Details of the Drug

General Information of Drug (ID: DMAEI51)

Drug Name
Dichloroindophenol
Synonyms
Dichlorophenolindophenol; Indochlorophenol; Tillmans Reagent; 2,5-Cyclohexadien-1-one, 2,6-dichloro-4-((4-hydroxyphenyl)imino)-; 2,6-Dichlorophenolindophenol; 2,5-cyclohexadien-1-one, 2,6-dichloro-4-[(4-hydroxyphenyl)imino]-; 2,6-DICHLOROINDOPHENOL; 2,6-Dichloro-N-4-hydroxyphenyl-p-benzoquinone monoimine; 4-[(3,5-dichloro-4-hydroxyphenyl)imino]cyclohexa-2,5-dien-1-one; 956-48-9; C35QN2Z58B; CHEBI:27451; CHEBI:945; DCPIP; DPIP; N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine; UNII-C35QN2Z58B
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 268.09
Logarithm of the Partition Coefficient (xlogp) 2.8
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C12H7Cl2NO2
IUPAC Name
4-(3,5-dichloro-4-hydroxyphenyl)iminocyclohexa-2,5-dien-1-one
Canonical SMILES
C1=CC(=O)C=CC1=NC2=CC(=C(C(=C2)Cl)O)Cl
InChI
FBWADIKARMIWNM-UHFFFAOYSA-N
InChIKey
1S/C12H7Cl2NO2/c13-10-5-8(6-11(14)12(10)17)15-7-1-3-9(16)4-2-7/h1-6,17H
Cross-matching ID
PubChem CID
13726
ChEBI ID
CHEBI:945
CAS Number
956-48-9
INTEDE ID
DR2045

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Methionine synthase reductase (MTRR)
Main DME 		DE6NIY9 MTRR_HUMAN Substrate [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
NAD(P)H dehydrogenase 1 (NQO1) OTZGGIVK NQO1_HUMAN Drug Response [2]
Ribosyldihydronicotinamide dehydrogenase (NQO2) OTGDAJRZ NQO2_HUMAN Biotransformations [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Differences in the efficiency of reductive activation of methionine synthase and exogenous electron acceptors between the common polymorphic variants of human methionine synthase reductase. Biochemistry. 2002 Nov 12;41(45):13378-85.
2 DCPIP (2,6-dichlorophenolindophenol) as a genotype-directed redox chemotherapeutic targeting NQO1*2 breast carcinoma. Free Radic Res. 2011 Mar;45(3):276-92. doi: 10.3109/10715762.2010.526766. Epub 2010 Nov 1.
3 Reduction and scavenging of chemically reactive drug metabolites by NAD(P)H:quinone oxidoreductase 1 and NRH:quinone oxidoreductase 2 and variability in hepatic concentrations. Chem Res Toxicol. 2018 Feb 19;31(2):116-126.