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Identification
YMDB IDYMDB00115
NameD-Glyceraldehyde 3-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGlyceraldehyde 3-phosphate (G3P) is an aldotriose. It is an important metabolic intermediate in both glycolysis and gluconeogenesis, and in tryptophan biosynthesis.
Structure
Thumb
Synonyms
  • (2r)-2-hydroxy-3-(phosphonooxy)-propanal
  • 2-hydroxy-3-(phosphonooxy)-Propanal
  • 2-hydroxy-3-(phosphonooxy)propanal
  • 3-Phosphoglyceraldehyde
  • D-Glyceraldehyde 3-phosphate
  • D-Glyceraldehyde 3-phosphic acid
  • D-glyceraldehyde-3-P
  • DL-Glyceraldehyde 3-phosphate
  • GAP
  • gliceraldehido-3-fosfato
  • glyceraldehyde 3-(dihydrogen phosphate)
  • Glyceraldehyde 3-phosphate
  • glyceraldehyde-3-P
  • Glyceraldehyde-3-phosphate
  • glyceraldehyde-P
  • glyceraldehyde-phosphate
  • Glycerinaldehyd-3-phosphat
  • Glyzerinaldehyd-3-phosphat
  • Propanal, 2-hydroxy-3-(phosphonooxy)-
  • DL-Glyceraldehyde 3-phosphoric acid
  • Glyceraldehyde 3-(dihydrogen phosphoric acid)
  • Glyceraldehyde-3-phosphoric acid
  • D-Glyceraldehyde 3-phosphoric acid
  • 3 Phosphoglyceraldehyde
  • Glyceraldehyde 3 phosphate
CAS number142-10-9
WeightAverage: 170.0578
Monoisotopic: 169.998024468
InChI KeyLXJXRIRHZLFYRP-UHFFFAOYSA-N
InChIInChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
IUPAC Name(2-hydroxy-3-oxopropoxy)phosphonic acid
Traditional IUPAC Nameglyceraldehyde 3 phosphate
Chemical FormulaC3H7O6P
SMILES[H]OC([H])(C([H])=O)C([H])([H])OP(=O)(O[H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as glyceraldehyde-3-phosphates. Glyceraldehyde-3-phosphates are compounds containing a glyceraldehyde substituted at position O3 by a phosphate group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlyceraldehyde-3-phosphates
Alternative Parents
Substituents
  • Glyceraldehyde-3-phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • 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 Solubility20.5 g/LALOGPS
logP-1.7ALOGPS
logP-1.8ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.4ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.33 m³·mol⁻¹ChemAxon
Polarizability12.61 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Organoleptic PropertiesNot Available
SMPDB Pathways
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
Inositol phosphate metabolismPW002495 ThumbThumb?image type=greyscaleThumb?image type=simple
RiboneogenesisPW002511 ThumbThumb?image type=greyscaleThumb?image type=simple
Terpenoid backbone biosynthesisPW002485 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fructose and mannose metabolismec00051 Map00051
Galactose metabolismec00052 Map00052
Glycolysis / Gluconeogenesisec00010 Map00010
Inositol phosphate metabolismec00562 Map00562
Methane metabolismec00680 Map00680
SMPDB Reactions
Fructose 1,6-bisphosphateD-Glyceraldehyde 3-phosphate + Dihydroxyacetone phosphate
Dihydroxyacetone phosphateD-Glyceraldehyde 3-phosphate
D-Glyceraldehyde 3-phosphate + NAD + Phosphoric acidGlyceric acid 1,3-biphosphate + NADH
Xylulose 5-phosphate + D-Ribose 5-phosphateD-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate
D-Erythrose 4-phosphate + Xylulose 5-phosphateβ-D-fructofuranose 6-phosphate + D-Glyceraldehyde 3-phosphate
KEGG Reactions
Fructose 1,6-bisphosphateD-Glyceraldehyde 3-phosphate + Dihydroxyacetone phosphate
NAD + D-Glyceraldehyde 3-phosphate + phosphateNADH + 3-phospho-D-glyceroyl dihydrogen phosphate + hydron
D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphateD-Erythrose 4-phosphate + Fructose 6-phosphate
alpha-D-ribose 5-phosphate + Xylulose 5-phosphateD-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate
D-Erythrose 4-phosphate + Xylulose 5-phosphateD-Glyceraldehyde 3-phosphate + Fructose 6-phosphate
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
46 ± 4 µM Synthetic medium with 2% glucoseaerobic;resting cellsBaker's yeastPMID: 6229402
100 ± 13 µM Synthetic medium with 2% galactoseaerobic;resting cellsBaker's yeastPMID: 6229402
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Bailey, C. J., Turner, P. D. (1983). "Purification and properties of tryptophan synthase from baker's yeast (Saccharomyces cerevisiae)." Biochem J 209:151-157.6342605
  • Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
  • Senac, T., Hahn-Hagerdal, B. (1990). "Intermediary Metabolite Concentrations in Xylulose- and Glucose-Fermenting Saccharomyces cerevisiae Cells." Appl Environ Microbiol 56:120-126.16348083
  • Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). "Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae." Eur J Biochem 153:243-247.3908097
  • Banki, K., Halladay, D., Perl, A. (1994). "Cloning and expression of the human gene for transaldolase. A novel highly repetitive element constitutes an integral part of the coding sequence." J Biol Chem 269:2847-2851.8300619
  • McAlister, L., Holland, M. J. (1985). "Differential expression of the three yeast glyceraldehyde-3-phosphate dehydrogenase genes." J Biol Chem 260:15019-15027.3905788
  • Boles, E., Zimmermann, F. K. (1993). "Saccharomyces cerevisiae phosphoglucose isomerase and fructose bisphosphate aldolase can be replaced functionally by the corresponding enzymes of Escherichia coli and Drosophila melanogaster." Curr Genet 23:187-191.8435847
  • Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402
Synthesis Reference:Ballou, Clinton E.; Fischer, Hermann O. L. The synthesis of D-glyceraldehyde 3-phosphate. Journal of the American Chemical Society (1955), 77 3329-31.
External Links:
ResourceLink
CHEBI ID29052
HMDB IDHMDB01112
Pubchem Compound ID729
Kegg IDC00118
ChemSpider ID709
FOODB IDFDB001619
WikipediaGlyceraldehyde_3-phosphate
BioCyc IDGAP

Enzymes

General function:
Involved in catalytic activity
Specific function:
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:
TKL2
Uniprot ID:
P33315
Molecular weight:
75028.79688
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-ribose 5-phosphate + D-xylulose 5-phosphate.
General function:
Involved in catalytic activity
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:
NQM1
Uniprot ID:
P53228
Molecular weight:
37253.30078
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-erythrose 4-phosphate + D-fructose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:
TKL1
Uniprot ID:
P23254
Molecular weight:
73805.0
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-ribose 5-phosphate + D-xylulose 5-phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the aldol condensation of dihydroxyacetone phosphate (DHAP or glycerone-phosphate) with glyceraldehyde 3- phosphate (G3P) to form fructose 1,6-bisphosphate (FBP) in gluconeogenesis and the reverse reaction in glycolysis
Gene Name:
FBA1
Uniprot ID:
P14540
Molecular weight:
39620.5
Reactions
D-fructose 1,6-bisphosphate → glycerone phosphate + D-glyceraldehyde 3-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:
L-serine + 1-C-(indol-3-yl)glycerol 3- phosphate = L-tryptophan + glyceraldehyde 3-phosphate + H(2)O
Gene Name:
TRP5
Uniprot ID:
P00931
Molecular weight:
76625.5
Reactions
L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate → L-tryptophan + glyceraldehyde 3-phosphate + H(2)O.
General function:
Involved in catalytic activity
Specific function:
D-glyceraldehyde 3-phosphate = glycerone phosphate
Gene Name:
TPI1
Uniprot ID:
P00942
Molecular weight:
26795.30078
Reactions
D-glyceraldehyde 3-phosphate → glycerone phosphate.
General function:
Involved in catalytic activity
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:
TAL1
Uniprot ID:
P15019
Molecular weight:
37036.0
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-erythrose 4-phosphate + D-fructose 6-phosphate.