2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid

• ChemBase ID: 103839
• Molecular Formular: C11H16N2O8
• Molecular Mass: 304.25334
• Monoisotopic Mass: 304.09066548
• SMILES: CC(=O)NC(CC(=O)O)C(=O)NC(CCC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CCC(C(=O)O)NC(=O)C(NC(=O)C)CC(=O)O
• InChI: InChI=1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21)
• InChIKey: OPVPGKGADVGKTG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid
• IUPAC Traditional name: 2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid
• Synonyms: NAAG; Spaglumic acid; N-Acetyl-Asp-Glu; N-Acetyl-Aspartic Acid-glutamic acid-OH; N-Ac-D-E; N-ACETYL-ASP-GLU

Database IDs

• CAS Number: 3106-85-2
• MDL Number: MFCD00076652
• PubChem SID: 24891036; 162091034
• PubChem CID: 5255

CALCULATED PROPERTIES

• Acid pKa: 3.127459
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -7.5994043
• LogD (pH = 7.4): -12.0718355
• Log P: -2.2913463
• Molar Refractivity: 64.0643 cm^3
• Polarizability: 25.43706 Å^3
• Polar Surface Area: 170.1 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: white powder
• Optical Rotation: [α]22/D -34.5°, c = 1.1 in H2O(lit.)

Safety Information

• Storage Condition: -20°C, Desiccate
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRIN3A(116443), GRIN3B(116444), GRINA(2907), GRM3(2913)mouse ... GRIN1(14810), GRIN2A(14811), GRIN2B(14812), GRIN2C(14813), GRIN2D(14814), GRIN3A(242443), GRIN3B(170483), GRINA(66168), GRM3(108069)rat ... GRIN1(24408), GRIN2A(24409), GRIN2B(24410), GRIN2C(24411), GRIN2D(24412), GRIN3A(191573), GRIN3B(170796), GRINA(266668), GRM3(24416)

Product Information

• Purity: ≥97% (TLC)

DETAILS

MP Biomedicals - 02153036

An endogenous neuropeptide with high affinity for a brain "Glutamate" receptor.

Sigma Aldrich - A5930

Amino Acid Sequence
NAc-Asp-Glu
Caution
Store desiccated.
Biochem/physiol Actions
Endogenous neurotransmitter localized to neurons with high affinity for metabotropic glutamate receptors, mGluR3. It is an antagonist at NMDA receptors. Catabolized by carboxypeptidase II, which is expressed on astrocyte membranes, to N-acetylaspartate and glutamate.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A5930.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Zaczek, R., et al., Proc. Natl. Acad. Sci. (USA), 80: 1116, (1983).