(+)-Nicotine

Details

• Internal ID: 95a46c4d-e2ca-40c3-b9ac-94d0714378fa
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Pyrrolidinylpyridines
• IUPAC Name: 3-[(2R)-1-methylpyrrolidin-2-yl]pyridine
• SMILES (Canonical): CN1CCCC1C2=CN=CC=C2
• SMILES (Isomeric): CN1CCC[C@@H]1C2=CN=CC=C2
• 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-/m1/s1
• InChI Key: SNICXCGAKADSCV-SNVBAGLBSA-N
• Popularity: 226 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.23 g/mol
• Exact Mass: 162.115698455 g/mol
• Topological Polar Surface Area (TPSA): 16.10 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• D-Nicotine
• Pseudonicotine
• (R)-nicotine
• 25162-00-9
• R-(+)-Nicotine
• 2'-beta-H-Nicotine
• Nicotine, (+)-
• (R)-3-(1-Methyl-2-pyrrolidinyl)pyridine
• 3-[(2R)-1-methylpyrrolidin-2-yl]pyridine
• Pyridine, 3-[(2R)-1-methyl-2-pyrrolidinyl]-
• (R)-(+)-Nicotine
• BRN 4666243
• CHEMBL9732
• UNII-42XNU684Z1
• DTXSID0046351
• CHEBI:39162
• 42XNU684Z1
• Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (R)-
• NCGC00163360-01
• 5-23-06-00064 (Beilstein Handbook Reference)
• DTXCID8026351
• Nicotine-D salicylate
• CAS-25162-00-9
• D-(+)-Nicotine
• PYRIDINE, 3-((2R)-1-METHYL-2-PYRROLIDINYL)-
• Nicotine-L salicylate
• (R)-3-(1-Methylpyrrolidin-2-yl)pyridine
• 3-[(2R)-1-Methyl-2-pyrrolidinyl]pyridine
• 352-(+)-Nicotine
• 2'.BETA.H-NICOTINE
• SCHEMBL20518
• BDBM82068
• SNICXCGAKADSCV-SNVBAGLBSA-N
• Tox21_112053
• PDSP1_000557
• PDSP2_000113
• AKOS006238318
• Tox21_112053_1
• NCGC00090693-11
• NCGC00163360-02
• AC-12917
• LS-96490
• J-015844
• Q27119762

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	+	0.9426	94.26%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.4196	41.96%
OATP2B1 inhibitior	-	0.8636	86.36%
OATP1B1 inhibitior	+	0.9603	96.03%
OATP1B3 inhibitior	+	0.9475	94.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.8806	88.06%
P-glycoprotein inhibitior	-	0.9957	99.57%
P-glycoprotein substrate	-	0.7747	77.47%
CYP3A4 substrate	-	0.5825	58.25%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	+	0.6763	67.63%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.8433	84.33%
CYP2C19 inhibition	-	0.8543	85.43%
CYP2D6 inhibition	-	0.8838	88.38%
CYP1A2 inhibition	-	0.6347	63.47%
CYP2C8 inhibition	-	0.8418	84.18%
CYP inhibitory promiscuity	-	0.7589	75.89%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7042	70.42%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8658	86.58%
Skin irritation	+	0.8032	80.32%
Skin corrosion	-	0.5826	58.26%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5145	51.45%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.8770	87.70%
skin sensitisation	-	0.9436	94.36%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8018	80.18%
Acute Oral Toxicity (c)	II	0.7410	74.10%
Estrogen receptor binding	-	0.9297	92.97%
Androgen receptor binding	-	0.9392	93.92%
Thyroid receptor binding	-	0.8383	83.83%
Glucocorticoid receptor binding	-	0.6638	66.38%
Aromatase binding	-	0.8745	87.45%
PPAR gamma	-	0.8154	81.54%
Honey bee toxicity	-	0.9726	97.26%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.8400	84.00%
Fish aquatic toxicity	+	0.6563	65.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	4466.8 nM	Potency	via CMAUP
CHEMBL3068	P32297	Neuronal acetylcholine receptor subunit alpha-3	45 nM	IC50	via Super-PRED
CHEMBL2109233	P17787	Neuronal acetylcholine receptor; alpha3/alpha6/beta2/beta3	84.8 nM	IC50	via Super-PRED
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	0.045 nM	Ki	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	4.5 nM; 4.5 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	141.3 nM; 141.3 nM	Potency; Potency	via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.88%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.14%	91.49%
CHEMBL2581	P07339	Cathepsin D	91.83%	98.95%
CHEMBL5203	P33316	dUTP pyrophosphatase	91.60%	99.18%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.16%	95.89%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.63%	93.65%
CHEMBL1907599	P05556	Integrin alpha-4/beta-1	84.56%	92.86%
CHEMBL1902	P62942	FK506-binding protein 1A	84.53%	97.05%
CHEMBL3920	Q04759	Protein kinase C theta	83.36%	97.69%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.98%	96.00%
CHEMBL1938212	Q9UPP1	Histone lysine demethylase PHF8	81.90%	98.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.19%	97.09%
CHEMBL5805	Q9NR97	Toll-like receptor 8	80.77%	96.25%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	80.61%	91.43%

Plants that contains it

• Piper nigrum

Cross-Links

• PubChem: 157672
• NPASS: NPC265605
• ChEMBL: CHEMBL9732