asparagine (CHEBI:22653)

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ChEBI Name	asparagine

ChEBI ID	CHEBI:22653

Definition	An α-amino acid in which one of the hydrogens attached to the α-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	eMolecules:27677620, eMolecules:478704

Download	Molfile XML SDF

Wikipedia	License
Asparagine (symbol Asn or N) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH+3 form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain carboxamide, classifying it as a polar (at physiological pH), aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it. It is encoded by the codons AAU and AAC. The one-letter symbol N for asparagine was assigned arbitrarily, with the proposed mnemonic asparagiNe;
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Formula

C4H8N2O3

Net Charge

Average Mass

132.11800

Monoisotopic Mass

132.05349

InChI

InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)

InChIKey

DCXYFEDJOCDNAF-UHFFFAOYSA-N

SMILES

NC(CC(N)=O)C(O)=O

Metabolite of Species	Details
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Daphnia magna (NCBI:txid35525)	See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268

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):	algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna.

ChEBI Ontology
Outgoing	asparagine (CHEBI:22653) has part 2-amino-2-oxoethyl group (CHEBI:50330) asparagine (CHEBI:22653) has role Daphnia magna metabolite (CHEBI:83056) asparagine (CHEBI:22653) has role algal metabolite (CHEBI:84735) asparagine (CHEBI:22653) is a α-amino acid (CHEBI:33704) asparagine (CHEBI:22653) is a dicarboxylic acid monoamide (CHEBI:35735) asparagine (CHEBI:22653) is a polar amino acid (CHEBI:26167) asparagine (CHEBI:22653) is conjugate acid of asparaginate (CHEBI:32660) asparagine (CHEBI:22653) is conjugate base of asparaginium (CHEBI:32661)

Incoming	N-ethylasparagine (CHEBI:64308) has functional parent asparagine (CHEBI:22653) asparagine derivative (CHEBI:22654) has functional parent asparagine (CHEBI:22653) D-asparagine (CHEBI:28159) is a asparagine (CHEBI:22653) L-asparagine (CHEBI:17196) is a asparagine (CHEBI:22653) asparaginium (CHEBI:32661) is conjugate acid of asparagine (CHEBI:22653) asparaginate (CHEBI:32660) is conjugate base of asparagine (CHEBI:22653) N²-asparagino group (CHEBI:32662) is substituent group from asparagine (CHEBI:22653) N⁴-asparagino group (CHEBI:22655) is substituent group from asparagine (CHEBI:22653) asparagine residue (CHEBI:32664) is substituent group from asparagine (CHEBI:22653) asparaginyl group (CHEBI:22656) is substituent group from asparagine (CHEBI:22653)

IUPAC Name

asparagine

Synonyms	Sources
2,4-diamino-4-oxobutanoic acid	IUPAC
2-amino-3-carbamoylpropanoic acid	JCBN
Asn	ChEBI
ASN	ChEBI
Asparagin	ChEBI
asparagina	ChEBI
DL-Asparagine	KEGG COMPOUND
Hasp	IUPAC
N	ChEBI

Citations

Last Modified

29 July 2019