,4-benzoquinone-induced apoptosis and DNA damage by suppressing oxidative stress and promoting fatty acid oxidation in K562 cells. Environ Toxicol. 2020 Oct;35(10):1033-1042. doi: 10.1002/tox.22939. Epub 2020 Jun 1.