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Identification
YMDB IDYMDB00672
Name3-phospho-D-glyceroyl dihydrogen phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-phospho-D-glyceroyl phosphate, also known as 1,3-bisphospho-D-glycerate or D-glycerate 1,3-diphosphate, belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl. 3-phospho-D-glyceroyl phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-phospho-D-glyceroyl phosphate exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • (R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoic acid
  • 1,3-bis-phosphoglycerate
  • 1,3-Bisphospho-D-glycerate
  • 1,3-bisphosphoglycerate
  • 3-phospho-d-glyceroyl phosphate
  • D-Glycerate 1,3-diphosphate
  • (R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoate
  • 1,3-Bisphospho-D-glyceric acid
  • D-Glyceric acid 1,3-diphosphoric acid
  • 3-Phospho-D-glyceroyl phosphoric acid
  • 3-Phospho-D-glyceroyl dihydrogen phosphoric acid
  • 1,3-Biphosphoglycerate
  • 1,3-Bisphosphoglyceric acid
  • 1,3-Diphosphoglycerate
  • 1,3-Diphosphoglyceric acid
  • 3-Phospho-D-glyceroyl-phosphate
  • 3-Phosphoglyceroyl phosphate
  • 3-Phosphoglyceroyl-p
  • 3-Phosphoglyceroyl-phosphate
  • 3-Phosphonato-D-glyceroyl phosphate
  • 3-Phosphonatoglyceroyl phosphate
  • 3-p-Glyceroyl-p
  • D-Glycerate 1,3-biphosphate
  • D-Glycerate 1,3-bisphosphate
  • D-Glyceric acid 1,3-biphosphate
  • D-Glyceric acid 1,3-bisphosphate
  • D-Glyceric acid 1,3-diphosphate
  • DPG
  • Glycerate 1,3-biphosphate
  • Glycerate 1,3-bisphosphate
  • Glycerate 1,3-diphosphate
  • Glyceric acid 1,3-biphosphate
  • Glyceric acid 1,3-bisphosphate
  • Glyceric acid 1,3-diphosphate
  • Phosphoglyceroyl-p
  • p-Glyceroyl-p
CAS number38168-82-0
WeightAverage: 266.0371
Monoisotopic: 265.9592695
InChI KeyLJQLQCAXBUHEAZ-UWTATZPHSA-N
InChIInChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1
IUPAC Name{[(2R)-2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid
Traditional IUPAC Name1,3-bisphospho-D-glycerate
Chemical FormulaC3H8O10P2
SMILESO[C@H](COP(O)(O)=O)C(=O)OP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentAcyl monophosphates
Alternative Parents
Substituents
  • Acyl monophosphate
  • Glyceric_acid
  • Monoalkyl phosphate
  • Monosaccharide
  • Alkyl phosphate
  • Carboxylic acid salt
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.64 g/LALOGPS
logP-1.1ALOGPS
logP-2.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.01ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.42 m³·mol⁻¹ChemAxon
Polarizability18.01 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 PathwaysNot Available
KEGG Pathways
Glycolysis / Gluconeogenesisec00010 Map00010
SMPDB ReactionsNot Available
KEGG Reactions
3-phospho-D-glyceroyl dihydrogen phosphate2,3-bisphospho-D-glyceric acid + hydron
NAD + D-Glyceraldehyde 3-phosphate + phosphateNADH + 3-phospho-D-glyceroyl dihydrogen phosphate + hydron
Adenosine triphosphate + 3-phospho-D-glyceric acid3-phospho-D-glyceroyl dihydrogen phosphate + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9500000000-cb3071f9249ee92b7d2cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1950000000-2cde7b5739871a882542JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-3910000000-72f2c46eab2036938056JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9500000000-c835034f0ac11618922dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-6190000000-6f4870543fc6131d14a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-d9d9c6d217a255d791fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1fef400a1ea8ca54c802JSpectraViewer
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
  • McAlister, L., Holland, M. J. (1985). "Differential expression of the three yeast glyceraldehyde-3-phosphate dehydrogenase genes." J Biol Chem 260:15019-15027.3905788
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16001
HMDB IDNot Available
Pubchem Compound ID439191
Kegg IDC00236
ChemSpider ID388331
FOODB IDFDB030188
Wikipedia ID1,3-Bisphosphoglyceric acid
BioCyc IDDPG

Enzymes

General function:
Involved in phosphoglycerate kinase activity
Specific function:
ATP + 3-phospho-D-glycerate = ADP + 3-phospho- D-glyceroyl phosphate
Gene Name:
PGK1
Uniprot ID:
P00560
Molecular weight:
44738.0
Reactions
ATP + 3-phospho-D-glycerate → ADP + 3-phospho-D-glyceroyl phosphate.
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, NAD or NADP as acceptor
Specific function:
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH
Gene Name:
TDH1
Uniprot ID:
P00360
Molecular weight:
35749.60156
Reactions
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) → 3-phospho-D-glyceroyl phosphate + NADH.
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, NAD or NADP as acceptor
Specific function:
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH
Gene Name:
TDH2
Uniprot ID:
P00358
Molecular weight:
35846.60156
Reactions
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) → 3-phospho-D-glyceroyl phosphate + NADH.
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, NAD or NADP as acceptor
Specific function:
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH
Gene Name:
TDH3
Uniprot ID:
P00359
Molecular weight:
35746.39844
Reactions
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) → 3-phospho-D-glyceroyl phosphate + NADH.
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.