P. aeruginosa Metabolome Database: N-Acetylglutamic acid (PAMDB001824)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001824

Identification

Name:

N-Acetylglutamic acid

Description:

N-acetylglutamic acid is an acetylated amino acid. It is involved in arginine biosynthesis and is a substrate for both ArgA and ArgB in Pseudomonas aeruginosa.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-acetamido-L-Glutaraldehydate
2-acetamido-L-Glutaraldehydic acid
Ac-Glu-OH
Acetyl-glutamate
Acetyl-glutamic acid
Acetyl-L-glutamate
Acetyl-L-glutamic acid
Acetylglutamate
Acetylglutamic acid
DL-Acetylglutamate
DL-Acetylglutamic acid
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-glutamate-g-semialdehyde
N-Acetyl-L-glutamate-gamma-semialdehyde
N-Acetyl-L-glutamate-γ-semialdehyde
N-Acetyl-L-glutamic acid
N-Acetyl-L-glutamic acid-g-semialdehyde
N-Acetyl-L-glutamic acid-gamma-semialdehyde
N-Acetyl-L-glutamic acid-γ-semialdehyde
N-Acetylglutamate
N-Acetylglutamic g-semialdehyde
N-Acetylglutamic gamma-semialdehyde
N-Acetylglutamic γ-semialdehyde
N-AcGlu

Chemical Formula:

C₇H₁₁NO₅

Average Molecular Weight:

189.1659

Monoisotopic Molecular Weight:

189.063722467

InChI Key:

RFMMMVDNIPUKGG-UHFFFAOYSA-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)

CAS number:

1188-37-0

IUPAC Name:

2-acetamidopentanedioic acid

Traditional IUPAC Name:

acetylglutamate

SMILES:

CC(=O)NC(CCC(O)=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-aliphatic-alpha amino acids

Alternative Parents

Substituents

N-acyl-aliphatic-alpha amino acid
Amino fatty acid
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Acetamide
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Carboxylic acid amide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-2

Melting point:

199 - 201 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	52 mg/mL [HMP experimental]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	18.6 mg/mL	ALOGPS
logP	-0.67	ALOGPS
logP	-1.1	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-1.2	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	17.28 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:

Cytoplasm

Reactions:

Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid
N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP
L-Glutamic acid + Acetyl-CoA + L-Glutamate > Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetylglutamic acid
N-Acetylglutamic acid + Adenosine triphosphate + N-Acetylglutamic acid > Adenosine diphosphate + N-Acetyl-L-glutamyl 5-phosphate + ADP
Acetyl-CoA + L-Glutamic acid + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetyl-L-alanine + N-Acetylglutamic acid

Pathways:

Arginine and proline metabolism pae00330
Metabolic pathways pae01100

Spectra

Spectra:

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-006y-0900000000-253a2008e5434e261a26	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9600000000-784f477a051434e9ba82	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-053u-9000000000-3f296192137041b66c1a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-5900000000-9cc96458c06943e10820	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0ug0-0900000000-00353ebbdcea9aaf232d	View in MoNA
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. Pubmed: 7952062
Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. Pubmed: 16139832
Tuchman M, Holzknecht RA: N-acetylglutamate content in liver and gut of normal and fasted mice, normal human livers, and livers of individuals with carbamyl phosphate synthetase or ornithine transcarbamylase deficiency. Pediatr Res. 1990 Apr;27(4 Pt 1):408-12. Pubmed: 2342831
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Vockley J, Vockley CM, Lin SP, Tuchman M, Wu TC, Lin CY, Seashore MR: Normal N-acetylglutamate concentration measured in liver from a new patient with N-acetylglutamate synthetase deficiency: physiologic and biochemical implications. Biochem Med Metab Biol. 1992 Feb;47(1):38-46. Pubmed: 1562355
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Zhang W, Holzknecht RA, Butkowski RJ, Tuchman M: Immunochemical analysis of carbamyl phosphate synthetase I and ornithine transcarbamylase deficient livers: elevated N-acetylglutamate level in a liver lacking carbamyl phosphate synthetase protein. Clin Invest Med. 1990 Aug;13(4):183-8. Pubmed: 2208834

Synthesis Reference:

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

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	12575
HMDB ID	HMDB01138
Pubchem Compound ID	185
Kegg ID	C00624
ChemSpider ID	180
Wikipedia	N-Acetylglutamic acid
BioCyc ID	Not Available

N-Acetylglutamic acid (PAMDB001824)

Structure for N-Acetylglutamic acid (PAMDB001824)