ECMDB: L-Glutamic acid 5-phosphate (ECMDB01228) (M2MDB000304)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (759)

Record Information

Version

2.0

Creation Date

2012-05-31 13:48:00 -0600

Update Date

2015-06-03 15:53:51 -0600

Secondary Accession Numbers

ECMDB01228

Identification

Name:

L-Glutamic acid 5-phosphate

Description

L-Glutamic acid 5-phosphate is an intermediate in the urea cycle and metabolism of amino groups, a substrate of aldehyde dehydrogenase 18 family, member A1 [EC:2.7.2.11 1.2.1.41] (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Glu-5-P
L-γ-glutamyl-5-P
L-γ-glutamyl-5-phosphate
L-γ-glutamyl-5-phosphoric acid
L-g-Glutamyl-5-P
L-g-Glutamyl-5-phosphate
L-g-Glutamyl-5-phosphoric acid
L-gamma-Glutamyl-5-P
L-gamma-Glutamyl-5-phosphate
L-gamma-Glutamyl-5-phosphoric acid
L-Glutamate 5-phosphate
L-Glutamate-5-phosphate
L-Glutamic acid 5-phosphate
L-Glutamic acid 5-phosphoric acid
L-Glutamic acid-5-phosphoric acid
L-Glutamyl 5-phosphate
L-Glutamyl 5-phosphoric acid
L-Glutamyl-5-P
L-Glutamyl-5-phosphate
L-Glutamyl-5-phosphoric acid
L-γ-Glutamyl-5-P
L-γ-Glutamyl-5-phosphate
L-γ-Glutamyl-5-phosphoric acid

Chemical Formula:

C₅H₁₀NO₇P

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

CAS number:

13254-53-0

IUPAC Name:

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

Traditional IUPAC Name:

L-gamma-glutamyl phosphate

SMILES:

N[C@@H](CCC(=O)OP(O)(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
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:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

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

Reactions:

SMPDB Pathways:

proline metabolism

PW000794

KEGG Pathways:

Arginine and proline metabolism ec00330
Metabolic pathways eco01100

EcoCyc Pathways:

proline biosynthesis I PROSYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9100000000-1f025e73303e86357c09	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-9830000000-dfd0fdd7b5d37360bace	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01qa-4940000000-e0efc97dbf5f13f5b035	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9700000000-a154ebeef5e0f0f43204	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-b1be60027526c9bde31b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9040000000-9de98862247938227647	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-800f97e7da351e4f9a42	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a620dcfe7b9e2908b2a5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9010000000-fd2b2036f447f482b04a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3970000000-225c75caa9353c31ca4c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-5acb01b87dc2c83bc22f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9000000000-a92b4200472a0a756a42	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

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

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

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

Enzymes

Protein Details

1. 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:: proA
Uniprot ID:: P07004
Molecular weight:: 44630

Reactions

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

Protein Details

2. 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:: proB
Uniprot ID:: P0A7B5
Molecular weight:: 39056

Reactions

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

L-Glutamic acid 5-phosphate (ECMDB01228) (M2MDB000304)

Structure for #<Compound:0xaa85cd84>

Enzymes

Reactions

Reactions