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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:36 UTC
HMDB IDHMDB0001321
Secondary Accession Numbers
  • HMDB01321
Metabolite Identification
Common NameD-Erythrose 4-phosphate
DescriptionD-Erythrose 4-phosphate, also known as D-erythrose-4-p or 4-O-phosphono-D-erythrose, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. D-Erythrose 4-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Erythrose 4-phosphate exists in all living species, ranging from bacteria to humans. Within humans, D-erythrose 4-phosphate participates in a number of enzymatic reactions. In particular, D-erythrose 4-phosphate and fructose 6-phosphate can be converted into D-glyceraldehyde 3-phosphate and D-sedoheptulose 7-phosphate; which is catalyzed by the enzyme transaldolase. In addition, D-erythrose 4-phosphate and xylulose 5-phosphate can be converted into fructose 6-phosphate and D-glyceraldehyde 3-phosphate through its interaction with the enzyme transketolase. In humans, D-erythrose 4-phosphate is involved in the metabolic disorder called the glucose-6-phosphate dehydrogenase deficiency pathway.
Structure
Thumb
Synonyms
Chemical FormulaC4H9O7P
Average Molecular Weight200.0838
Monoisotopic Molecular Weight200.008589154
IUPAC Name[(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid
Traditional Name4-O-phosphono-D-erythrose
CAS Registry Number585-18-2
SMILES
O[C@H](COP(O)(O)=O)[C@@H](O)C=O
InChI Identifier
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)/t3-,4+/m0/s1
InChI KeyNGHMDNPXVRFFGS-IUYQGCFVSA-N
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker149.16430932474
[M-H]-Not Available149.164http://allccs.zhulab.cn/database/detail?ID=AllCCS00001801
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Cellular Cytoplasm
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified1770 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03937
Phenol Explorer Compound IDNot Available
FooDB IDFDB001614
KNApSAcK IDC00007472
Chemspider ID109096
KEGG Compound IDC00279
BioCyc IDERYTHROSE-4P
BiGG ID34479
Wikipedia LinkErythrose_4-phosphate
METLIN ID6158
PubChem Compound122357
PDB IDNot Available
ChEBI ID48153
Food Biomarker OntologyNot Available
VMH IDE4P
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate (By similarity).
Gene Name:
TKTL1
Uniprot ID:
P51854
Molecular weight:
59302.195
Reactions
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
Gene Name:
TALDO1
Uniprot ID:
P37837
Molecular weight:
37539.74
Reactions
D-Sedoheptulose 7-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Fructose 6-phosphatedetails
D-Sedoheptulose 7-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Beta-D-Fructose 6-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:
TKT
Uniprot ID:
P29401
Molecular weight:
67876.95
Reactions
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Plays a key role in glycolysis and gluconeogenesis. In addition, may also function as scaffolding protein (By similarity).
Gene Name:
ALDOA
Uniprot ID:
P04075
Molecular weight:
39419.675
Reactions
Sedoheptulose 1,7-bisphosphate → Dihydroxyacetone phosphate + D-Erythrose 4-phosphatedetails
Dihydroxyacetone phosphate + D-Erythrose 4-phosphate → Sedoheptulose 1,7-bisphosphatedetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Not Available
Gene Name:
ALDOC
Uniprot ID:
P09972
Molecular weight:
39455.505
Reactions
Sedoheptulose 1,7-bisphosphate → Dihydroxyacetone phosphate + D-Erythrose 4-phosphatedetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
P05062
Molecular weight:
39472.715
Reactions
Sedoheptulose 1,7-bisphosphate → Dihydroxyacetone phosphate + D-Erythrose 4-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Plays an essential role in total transketolase activity and cell proliferation in cancer cells; after transfection with anti-TKTL1 siRNA, total transketolase activity dramatically decreases and proliferation was significantly inhibited in cancer cells. Plays a pivotal role in carcinogenesis.
Gene Name:
TKTL2
Uniprot ID:
Q9H0I9
Molecular weight:
67876.625
Reactions
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails