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Identification
YMDB IDYMDB00675
Name2-phospho-D-glyceric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Phospho-D-glyceric acid, also known as 2-phospho-D-glycerate or D-glycerate 2-phosphate, 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. 2-Phospho-D-glyceric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Phospho-D-glyceric acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • (2R)-3-hydroxy-2-(phosphonooxy)propanoate
  • (2R)-3-hydroxy-2-(phosphonooxy)propanoic acid
  • 2-Phospho-(R)-glycerate
  • 2-phospho-d-glycerate
  • 2-Phospho-D-glyceric acid
  • 2-phosphoglyceric acid
  • 3-D-Hydroxy-2-phosphonooxy-propanoate
  • 3-D-Hydroxy-2-phosphonooxy-propanoic acid
  • D-Glycerate 2-phosphate
  • 2-PHOSPHOGLYCERate
  • D-Glyceric acid 2-phosphoric acid
  • 2-Phospho-(R)-glyceric acid
  • D-(+)-2-Phosphoglyceric acid
  • D-2-Phosphoglyceric acid
  • D-Glyceric acid 2-phosphate
CAS numberNot Available
WeightAverage: 186.0572
Monoisotopic: 185.99293909
InChI KeyGXIURPTVHJPJLF-UWTATZPHSA-N
InChIInChI=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
IUPAC Name(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid
Traditional IUPAC Name(+-)-2-phosphoglycerate
Chemical FormulaC3H7O7P
SMILES[H][C@](CO)(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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility20.3 g/LALOGPS
logP-2.2ALOGPS
logP-1.6ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)0.81ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.26 m³·mol⁻¹ChemAxon
Polarizability13.36 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycolysis / Gluconeogenesisec00010 Map00010
Methane metabolismec00680 Map00680
Pentose phosphate pathwayec00030 Map00030
SMPDB Reactions
3-Phosphoglyceric acid2-phospho-D-glyceric acid
2-phospho-D-glyceric acidPhosphoenolpyruvic acid + water
KEGG Reactions
2-phospho-D-glyceric acidPhosphoenolpyruvic acid + water
2-phospho-D-glyceric acid3-phospho-D-glyceric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • 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
  • Furukawa, K., Yamada, T., Mizoguchi, H., Hara, S. (2003). "Increased ethyl caproate production by inositol limitation in Saccharomyces cerevisiae." J Biosci Bioeng 95:448-454.16233438
  • Cabral, M. G., Viegas, C. A., Sa-Correia, I. (2001). "Mechanisms underlying the acquisition of resistance to octanoic-acid-induced-death following exposure of Saccharomyces cerevisiae to mild stress imposed by octanoic acid or ethanol." Arch Microbiol 175:301-307.11382226
  • Schwartz, J. M., Kanehisa, M. (2006). "Quantitative elementary mode analysis of metabolic pathways: the example of yeast glycolysis." BMC Bioinformatics 7:186.16584566
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Hannaert, V., Albert, M. A., Rigden, D. J., da Silva Giotto, M. T., Thiemann, O., Garratt, R. C., Van Roy, J., Opperdoes, F. R., Michels, P. A. (2003). "Kinetic characterization, structure modelling studies and crystallization of Trypanosoma brucei enolase." Eur J Biochem 270:3205-3213.12869196
  • Rodicio, R., Heinisch, J. (1987). "Isolation of the yeast phosphoglyceromutase gene and construction of deletion mutants." Mol Gen Genet 206:133-140.3033435
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17835
HMDB IDHMDB03391
Pubchem Compound ID439278
Kegg IDC00631
ChemSpider ID388411
FOODB IDFDB001407
Wikipedia2-Phosphoglyceric_acid
BioCyc ID2-PG

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:
ERR1
Uniprot ID:
Q12007
Molecular weight:
47327.10156
Reactions
2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.
General function:
Involved in magnesium ion binding
Specific function:
2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:
ERR3
Uniprot ID:
P42222
Molecular weight:
47312.10156
Reactions
2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.
General function:
Involved in magnesium ion binding
Specific function:
2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:
ENO1
Uniprot ID:
P00924
Molecular weight:
46815.69922
Reactions
2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.
General function:
Involved in magnesium ion binding
Specific function:
2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:
ENO2
Uniprot ID:
P00925
Molecular weight:
46913.69922
Reactions
2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.
General function:
Involved in catalytic activity
Specific function:
Interconversion of 3- and 2-phosphoglycerate with 2,3- bisphosphoglycerate as the primer of the reaction. Can also Catalyze the reaction of EC 5.4.2.4 (synthase) and EC 3.1.3.13 (phosphatase), but with a reduced activity
Gene Name:
GPM1
Uniprot ID:
P00950
Molecular weight:
27608.30078
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Involved, either directly or indirectly, in the bidirectional transport of sterols between the endoplasmic reticulum and the plasma membrane
Gene Name:
DET1
Uniprot ID:
Q99288
Molecular weight:
39171.80078
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the interconversion of 2-phosphoglycerate and 3-phosphoglycerate
Gene Name:
Not Available
Uniprot ID:
Q12040
Molecular weight:
26176.5
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Could be non-functional
Gene Name:
GPM3
Uniprot ID:
Q12326
Molecular weight:
34863.19922
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.
General function:
Involved in catalytic activity
Specific function:
Could be non-functional
Gene Name:
GPM2
Uniprot ID:
Q12008
Molecular weight:
36072.80078
Reactions
2-phospho-D-glycerate → 3-phospho-D-glycerate.