Livestock Metabolome Database: Showing metabocard for D-Glutamic acid (LMDB00427)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:49:37 UTC

Update Date

2016-07-19 23:38:07 UTC

Lmdb

LMDB00427

Secondary Accession Numbers

None

Metabolite Identification

Common Name

D-Glutamic acid

Description

There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid, is not endogenously produced in higher mammals. It is found naturally primarily in the cell walls of certain bacteria. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). Free D-glutamate is found in mammalian tissue at surprisingly high levels, with D-glutamate accounting for 9% of the total glutamate present in liver. D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date and this may account for its localization to the liver, since circulating D-glutamate may alter redox stabiity (PMID 11158923 ). Certain eels are known to use D-glutamic acid as a phermone for chemical communication.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-2-Aminopentanedioic acid	ChEBI
D-2-Aminoglutaric acid	ChEBI
D-Glutaminic acid	ChEBI
D-Glutaminsaeure	ChEBI
DGL	ChEBI
Glutamic acid D-form	ChEBI
(R)-2-Aminopentanedioate	Generator
D-2-Aminoglutarate	Generator
D-Glutaminate	Generator
Glutamate D-form	Generator
D-Glutamate	Generator
(2R)-2-Aminopentanedioate	HMDB
(2R)-2-Aminopentanedioic acid	HMDB
D-2-Aminopentanedioate	HMDB
D-2-Aminopentanedioic acid	HMDB
delta-2-Aminoglutarate	HMDB
delta-2-Aminoglutaric acid	HMDB
delta-2-Aminopentanedioate	HMDB
delta-2-Aminopentanedioic acid	HMDB
delta-Glutamate	HMDB
delta-Glutamic acid	HMDB
delta-Glutaminate	HMDB
delta-Glutaminic acid	HMDB
delta-Glutaminsaeure	HMDB
Glutamate	HMDB
Lopac-g-2128	HMDB
Lopac-gamma-2128	HMDB
R-(-)-Glutamate	HMDB
R-(-)-Glutamic acid	HMDB
Tocris-0217	HMDB
Glutamic acid, (D)-isomer	HMDB
L Glutamic acid	HMDB
L-Glutamate	HMDB
L-Glutamic acid	HMDB
D Glutamate	HMDB
Glutamate, potassium	HMDB
L-Glutamate, aluminum	HMDB
Aluminum L glutamate	HMDB
Glutamic acid	HMDB
L Glutamate	HMDB
Aluminum L-glutamate	HMDB
Potassium glutamate	HMDB

Chemical Formula

C₅H₉NO₄

Average Molecular Weight

147.1293

Monoisotopic Molecular Weight

147.053157781

IUPAC Name

(2R)-2-aminopentanedioic acid

Traditional Name

D-glutamic acid

CAS Registry Number

6893-26-1

SMILES

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

InChI Identifier

InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1

InChI Key

WHUUTDBJXJRKMK-GSVOUGTGSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic 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

Glutamic acid and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:15966 )
glutamic acid (CHEBI:15966 )
Other amino acids (C00217 )

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	-3.2	ChemAxon
logS	-0.26	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	9.54	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	4	ChemAxon
Refractivity	31.29 m³·mol⁻¹	ChemAxon
Polarizability	13.19 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	splash10-0k9x-9300000000-a43e0122a45b9abf09d6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9240000000-53c8c708191dfcd550d0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-ad4a2989e599a67182c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-c449cfd2231fe941d44f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-1900000000-f71458032a132069f94f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-7900000000-810570c8cfcea8da64f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d5167570d11d77fd541e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-0900000000-c7d42b011a328bb7991d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9300000000-9fd882f84339f600b5eb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-407a30a35de9c1cceb3a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-8610ea89d52ef116caf5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-331b7ed6ea33880c306e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3900000000-58248bb2a0c7ddc905cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zgi-9600000000-076b628a6858a60a475f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-bd3823a5fab8a2d9b62c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-11233b5887638266e512	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fba-4900000000-1e8ea62e3fbd8467396f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-9100000000-6c956e122b59de69a472	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-4900000000-c467fa409affedc9ab85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-ddda6500978ea1670dcf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-4c6639c8639f077b57a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-4900000000-503f6a47bc72662de09c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ugi-3900000000-ec06b29308ff068bf7a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e06c31345e8a86e71de1	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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Follicular Fluid
Lung
Plasma
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected and Quantified	250 +/- 10-460+/-10 uM	Not Available	Porcine	183842	details
Follicular Fluid	Detected and Quantified	540 +/- 30-640+/-80 uM	Not Available	Porcine	183842	details
Lung	Detected and Quantified	2.70+/-0.20 umol/g	Not Available	Porcine	23412987	details
Plasma	Detected and Quantified	115.4 +/- 38.2 uM	Not Available	Ovine	17900638	details
Plasma	Detected and Quantified	166.0-87.6 uM	Not Available	Ovine	17900638	details
Plasma	Detected and Quantified	200.85 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	221.43 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	232.9 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	329.16 uM	Not Available	Porcine	25820777	details
Ruminal Fluid	Detected and Quantified	811 +/- 76 uM	Not Available	Caprine	22706048	details
Serum	Detected and Quantified	200 +/- 40 uM	Not Available	Porcine	183842	details
Serum	Detected and Quantified	315.4 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	317.8 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	333.7 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	418.5 uM	Not Available	Porcine	Barbara U. Metzle...	details

External Links

DrugBank ID

DB02517

HMDB ID

HMDB0003339

FooDB ID

FDB023148

Phenol Explorer ID

Not Available

KNApSAcK ID

C00019577

BiGG ID

Not Available

BioCyc ID

D-GLT

METLIN ID

6895

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB03339

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Raj D, Langford M, Krueger S, Shelton M, Welbourne T: Regulatory responses to an oral D-glutamate load: formation of D-pyrrolidone carboxylic acid in humans. Am J Physiol Endocrinol Metab. 2001 Feb;280(2):E214-20. [11158923 ]

Showing metabocard for D-Glutamic acid (LMDB00427)

Structure for LMDB00427 (D-Glutamic acid)