MiMeDB: Showing metabocard for gamma-L-Glutamyl 5-phosphate (MMDBc0032118)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:03:09 UTC

Update Date

2023-02-23 19:39:50 UTC

Metabolite ID

MMDBc0032118

Metabolite Identification

Common Name

gamma-L-Glutamyl 5-phosphate

Description

gamma-L-Glutamyl 5-phosphate is an intermediate in L-proline biosynthesis I pathway in E.coli. It is a product for the enzyme gamma-glutamyl kinase which catalyzes the reaction L-glutamate + ATP -> gamma-L-glutamyl 5-phosphate + ADP. It is also the substrate for the enzyme glutamate-5-semialdehyde dehydrogenase which catalyzes the reaction gamma-L-glutamyl 5-phosphate + NADPH + H+ -> L-glutamate-5-semialdehyde + NADP+ + phosphate (BioCyc compound: L-GLUTAMATE-5-P).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533005221515152D          

 15 14  0  0  0  0            999 V2000
    0.7144   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7144   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.0312    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.8578   -0.6187    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.5559    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.2062    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.6187    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  1  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 13  4  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
  3 15  1  1  0  0  0
M  CHG  2   9  -1  10  -1
M  END
> <DATABASE_ID>
MMDBc0032118

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCC(=O)OP(O)([O-])=O)C([O-])=O

> <INCHI_IDENTIFIER>
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)/p-2/t3-/m0/s1

> <INCHI_KEY>
PJRXVIJAERNUIP-VKHMYHEASA-L

> <FORMULA>
C5H8NO7P

> <MOLECULAR_WEIGHT>
225.094

> <EXACT_MASS>
225.004935759

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.27512480832278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-5-(hydrogen phosphonatooxy)-5-oxopentanoate

> <ALOGPS_LOGP>
-1.46

> <JCHEM_LOGP>
-3.0424739962552194

> <ALOGPS_LOGS>
-0.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
1.976858456614289

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1185265364746844

> <JCHEM_PKA_STRONGEST_BASIC>
9.511214443237481

> <JCHEM_POLAR_SURFACE_AREA>
152.81

> <JCHEM_REFRACTIVITY>
52.162800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.82e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-5-(hydrogen phosphonatooxy)-5-oxopentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-15         0                                  
HETATM    1  C   UNK     0       1.334  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.385   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.667   1.925   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      -1.334  -1.925   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.335   0.385   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001  -1.925   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0      -5.335  -1.155   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0      -4.771   0.949   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.231  -1.719   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.667   0.385   0.000  0.00  0.00           O+0
HETATM   14  P   UNK     0      -4.001  -0.385   0.000  0.00  0.00           P+0
HETATM   15  H   UNK     0       2.667  -1.155   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    6   15                                             
CONECT    4    2    7   13                                                  
CONECT    5    3    8    9                                                  
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10   14                                                            
CONECT   11   14                                                            
CONECT   12   14                                                            
CONECT   13    4   14                                                       
CONECT   14   10   11   12   13                                             
CONECT   15    3                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

Synonyms

Value	Source
(2S)-2-Ammonio-5-oxo-5-(phosphonatooxy)pentanoate	ChEBI
L-gamma-Glutamyl phosphate dianion	ChEBI
L-Glutamyl 5-phosphate	ChEBI
(2S)-2-Ammonio-5-oxo-5-(phosphonatooxy)pentanoic acid	Generator
L-g-Glutamyl phosphate dianion	Generator
L-g-Glutamyl phosphoric acid dianion	Generator
L-gamma-Glutamyl phosphoric acid dianion	Generator
L-Γ-glutamyl phosphate dianion	Generator
L-Γ-glutamyl phosphoric acid dianion	Generator
L-Glutamyl 5-phosphoric acid	Generator
Γ-L-glutamyl 5-phosphoric acid	Generator
L-g-Glutamyl phosphate(2-)	Generator
L-g-Glutamyl phosphoric acid(2-)	Generator
L-gamma-Glutamyl phosphoric acid(2-)	Generator
L-γ-glutamyl phosphate(2-)	Generator
L-γ-glutamyl phosphoric acid(2-)	Generator

Molecular Formula

C₅H₈NO₇P

Average Mass

225.094

Monoisotopic Mass

225.004935759

IUPAC Name

(2S)-2-amino-5-(hydrogen phosphonatooxy)-5-oxopentanoate

Traditional Name

(2S)-2-amino-5-(hydrogen phosphonatooxy)-5-oxopentanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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)/p-2/t3-/m0/s1

InChI Key

PJRXVIJAERNUIP-VKHMYHEASA-L

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
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organophosphate oxoanion (CHEBI:58274 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	38.2 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-3	ChemAxon
logS	-0.84	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	2	ChemAxon
Polar Surface Area	152.81 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	52.16 m³·mol⁻¹	ChemAxon
Polarizability	17.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00os-4190000000-279617a245563de99342	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-6980000000-2216bcacb99d0e169718	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9100000000-c28fdad4962b923def30	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1190000000-19c13abe3fcd1b4a4b41	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-9120000000-c6489da4308b888f1240	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-fb6fc0527ea3c11a85c8	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	337	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Turkey ; Sheep ; Pig ; Chicken ; Cattle ; River trout ; Rat	Unknown
Bacteria	Cyanobacteria	34	Human
Bacteria	Firmicutes	115	Human feces; Human ; Catfish ; Cattle
Bacteria	Aquificae	4
Bacteria	Bacteroidetes	7	Human ; Human feces
Bacteria	Actinobacteria	47	Human ; Human feces; Cattle
Bacteria	Chlorobi	8
Bacteria	Chloroflexi	9
Bacteria	Deinococcus-thermus	5
Bacteria	Dictyoglomi	2
Bacteria	Thermotogae	5
Bacteria	Spirochaetes	9	Human ; Pig
Archaea/Archaea	Euryarchaeota	6
Bacteria	Planctomycetes	1
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown
Bacteria	nah	1
Bacteria	Acidobacteria	1
Bacteria	Verrucomicrobia	1
Bacteria	Nitrospirae	1

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

58274

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for gamma-L-Glutamyl 5-phosphate (MMDBc0032118)

MOL for #<Metabolite:0x00007fdb50256178>

3D MOL for #<Metabolite:0x00007fdb50256178>

3D SDF for #<Metabolite:0x00007fdb50256178>

3D-SDF for #<Metabolite:0x00007fdb50256178>

PDB for #<Metabolite:0x00007fdb50256178>

3D PDB for #<Metabolite:0x00007fdb50256178>

SMILES for #<Metabolite:0x00007fdb50256178>

INCHI for #<Metabolite:0x00007fdb50256178>

Structure for #<Metabolite:0x00007fdb50256178>

3D Structure for #<Metabolite:0x00007fdb50256178>