N-Oxalylglycine - ≥98% , CAS No.5262-39-5

CAS: 5262-39-5 Cat. No.: N341017 Molecular Weight: 147.09 EC Number: 687-281-9

GRADE & PURITY ≥98%

Synonyms

NOG | Oxalylglycine | 2-[(Carboxymethyl)amino]-2-oxoacetic Acid | N-Oxalylglycine | 4idz | 2-(carboxyformamido)acetic acid | oxamic acid, (carboxymethyl)- | AS-60026 | CHEBI:44482 | Glycine, N-(carboxycarbonyl)- | MFCD00913253 | n-oxalyl glycine | Pokkuri

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

N-Oxalylglycine is a cell permeable α-ketoglutarate analogue that functions as a competitive inhibitor of P4HA and PDI (prolyl 4-hydroxylase) which hydroxylates proline-rich peptides|in vitro|. Studies show that the glycine moiety of N-Oxalylglycine can be modified stereoselectively by acylsulfonamides or anilides binding to the ω-carboxylate group of the molecule resulting in a sharp reduction in activity. In addition, N-Oxalylglycine competes with αKG to bind to taurine/αKG dioxygenase resulting in inhibition of the enzyme. N-Oxalylglycine is an inhibitor of HIF PHD1 and HIF PHD2.

Specifications

Synonyms

NOG | Oxalylglycine | 2-[(Carboxymethyl)amino]-2-oxoacetic Acid | N-Oxalylglycine | 4idz | 2-(carboxyformamido)acetic acid | oxamic acid, (carboxymethyl)- | AS-60026 | CHEBI:44482 | Glycine, N-(carboxycarbonyl)- | MFCD00913253 | n-oxalyl glycine | Pokkuri

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

N-oxalyl glycine is an inhibitor of α-ketoglutaric acid dependent enzymes and mimics the initial step, but does not initiate the hydroxylation process. N-oxalyl-glycine has been used to inhibit histone lysine demethylases containing the Jumonji C domain.

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Product Properties

• pKa: pKa: 2.83 (Predicted)
• Ki Data: Prolyl 4-hydroxylase alpha-1 subunit: Ki= 540 nM (rat); P4HA1: Ki= 8 μM (human); HIF-1α: Ki= 1.2 mM (human)

Names and Identifiers

• Pubchem Sid: 488194237
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488194237
• Canonical Smiles: C(C(=O)O)NC(=O)C(=O)O
• IUPAC Name: 2-(carboxymethylamino)-2-oxoacetic acid
• InChIKey: BIMZLRFONYSTPT-UHFFFAOYSA-N
• INCHI: 1S/C4H5NO5/c6-2(7)1-5-3(8)4(9)10/h1H2,(H,5,8)(H,6,7)(H,9,10)
• Isomeric SMILES: C(C(=O)O)NC(=O)C(=O)O
• WGK Germany: 3
• Molecular Weight: 147.09
• Reaxy-Rn: 1771016
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1771016&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 N-acyl-alpha amino acids and derivatives
              • Level8 N-acyl-alpha amino acids

• 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 - N-acyl-alpha amino acids and derivatives
• Direct Parent: N-acyl-alpha amino acids
• Alternative Parents: Dicarboxylic acids and derivatives Secondary carboxylic acid amides Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: N-acyl-alpha-amino acid - Dicarboxylic acid or derivatives - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
• External Descriptors: amino dicarboxylic acid - N-acylglycine

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)

EGLN2 Tclin Egl nine homolog 2 (1 Activities)

Discover Target: EGLN2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

KDM6B Tchem Lysine-specific demethylase 6B (1 Activities)

Discover Target: KDM6B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

EGLN2 Tclin Hypoxia-inducible factor prolyl hydroxylase 1 (404 Activities)

Discover Target: EGLN2

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

HeLa (62764 Activities)

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

KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

Discover Target: KDM4A

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

EGLN1 Tclin Egl nine homolog 1 (1702 Activities)

Discover Target: EGLN1

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

HIF1AN Tbio Hypoxia-inducible factor 1-alpha inhibitor (79 Activities)

Discover Target: HIF1AN

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

KDM4D Tchem Lysine-specific demethylase 4D (224 Activities)

Discover Target: KDM4D

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

KDM4C Tchem Lysine-specific demethylase 4C (1129 Activities)

Discover Target: KDM4C

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

KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

Discover Target: KDM4E

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

KDM3A Tchem Lysine-specific demethylase 3A (116 Activities)

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

KDM2A Tchem Lysine-specific demethylase 2A (198 Activities)

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

KDM6B Tchem Lysine-specific demethylase 6B (280 Activities)

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

PHF8 Tchem Histone lysine demethylase PHF8 (151 Activities)

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

KDM5C Tchem Lysine-specific demethylase 5C (224 Activities)

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

KDM7A Tchem Lysine-specific demethylase 7 (35 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)

Discover Target: FTO

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

KDM5A Tchem Lysine-specific demethylase 5A (893 Activities)

Discover Target: KDM5A

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

ALKBH3 Tchem Alpha-ketoglutarate-dependent dioxygenase alkB homolog 3 (119 Activities)

Discover Target: ALKBH3

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

ALKBH5 Tchem RNA demethylase ALKBH5 (134 Activities)

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

KDM5B Tchem Lysine-specific demethylase 5B (814 Activities)

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

TET2 Tchem Methylcytosine dioxygenase TET2 (57 Activities)

Discover Target: TET2

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

ALKBH2 Tbio DNA oxidative demethylase ALKBH2 (19 Activities)

Discover Target: ALKBH2

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

Associated Targets(non-human)

P4ha1 Prolyl 4-hydroxylase alpha-1 subunit (36 Activities)

Discover Target: P4ha1

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

rep Replicase polyprotein 1ab (378 Activities)

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

SARS-CoV-2 (38078 Activities)

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A085R Prolyl 4-hydroxylase (72 Activities)

Discover Target: A085R

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water, DMSO (~10 mg/ml, purged with inert gas), ethanol (~10 mg/ml, purged with inert gas), and DMF (~5 mg/ml, purged with inert gas).
• Sensitivity: moisture sensitive
• Refractive Index: n20D1.52 (Predicted)
• Molecular Weight: 147.090 g/mol
• XLogP3: -0.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 147.017 Da
• Monoisotopic Mass: 147.017 Da
• Topological Polar Surface Area: 104.000 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 174.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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