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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-07-23 05:44:53 UTC |
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HMDB ID | HMDB0001321 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | D-Erythrose 4-phosphate |
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Description | D-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. |
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Structure | |
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Synonyms | Value | Source |
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4-O-Phosphono-D-erythrose | ChEBI | ERYTHOSE-4-phosphATE | ChEBI | ERYTHOSE-4-phosphoric acid | Generator | D-Erythrose 4-phosphoric acid | Generator | D-Erythrose 4-PO4 | HMDB | D-Erythrose-4-p | HMDB | D-Erythrose-4-phosphate | HMDB | Erythrose 4-phosphate | HMDB | Erythrose 4-PO4 | HMDB | Erythrose-4-p | HMDB | Erythrose-4-phosphate | HMDB | Erythrose-4P | HMDB | Threose 4-phosphate | HMDB | Erythrose 4-phosphate, (r*,r*)-isomer | HMDB | Erythrose 4-phosphate, ((r*,r*)-(+-))-isomer | HMDB | Erythrose 4-phosphate, 14c4-labeled, (r*,r*)-isomer | HMDB | Erythrose 4-phosphate, ((r*,s*)-(+-))-isomer | HMDB |
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Chemical Formula | C4H9O7P |
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Average Molecular Weight | 200.0838 |
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Monoisotopic Molecular Weight | 200.008589154 |
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IUPAC Name | [(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid |
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Traditional Name | 4-O-phosphono-D-erythrose |
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CAS Registry Number | 585-18-2 |
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SMILES | O[C@H](COP(O)(O)=O)[C@@H](O)C=O |
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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 |
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InChI Key | NGHMDNPXVRFFGS-IUYQGCFVSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Monosaccharide phosphates |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 4 TMS) | splash10-0a4i-2946000000-9443f2e925fd6a35c72c | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 4 TMS) | splash10-0a4i-2967000000-d813d71e392e180e1a1a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0a4i-2946000000-9443f2e925fd6a35c72c | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0a4i-2967000000-d813d71e392e180e1a1a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0pba-1933000000-ce3489351efc49bf69f3 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0ka2-2923000000-16fa49e06a727e2d6a47 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9600000000-9d57877fd2f223b326b3 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-01di-8973000000-4793f4bb7564afb5ca7b | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-002b-9000000000-06d71bced6df9b8baad3 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-054k-8900000000-951c8d2dad21e2f2c479 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9100000000-4106e1504853e25f6dff | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-150345a1ab7b74a502c9 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ue9-3940000000-b2cf1408c63fcd508190 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-114m-9800000000-ca839aa0d4b5ed1d26a8 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052v-9100000000-ce3e3be16de64b5ce20e | JSpectraViewer |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Cellular Cytoplasm | Detected and Quantified | 1770 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB03937 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB001614 |
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KNApSAcK ID | C00007472 |
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Chemspider ID | 109096 |
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KEGG Compound ID | C00279 |
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BioCyc ID | Not Available |
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BiGG ID | 34479 |
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Wikipedia Link | Erythrose_4-phosphate |
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METLIN ID | 6158 |
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PubChem Compound | 122357 |
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PDB ID | Not Available |
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ChEBI ID | 48153 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Takeuchi T, Nishino K, Itokawa Y: Improved determination of transketolase activity in erythrocytes. Clin Chem. 1984 May;30(5):658-61. [PubMed:6713626 ]
- 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 ]
- 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 ]
- 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 ]
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