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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:46:58 UTC

HMDB ID

HMDB0001010

Secondary Accession Numbers

HMDB01010

Metabolite Identification

Common Name

Nicotine imine

Description

Nicotine imine belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. In humans, nicotine imine is involved in the nicotine metabolism pathway. Nicotine imine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make nicotine imine a potential biomarker for the consumption of these foods. Nicotine imine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Nicotine imine.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       5.235  -3.432   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.775  -3.432   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.251  -4.897   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.005  -5.802   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.760  -4.897   0.000  0.00  0.00           N+1
HETATM    6  C   UNK     0       3.295  -5.373   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.005  -7.342   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.339  -8.112   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.339  -9.652   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.005 -10.422   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.672  -9.652   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.672  -8.112   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5                                                            
CONECT    7    4    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-1-(Methylene-11C)-2-(3-pyridinyl)-pyrrolidium	HMDB
(S)-1-(Methylene-11C)-2-(3-pyridinyl)pyrrolidinium	HMDB
11C-Nicotine imine	HMDB
Nicotine iminium	HMDB, MeSH
Nicotine-delta 1'-(5')-iminium	HMDB
Nicotine delta 1'(5)' iminium ion	MeSH, HMDB

Chemical Formula

C₁₀H₁₃N₂

Average Molecular Weight

161.2236

Monoisotopic Molecular Weight

161.107873426

IUPAC Name

1-methyl-2-(pyridin-3-yl)-3,4-dihydro-2H-pyrrol-1-ium

Traditional Name

1-methyl-2-(pyridin-3-yl)-3,4-dihydro-2H-pyrrol-1-ium

CAS Registry Number

74710-78-4

SMILES

C[N+]1=CCCC1C1=CC=CN=C1

InChI Identifier

InChI=1S/C10H13N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6-8,10H,3,5H2,1H3/q+1

InChI Key

GTQXYYYOJZZJHL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Pyridine
Heteroaromatic compound
Pyrroline
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD-3186 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.21 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.9	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	4.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	15.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	59.8 m³·mol⁻¹	ChemAxon
Polarizability	18.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	133.026	32859911
AllCCS	[M-H]-	139.576	32859911
DeepCCS	[M+H]+	134.604	30932474
DeepCCS	[M-H]-	131.858	30932474
DeepCCS	[M-2H]-	167.989	30932474
DeepCCS	[M+Na]+	143.285	30932474
AllCCS	[M+H]+	133.0	32859911
AllCCS	[M+H-H2O]+	128.3	32859911
AllCCS	[M+NH4]+	137.4	32859911
AllCCS	[M+Na]+	138.7	32859911
AllCCS	[M-H]-	139.6	32859911
AllCCS	[M+Na-2H]-	140.3	32859911
AllCCS	[M+HCOO]-	141.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nicotine imine	C[N+]1=CCCC1C1=CC=CN=C1	1937.1	Standard polar	33892256
Nicotine imine	C[N+]1=CCCC1C1=CC=CN=C1	1368.6	Standard non polar	33892256
Nicotine imine	C[N+]1=CCCC1C1=CC=CN=C1	1450.7	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 - Nicotine imine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ge9-3900000000-031e674b4f7ade3be8ee	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotine imine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotine imine 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 - Nicotine imine 10V, Positive-QTOF	splash10-03di-0900000000-1467b2a33df3b3f6ae32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine imine 20V, Positive-QTOF	splash10-03di-2900000000-92c1c5fe0d000faa4561	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine imine 40V, Positive-QTOF	splash10-000x-9700000000-4792328a8ade7540ad76	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine imine 10V, Negative-QTOF	splash10-03di-0900000000-f56164d22376a5571748	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine imine 20V, Negative-QTOF	splash10-03di-0900000000-90a5d859971b907f6da1	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine imine 40V, Negative-QTOF	splash10-0006-9500000000-90db76b0d90048cdaa0b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine imine 10V, Positive-QTOF	splash10-03di-0900000000-28023f8ea3eb3a869265	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine imine 20V, Positive-QTOF	splash10-01wf-5900000000-55e307471eec301a18e6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine imine 40V, Positive-QTOF	splash10-0006-9600000000-fb3d3407bc3e24820073	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Nicotine Action Pathway		Not Available
Nicotine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

FDB022368

KNApSAcK ID

Not Available

Chemspider ID

418

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5940

PubChem Compound

431

PDB ID

Not Available

ChEBI ID

173425

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 Nicotine imine (HMDB0001010)

MOL for HMDB0001010 (Nicotine imine)

3D MOL for HMDB0001010 (Nicotine imine)

3D SDF for HMDB0001010 (Nicotine imine)

3D-SDF for HMDB0001010 (Nicotine imine)

PDB for HMDB0001010 (Nicotine imine)

3D PDB for HMDB0001010 (Nicotine imine)

SMILES for HMDB0001010 (Nicotine imine)

INCHI for HMDB0001010 (Nicotine imine)

Structure for HMDB0001010 (Nicotine imine)

3D Structure for HMDB0001010 (Nicotine imine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra