Showing metabocard for Nornicotine (BMDB0001126)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:41:26 UTC
Update Date2020-05-11 20:13:29 UTC
BMDB IDBMDB0001126
Secondary Accession Numbers
  • BMDB01126
Metabolite Identification
Common NameNornicotine
DescriptionNornicotine, 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-1'-Demethyl-nicotineHMDB
(+-)-1'-DemethylnicotineHMDB
(+-)-3-(2-Pyrrolidinyl)pyridineHMDB
(+-)-NornicotineHMDB
(R)-3-(Pyrrolidin-2-yl)pyridineHMDB
(R,S)-NornicotineHMDB
(S)-2-(3-Pyridyl)pyrrolidineHMDB
2-(3-Pyridyl)pyrrolidineHMDB
3-(2-Pyrrolidinyl)pyridineHMDB
DL-NorcitineHMDB
L-Nor-nicotineHMDB
NornicotinHMDB
S-(-)-NornicotineHMDB
Nornicotine tartrate, (S)-(R-(r*,r*))-isomerHMDB
Nornicotine, (R)-isomerHMDB
Nornicotine, (S)-isomerHMDB
Chemical FormulaC9H12N2
Average Molecular Weight148.205
Monoisotopic Molecular Weight148.100048394
IUPAC Name3-(pyrrolidin-2-yl)pyridine
Traditional Name(+-)-nornicotine
CAS Registry Number494-97-3
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 KeyMYKUKUCHPMASKF-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyrrolidinylpyridines
Direct ParentPyrrolidinylpyridines
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point270 °CNot Available
Water SolubilityNot AvailableNot Available
LogP0.17HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP0.66ALOGPS
logP0.78ChemAxon
logS-0.76ALOGPS
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.36 m³·mol⁻¹ChemAxon
Polarizability16.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001126
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022439
KNApSAcK IDC00042792
Chemspider ID21108497
KEGG Compound IDC06524
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNornicotine
METLIN ID1534
PubChem Compound412
PDB IDNot Available
ChEBI ID28313
References
Synthesis ReferencePapadopoulos, 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 ReferencesNot Available