N-acetyl-L-glutamic acid (YMDB00066)

Identification

YMDB ID

YMDB00066

Name

N-acetyl-L-glutamic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

N-Acetyl-L-glutamic acid, also known as acetylglutamate or ac-glu-OH, 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. N-Acetyl-L-glutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-L-glutamic acid exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(S)-2-(acetylamino)pentanedioate
2-acetamido-L-Glutaraldehydate
2-acetamido-L-Glutaraldehydic acid
Ac-Glu-OH
acetyl-glutamate
Acetyl-L-glutamate
Acetyl-L-glutamic acid
acetylglutamate
acetylglutamic acid
DL-Acetylglutamate
DL-Acetylglutamic acid
L-Glutamic acid, N-acetyl-
N-Ac-Glu-OH
N-acetyl L-glutamate
N-acetyl L-glutamic acid
N-Acetyl-DL-glutamate
N-Acetyl-DL-glutamic acid
N-acetyl-Glutamate
N-acetyl-Glutamic acid
N-Acetyl-L-glutamate
N-Acetyl-L-glutamic acid
N-Acetyl-L-glutamic acid-gamma-semialdehyde
N-Acetylglutamate
N-Acetylglutamic acid
N-Acetylglutamic gamma-semialdehyde
NAG
(S)-2-(Acetylamino)pentanedioic acid
L-N-Acetylglutamic acid
L-N-Acetylglutamate
N-Acetylglutamic acid semialdehyde
N-Acetylglutamate, potassium salt, (L)-isomer
N-Acetylglutamate, (D)-isomer
N-Acetylglutamate, calcium salt (1:1), (L)-isomer
N-Acetylglutamate, dipotassium salt, (L)-isomer
N-Acetylglutamate, disodium salt, (L)-isomer
N-Acetylglutamate, calcium salt, (L)-isomer
N-Acetylglutamate, magnesium salt, (L)-isomer
Sodium N-acetylglutamate
N-Acetylglutamate, (DL)-isomer
N-Acetylglutamate, monosodium salt, (L)-isomer
N-Acetyl-L-glutaminic acid
alpha-(N-Acetyl)-L-glutamic acid
Α-(N-acetyl)-L-glutamic acid
NAcGlu

CAS number

1188-37-0

Weight

Average: 189.1659
Monoisotopic: 189.063722467

InChI Key

RFMMMVDNIPUKGG-YFKPBYRVSA-N

InChI

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

IUPAC Name

(2S)-2-acetamidopentanedioic acid

Traditional IUPAC Name

N-acetyl-L-glutamate

Chemical Formula

C₇H₁₁NO₅

SMILES

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

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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Dicarboxylic acid or derivatives
Fatty acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:17533 )
N-acyl-L-glutamic acid (CHEBI:17533 )

Physical Properties

State

Solid

Charge

Melting point

199 - 201 °C

Experimental Properties

Property	Value	Reference
Water Solubility	52 mg/mL [HMP experimental]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	18.6 g/L	ALOGPS
logP	-0.67	ALOGPS
logP	-1.1	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.73 m³·mol⁻¹	ChemAxon
Polarizability	17.44 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Mitochondrion

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Arginine and proline metabolism

ec00330

SMPDB Reactions

Not Available

KEGG Reactions

Adenosine triphosphate + N-acetyl-L-glutamic acid → N-Acetyl-L-glutamyl 5-phosphate + ADP

Acetyl-CoA + L-Glutamic acid → N-acetyl-L-glutamic acid + hydron + Coenzyme A

L-Glutamic acid + N-Acetylornithine → N-acetyl-L-glutamic acid + Ornithine

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0a4i-1940000000-78ee4843d1eab79c7ca3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0api-3930000000-e499004b087e5d741b02	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4j-0920000000-2d39b0eff0ff23756843	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0aor-1920000000-a2fe62d19e50f9db103f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4j-0920000000-546571923f012476b58b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ap0-1910000000-d18f7c4035b189c1f4b6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4r-1900000000-fc8347700abd012bf349	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-cdb488a97c5bf1952810	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-1f9f80a37aa4e37ee878	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0fb9-0900000000-5423b76f7eb4b2a17fac	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-2900000000-38410c884a2999611065	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0zfr-9700000000-85acd9611312dd7df0db	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0pb9-9100000000-0d780e23d772cf133da2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0ufr-1900000000-7a57de84cf9c6671cfc2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-0900000000-7b58c7204405ece93fca	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-1900000000-515b33cc5674fc8985c8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9300000000-b379a6e4d794e810c478	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-2ce098bb9e1b35433878	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-8e7d8abde262b7d5cb45	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-1900000000-a3bdc3627857c5f47f4b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0ufr-2900000000-b074eaccd0b3864766b3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0fb9-0900000000-54faa7b7182f5cceca84	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-6900000000-0f14d0a7c8fb67a381b2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-053r-9000000000-333b6aa44450dbd0c754	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-adf2d3645b4231cbddc3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-d7df112ff7af7e076d70	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0536-9000000000-d70c37086adaa1636750	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0900000000-88345aaf9776c7fb8676	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udl-2900000000-5fca3bd987ebf6b42946	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udj-9500000000-be58124b136b37456414	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-a56ffb8d475d132443a8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004v-2900000000-c32612499c0a2ceb8298	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9300000000-75dbbc130d00cfec5880	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Abadjieva, A., Pauwels, K., Hilven, P., Crabeel, M. (2001). "A new yeast metabolon involving at least the two first enzymes of arginine biosynthesis: acetylglutamate synthase activity requires complex formation with acetylglutamate kinase." J Biol Chem 276:42869-42880.11553611
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

hang, Xiaolin; Yang, Qiyong; Sun, Yuesheng. Preparation of N-acetyl-L-glutamic acid. Huaxue Shijie (2002), 43(7), 363-365.

External Links:

Resource	Link
CHEBI ID	17533
HMDB ID	HMDB01138
Pubchem Compound ID	185
Kegg ID	C00624
ChemSpider ID	64077
FOODB ID	FDB031019
Wikipedia	N-Acetylglutamic_acid
BioCyc ID	ACETYL-GLU

Enzymes

Protein Details

1. Arginine biosynthesis bifunctional protein ArgJ, mitochondrial

General function:: Involved in glutamate N-acetyltransferase activity
Specific function:: Catalyzes two activities which are involved in the cyclic version of arginine biosynthesis:the synthesis of acetylglutamate from glutamate and acetyl-CoA, and of ornithine by transacetylation between acetylornithine and glutamate
Gene Name:: ARG7
Uniprot ID:: Q04728
Molecular weight:: 47848.30078

Reactions

N(2)-acetyl-L-ornithine + L-glutamate → L-ornithine + N-acetyl-L-glutamate.
Acetyl-CoA + L-glutamate → CoA + N-acetyl-L-glutamate.

Protein Details

2. Amino-acid acetyltransferase, mitochondrial

General function:: Involved in arginine biosynthetic process
Specific function:: N-acetylglutamate synthase involved in arginine biosynthesis
Gene Name:: ARG2
Uniprot ID:: P40360
Molecular weight:: 65609.5

Reactions

Acetyl-CoA + L-glutamate → CoA + N-acetyl-L-glutamate.

Protein Details

3. Protein ARG5,6, mitochondrial

General function:: Involved in acetylglutamate kinase activity
Specific function:: N-acetyl-L-glutamate 5-semialdehyde + NADP(+) + phosphate = N-acetyl-5-glutamyl phosphate + NADPH
Gene Name:: ARG5
Uniprot ID:: Q01217
Molecular weight:: 94868.39844

Reactions

N-acetyl-L-glutamate 5-semialdehyde + NADP(+) + phosphate → N-acetyl-5-glutamyl phosphate + NADPH.
ATP + N-acetyl-L-glutamate → ADP + N-acetyl-L-glutamate 5-phosphate.

Structure for #<Compound:0xabbbdab8>

Enzymes

Reactions

Reactions

Reactions