FComEx: L-Asparagine (PC000083)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:05 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000083

FoodDB Record

FDB000787

Chemical Information

Name

L-Asparagine

Description

L-Asparagine, also known as Asn or aspartamic acid, belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Asparagine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. L-Asparagine is a very strong basic compound (based on its pKa). L-Asparagine exists in all living species, ranging from bacteria to humans. Within humans, L-asparagine participates in a number of enzymatic reactions. In particular, L-asparagine and L-glutamic acid can be biosynthesized from L-aspartic acid and L-glutamine through the action of the enzyme asparagine synthetase [glutamine-hydrolyzing]. In addition, L-asparagine can be converted into L-aspartic acid through the action of the enzyme isoaspartyl peptidase/l-asparaginase. In humans, L-asparagine is involved in aspartate metabolism. L-Asparagine is an odorless tasting compound. Outside of the human body, L-Asparagine is found, on average, in the highest concentration within a few different foods, such as white lupines, wheats, and oats and in a lower concentration in sacred lotus, parsnips, and pineapples. L-Asparagine has also been detected, but not quantified in, several different foods, such as colorado pinyons, opium poppies, lentils, green beans, and watermelons. This could make L-asparagine a potential biomarker for the consumption of these foods. L-Asparagine is a potentially toxic compound. An optically active form of asparagine having L-configuration.

CAS Number

70-47-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-Asparagine	biospider
(2S)-2-amino-3-Carbamoylpropanoate	Generator
(2S)-2-Amino-3-carbamoylpropanoic acid	biospider
(2S)-2,4-Diamino-4-oxobutanoate	Generator
(2S)-2,4-Diamino-4-oxobutanoic acid	biospider
(S)-2-amino-3-Carbamoylpropanoate	Generator
(S)-2-Amino-3-carbamoylpropanoic acid	biospider
(S)-2-Aminosuccinic acid 4-amide	biospider
(S)-2,4-Diamino-4-oxobutanoate	biospider
(S)-2,4-Diamino-4-oxobutanoic acid	biospider
(S)-Asparagine	biospider
2-Aminosuccinamate	Generator
2-Aminosuccinamic acid	ChEBI
2-Aminosuccinamic acid, L-	biospider
a-Aminosuccinamate	Generator
a-Aminosuccinamic acid	Generator
Agedoite	HMDB
alpha Amminosuccinamate	HMDB
alpha Amminosuccinamic acid	HMDB
alpha-Aminosuccinamate	Generator
alpha-Aminosuccinamic acid	ChEBI
Altheine	HMDB
Asn	ChEBI
ASPARAGINE	ChEBI
Asparagine acid	HMDB
Asparagine, 9CI; L-form	db_source
Asparagine, L- (8CI)	biospider
Asparamide	HMDB
Aspartamate	Generator
Aspartamic acid	ChEBI
Aspartic acid amide	HMDB
Aspartic acid b-amide	HMDB
Aspartic acid beta amide	HMDB
b2,4-(S)-Diamino-4-oxo-utanoate	HMDB
b2,4-(S)-Diamino-4-oxo-utanoic acid	HMDB
Crystal VI	HMDB
L-2-Aminosuccinamate	Generator
L-2-Aminosuccinamic acid	biospider
L-2,4-Diamino-4-oxobutanoate	biospider
L-2,4-Diamino-4-oxobutanoic acid	biospider
L-Asparagin	ChEBI
L-Asparagine (9CI)	biospider
L-Asparatamine	biospider
L-Aspartamine	biospider
L-Aspartate b-amide	Generator
L-Aspartate beta-amide	Generator
L-Aspartate β-amide	Generator
L-Aspartic acid 4-amide	biospider
L-Aspartic acid b-amide	Generator
L-Aspartic acid beta-amide	biospider
L-Aspartic acid β-amide	Generator
L-b-Asparagine	biospider
L-beta-Asparagine	biospider
N	ChEBI
α-aminosuccinamate	Generator
α-aminosuccinamic acid	Generator

Chemical Formula

C4H8N2O3

IUPAC name

(2S)-2-amino-3-carbamoylpropanoic acid

InChI Identifier

InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1

InChI Key

DCXYFEDJOCDNAF-REOHCLBHSA-N

Isomeric SMILES

N[C@@H](CC(N)=O)C(O)=O

Average Molecular Weight

132.1179

Monoisotopic Molecular Weight

132.053492132

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Asparagine and derivatives

Alternative Parents

Substituents

Asparagine or derivatives
Alpha-amino acid
L-alpha-amino acid
Fatty amide
Fatty acyl
Fatty acid
Carboxamide group
Amino acid
Primary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aspartate family amino acid (CHEBI:17196 )
proteinogenic amino acid (CHEBI:17196 )
L-alpha-amino acid (CHEBI:17196 )
asparagine (CHEBI:17196 )
Common amino acids (C00152 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-3.82	CHMELIK,J ET AL. (1991)
Experimental Water Solubility	29.4 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 226-227 dec. (slow heat)	DFC

Foods of Origin