IMPPAT Phytochemical information: 
Nicotine

Nicotine
Summary

SMILES: CN1CCC[C@H]1c1cccnc1
InChI: 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
InChIKey: SNICXCGAKADSCV-JTQLQIEISA-N
DeepSMILES: CNCCC[C@H]5ccccnc6
Scaffold Graph/Node/Bond level: c1cncc(C2CCCN2)c1
Scaffold Graph/Node level: C1CNCC(C2CCCN2)C1
Scaffold Graph level: C1CCC(C2CCCC2)CC1
Functional groups: CN(C)C; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Pyridines and derivatives
ClassyFire Subclass: Pyrrolidinylpyridines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Nicotinic acid alkaloids
NP Classifier Class: Pyridine alkaloids
Synonymous chemical names:
nicotine, β-pyridyl-α-n-methylpyrrolidine (nicotine), nicotin, Nicotine
External chemical identifiers:
CID:CID_89594; ChEMBL:CHEMBL3; ChEBI:CHEBI:17688; ZINC:ZINC000000391812; FDASRS:6M3C89ZY6R; SureChEMBL:SCHEMBL20192; MolPort-000-744-731
Chemical structure download


Nicotine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 162.24
Log P RDKit 1.85
Topological polar surface area (Å2) RDKit 16.13
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Nicotine
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.626152


Nicotine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.46
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Nicotine
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001207ENSG00000154229PRKCA5578ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001378ENSG00000143365RORC6097NPASS
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001320ENSG00000262418PTPRC5788ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_000405ENSG00000180210F22147ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001289ENSG00000169403PTAFR5724ChEMBL
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001056ENSG00000065989PDE4A5141ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001186ENSG00000138814PPP3CA5530ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001538ENSG00000175003SLC22A16580ChEMBL, NPASS
TAR_EXP_001852ENSG00000147434CHRNA68973ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001816ENSG00000108846ABCC38714BindingDB, NPASS
TAR_EXP_001811ENSG00000138735PDE5A8654ChEMBL
TAR_EXP_001810ENSG00000067955CBFB865NPASS
TAR_EXP_001808ENSG00000276582ABCB118647NPASS
TAR_EXP_001753ENSG00000137752CASP1834ChEMBL
TAR_EXP_001727ENSG00000004948CALCR799ChEMBL
TAR_EXP_001880ENSG00000149305HTR3B9177ChEMBL
TAR_EXP_001684ENSG00000104267CA2760ChEMBL
TAR_EXP_001642ENSG00000121807CCR2729230ChEMBL
TAR_EXP_001592ENSG00000059377TBXAS16916ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001587ENSG00000115353TACR16869ChEMBL
TAR_EXP_001585ENSG00000075073TACR26865ChEMBL
TAR_EXP_001542ENSG00000197375SLC22A56584ChEMBL, NPASS
TAR_EXP_001541ENSG00000197208SLC22A46583ChEMBL, NPASS
TAR_EXP_001540ENSG00000112499SLC22A26582ChEMBL
TAR_EXP_001669ENSG00000114812VIPR17433ChEMBL
TAR_EXP_001857ENSG00000104321TRPA18989ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000263ENSG00000140505CYP1A21544BindingDB, ChEMBL, NPASS
TAR_EXP_000265ENSG00000255974CYP2A61548BindingDB, ChEMBL, NPASS
TAR_EXP_000267ENSG00000188778ADRB3155ChEMBL
TAR_EXP_000269ENSG00000197838CYP2A131553BindingDB, ChEMBL, NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL
TAR_EXP_000277ENSG00000130649CYP2E11571ChEMBL
TAR_EXP_000760ENSG00000163464CXCR13577ChEMBL
TAR_EXP_000759ENSG00000169429CXCL83576NPASS
TAR_EXP_000738ENSG00000158748HTR63362ChEMBL
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000308ENSG00000178084HTR3C170572ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL, NPASS
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000327ENSG00000069696DRD41815ChEMBL
TAR_EXP_000332ENSG00000180772AGTR2186ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000761ENSG00000180871CXCR23579ChEMBL
TAR_EXP_000357ENSG00000277571ELANE1991ChEMBL
TAR_EXP_000362ENSG00000186090HTR3D200909ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000250ENSG00000100448CTSG1511ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000773ENSG00000169083AR367ChEMBL, NPASS
TAR_EXP_000798ENSG00000055118KCNH23757BindingDB, ChEMBL, NPASS
TAR_EXP_000810ENSG00000128052KDR3791ChEMBL
TAR_EXP_000822ENSG00000182866LCK3932ChEMBL
TAR_EXP_000845ENSG00000166949SMAD34088NPASS
TAR_EXP_000846ENSG00000100299ARSA410NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_000863ENSG00000176136MC5R4161ChEMBL
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL
TAR_EXP_000888ENSG00000100985MMP94318ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_000988ENSG00000185149NPY2R4887ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000178ENSG00000160791CCR51234ChEMBL
TAR_EXP_000182ENSG00000023839ABCC21244ChEMBL, NPASS
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000081ENSG00000173198CYSLTR110800ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL
TAR_EXP_000233ENSG00000171873ADRA1D146ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000348ENSG00000146648EGFR1956ChEMBL
TAR_EXP_000139ENSG00000138435CHRNA11134BindingDB, ChEMBL, NPASS
TAR_EXP_000132ENSG00000137491SLCO2B111309NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000461ENSG00000102755FLT12321ChEMBL
TAR_EXP_000431ENSG00000164638SLC29A4222962ChEMBL, NPASS
TAR_EXP_000134ENSG00000180720CHRM41132ChEMBL
TAR_EXP_000137ENSG00000184984CHRM51133ChEMBL
TAR_EXP_000153ENSG00000135902CHRND1144ChEMBL, NPASS
TAR_EXP_000141ENSG00000120903CHRNA21135BindingDB, ChEMBL, NPASS
TAR_EXP_000142ENSG00000080644CHRNA31136BindingDB, ChEMBL, NPASS
TAR_EXP_000144ENSG00000101204CHRNA41137BindingDB, ChEMBL, NPASS
TAR_EXP_000145ENSG00000169684CHRNA51138ChEMBL, NPASS
TAR_EXP_000146ENSG00000175344CHRNA71139BindingDB, ChEMBL, NPASS
TAR_EXP_000177ENSG00000183813CCR41233ChEMBL
TAR_EXP_000148ENSG00000283946CHRNB11140ChEMBL
TAR_EXP_000149ENSG00000160716CHRNB21141ChEMBL
TAR_EXP_000151ENSG00000147432CHRNB31142ChEMBL, NPASS
TAR_EXP_000152ENSG00000117971CHRNB41143ChEMBL, NPASS
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000515ENSG00000010810FYN2534ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000154ENSG00000108556CHRNE1145ChEMBL, NPASS
TAR_EXP_000156ENSG00000196811CHRNG1146ChEMBL
TAR_EXP_000041ENSG00000147955SIGMAR110280BindingDB, ChEMBL, NPASS
TAR_EXP_000039ENSG00000125257ABCC410257BindingDB, NPASS
TAR_EXP_000387ENSG00000141736ERBB22064ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000692ENSG00000113161HMGCR3156ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL
TAR_EXP_000624ENSG00000186038HTR3E285242ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL