CHEBI:37024 - 2-aminoadipic acid

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ChEBI Name 2-aminoadipic acid
ChEBI ID CHEBI:37024
Definition An α-amino acid that is adipic acid bearing a single amino substituent at position 2. An intermediate in the formation of lysine.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Paola Roncaglia
Secondary ChEBI IDs CHEBI:64698
Supplier Information ChemicalBook:CB1130111, eMolecules:27678415, eMolecules:490874, Selleckchem:Nicotinamide(Niacinamide), ZINC000000005878
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Nicotinamide (INN, BAN UK) or niacinamide (USAN US) is a form of vitamin B3 found in food and used as a dietary supplement and medication. As a supplement, it is used orally (swallowed by mouth) to prevent and treat pellagra (niacin deficiency). While nicotinic acid (niacin) may be used for this purpose, nicotinamide has the benefit of not causing skin flushing. As a cream, it is used to treat acne, and has been observed in clinical studies to improve the appearance of aging skin by reducing hyperpigmentation and redness. It is a water-soluble vitamin. Side effects are minimal. At high doses, liver problems may occur. Normal amounts are safe for use during pregnancy. Nicotinamide is in the vitamin B family of medications, specifically the vitamin B3 complex. It is an amide of nicotinic acid. Foods that contain nicotinamide include yeast, meat, milk, and green vegetables. Nicotinamide was discovered between 1935 and 1937. It is on the World Health Organization's List of Essential Medicines. Nicotinamide is available as a generic medication and over the counter. Commercially, nicotinamide is made from either nicotinic acid (niacin) or nicotinonitrile. In some countries, grains have nicotinamide added to them. Extra-terrestrial nicotinamide has been found in carbonaceous chondrite meteorites.
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Formula C6H11NO4
Net Charge 0
Average Mass 161.15588
Monoisotopic Mass 161.06881
InChI InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)
InChIKey OYIFNHCXNCRBQI-UHFFFAOYSA-N
SMILES NC(CCCC(O)=O)C(O)=O
Metabolite of Species Details
Caenorhabditis elegans (NCBI:txid6239) See: PubMed
Sus scrofa domesticus (NCBI:txid9825) See: MetaboLights Study
Sus scrofa domesticus (NCBI:txid9825) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): mammalian metabolite
Any animal metabolite produced during a metabolic reaction in mammals.
Caenorhabditis elegans metabolite
A nematode metabolite produced by Caenorhabditis elegans.
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ChEBI Ontology
Outgoing 2-aminoadipic acid (CHEBI:37024) has role Caenorhabditis elegans metabolite (CHEBI:78804)
2-aminoadipic acid (CHEBI:37024) has role mammalian metabolite (CHEBI:75768)
2-aminoadipic acid (CHEBI:37024) is a amino dicarboxylic acid (CHEBI:36164)
2-aminoadipic acid (CHEBI:37024) is a dicarboxylic fatty acid (CHEBI:189840)
2-aminoadipic acid (CHEBI:37024) is a non-proteinogenic α-amino acid (CHEBI:83925)
2-aminoadipic acid (CHEBI:37024) is conjugate acid of 2-aminoadipate(2−) (CHEBI:84981)
Incoming D-2-aminoadipic acid (CHEBI:37025) is a 2-aminoadipic acid (CHEBI:37024)
L-2-aminoadipic acid (CHEBI:37023) is a 2-aminoadipic acid (CHEBI:37024)
2-aminoadipate(2−) (CHEBI:84981) is conjugate base of 2-aminoadipic acid (CHEBI:37024)
IUPAC Name
2-aminohexanedioic acid
Synonyms Sources
(+/-)-2-Aminoadipic acid HMDB
2-aminoadipic acid ChemIDplus
Aad ChEBI
alpha-Aminoadipic acid HMDB
α-aminoadipic acid ChemIDplus
aminoadipic acid ChEBI
DL-2-Aminoadipic acid HMDB
DL-2-Aminohexanedioic acid HMDB
DL-alpha-Aminoadipic acid HMDB
DL-α-Aminoadipic acid HMDB
Manual Xrefs Databases
Alpha-Aminoadipic_acid Wikipedia
HMDB0000510 HMDB
View more database links
Registry Numbers Types Sources
1724349 Reaxys Registry Number Reaxys
1773077 Beilstein Registry Number ChemIDplus
542-32-5 CAS Registry Number ChemIDplus
Citations Types Sources
22264337 PubMed citation Europe PMC
31148 PubMed citation Europe PMC
6462455 PubMed citation Europe PMC
Last Modified
24 February 2022