FComEx: D-Aspartic acid (PC000937)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:28 UTC

Update date

2017-01-19 02:36:42 UTC

FoodComEx ID

PC000937

FoodDB Record

FDB023933

Chemical Information

Name

D-Aspartic acid

Description

D-Aspartic acid is the D-isomer of aspartic acid. Since its discovery in invertebrates, free D-aspartate (D-Asp) has been identified in a variety of organisms, including microorganisms, plants, and lower animals, mammals and humans. D-Asp in mammalian tissues is present in specific cells, indicating the existence of specific molecular components that regulate D-Asp levels and localization in tissues. In the rat adrenal medulla, D-Asp is closely associated with adrenaline-cells (A-cells), which account for approximately 80% of the total number of chromaffin cells in the tissue, and which make and store adrenaline. D-Asp appears to be absent from noradrenaline-cells (NA-cells), which comprise approximately 20% of the total number of chromaffin cells in the adrenal medulla, and which make and store noradrenaline. D-aspartate oxidase (EC 1.4.3.1, D-AspO), which catalyzes oxidative deamination of D-Asp, appears to be present only in NA-cells, suggesting that the lack of D-Asp in these cells is due to D-Asp oxidase-mediated metabolism of D-Aspecies In the rat adrenal cortex, the distribution of D-Asp changes during development. It has been suggested that developmental changes in the localization of D-Asp reflects the participation of D-Asp in the development and maturation of steroidogenesis in rat adrenal cortical cells. D-Asp is involved in steroid hormone synthesis and secretion in mammals as well. D-Asp is synthesized intracellularly, most likely by Asp racemase (EC 5.1.1.13). Endogenous D-Asp apparently has two different intracellular localization patterns: cytoplasmic and vesicular. D-Asp release can occur through three distinct pathways: 1) spontaneous, continuous release of cytoplasmic D-Asp, which is not associated with a specific stimulus; 2) release of cytoplasmic D-Asp via a volume-sensitive organic anion channel that connects the cytoplasm and extracellular space; 3) exocytotic discharge of vesicular D-Aspecies D-Asp can be released via a mechanism that involves the L-Glu transporter. D-Asp is thus apparently in dynamic flux at the cellular level to carry out its physiological function(s) in mammals. (PMID: 16755369) [HMDB]

CAS Number

1783-96-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(-)-Aspartic acid	hmdb
(2R)-2-Aminobutanedioate	hmdb
(2R)-2-Aminobutanedioic acid	hmdb
(R)-2-Aminobutanedioate	hmdb
(R)-2-Aminobutanedioic acid	hmdb
(R)-2-Aminosuccinic acid	hmdb
(R)-Aspartic acid	hmdb
1-Amino-1,2-carboxyethane	hmdb
Aspartate D-form	Generator
aspartic acid	hmdb
Aspartic acid D-form	ChEBI
D-(-)-Aspartic acid	hmdb
D-Asparaginsaeure	hmdb
D-aspartate	hmdb
D-aspartic acid	hmdb
delta-(-)-Aspartic acid	hmdb
delta-asparaginsaeure	hmdb
delta-aspartate	hmdb
delta-aspartic acid	hmdb
Lopac-alpha-9256	hmdb
Tocris-0213	hmdb

Chemical Formula

C4H7NO4

IUPAC name

(2R)-2-aminobutanedioic acid

InChI Identifier

InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m1/s1

InChI Key

CKLJMWTZIZZHCS-UWTATZPHSA-N

Isomeric SMILES

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

Average Molecular Weight

133.1027

Monoisotopic Molecular Weight

133.037507717

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid 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

Aspartic acid and derivatives

Alternative Parents