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(S)-nicotine

AlkaPlorer ID: AK001882

Synonym: '', 'SMR000471862', '3-(N-methylpyrollidino)pyridine', '(S)-nicotine', '(S)-(-)-nicotine', '(-)-3-(1-Methyl-2-pyrrolidyl)pyridine', '1-Methyl-2-(3-pyridyl)pyrrolidine', 'L-3-(1-Methyl-2-pyrrolidyl)pyridine', '(S)-3-(1-methylpyrrolidin-2-yl)pyridine', '(-)-nicotine', '(-)-3-(N-Methylpyrrolidino)pyridine', '(-)-Nicotine', '3-(2-(N-methylpyrrolidinyl))pyridine', '3-(1-Methyl-2-pyrollidinyl)pyridine', '(S)-3-(N-methylpyrrolidin-2-yl)pyridine', 'L-Nicotine', '(R)-3-(1-Methyl-2-pyrrolidinyl)pyridine', 'MLS001332491', 'MLSMR', '(S)-Nicotine', '3-(1-Methylpyrrolidin-2-yl)pyridine', 'MLS001066400', 'Nicotine', 'L(-)-nicotine'

IUPAC Name: None

Structure

SMILES: CN1CCC[C@@H]1C1=CC=C[NH+]=C1

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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/p+1/t10-/m1/s1

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InChIKey: SNICXCGAKADSCV-SNVBAGLBSA-O

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Reference

PubChem CID: 6950509

SuperNatural Ⅲ: SN0350212-02

NPASS: NPC265605

Source

Species Genus Family Order Class Phylum Kingdom Domain
Piper nigrum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 163.244

TPSA？: 17.380000000000003

MolLogP？: 1.2674

Number of H-Donors: 0

Number of H-Acceptors: 1

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 4466.8 nM None
Homo sapiens Cytochrome P450 2A6 IC50 580000.0 nM 10.1021/jm049536b
Homo sapiens Histone acetyltransferase GCN5 Potency 35481.3 nM None
Homo sapiens Prelamin-A/C Potency 4.5 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 141.3 nM None
Musca domestica Musca domestica Activity 40.0 % 10.1584/jpestics.29.43
Musca domestica Nicotinic acetylcholine receptor alpha 5 subunit Activity 422.0 uM 10.1584/jpestics.29.43
Musca domestica Nicotinic acetylcholine receptor alpha 5 subunit IC50 422000.0 nM 10.1271/bbb.67.980
Mus musculus Cytochrome P450 2A5 IC50 160000.0 nM 10.1021/jm049536b
Mus musculus Mus musculus ED50 2.9 mg.kg-1 10.1021/jm060122n
Mus musculus Mus musculus ED50 3.9 mg.kg-1 10.1021/jm060122n
Mus musculus Mus musculus ED50 7.6 mg.kg-1 10.1021/jm060122n
Mus musculus Mus musculus ED50 8.0 mg.kg-1 10.1021/jm060122n
Periplaneta americana Periplaneta americana MLD 160.0 nmol 10.1584/jpestics.29.43
Periplaneta americana Periplaneta americana MLD 320.0 nmol 10.1584/jpestics.29.43
Plasmodium falciparum Plasmodium falciparum Potency 15101.4 nM None
Rattus norvegicus Neuronal acetylcholine receptor Dopamine release 114.0 % 10.1021/jm00052a005
Rattus norvegicus Neuronal acetylcholine receptor Ki 16.0 nM 10.1021/jm00052a005
Rattus norvegicus Neuronal acetylcholine receptor; alpha4/beta2 Ki 35.0 nM 10.1021/jm060122n
Rattus norvegicus Neuronal acetylcholine receptor; alpha4/beta2 Ki 38.0 nM 10.1016/j.bmcl.2004.02.007
Rattus norvegicus Neuronal acetylcholine receptor; alpha4/beta2 Ki 87.0 nM 10.1021/jm0103561
Torpedo californica Acetylcholine receptor protein alpha chain Activity nan None 10.1584/jpestics.20.49
Torpedo californica Acetylcholine receptor protein alpha chain IC50 54400.0 nM 10.1584/jpestics.20.49
None ADMET Ratio 3.8 None 10.1021/jm049536b
None NON-PROTEIN TARGET Activity 57.3 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 61.5 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 63.8 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 64.6 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 65.4 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 65.8 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 66.4 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 66.5 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 67.1 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 68.1 % 10.1016/j.bmcl.2014.02.008
None Unchecked Ac50 0.631 uM None
None Unchecked AC50 631.0 nM None
None Unchecked Ki 16.0 nM 10.1021/jm00034a002
None Unchecked Ki 32.0 nM 10.1021/jm00034a002
None Unchecked Ki 1500.0 nM 10.1021/jm00034a002
None Unchecked Ki 20000.0 nM 10.1021/jm00034a002
None Unchecked Potency 14125.4 nM None
None Unchecked Potency 20587.8 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010552 CN1CCC[C@@H]1c1cccnc1.C[SAH]>>CN1CCC[C@@H]1c1ccc[n+](C)c1 RXN66-82
AKRT010553 CN1CCC[C@@H]1c1cccnc1>>CN1CCC[C@@H]1c1ccc(O)nc1 R161-RXN
AKRT010558 CN1CCC[C@H]1c1ccc(O)nc1>>CN1CCC[C@@H]1c1cccnc1 MNXR173318