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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:53 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 a drug. 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 through its interaction with 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. Outside of the human body, D-erythrose 4-phosphate has been detected, but not quantified in, several different foods, such as rapes, pomegranates, evening primroses, soursops, and amaranths. This could make D-erythrose 4-phosphate a potential biomarker for the consumption of these foods.
Structure
Data?1563860693
Synonyms
ValueSource
4-O-Phosphono-D-erythroseChEBI
ERYTHOSE-4-phosphATEChEBI
ERYTHOSE-4-phosphoric acidGenerator
D-Erythrose 4-phosphoric acidGenerator
D-Erythrose 4-PO4HMDB
D-Erythrose-4-pHMDB
D-Erythrose-4-phosphateHMDB
Erythrose 4-phosphateHMDB
Erythrose 4-PO4HMDB
Erythrose-4-pHMDB
Erythrose-4-phosphateHMDB
Erythrose-4PHMDB
Threose 4-phosphateHMDB
Erythrose 4-phosphate, (r*,r*)-isomerHMDB
Erythrose 4-phosphate, ((r*,r*)-(+-))-isomerHMDB
Erythrose 4-phosphate, 14c4-labeled, (r*,r*)-isomerHMDB
Erythrose 4-phosphate, ((r*,s*)-(+-))-isomerHMDB
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Solubility23.7 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0a4i-2946000000-9443f2e925fd6a35c72cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0a4i-2967000000-d813d71e392e180e1a1aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-2946000000-9443f2e925fd6a35c72cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-2967000000-d813d71e392e180e1a1aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0pba-1933000000-ce3489351efc49bf69f3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ka2-2923000000-16fa49e06a727e2d6a47JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9600000000-9d57877fd2f223b326b3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01di-8973000000-4793f4bb7564afb5ca7bJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9000000000-06d71bced6df9b8baad3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054k-8900000000-951c8d2dad21e2f2c479JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-4106e1504853e25f6dffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-150345a1ab7b74a502c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-3940000000-b2cf1408c63fcd508190JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114m-9800000000-ca839aa0d4b5ed1d26a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052v-9100000000-ce3e3be16de64b5ce20eJSpectraViewer
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
FoodDB IDFDB001614
KNApSAcK IDC00007472
Chemspider ID109096
KEGG Compound IDC00279
BioCyc IDNot Available
BiGG ID34479
Wikipedia LinkErythrose_4-phosphate
METLIN ID6158
PubChem Compound122357
PDB IDNot Available
ChEBI ID48153
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot 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 ]
  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 ]
  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 ]
  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;2:18. [PubMed:15882454 ]
  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 ]
  6. Takeuchi T, Nishino K, Itokawa Y: Improved determination of transketolase activity in erythrocytes. Clin Chem. 1984 May;30(5):658-61. [PubMed:6713626 ]
  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 ]
  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 ]
  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 + 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