Details of the Drug

General Information of Drug (ID: DM4KXT0)

Drug Name
BRN-3548355
Synonyms
NNK (carcinogen); 1-Butanone, 4-(methylnitrosoamino)-1-(3-pyridinyl)-; 4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE; 4-(Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone; 4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone; 4-(N-Nitroso-N-methylamino)-1-(3-pyridyl)-1-butanone; 4-Methylnitrosoamino-1-(3-pyridinyl)-1-butanone; 4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one; 64091-91-4; 7S395EDO61; CCRIS 1150; CHEBI:32692; MFCD00274580; N-Methyl-N-nitroso-4-oxo-4-(3-pyridyl)butyl amine; NNK; UNII-7S395EDO61
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 207.23
Logarithm of the Partition Coefficient (xlogp) 0.8
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C10H13N3O2
IUPAC Name
N-methyl-N-(4-oxo-4-pyridin-3-ylbutyl)nitrous amide
Canonical SMILES
CN(CCCC(=O)C1=CN=CC=C1)N=O
InChI
InChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3
InChIKey
FLAQQSHRLBFIEZ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
47289
ChEBI ID
CHEMBL32692
CAS Number
64091-50-5
INTEDE ID
DR0011
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
NADPH-dependent carbonyl reductase 1 (CBR1) DE9JFMC CBR1_HUMAN Substrate [1]
Aldo-keto reductase 1C1 (AKR1C1) DE7P2FB AK1C1_HUMAN Substrate [1]
Aldo-keto reductase 1C2 (AKR1C2) DEOY5ZM AK1C2_HUMAN Substrate [1]
Aldo-keto reductase 1C4 (AKR1C4) DEAJN47 AK1C4_HUMAN Substrate [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
6-phosphogluconate dehydrogenase, decarboxylating (PGD) OTVG296F 6PGD_HUMAN Gene/Protein Processing [2]
Alpha-aminoadipic semialdehyde dehydrogenase (ALDH7A1) OTV57BZD AL7A1_HUMAN Gene/Protein Processing [2]
Argininosuccinate lyase (ASL) OTI2NGQR ARLY_HUMAN Gene/Protein Processing [2]
Baculoviral IAP repeat-containing protein 3 (BIRC3) OT3E95KB BIRC3_HUMAN Gene/Protein Processing [3]
Bcl2-associated agonist of cell death (BAD) OT63ERYM BAD_HUMAN Gene/Protein Processing [3]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [4]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [5]
Cadherin-2 (CDH2) OTH0Y56P CADH2_HUMAN Gene/Protein Processing [5]
Chromodomain-helicase-DNA-binding protein 1-like (CHD1L) OT7CZK7C CHD1L_HUMAN Gene/Protein Processing [2]
COMM domain-containing protein 1 (COMMD1) OT7WUD5R COMD1_HUMAN Gene/Protein Processing [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta. Chem Biol Interact. 2001 Jan 30;130-132(1-3):737-48.
2 Gene expression profiles in HPV-immortalized human cervical cells treated with the nicotine-derived carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Chem Biol Interact. 2009 Feb 12;177(3):173-80. doi: 10.1016/j.cbi.2008.10.051. Epub 2008 Nov 6.
3 Haem oxygenase-1 plays a central role in NNK-mediated lung carcinogenesis. Eur Respir J. 2008 Oct;32(4):911-23. doi: 10.1183/09031936.00064508. Epub 2008 May 28.
4 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, a component of tobacco smoke, modulates mediator release from human bronchial and alveolar epithelial cells. Clin Exp Immunol. 2005 Apr;140(1):46-53.
5 The cigarette smoke components induced the cell proliferation and epithelial to mesenchymal transition via production of reactive oxygen species in endometrial adenocarcinoma cells. Food Chem Toxicol. 2018 Nov;121:657-665. doi: 10.1016/j.fct.2018.09.023. Epub 2018 Sep 17.