An endogenous metabolite
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N-acetyl-L-Glutamic Acid

Item No. 37359

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
1188-37-0
Synonyms
  • N-Acetylglutamate
  • N-Acetylglutamic Acid
  • NAG
Molecular Formula
C7H11NO5
Formula Weight
189.2
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
OC(CC[C@H](NC(C)=O)C(O)=O)=O
InChi Code
InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1
InChi Key
RFMMMVDNIPUKGG-YFKPBYRVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 g

    $33

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    100 g

    $63

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    250 g

    $141

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    Product Description

    N-acetyl-L-Glutamic acid (NAG) is an endogenous metabolite.1 It is an allosteric activator of mitochondrial carbamoyl phosphate synthetase, an enzyme involved in the urea cycle, and the first intermediate in arginine biosynthesis in bacteria.2,3,4 NAG inhibits human liver NAG synthase (NAGS; Ki = 0.25 mM).5 It also inhibits several enzymes involved in mitochondrial bioenergetics, including isocitrate dehydrogenase 2 (IDH2), mitochondrial complex IV, also known as cytochrome c oxidase, and glutamate dehydrogenase (GDH), in rat brain mitochondrial preparations when used at a concentration of 1 mM.6 Increased urine levels of NAG are associated with mutations in the gene encoding aminoacylase-1 (ACY1), an enzyme involved in the hydrolysis of N-acetylated proteins.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sass, J.O., Mohr, V., Olbrich, H., et al. Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am. J. Hum. Genet. 78(3), 401-409 (2006).

    2. Alonso, E., and Rubio, V. Binding of N-acetyl-L-glutamate to rat liver carbamoyl phosphate synthetase (ammonia). Eur. J. Biochem. 135(2), 331-337 (1983).

    3. Marshall, M., Metzenberg, R.L., and Cohen, P.P. Physical and kinetic properties of carbamyl phosphate synthetase from frog liver. The Journal of Biological Chemisty 236(8), 2229-2237 (1961).

    4. Petri, K., Walter, F.R., Persicke, M., et al. A novel type of N-acetylglutamate synthase is involved in the first step of arginine biosynthesis in Corynebacterium glutamicum. BMC Genomics 14, 713 (2013).

    5. Coudé, F.X., Grimber, G., Parvy, P., et al. N-Acetyl glutamate synthetase in human liver: Regulation of activity by L-arginine and N-acetylglutamate. Biochem. Biophys. Res. Commun. 102(3), 1016-1020 (1981).

    6. Bortoluzzi, V.T., Ribeiro, R.T., Pinheiro, C.V., et al. N-Acetylglutamate and N-acetylmethionine compromise mitochondrial bioenergetics homeostasis and glutamate oxidation in brain of developing rats: Potential implications for the pathogenesis of ACY1 deficiency. Biochem. Biophys. Res. Commun. 684, 149123 (2023).