ECMDB: 2-Phospho-D-glyceric acid (ECMDB04129) (M2MDB000626)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)XML

Proteins (1709)

Record Information

Version

2.0

Creation Date

2012-05-31 14:05:56 -0600

Update Date

2015-06-03 15:54:46 -0600

Secondary Accession Numbers

ECMDB04129

Identification

Name:

2-Phospho-D-glyceric acid

Description

2-Phospho-D-glycerate or 2PG is an intermediate in gluconeogenesis. It is a glyceric acid which serves as the substrate in the ninth step of glycolysis. 2PG is converted by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. More specifically, 2PG can be generated from Glycerate-3-phosphate via phosphoglycerate mutase or from phosphoenolpyrvate via alpha enolase.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2R)-3-hydroxy-2-(phosphonooxy)propanoate
(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid
2-P-D-Glycerate
2-P-D-Glyceric acid
2-PG
2-Phospho-(D)-glycerate
2-Phospho-(D)-glyceric acid
2-Phospho-(R)-glycerate
2-Phospho-(R)-glyceric acid
2-Phospho-D-glycerate
2-Phospho-D-glyceric acid
3-D-Hydroxy-2-phosphonooxy-propanoate
3-D-Hydroxy-2-phosphonooxy-propanoic acid
D-2-Phosphoglycerate
D-2-Phosphoglyceric acid
D-Glycerate 2-phosphate
D-Glyceric acid 2-phosphate
D-Glyceric acid 2-phosphoric acid

Chemical Formula:

C₃H₇O₇P

Weight:

Average: 186.0572
Monoisotopic: 185.99293909

InChI Key:

GXIURPTVHJPJLF-UWTATZPHSA-N

InChI:

InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1

CAS number:

Not Available

IUPAC Name:

(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid

Traditional IUPAC Name:

(+-)-2-phosphoglycerate

SMILES:

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Glyceric_acid
Monoalkyl phosphate
Hydroxy acid
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alcohol
Organic oxide
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-phosphoglyceric acid (CHEBI:17835 )

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	20.3 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-1.6	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	0.81	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.26 m³·mol⁻¹	ChemAxon
Polarizability	13.36 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:

2-O-alpha-mannosyl-D-glycerate degradation	PW002096
fructose metabolism	PW000913
glycerol metabolism	PW000914
glycerol metabolism II	PW000915
glycerol metabolism III (sn-glycero-3-phosphoethanolamine)	PW000916
glycerol metabolism IV (glycerophosphoglycerol)	PW000917
glycerol metabolism V (glycerophosphoserine)	PW000918
glycolysis and pyruvate dehydrogenase	PW000785

KEGG Pathways:

Glycine, serine and threonine metabolism ec00260
Glycolysis / Gluconeogenesis ec00010
Metabolic pathways eco01100
Methane metabolism ec00680
Microbial metabolism in diverse environments ec01120
Pentose phosphate pathway ec00030

EcoCyc Pathways:

2-O-α-mannosyl-D-glycerate degradation PWY0-1300
D-glucarate degradation I GLUCARDEG-PWY
D-galactarate degradation I GALACTARDEG-PWY
gluconeogenesis I GLUCONEO-PWY
glycolysis I GLYCOLYSIS
respiration (anaerobic) ANARESP1-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-014j-1986100000-67b36247ae0c01d6630f	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014j-1986100000-67b36247ae0c01d6630f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9200000000-8ec7a644e48af8fc9f44	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0002-9030000000-cc4abc5e01c64cff2d87	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-80caf2498862e856c8fc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9100000000-1518e606c03a8697d1b9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-66ec419add3cb3e1fd32	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-b7f464912df9166dc597	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-d09faea5291df7a04b70	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udr-0900000000-09027263f64d0e1059c6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-1900000000-8eeb1d2a8432d1e44448	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0f6t-8900000000-3b714e664b948f61ac7e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0023-9000000000-ed83591fbfd15323cd6d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001m-9000000000-39cdf9729f381069e45f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-9300000000-24ac9683b32428f58197	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9600000000-b12281d6d89eef904e6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-a07c4a51c820b32ec8bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-4900000000-516a86a1a17689399892	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9500000000-b33f3e08e2e8b3d5aed5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-07016cc3ecca7d5e323b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9000000000-e2aa0f15a5d31307fa1e	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	splash10-000i-2900000000-e1c96e130069d9cf375a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-91835bf01523e3aceb24	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-9000000000-d48b603841c58b435069	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:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17835
HMDB ID	HMDB03391
Pubchem Compound ID	439278
Kegg ID	C00631
ChemSpider ID	388411
Wikipedia ID	Not Available
BioCyc ID	2-PG
EcoCyc ID	2-PG
Ligand Expo	PAG

Enzymes

Protein Details

1. Enolase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the reversible conversion of 2- phosphoglycerate into phosphoenolpyruvate. It is essential for the degradation of carbohydrates via glycolysis. It is also a component of the RNA degradosome, a multi-enzyme complex involved in RNA processing and messenger RNA degradation. Its interaction with RNase E is important for the turnover of mRNA, in particular on transcripts encoding enzymes of energy-generating metabolic routes. Its presence in the degradosome is required for the response to excess phosphosugar. May play a regulatory role in the degradation of specific RNAs, such as ptsG mRNA, therefore linking cellular metabolic status with post-translational gene regulation
Gene Name:: eno
Uniprot ID:: P0A6P9
Molecular weight:: 45655

Reactions

2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O.

Protein Details

2. Probable phosphoglycerate mutase gpmB

General function:: Involved in catalytic activity
Specific function:: 2-phospho-D-glycerate = 3-phospho-D-glycerate
Gene Name:: gpmB
Uniprot ID:: P0A7A2
Molecular weight:: 24065

Reactions

2-phospho-D-glycerate = 3-phospho-D-glycerate.

Protein Details

3. Glycerate kinase 2

General function:: Involved in glycerate kinase activity
Specific function:: ATP + (R)-glycerate = ADP + 3-phospho-(R)- glycerate
Gene Name:: garK
Uniprot ID:: P23524
Molecular weight:: 39104

Reactions

ATP + (R)-glycerate = ADP + 3-phospho-(R)-glycerate.

Protein Details

4. 2,3-bisphosphoglycerate-independent phosphoglycerate mutase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the interconversion of 2-phosphoglycerate and 3-phosphoglycerate
Gene Name:: gpmI
Uniprot ID:: P37689
Molecular weight:: 56193

Reactions

2-phospho-D-glycerate = 3-phospho-D-glycerate.

Protein Details

5. 2,3-bisphosphoglycerate-dependent phosphoglycerate mutase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the interconversion of 2-phosphoglycerate and 3-phosphoglycerate
Gene Name:: gpmA
Uniprot ID:: P62707
Molecular weight:: 28556

Reactions

2-phospho-D-glycerate = 3-phospho-D-glycerate.

2-Phospho-D-glyceric acid (ECMDB04129) (M2MDB000626)

Structure for #<Compound:0xad7a7f44>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions