Showing Compound 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (FDB028314)

Record Information

Version

1.0

Creation date

2011-09-21 01:37:48 UTC

Update date

2015-10-09 22:33:26 UTC

Primary ID

FDB028314

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone

Description

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is a potent tobacco-specific nitrosamine in animals. It has been suggested to play a role in human tobacco-related cancers. P450 1A2 catalyzed the formation of keto alcohol and 4-oxo-1-(3-pyridyl)-1-butanone (keto aldehyde) from NNK, with the keto alcohol being the major metabolite. Phenethyl isothiocyanate (PEITC0 is an effective inhibitor of the carcinogenicity or toxicity of chemicals that are activated by P450 1A2.( PMID: 8625495) [HMDB]

CAS Number

64091-91-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
4'-(Nitrosomethylamino)-1-(3-pyridyl)-1-butanone	HMDB
4-(Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone	HMDB
4-(Methylintrosamino)-1-(3-pyridyl)-1-butanone	HMDB
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone	ChEBI
4-(Methylnitrosoamino)-1-(3-pyridinyl)-1-butanone	HMDB
4-(Methylnitrosoamino)-1-(3-pyridyl)-1-butanone	HMDB
4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone	ChEBI
4-(N-Nitrosomethylamino)-1-(3-pyridyl)-1-butanone	HMDB
NNK	ChEBI
NNK (Carcinogen)	ChEBI

Showing 1 to 10 of 12 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.09 g/L	ALOGPS
logP	0.33	ALOGPS
logP	0.58	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	15.47	ChemAxon
pKa (Strongest Basic)	3.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	62.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	57.25 m³·mol⁻¹	ChemAxon
Polarizability	21.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H13N3O2

IUPAC name

4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one

InChI Identifier

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

InChI Key

FLAQQSHRLBFIEZ-UHFFFAOYSA-N

Isomeric SMILES

CN(CCCC(=O)C1=CC=CN=C1)N=O

Average Molecular Weight

207.2291

Monoisotopic Molecular Weight

207.100776675

Classification

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Pyridine
Heteroaromatic compound
Organic n-nitroso compound
Organic nitroso compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridines (CHEBI:32692 )
nitrosamine (CHEBI:32692 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Organ and components:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9800000000-57c49f29c9d7332bea22	Spectrum
Predicted GC-MS	4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1980000000-6eed182d10c9a03751b7	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-3910000000-5fed6b71985ed1afcab4	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001m-9600000000-1c5f7245d666beff11f2	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-3390000000-e76106f4b8f69d27d9aa	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a70-9840000000-3d022ffc7f1a61b3d6d0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9100000000-1782fbf95a7044f769a6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0920000000-1d8ea81c64d584ea02d1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1900000000-63e35eaa2366ca02b75d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-7900000000-5f96473ea00e041d2dcc	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-482b470c4a0ac6884d93	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-9820000000-35e475a0c732f383cc12	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-9300000000-37d4b4467865dbb44ac7	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

32692

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB11603

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

0QA

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB