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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:19 UTC
HMDB IDHMDB01321
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Erythrose 4-phosphate
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
  1. D-Erythrose 4-phosphate
  2. D-Erythrose 4-PO4
  3. D-Erythrose-4-P
  4. D-Erythrose-4-phosphate
  5. Erythrose 4-phosphate
  6. Erythrose 4-PO4
  7. Erythrose-4-P
  8. Erythrose-4-phosphate
  9. Erythrose-4P
  10. Threose 4-phosphate
Chemical FormulaC4H9O7P
Average Molecular Weight200.0838
Monoisotopic Molecular Weight200.008589154
IUPAC Name[(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid
Traditional Name(2R,3R)-2,3-dihydroxy-4-oxobutoxyphosphonic acid
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
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassMonosaccharide Phosphates
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
Substituents
  • 1,2 Diol
  • Aldehyde
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Secondary Alcohol
  • Tetrose Monosaccharide
Direct ParentMonosaccharide Phosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility23.7ALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.29 m3·mol-1ChemAxon
Polarizability15.41 Å3ChemAxon
Spectra
SpectraGC-MS
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Cellular Cytoplasm
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Pentose Phosphate PathwaySMP00031map00030
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified1770 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001614
KNApSAcK IDC00007472
Chemspider ID109096
KEGG Compound IDC00279
BioCyc IDERYTHROSE-4P
BiGG ID34479
Wikipedia Linkerythrose-4-phosphate
NuGOwiki LinkHMDB01321
Metagene LinkHMDB01321
METLIN ID6158
PubChem Compound122357
PDB IDE4P
ChEBI ID48153
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tanaka N, Haga A, Uemura H, Akiyama H, Funasaka T, Nagase H, Raz A, Nakamura KT: Inhibition mechanism of cytokine activity of human autocrine motility factor examined by crystal structure analyses and site-directed mutagenesis studies. J Mol Biol. 2002 May 10;318(4):985-97. Pubmed: 12054796
  2. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
  3. Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. Pubmed: 12881455
  4. Takeuchi T, Nishino K, Itokawa Y: Improved determination of transketolase activity in erythrocytes. Clin Chem. 1984 May;30(5):658-61. Pubmed: 6713626
  5. Talukder AH, Bagheri-Yarmand R, Williams RR, Ragoussis J, Kumar R, Raz A: Antihuman epidermal growth factor receptor 2 antibody herceptin inhibits autocrine motility factor (AMF) expression and potentiates antitumor effects of AMF inhibitors. Clin Cancer Res. 2002 Oct;8(10):3285-9. Pubmed: 12374700
  6. Stepanova NG: [Determination of aldolase A activity in the serum of patients with myocardial infarction] Vopr Med Khim. 1986 Sep-Oct;32(5):89-93. Pubmed: 3776121
  7. Mikami M, Sadahira Y, Haga A, Otsuki T, Wada H, Sugihara T: Hypoxia-inducible factor-1 drives the motility of the erythroid progenitor cell line, UT-7/Epo, via autocrine motility factor. Exp Hematol. 2005 May;33(5):531-41. Pubmed: 15850830
  8. Zanella A, Izzo C, Rebulla P, Perroni L, Mariani M, Canestri G, Sansone G, Sirchia G: The first stable variant of erythrocyte glucose-phosphate isomerase associated with severe hemolytic anemia. Am J Hematol. 1980;9(1):1-11. Pubmed: 7435496
  9. Williams JF, Blackmore PF, Duke CC, MacLeod JK: Fact, uncertainty and speculation concerning the biochemistry of D-erythrose-4-phosphate and its metabolic roles. Int J Biochem. 1980;12(3):339-44. Pubmed: 6998788

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 + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + D-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 + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Fructose 6-phosphatedetails
D-Sedoheptulose 7-phosphate + D-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 + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + D-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
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 + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails