| Record Information |
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| Version | 5.0 |
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| Status | Detected but not Quantified |
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| Creation Date | 2006-05-22 15:12:01 UTC |
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| Update Date | 2022-09-22 17:44:53 UTC |
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| HMDB ID | HMDB0002649 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Erythrose |
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| Description | Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose. It is a member of the class of compounds known as pentoses. Pentoses are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Erythrose is very soluble (in water). Erythrose can be found in blood, as well as in human cartilage tissue. Within the cell, erythrose is primarily located in the cytoplasm (predicted from logP). Erythrose exists in all living organisms, ranging from bacteria to humans. Erythrose is found to be associated with schizophrenia. Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869) and was named as such because of its red hue in the presence of alkali metals. |
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| Structure | [H][C@@]1(O)COC([H])(O)[C@]1([H])O InChI=1S/C4H8O4/c5-2-1-8-4(7)3(2)6/h2-7H,1H2/t2-,3-,4?/m1/s1 |
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| Synonyms | | Value | Source |
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| (R*,r*)-2,3,4-trihydroxybutanal | HMDB | | D-erythro-Tetrose | HMDB | | D-Erythrose | HMDB | | L-threo-Aldose | HMDB | | L-Threose | HMDB | | LTr | HMDB | | Threose | HMDB |
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| Chemical Formula | C4H8O4 |
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| Average Molecular Weight | 120.1039 |
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| Monoisotopic Molecular Weight | 120.042258744 |
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| IUPAC Name | (3R,4R)-oxolane-2,3,4-triol |
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| Traditional Name | D-erythro-tetrose |
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| CAS Registry Number | 1758-51-6 |
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| SMILES | [H][C@@]1(O)COC([H])(O)[C@]1([H])O |
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| InChI Identifier | InChI=1S/C4H8O4/c5-2-1-8-4(7)3(2)6/h2-7H,1H2/t2-,3-,4?/m1/s1 |
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| InChI Key | FMAORJIQYMIRHF-HERZVMAMSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. |
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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 | Pentoses |
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| Alternative Parents | |
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| Substituents | - Pentose monosaccharide
- Tetrahydrofuran
- Secondary alcohol
- Hemiacetal
- 1,2-diol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Alcohol
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | |
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| Disposition | |
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| Process | Not Available |
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| Role | Not Available |
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| Physical Properties |
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| State | Liquid |
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| Experimental Molecular 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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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 1.46 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 8.9173 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 2.69 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 248.7 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 641.9 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 330.9 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 45.8 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 208.3 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 72.8 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 273.7 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 220.2 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 643.1 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 573.5 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 40.6 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 708.5 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 205.3 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 257.8 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 600.3 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 323.3 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 283.2 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Erythrose,1TMS,isomer #1 | C[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O | 1261.6 | Semi standard non polar | 33892256 | | Erythrose,1TMS,isomer #2 | C[Si](C)(C)OC1OC[C@@H](O)[C@H]1O | 1275.9 | Semi standard non polar | 33892256 | | Erythrose,1TMS,isomer #3 | C[Si](C)(C)O[C@H]1C(O)OC[C@H]1O | 1264.5 | Semi standard non polar | 33892256 | | Erythrose,2TMS,isomer #1 | C[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C)[C@H]1O | 1357.7 | Semi standard non polar | 33892256 | | Erythrose,2TMS,isomer #2 | C[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O[Si](C)(C)C | 1348.0 | Semi standard non polar | 33892256 | | Erythrose,2TMS,isomer #3 | C[Si](C)(C)OC1OC[C@@H](O)[C@H]1O[Si](C)(C)C | 1346.5 | Semi standard non polar | 33892256 | | Erythrose,3TMS,isomer #1 | C[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C | 1412.6 | Semi standard non polar | 33892256 | | Erythrose,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O | 1487.0 | Semi standard non polar | 33892256 | | Erythrose,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1OC[C@@H](O)[C@H]1O | 1499.1 | Semi standard non polar | 33892256 | | Erythrose,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)O[C@H]1C(O)OC[C@H]1O | 1486.7 | Semi standard non polar | 33892256 | | Erythrose,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O | 1794.0 | Semi standard non polar | 33892256 | | Erythrose,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@@H]1COC(O)[C@@H]1O[Si](C)(C)C(C)(C)C | 1790.2 | Semi standard non polar | 33892256 | | Erythrose,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1OC[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C | 1797.5 | Semi standard non polar | 33892256 | | Erythrose,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C | 2074.2 | Semi standard non polar | 33892256 |
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| Spectra |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - Erythrose GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9100000000-446a7809c52925c9cccf | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Erythrose GC-MS (3 TMS) - 70eV, Positive | splash10-0079-9261000000-19140e354324df2a7807 | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Erythrose GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Experimental LC-MS/MS | LC-MS/MS Spectrum - Erythrose Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-00dl-6900000000-67190e070c91e864cf81 | 2012-07-25 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Erythrose Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-002f-9000000000-29833cdb41877882bc60 | 2012-07-25 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Erythrose Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0ufr-9000000000-9fb5c86d87b3809c8196 | 2012-07-25 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Erythrose LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF | splash10-0006-9100000000-15d26b9d7a9da6a71e33 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Erythrose LC-ESI-QTOF , positive-QTOF | splash10-0006-9100000000-15d26b9d7a9da6a71e33 | 2017-09-14 | HMDB team, MONA | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 10V, Positive-QTOF | splash10-0fk9-1900000000-474cbe56a3684e7601a4 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 20V, Positive-QTOF | splash10-0uk9-2900000000-361280ff6d6e52d3c4dd | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 40V, Positive-QTOF | splash10-0a4r-9000000000-eb0666b2d7a4245a8057 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 10V, Negative-QTOF | splash10-014i-0900000000-fef7e3c0dd5f8b112b13 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 20V, Negative-QTOF | splash10-0uxr-1900000000-8e6b0d5d085203ace9f7 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 40V, Negative-QTOF | splash10-0kfx-9100000000-e33833b098899221c99b | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 10V, Negative-QTOF | splash10-059i-9200000000-044dc2e77678dcbb9641 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 20V, Negative-QTOF | splash10-0a4l-9000000000-bbb949d2057a9d5e93e2 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 40V, Negative-QTOF | splash10-052f-9000000000-e7284f21f4112eb3ddea | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 10V, Positive-QTOF | splash10-0udj-9700000000-0d38e10775e45e5137ce | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 20V, Positive-QTOF | splash10-0006-9000000000-390349bf60b415ba3201 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Erythrose 40V, Positive-QTOF | splash10-0007-9000000000-a206c8b4add95411dcb6 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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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 | |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Schizophrenia | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Schizophrenia |
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- Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB023039 |
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| KNApSAcK ID | C00035355 |
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| Chemspider ID | 388659 |
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| KEGG Compound ID | C01796 |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Erythrose |
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| METLIN ID | 289 |
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| PubChem Compound | 439574 |
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| PDB ID | Not Available |
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| ChEBI ID | 23956 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| MarkerDB ID | Not Available |
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| Good Scents ID | Not Available |
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| References |
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| Synthesis Reference | Covimilla, Bernard M.; Ajiri, Masafumi; Arai, Kunio. Preparation of erythrose. Jpn. Kokai Tokkyo Koho (1998), 5 pp. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - Verzijl N, DeGroot J, Ben ZC, Brau-Benjamin O, Maroudas A, Bank RA, Mizrahi J, Schalkwijk CG, Thorpe SR, Baynes JW, Bijlsma JW, Lafeber FP, TeKoppele JM: Crosslinking by advanced glycation end products increases the stiffness of the collagen network in human articular cartilage: a possible mechanism through which age is a risk factor for osteoarthritis. Arthritis Rheum. 2002 Jan;46(1):114-23. [PubMed:11822407 ]
- DeGroot J, Verzijl N, Jacobs KM, Budde M, Bank RA, Bijlsma JW, TeKoppele JM, Lafeber FP: Accumulation of advanced glycation endproducts reduces chondrocyte-mediated extracellular matrix turnover in human articular cartilage. Osteoarthritis Cartilage. 2001 Nov;9(8):720-6. [PubMed:11795991 ]
- Jansen G, Muskiet FA, Schierbeek H, Berger R, van der Slik W: Capillary gas chromatographic profiling of urinary, plasma and erythrocyte sugars and polyols as their trimethylsilyl derivatives, preceded by a simple and rapid prepurification method. Clin Chim Acta. 1986 Jun 30;157(3):277-93. [PubMed:3731489 ]
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