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Identification
YMDB IDYMDB00223
NameD-Erythrose 4-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Erythrose 4-phosphate is a phosphorylated derivative of erythrose that serves as an important intermediate in the pentose phosphate pathway. It is also used in phenylalanine, tyrosine and tryptophan biosynthesis, and it plays a role in vitamin B6 metabolism. [KEGG]
Structure
Thumb
Synonyms
  • 4-O-phosphonato-D-erythrose
  • D-Erythrose 4-phosphate
  • D-Erythrose 4-phosphic acid
  • D-Erythrose 4-PO4
  • D-erythrose-4-P
  • D-erythrose-4-phosphate
  • Erythrose 4-phosphate
  • Erythrose 4-PO4
  • erythrose-4-P
  • erythrose-4-phosphate
  • erythrose-4P
  • threose 4-phosphate
  • 4-O-Phosphono-D-erythrose
  • ERYTHOSE-4-phosphATE
  • ERYTHOSE-4-phosphoric acid
  • D-Erythrose 4-phosphoric acid
  • Erythrose 4-phosphate, (r*,r*)-isomer
  • Erythrose 4-phosphate, ((r*,r*)-(+-))-isomer
  • Erythrose 4-phosphate, 14c4-labeled, (r*,r*)-isomer
  • Erythrose 4-phosphate, ((r*,s*)-(+-))-isomer
CAS number585-18-2
WeightAverage: 200.0838
Monoisotopic: 200.008589154
InChI KeyNGHMDNPXVRFFGS-IUYQGCFVSA-N
InChIInChI=1S/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/t3-,4+/m0/s1
IUPAC Name[(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid
Traditional IUPAC Name4-O-phosphono-D-erythrose
Chemical FormulaC4H9O7P
SMILES[H]O[C@@]([H])(C([H])=O)[C@]([H])(O[H])C([H])([H])OP(=O)(O[H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • 1,2-diol
  • 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 Solubility23.7 g/LALOGPS
logP-1.9ALOGPS
logP-2.4ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.29 m³·mol⁻¹ChemAxon
Polarizability15.41 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
RiboneogenesisPW002511 ThumbThumb?image type=greyscaleThumb?image type=simple
Vitamin B6PW002488 ThumbThumb?image type=greyscaleThumb?image type=simple
xylitol degradationPW002433 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pentose phosphate pathwayec00030 Map00030
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
Vitamin B6 metabolismec00750 Map00750
SMPDB Reactions
D-Erythrose 4-phosphate + Xylulose 5-phosphateβ-D-fructofuranose 6-phosphate + D-Glyceraldehyde 3-phosphate
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphateXylulose 5-phosphate + D-Erythrose 4-phosphate
D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphateD-Erythrose 4-phosphate + β-D-fructofuranose 6-phosphate
D-Erythrose 4-phosphate + NAD + waterNADH + hydron + 4-Phospho-D-erythronate
Erythrose → D-Erythrose 4-phosphate + [PTS enzyme I]-L-histidine + [PTS enzyme I]-Nπ-phospho-L-histidine
KEGG Reactions
D-Erythrose 4-phosphate + Phosphoenolpyruvic acid + waterphosphate + 7-phospho-2-dehydro-3-deoxy-D-arabino-heptonic acid
sedoheptulose 1,7-bisphosphateD-Erythrose 4-phosphate + Dihydroxyacetone phosphate
D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphateD-Erythrose 4-phosphate + Fructose 6-phosphate
D-Erythrose 4-phosphate + Xylulose 5-phosphateD-Glyceraldehyde 3-phosphate + Fructose 6-phosphate
Concentrations
Intracellular ConcentrationsNot Available
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
  • Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
  • Braus, G. H. (1991). "Aromatic amino acid biosynthesis in the yeast Saccharomyces cerevisiae: a model system for the regulation of a eukaryotic biosynthetic pathway." Microbiol Rev 55:349-370.1943992
  • Teshiba, S., Furter, R., Niederberger, P., Braus, G., Paravicini, G., Hutter, R. (1986). "Cloning of the ARO3 gene of Saccharomyces cerevisiae and its regulation." Mol Gen Genet 205:353-357.2880280
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID48153
HMDB IDHMDB01321
Pubchem Compound ID697
Kegg IDC00279
ChemSpider ID109096
FOODB IDFDB001614
Wikipediaerythrose-4-phosphate
BioCyc IDERYTHROSE-4P

Enzymes

General function:
Involved in catalytic activity
Specific function:
Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
Gene Name:
ARO4
Uniprot ID:
P32449
Molecular weight:
39748.80078
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O → 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate.
General function:
Involved in catalytic activity
Specific function:
Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
Gene Name:
ARO3
Uniprot ID:
P14843
Molecular weight:
41069.5
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O → 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + 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:
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 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.