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:
nicotin, nicotine, β-pyridyl-α-n-methylpyrrolidine (nicotine)
External chemical identifiers:
CID:89594; ChEMBL:CHEMBL3; 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 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit


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 0.6262


Nicotine
ADMET 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 0.0
Number of Brenk structural alerts SwissADME 0.0
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 - Predicted human target protein associations
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000013222INMT900
ENSP00000155858TRPM5814
ENSP00000165524PRLH826
ENSP00000168712FGF4786
ENSP00000209929FMO2900
ENSP00000215832MAPK1700
ENSP00000216117HMOX1819
ENSP00000216492CHGA851
ENSP00000217420SLC32A1846
ENSP00000218316GPR50700
ENSP00000219070MMP2844
ENSP00000220809PLAT824
ENSP00000222381PON1724
ENSP00000222390HGF834
ENSP00000223095SERPINE1824
ENSP00000225245CCL3816
ENSP00000225655PFN1800
ENSP00000226574NFKB1748
ENSP00000226730IL2940
ENSP00000228837FGF6786
ENSP00000230859PAPD7700
ENSP00000231509NR3C1872
ENSP00000234091ID2700
ENSP00000236166FMO6P900
ENSP00000237014TTR800
ENSP00000239849TNFSF11833
ENSP00000239938EGR1831
ENSP00000240662KCNJ8800
ENSP00000242152NPY862
ENSP00000243997ATP5E700
ENSP00000244050SNAI1700
ENSP00000248673ZFP36727
ENSP00000251849RAF1700
ENSP00000252321KCNA5800
ENSP00000252945CYP2E1988
ENSP00000253024TRIM28700
ENSP00000254090FMO5900
ENSP00000254521HSD17B7700
ENSP00000255030CRP860
ENSP00000258743IL6859
ENSP00000259455GABBR2874
ENSP00000261007CHRNA1749
ENSP00000261233IRAK3800
ENSP00000261707SLC6A4872
ENSP00000261751CHRNB4933
ENSP00000261769CDH1824
ENSP00000262209TRPA1862
ENSP00000262352SLC1A1820
ENSP00000262999UCP1800
ENSP00000263025MAPK3734
ENSP00000263341IL1B860
ENSP00000263895RND3700
ENSP00000264381BCHE790
ENSP00000264498FGF2943
ENSP00000264657STAT3736
ENSP00000264708POMC875
ENSP00000265403UGT2B10915
ENSP00000266744ASCL1800
ENSP00000267163RB1700
ENSP00000269305TP53849
ENSP00000269582PNMT923
ENSP00000270202AKT1948
ENSP00000270349SLC6A3983
ENSP00000271651CTSK814
ENSP00000275428GGCT700
ENSP00000275493EGFR736
ENSP00000276410CHRNA6900
ENSP00000276449STAR938
ENSP00000276571CRH859
ENSP00000277120NTRK2886
ENSP00000277903HABP2800
ENSP00000280612SLC7A11800
ENSP00000281043MYCN800
ENSP00000281455ACSL1700
ENSP00000282441YAP1800
ENSP00000282561GJA1817
ENSP00000285379CA2827
ENSP00000287820PPARG834
ENSP00000289957CHRNB3799
ENSP00000293288BAX700
ENSP00000293330HCRT853
ENSP00000295108NEUROD1800
ENSP00000295887CDS1700
ENSP00000296545IL15831
ENSP00000296684NDUFS4800
ENSP00000296869ACSL6800
ENSP00000296871CSF2723
ENSP00000297494NOS3700
ENSP00000297785ALDH1A1722
ENSP00000299565CHRNA5975
ENSP00000299847CHRFAM7A812
ENSP00000301141CYP2A6999
ENSP00000301146CYP2A7940
ENSP00000302564BCL2L1816
ENSP00000302913SH3D19700
ENSP00000302961HSPA4825
ENSP00000304895IRS1800
ENSP00000306245FOS987
ENSP00000306253ITPR1800
ENSP00000306512IL8851
ENSP00000307235EIF2AK3800
ENSP00000307786CYCS700
ENSP00000308032CYP2S1900
ENSP00000311032CASP3736
ENSP00000312999GNAI2700
ENSP00000315602CHRNA3981
ENSP00000318607LDLRAD3700
ENSP00000320084CD276786
ENSP00000324173HSPA5854
ENSP00000324648CYP2B6932
ENSP00000327048MAF800
ENSP00000329623BCL2700
ENSP00000329967TBK1825
ENSP00000330382PDGFB700
ENSP00000331736SELE852
ENSP00000332679CYP2A13986
ENSP00000333212CYP2U1922
ENSP00000335657CCK806
ENSP00000337103CHAT898
ENSP00000337459NOS1802
ENSP00000337825LCK700
ENSP00000337915CYP3A4818
ENSP00000337949HTR7865
ENSP00000338018HIF1A824
ENSP00000338130KLRD1837
ENSP00000338345SNCA757
ENSP00000338548FGF1800
ENSP00000339328PLAUR824
ENSP00000342007CYP1A2736
ENSP00000342307FOXM1800
ENSP00000346671FYN725
ENSP00000346768UGT1A9700
ENSP00000346839FN1851
ENSP00000346901FMO1916
ENSP00000347754HTR3A796
ENSP00000347999ZC3H7A700
ENSP00000349687GM2A700
ENSP00000350941SRC950
ENSP00000352208MYOF700
ENSP00000352516DNMT1831
ENSP00000353483MAPK8733
ENSP00000354855NFE2L1700
ENSP00000355627AGT786
ENSP00000355902GPATCH2700
ENSP00000356438PTGS2951
ENSP00000356723FMO4915
ENSP00000356729FMO3933
ENSP00000357255BGLAP838
ENSP00000357461CHRNB2917
ENSP00000358022MCL1700
ENSP00000358301ADRB1824
ENSP00000358511CNR1906
ENSP00000358525NGF820
ENSP00000359285CHRNA4999
ENSP00000359635FGF13800
ENSP00000360266JUN856
ENSP00000360493RUNX2800
ENSP00000360968CYP4X1910
ENSP00000361125VEGFA947
ENSP00000361405MMP9849
ENSP00000361512PRPS1700
ENSP00000362410MAFB712
ENSP00000362508UGT1A4900
ENSP00000363189TMEM222700
ENSP00000363868ABCA1800
ENSP00000365280ID1803
ENSP00000365380FOXP3800
ENSP00000366248CORT817
ENSP00000367203KDM6A800
ENSP00000367207MYC726
ENSP00000367830PRKCZ700
ENSP00000367959HTR2A907
ENSP00000369050CYP1A1914
ENSP00000369071POSTN800
ENSP00000369647AVP853
ENSP00000369889COL2A1786
ENSP00000370223IDH3B800
ENSP00000370571TH992
ENSP00000371419PARP4700
ENSP00000374265GPX2740
ENSP00000378517SPP1840
ENSP00000379213PTHLH800
ENSP00000383938CRELD2800
ENSP00000385026CHRNA2882
ENSP00000385834TF800
ENSP00000386284ALAD700
ENSP00000387683UGT2B11900
ENSP00000396538NFAT5800
ENSP00000398131GSPT1841
ENSP00000398632CD44800
ENSP00000398698TNF947
ENSP00000401399MYD88800
ENSP00000407375GPX1772
ENSP00000407546CHRNA7954
ENSP00000408695PRKCA739
ENSP00000412237IL10966
ENSP00000414303BDNF830
ENSP00000414321RPS24700
ENSP00000417498MUC4800
ENSP00000418532UGT1A3700
ENSP00000431418NTRK1800
ENSP00000454071LDLR824
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.