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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:49:04 UTC

Update Date

2023-02-21 17:29:04 UTC

HMDB ID

HMDB0041940

Secondary Accession Numbers

HMDB41940

Metabolite Identification

Common Name

N'-nitrosonornicotine

Description

N'-nitrosonornicotine, also known as NNN, belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. N'-nitrosonornicotine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. N'-nitrosonornicotine is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review very few articles have been published on N'-nitrosonornicotine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       3.802   3.735   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.906  -2.485   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.381  -1.020   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.136   4.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.366  -2.485   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       6.469   3.735   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.425  -0.544   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.890  -1.020   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       1.281  -1.575   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    8                                                       
CONECT    4    2    9                                                       
CONECT    5    1   10                                                       
CONECT    6    2   12                                                       
CONECT    7    8   10                                                       
CONECT    8    3    7    9                                                  
CONECT    9    4    8   12                                                  
CONECT   10    5    7                                                       
CONECT   11   12   13                                                       
CONECT   12    6    9   11                                                  
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
NNN	Kegg
N-Nitrosonornicotine	HMDB
Nitrosonornicotine	HMDB
N-Nitrosonor-nicotine	HMDB
N'-nitrosonornicotine, (+-)-isomer	HMDB
N'-nitrosonornicotine, (S)-isomer	HMDB

Chemical Formula

C₉H₁₁N₃O

Average Molecular Weight

177.2031

Monoisotopic Molecular Weight

177.090211989

IUPAC Name

3-(1-nitrosopyrrolidin-2-yl)pyridine

Traditional Name

nitrosonornicotine

CAS Registry Number

16543-55-8

SMILES

O=NN1CCCC1C1=CN=CC=C1

InChI Identifier

InChI=1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2

InChI Key

XKABJYQDMJTNGQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyrrolidinylpyridines

Direct Parent

Pyrrolidinylpyridines

Alternative Parents

Substituents

Pyrrolidinylpyridine
Heteroaromatic compound
Pyrrolidine
Organic n-nitroso compound
Organic nitroso compound
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrrolidines (CHEBI:80502 )
pyridines (CHEBI:80502 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0041940)
Extracellular (HMDB: HMDB0041940)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	47 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.19 g/L	ALOGPS
logP	0.71	ALOGPS
logP	1.01	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	4.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	45.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.72 m³·mol⁻¹	ChemAxon
Polarizability	18.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.918	31661259
DarkChem	[M-H]-	134.601	31661259
DeepCCS	[M+H]+	138.916	30932474
DeepCCS	[M-H]-	135.677	30932474
DeepCCS	[M-2H]-	172.802	30932474
DeepCCS	[M+Na]+	148.34	30932474
AllCCS	[M+H]+	139.0	32859911
AllCCS	[M+H-H2O]+	134.5	32859911
AllCCS	[M+NH4]+	143.2	32859911
AllCCS	[M+Na]+	144.4	32859911
AllCCS	[M-H]-	140.4	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	141.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N'-nitrosonornicotine	O=NN1CCCC1C1=CN=CC=C1	2272.9	Standard polar	33892256
N'-nitrosonornicotine	O=NN1CCCC1C1=CN=CC=C1	1641.9	Standard non polar	33892256
N'-nitrosonornicotine	O=NN1CCCC1C1=CN=CC=C1	1786.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N'-nitrosonornicotine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-6900000000-fd2ef6c01a4b17ce5273	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N'-nitrosonornicotine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N'-nitrosonornicotine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 10V, Positive-QTOF	splash10-004i-0900000000-12f56e19de9cbe398565	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 20V, Positive-QTOF	splash10-002b-0900000000-91649128a892cc839eb6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 40V, Positive-QTOF	splash10-00kf-9700000000-873fd2c47c2d68c83594	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 10V, Negative-QTOF	splash10-004i-0900000000-c12c118d1c7651944f81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 20V, Negative-QTOF	splash10-0a6r-2900000000-e35c2cff64ce3c329c36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 40V, Negative-QTOF	splash10-056r-9700000000-fae379e939e02b828337	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 10V, Positive-QTOF	splash10-004i-0900000000-5e75feafb4c32781d478	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 20V, Positive-QTOF	splash10-004i-0900000000-ec7ff1c81f701ccb3c4b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 40V, Positive-QTOF	splash10-0036-9500000000-34ad449443dff74d1f2f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 10V, Negative-QTOF	splash10-004i-2900000000-0f48d5bc2f759fd6c2bb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 20V, Negative-QTOF	splash10-004i-3900000000-794ade8a28d915dff371	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N'-nitrosonornicotine 40V, Negative-QTOF	splash10-002e-9400000000-6c58cf9f856143d2092f	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

25973

KEGG Compound ID

C16452

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Nitrosonornicotine

METLIN ID

Not Available

PubChem Compound

27919

PDB ID

Not Available

ChEBI ID

80502

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N'-nitrosonornicotine (HMDB0041940)

MOL for HMDB0041940 (N'-nitrosonornicotine)

3D MOL for HMDB0041940 (N'-nitrosonornicotine)

3D SDF for HMDB0041940 (N'-nitrosonornicotine)

3D-SDF for HMDB0041940 (N'-nitrosonornicotine)

PDB for HMDB0041940 (N'-nitrosonornicotine)

3D PDB for HMDB0041940 (N'-nitrosonornicotine)

SMILES for HMDB0041940 (N'-nitrosonornicotine)

INCHI for HMDB0041940 (N'-nitrosonornicotine)

Structure for HMDB0041940 (N'-nitrosonornicotine)

3D Structure for HMDB0041940 (N'-nitrosonornicotine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra