L-Glutamic acid 5-phosphate (YMDB00233)

Identification

YMDB ID

YMDB00233

Name

L-Glutamic acid 5-phosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

L-Glutamic acid 5-phosphate, also known as L-glutam-5-yl phosphate or L-glutamyl 5-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. L-Glutamic acid 5-phosphate exists in all living species, ranging from bacteria to plants to humans. In yeast, L-glutamic acid 5-phosphate is involved in the metabolic pathway called the proline metabolism pathway. Based on a literature review very few articles have been published on L-Glutamic acid 5-phosphate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

L-gamma-glutamyl-5-P
L-gamma-glutamyl-5-phosphate
L-Glutamate 5-phosphate
L-glutamate-5-phosphate
L-Glutamic acid 5-phosphate
L-Glutamic acid 5-phosphic acid
L-glutamyl 5-phosphate
L-glutamyl-5-P
(2S)-2-Amino-5-oxo-5-(phosphonooxy)pentanoic acid
5-oxo-5-(Phosphonooxy)-L-norvaline
L-Glutam-5-yl phosphate
(2S)-2-Amino-5-oxo-5-(phosphonooxy)pentanoate
L-Glutam-5-yl phosphoric acid
L-Glutamic acid 5-phosphoric acid
L-Glutamyl 5-phosphoric acid
gamma-Glutamyl phosphate
γ-Glutamyl phosphate

CAS number

13254-53-0

Weight

Average: 227.1092
Monoisotopic: 227.019488191

InChI Key

PJRXVIJAERNUIP-VKHMYHEASA-N

InChI

InChI=1S/C5H10NO7P/c6-3(5(8)9)1-2-4(7)13-14(10,11)12/h3H,1-2,6H2,(H,8,9)(H2,10,11,12)/t3-/m0/s1

IUPAC Name

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

Traditional IUPAC Name

L-gamma-glutamyl phosphate

Chemical Formula

C₅H₁₀NO₇P

SMILES

[H]OC(=O)[C@@]([H])(N([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
Alpha-amino acid
L-alpha-amino acid
Acyl monophosphate
Acyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Fatty acid
Carboxylic acid salt
Amino acid
Carboxylic acid
Primary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Amine
Organic oxygen compound
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

gamma-glutamyl phosphate (CHEBI:17798 )

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	10.9 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.12	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	147.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	42.45 m³·mol⁻¹	ChemAxon
Polarizability	18.09 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

Organoleptic Properties

Not Available

SMPDB Pathways

Proline Metabolism

PW002365

KEGG Pathways

Arginine and proline metabolism

ec00330

SMPDB Reactions

L-Glutamic acid 5-phosphate + hydron + NADPH → l-Glutamic-gamma-semialdehyde + NADP + phosphate

KEGG Reactions

Adenosine triphosphate + L-Glutamic acid → L-Glutamic acid 5-phosphate + ADP

L-Glutamic acid 5-phosphate + NADPH + hydron → NADP + phosphate + l-Glutamic-gamma-semialdehyde

NADH + L-Glutamic acid 5-phosphate + hydron → NAD + phosphate + l-Glutamic-gamma-semialdehyde

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	splash10-0002-9100000000-1f025e73303e86357c09	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-9830000000-dfd0fdd7b5d37360bace	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01qa-4940000000-e0efc97dbf5f13f5b035	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9700000000-a154ebeef5e0f0f43204	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-b1be60027526c9bde31b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9040000000-9de98862247938227647	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-800f97e7da351e4f9a42	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a620dcfe7b9e2908b2a5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9010000000-fd2b2036f447f482b04a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3970000000-225c75caa9353c31ca4c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-5acb01b87dc2c83bc22f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9000000000-a92b4200472a0a756a42	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

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

Synthesis Reference:

Journal of Heterocyclic Chemistry (1987), 24(1), 279-82.

External Links:

Resource	Link
CHEBI ID	17798
HMDB ID	HMDB01228
Pubchem Compound ID	193475
Kegg ID	C03287
ChemSpider ID	167893
FOODB ID	FDB022500
Wikipedia ID	Not Available
BioCyc ID	L-GLUTAMATE-5-P

Enzymes

Protein Details

1. Glutamate 5-kinase

General function:: Involved in cellular amino acid biosynthetic process
Specific function:: Catalyzes the transfer of a phosphate group to glutamate to form glutamate 5-phosphate which rapidly cyclizes to 5- oxoproline
Gene Name:: PRO1
Uniprot ID:: P32264
Molecular weight:: 47161.69922

Reactions

ATP + L-glutamate → ADP + L-glutamate 5-phosphate.

Protein Details

2. Gamma-glutamyl phosphate reductase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADPH dependent reduction of L-gamma- glutamyl 5-phosphate into L-glutamate 5-semialdehyde and phosphate. The product spontaneously undergoes cyclization to form 1-pyrroline-5-carboxylate
Gene Name:: PRO2
Uniprot ID:: P54885
Molecular weight:: 49740.0

Reactions

L-glutamate 5-semialdehyde + phosphate + NADP(+) → L-glutamyl 5-phosphate + NADPH.

Structure for #<Compound:0xaf6b6b74>

Enzymes

Reactions

Reactions