N-Acetyl-L-glutamyl 5-phosphate (YMDB00047)

Identification

YMDB ID

YMDB00047

Name

N-Acetyl-L-glutamyl 5-phosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

N-Acetyl-L-glutamyl 5-phosphate, also known as N-acetyl-5-glutamyl phosphoric acid, 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-glutamyl 5-phosphate exists in all living species, ranging from bacteria to plants to humans. Based on a literature review very few articles have been published on N-Acetyl-L-glutamyl 5-phosphate.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

(2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoate
(2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid
N-acetyl-5-glutamyl phosphate
N-Acetyl-5-glutamyl phosphoric acid
N-acetyl-5-oxo-5-(phosphonooxy)-L-norvaline
N-acetyl-gamma-l-glutamyl phosphate
N-acetyl-L-glutamate 5-phosphate
N-Acetyl-L-glutamic acid 5-phosphoric acid
N-Acetyl-L-glutamyl 5-phosphoric acid
N-Acetyl-gamma-glutamyl phosphate
N-Acetyl-γ-glutamyl phosphate

CAS number

15383-57-0

Weight

Average: 269.1458
Monoisotopic: 269.030052877

InChI Key

FCVIHFVSXHOPSW-YFKPBYRVSA-N

InChI

InChI=1S/C7H12NO8P/c1-4(9)8-5(7(11)12)2-3-6(10)16-17(13,14)15/h5H,2-3H2,1H3,(H,8,9)(H,11,12)(H2,13,14,15)/t5-/m0/s1

IUPAC Name

(2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid

Traditional IUPAC Name

(2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid

Chemical Formula

C₇H₁₂NO₈P

SMILES

[H]OC(=O)[C@@]([H])(N([H])C(=O)C([H])([H])[H])C([H])([H])C([H])([H])C(=O)OP(=O)(O[H])O[H]

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
N-acyl-l-alpha-amino acid
Acyl monophosphate
Acyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Fatty acid
Acetamide
Secondary carboxylic acid amide
Carboxylic acid salt
Carboxamide group
Carboxylic acid
Carbonyl group
Organic salt
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-glutamic acid derivative (CHEBI:16878 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	3.64 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.8	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.23 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	51.89 m³·mol⁻¹	ChemAxon
Polarizability	21.95 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

N-Acetyl-L-glutamyl 5-phosphate + NADPH + hydron → NADP + phosphate + 2-Acetamido-5-oxopentanoic acid

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9010000000-b0a55da1a5a5b19cb1d4	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006t-9010000000-42bde2dc702d9b13da76	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9050000000-71b3eb12e2ae4f419455	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-eb5a9659d9563f71cfed	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9428bc78f2587e624b2e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9010000000-fdf484605ec8efcf1973	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-5c2f91e14126fc9d0952	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-7084495cb0b628b5da4a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fka-3690000000-1006721922db38442ba6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-007k-4930000000-eb999b44d4988128c1c9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9500000000-78a70933fe87b25941ad	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00b9-0090000000-041c62aaf9a011fbf28a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003r-2930000000-e4bd8858ef8860dc9111	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0035-9400000000-2015735feb749a5b240b	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

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
Jauniaux, J. C., Urrestarazu, L. A., Wiame, J. M. (1978). "Arginine metabolism in Saccharomyces cerevisiae: subcellular localization of the enzymes." J Bacteriol 133:1096-1107.205532
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

Synthesis Reference:

Kuramitsu, Shigenori; Masui, Ryoji. Cloning of thermostable acetylglutamate kinase gene from Sulfolobus tokodaii and use for N-acetyl-L-glutamate-5-phosphate biosynthesis. Jpn. Kokai Tokkyo Koho (2004), 12 pp. CODEN: JKXXAF JP 2004298187 A 2

External Links:

Resource	Link
CHEBI ID	16878
HMDB ID	HMDB06456
Pubchem Compound ID	440236
Kegg ID	C04133
ChemSpider ID	389220
FOODB ID	FDB023917
Wikipedia ID	Not Available
BioCyc ID	N-ACETYL-GLUTAMYL-P

Enzymes

Protein Details

1. 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.

N-Acetyl-L-glutamyl 5-phosphate (YMDB00047)

Structure for #<Compound:0xb0a65b98>

Enzymes

Reactions