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MetaCyc Compound: D-erythrose 4-phosphate

Synonyms: erythrose-4P, threose 4-phosphate, erythrose-4-phosphate, erythrose-4-P, D-erythrose-4-P

Superclasses: all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate

Chemical Formula: C4H7O7P

Molecular Weight: 198.07 Daltons

Monoisotopic Molecular Weight: 200.0085891536 Daltons

SMILES: [CH](C(C(COP([O-])([O-])=O)O)O)=O

InChI: InChI=1S/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/p-2/t3-,4+/m0/s1

InChIKey: InChIKey=NGHMDNPXVRFFGS-IUYQGCFVSA-L

Unification Links: CAS:585-18-2 , ChEBI:16897 , ChemSpider:4573609 , HMDB:HMDB01321 , IAF1260:34479 , KEGG:C00279 , MetaboLights:MTBLC16897 , PubChem:5459862

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -284.9704 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

pyridoxal 5'-phosphate biosynthesis I :
D-erythrose 4-phosphate + NAD+ + H2O → erythronate-4-phosphate + NADH + 2 H+

Not in pathways:
a sugar phosphate + H2O → a sugar + phosphate

Reactions known to produce the compound:

5,6-dimethylbenzimidazole biosynthesis , adenosylcobalamin biosynthesis from cobyrinate a,c-diamide II :
FMNH2 + oxygen → 5,6-dimethylbenzimidazole + D-erythrose 4-phosphate + dialurate

Bifidobacterium shunt :
β-D-fructofuranose 6-phosphate + phosphate → D-erythrose 4-phosphate + acetyl phosphate + H2O

methylthiolincosamide biosynthesis :
D-ribose 5-phosphate + D-sedoheptulose 7-phosphate → D-glycero-D-altro-octulose 8-phosphate + D-erythrose 4-phosphate

Not in pathways:
an N-acetyl-β-D-galactosalaminyl-[glycan] + H2O → a glycan + N-acetyl-β-D-galactosamine

Reactions known to both consume and produce the compound:

3-dehydroquinate biosynthesis I :
phosphoenolpyruvate + D-erythrose 4-phosphate + H2O ↔ 3-deoxy-D-arabino-heptulosonate-7-phosphate + phosphate

Bifidobacterium shunt :
D-glyceraldehyde 3-phosphate + D-sedoheptulose 7-phosphate ↔ β-D-fructofuranose 6-phosphate + D-erythrose 4-phosphate

Calvin-Benson-Bassham cycle :
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate
dihydroxyacetone phosphate + D-erythrose 4-phosphate ↔ D-sedoheptulose-1,7-bisphosphate

formaldehyde assimilation II (RuMP Cycle) :
D-glyceraldehyde 3-phosphate + D-sedoheptulose 7-phosphate ↔ β-D-fructofuranose 6-phosphate + D-erythrose 4-phosphate
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate

formaldehyde assimilation III (dihydroxyacetone cycle) :
D-glyceraldehyde 3-phosphate + D-sedoheptulose 7-phosphate ↔ β-D-fructofuranose 6-phosphate + D-erythrose 4-phosphate
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate

pentose phosphate pathway (non-oxidative branch) :
D-glyceraldehyde 3-phosphate + D-sedoheptulose 7-phosphate ↔ β-D-fructofuranose 6-phosphate + D-erythrose 4-phosphate
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate

pentose phosphate pathway (partial) , superpathway of glucose and xylose degradation :
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate

Rubisco shunt :
D-glyceraldehyde 3-phosphate + D-sedoheptulose 7-phosphate ↔ β-D-fructofuranose 6-phosphate + D-erythrose 4-phosphate
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate

sedoheptulose bisphosphate bypass :
dihydroxyacetone phosphate + D-erythrose 4-phosphate ↔ D-sedoheptulose-1,7-bisphosphate

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[out] → a [PTS enzyme I]-L-histidine + a sugar phosphate[in]

Enzymes inhibited by D-erythrose 4-phosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: phosphomannose isomerase [Lee84] , 6-phosphogluconate dehydrogenase

Inhibitor (Mechanism unknown) of: NADP-dependent glyceraldehyde-3-phosphate dehydrogenase [Crow79]


References

Crow79: Crow VL, Wittenberger CL (1979). "Separation and properties of NAD+- and NADP+-dependent glyceraldehyde-3-phosphate dehydrogenases from Streptococcus mutans." J Biol Chem 254(4);1134-42. PMID: 33184

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lee84: Lee B.T., Matheson N.K. "Phosphomannoisomerase and phosphoglucoisomerase in seeds of Cassia coluteoides and some other legumes that synthesize galactomannan." Phytochemistry (1984) 23(5) : 983-987.


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Wed Nov 26, 2014, biocyc14.