Record Information
Version2.0
Creation Date2012-05-31 14:51:45 -0600
Update Date2015-06-03 17:20:20 -0600
Secondary Accession Numbers
  • ECMDB20581
Identification
Name:L-Glyceraldehyde 3-phosphate
DescriptionL-glyceraldehyde 3-phosphate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. L-Glyceraldehyde 3-phosphate is a competitive inhibitor of sn-glycerol 3-phosphate in the reactions catalyzed by acyl coenzyme A:sn-glycerol 3-phosphate acyltransferase (K(i) of 1. (PMID 319747) L-glyceraldehyde 3-phosphate reductase from Escherichia coli is a heme binding protein. It has been shown that YghZ from Escherichia coli functions as an efficient L-glyceraldehyde 3-phosphate reductase (Gpr). (PMID 20015532)
Structure
Thumb
Synonyms:
  • L-Gap
  • L-Glyceraldehyde 3-phosphoric acid
  • L-GLYCERALDEHYDE-3-PHOSPHATE
  • L-GLYCERALDEHYDE-3-phosphoric acid
Chemical Formula:C3H5O6P
Weight:Average: 168.042
Monoisotopic: 167.982374404
InChI Key:GXXAGHMDFNBLAG-GSVOUGTGSA-N
InChI:InChI=1S/C3H5O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2/q-1/t3-/m1/s1
CAS number:Not Available
IUPAC Name:{[(2S)-2-hydroxy-3-oxopropoxy]dioxo-λ⁵-phosphanuidyl}oxidanyl
Traditional IUPAC Name:{[(2S)-2-hydroxy-3-oxopropoxy]dioxo-λ⁵-phosphanuidyl}oxidanyl
SMILES:[H][C@](O)(CO[P-]([O])(=O)=O)C=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.51 g/LALOGPS
logP-1.6ALOGPS
logP-2.3ChemAxon
logS-1.5ALOGPS
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity28.09 m³·mol⁻¹ChemAxon
Polarizability11.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Desai, K. K., Miller, B. G. (2010). "L-glyceraldehyde 3-phosphate reductase from Escherichia coli is a heme binding protein." Bioorg Chem 38:37-41. Pubmed: 20015532
  • 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
  • Tang, C. T., Engel, R., Tropp, B. E. (1977). "L-Glyceraldehude 3-phosphate, a bactericidal agent." Antimicrob Agents Chemother 11:147-153. Pubmed: 319747
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID48932
HMDB IDNot Available
Pubchem Compound ID25201921
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDL-GLYCERALDEHYDE-3-PHOSPHATE
EcoCyc IDL-GLYCERALDEHYDE-3-PHOSPHATE

Enzymes

General function:
Energy production and conversion
Specific function:
Specific function unknown
Gene Name:
yghZ
Uniprot ID:
Q46851
Molecular weight:
38832