Livestock Metabolome Database: Showing metabocard for D-Aspartic acid (LMDB00478)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:50:44 UTC

Update Date

2021-04-30 20:57:41 UTC

Lmdb

LMDB00478

Secondary Accession Numbers

None

Metabolite Identification

Common 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 animals. 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-Asp. 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-Asp. 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 ).

Structure

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

Synonyms

Value	Source
(R)-2-Aminobutanedioic acid	ChEBI
(R)-2-Aminosuccinic acid	ChEBI
Aspartic acid D-form	ChEBI
D-Asparaginsaeure	ChEBI
DAS	ChEBI
(R)-2-Aminobutanedioate	Generator
(R)-2-Aminosuccinate	Generator
Aspartate D-form	Generator
D-Aspartate	Generator
D Aspartate	MeSH
D Aspartic acid	MeSH
(-)-Aspartic acid	HMDB
(2R)-2-Aminobutanedioate	HMDB
(2R)-2-Aminobutanedioic acid	HMDB
(R)-Aspartic acid	HMDB
1-amino-1,2-Carboxyethane	HMDB
Aspartic acid	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

Average Molecular Weight

133.1027

Monoisotopic Molecular Weight

133.037507717

IUPAC Name

(2R)-2-aminobutanedioic acid

Traditional Name

D-aspartic acid

CAS Registry Number

1783-96-6

SMILES

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

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

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

Substituents

Aspartic acid or derivatives
Alpha-amino acid
D-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty acid
Amino acid
Carboxylic acid
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:17364 )
aspartic acid (CHEBI:17364 )
Other amino acids (C00402 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.5	ALOGPS
logP	-3.5	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	1.7	ChemAxon
pKa (Strongest Basic)	9.61	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.53 m³·mol⁻¹	ChemAxon
Polarizability	11.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9100000000-b7db3377089f4c95001b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01w4-9610000000-0f1463c6395830708e12	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00lr-3900000000-162904f2efeb4d9ec1b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0079-9200000000-c986d1c1f93cfaaad024	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-a72e46d76472d24bc1c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-8d22977b40aa259a21d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9600000000-9c231a338120ef30d24c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9200000000-6c07b782a658249d199d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0019-9600000000-c2c3ca177b300379b9a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01c9-9700000000-43373fabf1f2a8251ac8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-36b20174fd207db22998	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-d6951a2ec44739673310	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-5900000000-b11760c7c2cfa2af3c7e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0019-9500000000-7269dcfd86ec82641ed9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05g3-9000000000-4403e122d1d449aace05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01p9-6900000000-10cf89ab499e02e19a92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-9000000000-fe190327aa4e06a02a41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9000000000-fe92c9aa9f1f1fb64042	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9100000000-0ac0dd6913d2586f7973	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-75d22f21955bd28b7dcb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-fb1c4f0680fc2dac53c7	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Embryo culture media
Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Embryo culture media	Detected but not Quantified	Not Applicable	Not Available	Bovine	20058302	details
Embryo culture media	Detected but not Quantified	Not Applicable	Not Available	Bovine	20058302	details
Plasma	Detected and Quantified	3.23 uM	Not Available	Bovine	17197001	details
Plasma	Detected and Quantified	3.23 uM	Not Available	Bovine	17197001	details
Plasma	Detected and Quantified	4.51 uM	Not Available	Bovine	17197001	details
Serum	Detected and Quantified	9.2859 +/- 9.3309 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	9.4016 +/- 3.9691 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.9988 +/- 5.6581 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.535 +/- 6.2699 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	11.1292 +/- 6.1496 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.8804 +/- 5.5351 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.5612 +/- 7.1174 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.6223 +/- 7.5224 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	11.4233 +/- 5.2843 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.9396 +/- 7.5902 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.9265 +/- 5.5579 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.3912 +/- 7.211 uM	Normal	Ovine	Goldansaz et al.,...	details