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Record Information
Version1.0
Created at2020-04-27 16:26:41 UTC
Updated at2021-01-04 20:37:45 UTC
CannabisDB IDCDB005499
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNicotine
Description
Structure
Thumb
Synonyms
Chemical FormulaC10H14N2
Average Molecular Weight162.23
Monoisotopic Molecular Weight162.1157
IUPAC Name3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
Traditional Namenicoderm CQ
CAS Registry Number54-11-5
SMILES
CN1CCC[C@H]1C1=CN=CC=C1
InChI Identifier
InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1
InChI KeySNICXCGAKADSCV-JTQLQIEISA-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
  • Alkaloid or derivatives
  • Aralkylamine
  • N-alkylpyrrolidine
  • Heteroaromatic compound
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-79 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
logP1.17HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP0.87ALOGPS
logP1.16ChemAxon
logS-0.24ALOGPS
pKa (Strongest Basic)8.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.66 m³·mol⁻¹ChemAxon
Polarizability18.59 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-9400000000-47a036aa305825218fa22014-09-20View Spectrum
GC-MSNicotine, non-derivatized, GC-MS Spectrumsplash10-001i-9500000000-f2d4835c504301f9410eSpectrum
GC-MSNicotine, non-derivatized, GC-MS Spectrumsplash10-01q9-7900000000-1e2c38b5e4e7aae10d37Spectrum
GC-MSNicotine, non-derivatized, GC-MS Spectrumsplash10-001i-9800000000-fe889308f7088d47c31dSpectrum
GC-MSNicotine, non-derivatized, GC-MS Spectrumsplash10-001i-9500000000-f2d4835c504301f9410eSpectrum
Predicted GC-MSNicotine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-4900000000-6d65165a4417a6129eebSpectrum
Predicted GC-MSNicotine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Amine oxidase [flavin-containing] BMAOBXp11.23P27338 details
Amine oxidase [flavin-containing] AMAOAXp11.3P21397 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Solute carrier family 22 member 5SLC22A55q31O76082 details
Solute carrier family 22 member 4SLC22A45q31.1Q9H015 details
Solute carrier family 22 member 1SLC22A16q26O15245 details
Solute carrier family 22 member 2SLC22A26q26O15244 details
Solute carrier family 22 member 3SLC22A36q25.3O75751 details
Neuronal acetylcholine receptor subunit alpha-10CHRNA1011p15.5Q9GZZ6 details
Neuronal acetylcholine receptor subunit alpha-9CHRNA94p14Q9UGM1 details
Neuronal acetylcholine receptor subunit alpha-2CHRNA28p21Q15822 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytochrome P450 3A4CYP3A47q21.1P08684 details
Cytochrome P450 2C9CYP2C910q24P11712 details
Cytochrome P450 2C19CYP2C1910q24P33261 details
Cytochrome P450 2E1CYP2E110q24.3-qterP05181 details
Cytochrome P450 2D6CYP2D622q13.1P10635 details
Cytochrome P450 2B6CYP2B619q13.2P20813 details
Cytochrome P450 1A1CYP1A115q24.1P04798 details
Cytochrome P450 2A13CYP2A1319q13.2Q16696 details
Cytochrome P450 1A2CYP1A215q24.1P05177 details
Cytochrome P450 2C8CYP2C810q23.33P10632 details
Cytochrome P450 2A6CYP2A619q13.2P11509 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Neuronal acetylcholine receptor subunit alpha-10CHRNA1011p15.5Q9GZZ6 details
Neuronal acetylcholine receptor subunit alpha-9CHRNA94p14Q9UGM1 details
Neuronal acetylcholine receptor subunit alpha-2CHRNA28p21Q15822 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001934
DrugBank IDDB00184
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003968
KNApSAcK IDC00002057
Chemspider ID80863
KEGG Compound IDC00745
BioCyc IDNICOTINE
BiGG IDNot Available
Wikipedia LinkNicotine
METLIN ID1526
PubChem Compound89594
PDB IDNot Available
ChEBI ID17688
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 24 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1
General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular weight:
62154.5
General function:
Involved in ion transmembrane transporter activity
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4
General function:
Involved in ion transmembrane transporter activity
Specific function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular weight:
62564.0
General function:
Involved in transmembrane transport
Specific function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular weight:
61279.5
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma
Gene Name:
CHRNA10
Uniprot ID:
Q9GZZ6
Molecular weight:
49704.3
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma. May also regulate keratinocyte adhesion
Gene Name:
CHRNA9
Uniprot ID:
Q9UGM1
Molecular weight:
54806.6
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular weight:
59764.8

Only showing the first 10 proteins. There are 24 proteins in total.