Human Metabolome Database Version 3.5

Showing metabocard for D-Erythrose 4-phosphate (HMDB01321)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:19 -0700
HMDB ID HMDB01321
Secondary Accession Numbers None
Metabolite Identification
Common Name D-Erythrose 4-phosphate
Description D-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C4H9O7P
Average Molecular Weight 200.0838
Monoisotopic Molecular Weight 200.008589154
IUPAC Name [(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid
Traditional IUPAC Name (2R,3R)-2,3-dihydroxy-4-oxobutoxyphosphonic acid
CAS Registry Number 585-18-2
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 Key NGHMDNPXVRFFGS-IUYQGCFVSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Monosaccharide 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 Parent Monosaccharide Phosphates
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 23.7 g/L ALOGPS
LogP -1.89 ALOGPS
LogP -2.4 ChemAxon
LogS -0.93 ALOGPS
pKa (strongest acidic) 1.48 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 124.29 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 36.29 ChemAxon
Polarizability 15.41 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Cellular Cytoplasm
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Pentose Phosphate Pathway SMP00031 map00030 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cellular Cytoplasm Detected and Quantified
1770 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB001614
KNApSAcK ID C00007472 Link_out
Chemspider ID 109096 Link_out
KEGG Compound ID C00279 Link_out
BioCyc ID ERYTHROSE-4P Link_out
BiGG ID 34479 Link_out
Wikipedia Link erythrose-4-phosphate Link_out
NuGOwiki Link HMDB01321 Link_out
Metagene Link HMDB01321 Link_out
METLIN ID 6158 Link_out
PubChem Compound 122357 Link_out
PDB ID E4P Link_out
ChEBI ID 48153 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. Takeuchi T, Nishino K, Itokawa Y: Improved determination of transketolase activity in erythrocytes. Clin Chem. 1984 May;30(5):658-61. Pubmed: 6713626 Link_out
  7. 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 Link_out
  8. 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 Link_out
  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 Link_out

Enzymes
Name: Transketolase-like protein 1
Reactions:
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
Gene Name: TKTL1
Uniprot ID: P51854 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transaldolase
Reactions:
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Fructose 6-phosphate details
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Beta-D-Fructose 6-phosphate details
Gene Name: TALDO1
Uniprot ID: P37837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transketolase
Reactions:
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
Gene Name: TKT
Uniprot ID: P29401 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase A
Reactions:
Sedoheptulose 1,7-bisphosphate unknown Dihydroxyacetone phosphate + D-Erythrose 4-phosphate details
Gene Name: ALDOA
Uniprot ID: P04075 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase C
Reactions:
Sedoheptulose 1,7-bisphosphate unknown Dihydroxyacetone phosphate + D-Erythrose 4-phosphate details
Gene Name: ALDOC
Uniprot ID: P09972 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase B
Reactions:
Sedoheptulose 1,7-bisphosphate unknown Dihydroxyacetone phosphate + D-Erythrose 4-phosphate details
Gene Name: ALDOB
Uniprot ID: P05062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transketolase-like protein 2
Reactions:
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
Gene Name: TKTL2
Uniprot ID: Q9H0I9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA