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D-Glyceraldehyde 3-phosphate (YMDB00115)

Identification
YMDB IDYMDB00115
NameD-Glyceraldehyde 3-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGlyceraldehyde 3-phosphate, also known as 3-phosphoglyceraldehyde or GAP, 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. Glyceraldehyde 3-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Glyceraldehyde 3-phosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
  • 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
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate ↔ Xylulose 5-phosphate + D-Erythrose 4-phosphate
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate ↔ Xylulose 5-phosphate + D-Ribose 5-phosphate
D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate → D-Erythrose 4-phosphate + β-D-fructofuranose 6-phosphate
1-C-(3-indolyl)-glycerol 3-phosphate → Indole + D-Glyceraldehyde 3-phosphate
D-Glyceraldehyde 3-phosphate + Pyruvic acid + hydron → 1-Deoxy-D-xylulose 5-phosphate + Carbon dioxide
KEGG Reactions
Dihydroxyacetone phosphate ↔ D-Glyceraldehyde 3-phosphate
L-Serine + 1-C-(indol-3-yl)glycerol 3-phosphate → D-Glyceraldehyde 3-phosphate + water + L-Tryptophan
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0m5s-3952000000-862ad552658a2dad7631JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03dj-2943000000-879f36e9ffb61cdb7e7eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0m5s-3952000000-862ad552658a2dad7631JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03dj-2943000000-879f36e9ffb61cdb7e7eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9300000000-7c325d284fb0e3770da5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xs-9720000000-2a59591392eaadc8cb67JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9000000000-6e7cef3b048204ad747cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-00di-1900000000-f7a7b256e1a0b030f168JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-00di-2900000000-eacc8d6b246e46b2340fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-00dj-4900000000-a66af0aa75aba70cb82aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-006t-7900000000-8b419c2e8472f9f74a49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-006t-9600000000-6504648a31d96ef44d49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-9400000000-5a167503e18109d4af5bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-9200000000-76cd396626689c9235beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-9100000000-9b592d8b0cba5a7af4c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-9100000000-7a7901afb70f6d8627c9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-9000000000-bcb4ecbf7bc0e3ce3164JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0002-9000000000-13cecd1b3662f69b69d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0002-9000000000-ad2b828477c8005d6ec0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0002-9000000000-c4278124075952af95f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0002-9000000000-4387fd6f7164cef7bd72JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0002-9000000000-4c200ed3c50ff96956b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0002-9000000000-c9b13016720f097cecbcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-0002-9000000000-f2389881e7483c78942fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0005-9700000000-3e08f8453aeb088eee03JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-4900000000-416f405681faaf774486JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9300000000-e5728592219561b9203cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-eeb354dbde88d3794c6dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-50b19733dd05329d82c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-22bcce954e030ff911edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5dbce0b156c269157c00JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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

Protein Details
1. Transketolase 2
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.
Protein Details
2. Transaldolase NQM1
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.
Protein Details
3. Transketolase 1
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.
Protein Details
4. Fructose-bisphosphate aldolase
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.
Protein Details
5. Glyceraldehyde-3-phosphate dehydrogenase 1
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.
Protein Details
6. Glyceraldehyde-3-phosphate dehydrogenase 2
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.
Protein Details
7. Glyceraldehyde-3-phosphate dehydrogenase 3
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.
Protein Details
8. Tryptophan synthase
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.
Protein Details
9. Triosephosphate isomerase
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.
Protein Details
10. Transaldolase
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.