CHEBI:17688 - (S)-nicotine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (S)-nicotine
ChEBI ID CHEBI:17688
ChEBI ASCII Name (S)-nicotine
Definition A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44268, CHEBI:14653, CHEBI:25536, CHEBI:7562
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C10H14N2
Net Charge 0
Average Mass 162.232
Monoisotopic Mass 162.116
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
SMILES C=1C=C([C@]2(N(CCC2)C)[H])C=NC1
Metabolite of Species Details
Nicotiana tabacum (NCBI:4097) See: PubMed
Roles Classification
Biological Role(s): teratogenic agent
A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
mitogen
A chemical substance that encourages a cell to commence cell division, triggering mitosis.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
neurotoxin
A poison that interferes with the functions of the nervous system.
nicotinic acetylcholine receptor agonist
An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): biomarker
A substance used as an indicator of a biological state.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
peripheral nervous system drug
A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
psychotropic drug
A loosely defined grouping of drugs that have effects on psychological function.
anxiolytic drug
Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
nicotinic acetylcholine receptor agonist
An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
phytogenic insecticide
An insecticide compound naturally occurring in plants.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (S)-nicotine (CHEBI:17688) has role anxiolytic drug (CHEBI:35474)
(S)-nicotine (CHEBI:17688) has role biomarker (CHEBI:59163)
(S)-nicotine (CHEBI:17688) has role immunomodulator (CHEBI:50846)
(S)-nicotine (CHEBI:17688) has role mitogen (CHEBI:52290)
(S)-nicotine (CHEBI:17688) has role neurotoxin (CHEBI:50910)
(S)-nicotine (CHEBI:17688) has role nicotinic acetylcholine receptor agonist (CHEBI:47958)
(S)-nicotine (CHEBI:17688) has role peripheral nervous system drug (CHEBI:49110)
(S)-nicotine (CHEBI:17688) has role phytogenic insecticide (CHEBI:22917)
(S)-nicotine (CHEBI:17688) has role plant metabolite (CHEBI:76924)
(S)-nicotine (CHEBI:17688) has role psychotropic drug (CHEBI:35471)
(S)-nicotine (CHEBI:17688) has role teratogenic agent (CHEBI:50905)
(S)-nicotine (CHEBI:17688) has role xenobiotic (CHEBI:35703)
(S)-nicotine (CHEBI:17688) is a 3-(1-methylpyrrolidin-2-yl)pyridine (CHEBI:138000)
(S)-nicotine (CHEBI:17688) is conjugate base of (S)-nicotinium(1+) (CHEBI:59806)
(S)-nicotine (CHEBI:17688) is enantiomer of (R)-nicotine (CHEBI:39162)
Incoming (S)-6-hydroxynicotine (CHEBI:17532) has functional parent (S)-nicotine (CHEBI:17688)
(S)-nicotine 1-N-oxide (CHEBI:132572) has functional parent (S)-nicotine (CHEBI:17688)
(S)-nicotinium N-α-D-glucosiduronate (CHEBI:63860) has functional parent (S)-nicotine (CHEBI:17688)
nicotine (CHEBI:18723) has part (S)-nicotine (CHEBI:17688)
(S)-nicotinium(1+) (CHEBI:59806) is conjugate acid of (S)-nicotine (CHEBI:17688)
(R)-nicotine (CHEBI:39162) is enantiomer of (S)-nicotine (CHEBI:17688)
IUPAC Name
3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
Synonyms Sources
(−)-nicotine ChemIDplus
(-)-3-(1-Methyl-2-pyrrolidyl)pyridine HMDB
(-)-3-(N-Methylpyrrolidino)pyridine HMDB
(R)-3-(1-Methyl-2-pyrrolidinyl)pyridine HMDB
(S)-(−)-nicotine NIST Chemistry WebBook
(S)-3-(1-methylpyrrolidin-2-yl)pyridine KEGG COMPOUND
(S)-3-(N-methylpyrrolidin-2-yl)pyridine IUBMB
(S)-Nicotine KEGG COMPOUND
(S)-nicotine ChemIDplus
1-Methyl-2-(3-pyridyl)pyrrolidine HMDB
3-(1-Methyl-2-pyrollidinyl)pyridine HMDB
3-(1-Methylpyrrolidin-2-yl)pyridine HMDB
3-(2-(N-methylpyrrolidinyl))pyridine NIST Chemistry WebBook
3-(N-methylpyrollidino)pyridine NIST Chemistry WebBook
L(−)-nicotine IUBMB
L-3-(1-Methyl-2-pyrrolidyl)pyridine HMDB
L-Nicotine HMDB
Nicotine KEGG COMPOUND
Nicotine HMDB
Database Links Databases
1920 DrugCentral
C00002057 KNApSAcK
C00745 KEGG COMPOUND
D03365 KEGG DRUG
DB00184 DrugBank
HMDB0001934 HMDB
LSM-2093 LINCS
NCT PDBeChem
Nicotine Wikipedia
NICOTINE MetaCyc
View more database links
Registry Numbers Types Sources
3604351 Beilstein Registry Number Beilstein
54-11-5 CAS Registry Number KEGG COMPOUND
54-11-5 CAS Registry Number ChemIDplus
54-11-5 CAS Registry Number NIST Chemistry WebBook
82109 Reaxys Registry Number Reaxys
82109 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11209966 PubMed citation Europe PMC
11322615 PubMed citation Europe PMC
11406005 PubMed citation Europe PMC
11719700 PubMed citation Europe PMC
11768184 PubMed citation Europe PMC
11821649 PubMed citation Europe PMC
11851194 PubMed citation Europe PMC
12575980 PubMed citation Europe PMC
12692774 PubMed citation Europe PMC
12769614 PubMed citation Europe PMC
12850578 PubMed citation Europe PMC
12971663 PubMed citation Europe PMC
13590907 PubMed citation Europe PMC
14674846 PubMed citation Europe PMC
14761239 PubMed citation Europe PMC
14975706 PubMed citation Europe PMC
15019421 PubMed citation Europe PMC
15027713 PubMed citation Europe PMC
15251917 PubMed citation Europe PMC
15276225 PubMed citation Europe PMC
15380834 PubMed citation Europe PMC
15502843 PubMed citation Europe PMC
15527885 PubMed citation Europe PMC
15707677 PubMed citation Europe PMC
15734728 PubMed citation Europe PMC
15826609 PubMed citation Europe PMC
15894687 PubMed citation Europe PMC
15902919 PubMed citation Europe PMC
15960296 PubMed citation Europe PMC
15963341 PubMed citation Europe PMC
16059663 PubMed citation Europe PMC
16212709 PubMed citation Europe PMC
16333621 PubMed citation Europe PMC
16370520 PubMed citation Europe PMC
16496293 PubMed citation Europe PMC
17023324 PubMed citation Europe PMC
17206646 PubMed citation Europe PMC
17292347 PubMed citation Europe PMC
17350101 PubMed citation Europe PMC
17498763 PubMed citation Europe PMC
17504235 PubMed citation Europe PMC
17525204 PubMed citation Europe PMC
17560039 PubMed citation Europe PMC
17683794 PubMed citation Europe PMC
18380035 PubMed citation Europe PMC
18383130 PubMed citation Europe PMC
18490768 PubMed citation Europe PMC
18683238 PubMed citation Europe PMC
18685152 PubMed citation Europe PMC
18805442 PubMed citation Europe PMC
18922921 PubMed citation Europe PMC
19100291 PubMed citation Europe PMC
19100331 PubMed citation Europe PMC
19287496 PubMed citation Europe PMC
19389046 PubMed citation Europe PMC
19448649 PubMed citation Europe PMC
19465085 PubMed citation Europe PMC
19850423 PubMed citation Europe PMC
19954906 PubMed citation Europe PMC
21521420 PubMed citation Europe PMC
21636612 PubMed citation Europe PMC
21822688 PubMed citation Europe PMC
21945235 PubMed citation Europe PMC
21947355 PubMed citation Europe PMC
22030716 PubMed citation Europe PMC
22129149 PubMed citation Europe PMC
22218403 PubMed citation Europe PMC
22265518 PubMed citation Europe PMC
22331007 PubMed citation Europe PMC
22377934 PubMed citation Europe PMC
22459798 PubMed citation Europe PMC
22529223 PubMed citation Europe PMC
22530136 PubMed citation Europe PMC
27951416 PubMed citation Europe PMC
28187919 PubMed citation Europe PMC
28391535 PubMed citation Europe PMC
28574230 PubMed citation Europe PMC
28641297 PubMed citation Europe PMC
28678400 PubMed citation Europe PMC
28683421 PubMed citation Europe PMC
28686840 PubMed citation Europe PMC
28698187 PubMed citation Europe PMC
28700952 PubMed citation Europe PMC
28704277 PubMed citation Europe PMC
28710519 PubMed citation Europe PMC
28711472 PubMed citation Europe PMC
28714396 PubMed citation Europe PMC
28718768 PubMed citation Europe PMC
28718828 PubMed citation Europe PMC
28726253 PubMed citation Europe PMC
28735272 PubMed citation Europe PMC
Last Modified
25 July 2017