D-Glyceraldehyde 3-phosphate (PAMDB000257)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000257
Identification
Name: D-Glyceraldehyde 3-phosphate
Description:Glyceraldehyde 3-phosphate (G3P) or triose phosphate is an aldotriose, an important metabolic intermediate in both glycolysis and gluconeogenesis, and in tryptophan biosynthesis. G3P is formed from Fructose-1,6-bisphosphate, Dihydroxyacetone phosphate (DHAP),and 1,3-bisphosphoglycerate, (1,3BPG), and this is how glycerol (as DHAP) enters the glycolytic and gluconeogenesis pathways.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2R)-2-hydroxy-3-(phosphonooxy)-propanal
  • (2R)-2-hydroxy-3-(phosphonooxy)-propanal
  • 2-Hydroxy-3-(phosphonooxy)-Propanal
  • 3-Phosphoglyceraldehyde
  • D-Glyceraldehyde 3-phosphate
  • D-Glyceraldehyde 3-phosphoric acid
  • D-Glyceraldehyde-3-P
  • DL-Glyceraldehyde 3-phosphate
  • DL-Glyceraldehyde 3-phosphoric acid
  • GAP
  • Glyceraldehyde 3-phosphate
  • Glyceraldehyde 3-phosphoric acid
  • Glyceraldehyde-3-P
  • Glyceraldehyde-3-phosphate
  • Glyceraldehyde-3-phosphoric acid
  • Glyceraldehyde-P
  • Glyceraldehyde-phosphate
  • Glyceraldehyde-phosphoric acid
  • Triose phosphate
  • Triose phosphoric acid
Chemical Formula: C3H7O6P
Average Molecular Weight: 170.0578
Monoisotopic Molecular Weight: 169.998024468
InChI Key: LXJXRIRHZLFYRP-UHFFFAOYSA-N
InChI:InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
CAS number: 142-10-9
IUPAC Name:[(2R)-2-hydroxy-3-oxopropoxy]phosphonic acid
Traditional IUPAC Name: glyceraldehyde-3-phosphate
SMILES:OC(COP(O)(O)=O)C=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glyceraldehyde-3-phosphates. These are compounds containing a glyceraldehyde substituted at position O3 by a phosphate group.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct Parent Glyceraldehyde-3-phosphates
Alternative Parents
Substituents
  • Glyceraldehyde-3-phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility20.5 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.33 m3·mol-1ChemAxon
Polarizability12.54 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
D-Tagatose 1,6-bisphosphate <> Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate
Fructose 6-phosphate <> Dihydroxyacetone + D-Glyceraldehyde 3-phosphate
Indoleglycerol phosphate + L-Serine > D-Glyceraldehyde 3-phosphate + Water + L-Tryptophan
Indoleglycerol phosphate > D-Glyceraldehyde 3-phosphate + Indole
Fructose 1,6-bisphosphate <> Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate
D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Erythrose 4-phosphate + Fructose 6-phosphate
D-Ribose-5-phosphate + Xylulose 5-phosphate <> D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate
D-Glyceraldehyde 3-phosphate + Hydrogen ion + Pyruvic acid <> Carbon dioxide + 1-Deoxy-D-xylulose 5-phosphate
D-Glyceraldehyde 3-phosphate + NAD + Phosphate <> Glyceric acid 1,3-biphosphate + Hydrogen ion + NADH + 3-phospho-D-glyceroyl phosphate
2-Keto-3-deoxy-6-phosphogluconic acid <> D-Glyceraldehyde 3-phosphate + Pyruvic acid
Dihydroxyacetone phosphate <> D-Glyceraldehyde 3-phosphate
D-Glyceraldehyde 3-phosphate + Phosphate + NAD <> Glyceric acid 1,3-biphosphate + NADH + Hydrogen ion
beta-D-Fructose 1,6-bisphosphate <> Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate
Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Ribose-5-phosphate + Xylulose 5-phosphate
Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + beta-D-Fructose 6-phosphate
beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate
Pyruvic acid + D-Glyceraldehyde 3-phosphate <> 1-Deoxy-D-xylulose 5-phosphate + Carbon dioxide
D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate
2-Dehydro-3-deoxy-D-galactonate-6-phosphate <> D-Glyceraldehyde 3-phosphate + Pyruvic acid
Deoxyribose 5-phosphate <> Acetaldehyde + D-Glyceraldehyde 3-phosphate
2-Dehydro-3-deoxy-D-galactonate 6-phosphate > Pyruvic acid + D-Glyceraldehyde 3-phosphate
D-Glyceraldehyde 3-phosphate + Inorganic phosphate + NAD > 3-phospho-D-glyceroyl phosphate + NADH
L-Serine + Indoleglycerol phosphate + Indole <> L-Tryptophan + D-Glyceraldehyde 3-phosphate + Water
D-Glyceraldehyde 3-phosphate + Pyruvic acid + Hydrogen ion + D-Glyceraldehyde 3-phosphate > 1-Deoxy-D-xylulose 5-phosphate + Carbon dioxide + 1-Deoxy-D-xylulose 5-phosphate
D-Glyceraldehyde 3-phosphate + Hydrogen ion + D-Glyceraldehyde 3-phosphate > Carbon dioxide + 1-Deoxy-D-xylulose 5-phosphate + 1-Deoxy-D-xylulose 5-phosphate
Xylulose 5-phosphate + D-Ribose-5-phosphate + Xylulose 5-phosphate <> D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> beta-D-Fructose 6-phosphate + D-Erythrose 4-phosphate
Fructose 1,6-bisphosphate + Fructose 1,6-bisphosphate <> D-Glyceraldehyde 3-phosphate + Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate
D-Glyceraldehyde 3-phosphate + NAD + Phosphate + D-Glyceraldehyde 3-phosphate > Glyceric acid 1,3-biphosphate + NADH + Hydrogen ion + Glyceric acid 1,3-biphosphate
(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate > D-Glyceraldehyde 3-phosphate + Indole + D-Glyceraldehyde 3-phosphate
D-Glyceraldehyde 3-phosphate + D-Glyceraldehyde 3-phosphate <> Dihydroxyacetone phosphate
2-dehydro-3-deoxy-D-galactonate 6-phosphate + 2-Dehydro-3-deoxy-D-galactonate 6-phosphate > Pyruvic acid + D-Glyceraldehyde 3-phosphate + D-Glyceraldehyde 3-phosphate
D-tagatofuranose 1,6-bisphosphate > Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate + D-Glyceraldehyde 3-phosphate
2-Keto-3-deoxy-6-phosphogluconic acid > D-Glyceraldehyde 3-phosphate + Pyruvic acid + D-Glyceraldehyde 3-phosphate
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-03gs-2974000000-49a55c276e0ad196e48bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-03dj-1954000000-b38d318554d6563bd853View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-4900000000-c2523768fc807c3c2be4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9300000000-f776376958b2b72f623aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e259d091dff097ba4725View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-c0ca9a77a4d78aab0dfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-0bed37562fdba4181b72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1a41399517f85b66b213View in MoNA
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: Ballou, Clinton E.; Fischer, Hermann O. L. The synthesis of D-glyceraldehyde 3-phosphate. Journal of the American Chemical Society (1955), 77 3329-31.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID17138
HMDB IDHMDB01112
Pubchem Compound ID729
Kegg IDC00118
ChemSpider ID709
WikipediaGAP
BioCyc IDGAP
EcoCyc IDGAP
Ligand ExpoG3H