Bovine Metabolome Database: Showing metabocard for Nornicotine (BMDB0001126)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:41:26 UTC

Update Date

2020-05-11 20:13:29 UTC

BMDB ID

BMDB0001126

Secondary Accession Numbers

BMDB01126

Metabolite Identification

Common Name

Nornicotine

Description

Nornicotine, also known as (+-)-nornicotine or DL-norcitine, 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. Based on a literature review a small amount of articles have been published on Nornicotine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-1'-Demethyl-nicotine	HMDB
(+-)-1'-Demethylnicotine	HMDB
(+-)-3-(2-Pyrrolidinyl)pyridine	HMDB
(+-)-Nornicotine	HMDB
(R)-3-(Pyrrolidin-2-yl)pyridine	HMDB
(R,S)-Nornicotine	HMDB
(S)-2-(3-Pyridyl)pyrrolidine	HMDB
2-(3-Pyridyl)pyrrolidine	HMDB
3-(2-Pyrrolidinyl)pyridine	HMDB
DL-Norcitine	HMDB
L-Nor-nicotine	HMDB
Nornicotin	HMDB
S-(-)-Nornicotine	HMDB
Nornicotine tartrate, (S)-(R-(r,r))-isomer	HMDB
Nornicotine, (R)-isomer	HMDB
Nornicotine, (S)-isomer	HMDB

Chemical Formula

C₉H₁₂N₂

Average Molecular Weight

148.205

Monoisotopic Molecular Weight

148.100048394

IUPAC Name

3-(pyrrolidin-2-yl)pyridine

Traditional Name

(+-)-nornicotine

CAS Registry Number

494-97-3

SMILES

C1CNC(C1)C1=CC=CN=C1

InChI Identifier

InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2

InChI Key

MYKUKUCHPMASKF-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
Aralkylamine
Heteroaromatic compound
Pyrrolidine
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Pyridine alkaloids (C06524 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	270 °C	Not Available
Water Solubility	Not Available	Not Available
LogP	0.17	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.66	ALOGPS
logP	0.78	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	24.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.36 m³·mol⁻¹	ChemAxon
Polarizability	16.66 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-1910000000-7aaa8177fe27a116f3e4	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-1910000000-7aaa8177fe27a116f3e4	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-4900000000-b1dd2fa89d2e3a6004b7	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0900000000-f2b0fa8b9c12821f2a96	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0900000000-f9d65ea20e70d97b17a7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00lr-0900000000-c15db03324adc5374c11	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0159-0900000000-c74af7c19e9329720e4e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0159-0900000000-128439754c8d0a69bec0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001j-0900000000-fbf9379b4dd1ba5915d1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001j-0900000000-3268f0d1161f7c767e39	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-1900000000-641ce2610f3b89a02853	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-2900000000-b3d63962e4ee5a7567ff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-3900000000-73abee1b55e5f70341cb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00lr-5900000000-df09cb3a631636459004	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00lr-9800000000-a45b0ff544bcd0281db0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0159-9300000000-13f626ee37faf5534153	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0fsc-9100000000-53e714e4328ef96344a9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0159-0900000000-c74af7c19e9329720e4e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00lr-0900000000-c03060e07c24d91fe2b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-6ffb5e4450055085bf5f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-d4059a90a539229953c9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-dabe42a76f889cfb9938	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-59737c2da8553c7ab03f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1900000000-c7de13e17b1e82a46e3f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v5c-9200000000-8eeb64be10e289cb9303	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1f7637ef9abf28475e71	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-3900000000-4580e77240a12f45be98	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-017l-9500000000-1af339f4c1a6a2b7ae6a	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001126

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nornicotine

METLIN ID

1534

PubChem Compound

412

PDB ID

Not Available

ChEBI ID

28313

References

Synthesis Reference

Papadopoulos, Nick M. Formation of nornicotine and other metabolites from nicotine in vitro and in vivo. Canadian Journal of Biochemistry and Physiology (1964), 42(4), 435-42.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Nornicotine (BMDB0001126)

Structure for BMDB0001126 (Nornicotine)