D-Glutamic acid - Moligand™, ≥98% , CAS No.6893-26-1

CAS: 6893-26-1 Cat. No.: G100444 Formula: C₅H₉NO₄ Molecular Weight: 147.13 Beilstein Registry Number: 1723800 EC Number: 230-000-8

GRADE & PURITY Moligand™, ≥98%

Synonyms

(r)-1-aminopropane-1,3-dicarboxylic acid | (2R)-2-aminopentanedioate | SR-01000597732 | CHEBI:53375 | GLUTAMIC ACID D-FORM [MI] | C00217 | D-Glutaminic acid | PDSP2_001470 | D-2-Aminoglutaric acid | delta-Glutaminate | D-Glutamic acid, >=99% (TLC) | DB025

Storage

Room temperature

Shipped In

Normal

Overview

D-Glutamic acid is an essential constituent of the bacterial peptidoglycan structure. It is added to UDP-N-acetylmuramyl-L-alanine (UDP-MurNAc-L-alanine) by the enzyme D-glutamic acid-adding enzyme (murD). This is, then, incorporated into the peptidoglycan precursor. Peptidoglycan makes up the cell walls of Gram-positive and -negative bacteria. The conversion of L-glutamate to D-glutamate by glutamate racemase (GR) enzyme is an essential step in the synthesis of peptidoglycan.

application：

D-Glutamic acid acts as a superior to alpha ketoglutarate. It helps in the growth of Lactobacillus arabinosus. It can inhibit the IgE binding to peanut allergens. It is widely used in pharmaceuticals and foods.

Specifications

Synonyms

(r)-1-aminopropane-1,3-dicarboxylic acid | (2R)-2-aminopentanedioate | SR-01000597732 | CHEBI:53375 | GLUTAMIC ACID D-FORM [MI] | C00217 | D-Glutaminic acid | PDSP2_001470 | D-2-Aminoglutaric acid | delta-Glutaminate | D-Glutamic acid, >=99% (TLC) | DB025

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Excitatory amino acid acting at NMDA receptors; less active than the L-isomer.L-isomeralso available.

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Purity

≥98%

Names and Identifiers

Pubchem Sid

488182816

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488182816

Canonical Smiles

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

IUPAC Name

(2R)-2-aminopentanedioic acid

InChIKey

WHUUTDBJXJRKMK-GSVOUGTGSA-N

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

Isomeric SMILES

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

WGK Germany

1

Molecular Weight

147.13

Beilstein

1723800

Reaxy-Rn

1723799

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1723799&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Glutamic acid and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Glutamic acid and derivatives
• Alternative Parents: D-alpha-amino acids Amino fatty acids Dicarboxylic acids and derivatives Amino acids Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• 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
• Description: This compound belongs to the class of organic compounds known as glutamic acid and derivatives. These 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.
• External Descriptors: Other amino acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRM3 Tchem Metabotropic glutamate receptor 3 (732 Activities)

Discover Target: GRM3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA1 Tclin Carbonic anhydrase I (13240 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRM4 Tchem Metabotropic glutamate receptor 4 (2320 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRM6 Tchem Metabotropic glutamate receptor 6 (361 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRM1 Tchem Metabotropic glutamate receptor 1 (2309 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRM5 Tchem Metabotropic glutamate receptor 5 (5733 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC1A3 Tchem Excitatory amino acid transporter 1 (586 Activities)

Discover Target: SLC1A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

THP-1 (11052 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FTO Tchem Alpha-ketoglutarate-dependent dioxygenase FTO (473 Activities)

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Associated Targets(non-human)

Grm2 Metabotropic glutamate receptor 2 (1326 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Grm7 Metabotropic glutamate receptor 7 (580 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

murI Glutamate racemase (2 Activities)

Discover Target: murI

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Rattus norvegicus (775804 Activities)

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lef Anthrax lethal factor (7585 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Gria2 Glutamate receptor ionotropic, AMPA (2103 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Grik1 Glutamate receptor ionotropic, kainate (722 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water, slightly soluble in ethanol, insoluble in ether
• x_specific_rotation: -30.0 to -33.0 deg(C=5, HCl(1+5))
• x_melt_point_char: 200-202°C
• Molecular Weight: 147.130 g/mol
• XLogP3: -3.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 147.053 Da
• Monoisotopic Mass: 147.053 Da
• Topological Polar Surface Area: 101.000 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 145.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1