CHEBI:17688 - (S)-nicotine

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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 ChemicalBook:CB4365169, eMolecules:499483
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Leucine (symbol Leu or L) is an essential amino acid that is used in the biosynthesis of proteins. Leucine is an α-amino acid, meaning it contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isobutyl group, making it a non-polar aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it; it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, and beans and other legumes. It is encoded by the codons UUA, UUG, CUU, CUC, CUA, and CUG. Leucine is named after the Greek word for "white": λευκός (leukós, "white"), after its common appearance as a white powder, a property it shares with many other amino acids. Like valine and isoleucine, leucine is a branched-chain amino acid. The primary metabolic end products of leucine metabolism are acetyl-CoA and acetoacetate; consequently, it is one of the two exclusively ketogenic amino acids, with lysine being the other. It is the most important ketogenic amino acid in humans. Leucine and β-hydroxy β-methylbutyric acid, a minor leucine metabolite, exhibit pharmacological activity in humans and have been demonstrated to promote protein biosynthesis via the phosphorylation of the mechanistic target of rapamycin (mTOR).
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Formula C10H14N2
Net Charge 0
Average Mass 162.236
Monoisotopic Mass 162.11570
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 [H][C@]1(CCCN1C)C1=CC=CN=C1
Metabolite of Species Details
Nicotiana tabacum (NCBI:txid4097) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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)-nicotine N1'-oxide (CHEBI:142659) 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
Manual Xrefs Databases
1920 DrugCentral
485 BPDB
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
Citations
Last Modified
13 February 2023