CHEBI:77761 - piperidin-2-one

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ChEBI Name piperidin-2-one
ChEBI ID CHEBI:77761
Definition A δ-lactam that is piperidine which is substituted by an oxo group at position 2.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB3750054, eMolecules:26755894, eMolecules:533030, ZINC000000083315
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Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic beta carbon substituent. Tryptophan is also a precursor to the neurotransmitter serotonin, the hormone melatonin, and vitamin B3 (niacin). It is encoded by the codon UGG. Like other amino acids, tryptophan is a zwitterion at physiological pH where the amino group is protonated (–NH+3; pKa = 9.39) and the carboxylic acid is deprotonated ( –COO−; pKa = 2.38). Humans and many animals cannot synthesize tryptophan: they need to obtain it through their diet, making it an essential amino acid. Tryptophan is named after the digestive enzymes trypsin, which were used in its first isolation from casein proteins. It was assigned the one-letter symbol W based on the double ring being visually suggestive to the bulky letter.
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Formula C5H9NO
Net Charge 0
Average Mass 99.13110
Monoisotopic Mass 99.06841
InChI InChI=1S/C5H9NO/c7-5-3-1-2-4-6-5/h1-4H2,(H,6,7)
InChIKey XUWHAWMETYGRKB-UHFFFAOYSA-N
SMILES O=C1CCCCN1
Roles Classification
Biological Role(s): EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor
An EC 1.2.1.* (oxidoreductase acting on donor aldehyde/oxo group with NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of L-glutamate gamma-semialdehyde dehydrogenase (EC 1.2.1.88).
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ChEBI Ontology
Outgoing piperidin-2-one (CHEBI:77761) has role EC 1.2.1.88 (L-glutamate γ-semialdehyde dehydrogenase) inhibitor (CHEBI:77763)
piperidin-2-one (CHEBI:77761) is a δ-lactam (CHEBI:77727)
piperidin-2-one (CHEBI:77761) is a piperidones (CHEBI:48589)
IUPAC Name
piperidin-2-one
Synonyms Sources
2-oxo-piperidine ChEBI
2-oxopiperidine ChEBI
5-pentanolactam ChemIDplus
α-piperidone NIST Chemistry WebBook
δ-valerolactam NIST Chemistry WebBook
piperidinone ChemIDplus
Piperidon ChemIDplus
piperidone ChemIDplus
piperidone-2 ChemIDplus
Manual Xref Database
2-Piperidinone Wikipedia
View more database links
Registry Numbers Types Sources
106434 Reaxys Registry Number Reaxys
27154-43-4 CAS Registry Number ChemIDplus
27154-43-4 CAS Registry Number NIST Chemistry WebBook
675-20-7 CAS Registry Number NIST Chemistry WebBook
675-20-7 CAS Registry Number ChemIDplus
Last Modified
23 October 2015
General Comment
2014-03-18 For inhibition of L-glutamate γ-semialdehyde dehydrogenase by piperidin-2-one, see Strecker, H.J., Methods Enzymol. 1971, 17B, 262-265.