| Record Information |
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| Version | 5.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2007-05-23 02:57:34 UTC |
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| Update Date | 2021-09-14 15:44:52 UTC |
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| HMDB ID | HMDB0006372 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | L-Glyceric acid |
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| Description | L-glyceric acid is a human urinary metabolite present in patients with L-Glyceric aciduria. The formation of L-glyceric acid from accumulated hydroxypyruvate is due to deficiency of human glyoxylate reductase/hydroxypyruvate reductase (GRHPR, EC 1.1.1.81), a D-2-hydroxy-acid dehydrogenase that plays a critical role in the removal of the metabolic by-product glyoxylate from within the liver. Deficiency of this enzyme is the underlying cause of primary hyperoxaluria type 2 (PH2) and leads to increased urinary oxalate levels, formation of kidney stones and renal failure. (PMID: 16756993 ). |
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| Structure | InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m0/s1 |
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| Synonyms | | Value | Source |
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| (S)-Glyceric acid | ChEBI | | (S)-Glycerate | Generator | | L-Glycerate | Generator | | (2S)-2,3-Dihydroxy-propanoate | HMDB | | (2S)-2,3-Dihydroxy-propanoic acid | HMDB | | (S)-2,3-Dihydroxy-propanoate | HMDB | | (S)-2,3-Dihydroxy-propanoic acid | HMDB | | (S)-2,3-Dihydroxypropanoate | HMDB | | (S)-2,3-Dihydroxypropanoic acid | HMDB |
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| Chemical Formula | C3H6O4 |
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| Average Molecular Weight | 106.0773 |
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| Monoisotopic Molecular Weight | 106.02660868 |
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| IUPAC Name | (2S)-2,3-dihydroxypropanoic acid |
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| Traditional Name | L-glycerate |
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| CAS Registry Number | 28305-26-2 |
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| SMILES | OC[C@H](O)C(O)=O |
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| InChI Identifier | InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m0/s1 |
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| InChI Key | RBNPOMFGQQGHHO-REOHCLBHSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. |
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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 | Sugar acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Beta-hydroxy acid
- Glyceric_acid
- Sugar acid
- Alpha-hydroxy acid
- Hydroxy acid
- Monosaccharide
- 1,2-diol
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Alcohol
- Carbonyl group
- Organic oxide
- Primary alcohol
- Hydrocarbon derivative
- 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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| 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 | Solid |
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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. | 1.1 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 9.4345 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 5.02 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 290.4 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 711.2 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 374.7 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 53.0 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 252.4 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 107.0 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 289.1 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 | 250.4 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 615.8 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 605.8 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 47.3 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 | 814.6 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 226.5 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 308.1 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 713.0 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 314.6 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 | 366.9 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| L-Glyceric acid,1TMS,isomer #1 | C[Si](C)(C)OC[C@H](O)C(=O)O | 1155.8 | Semi standard non polar | 33892256 | | L-Glyceric acid,1TMS,isomer #2 | C[Si](C)(C)O[C@@H](CO)C(=O)O | 1189.2 | Semi standard non polar | 33892256 | | L-Glyceric acid,1TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H](O)CO | 1085.5 | Semi standard non polar | 33892256 | | L-Glyceric acid,2TMS,isomer #1 | C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(=O)O | 1258.6 | Semi standard non polar | 33892256 | | L-Glyceric acid,2TMS,isomer #2 | C[Si](C)(C)OC[C@H](O)C(=O)O[Si](C)(C)C | 1223.2 | Semi standard non polar | 33892256 | | L-Glyceric acid,2TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@H](CO)O[Si](C)(C)C | 1220.3 | Semi standard non polar | 33892256 | | L-Glyceric acid,3TMS,isomer #1 | C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1328.0 | Semi standard non polar | 33892256 | | L-Glyceric acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H](O)C(=O)O | 1419.6 | Semi standard non polar | 33892256 | | L-Glyceric acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@@H](CO)C(=O)O | 1442.1 | Semi standard non polar | 33892256 | | L-Glyceric acid,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O)CO | 1338.7 | Semi standard non polar | 33892256 | | L-Glyceric acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O | 1703.4 | Semi standard non polar | 33892256 | | L-Glyceric acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC[C@H](O)C(=O)O[Si](C)(C)C(C)(C)C | 1658.5 | Semi standard non polar | 33892256 | | L-Glyceric acid,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CO)O[Si](C)(C)C(C)(C)C | 1675.1 | Semi standard non polar | 33892256 | | L-Glyceric acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1960.9 | 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 - L-Glyceric acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-01po-9000000000-88f14f02029fc1ed3f09 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - L-Glyceric acid GC-MS (3 TMS) - 70eV, Positive | splash10-0avr-9362000000-4ae43a853db514e46cc7 | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - L-Glyceric acid 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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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 10V, Positive-QTOF | splash10-0a4r-9600000000-6c887f0d5bb5b5b43e47 | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 20V, Positive-QTOF | splash10-01p9-9100000000-4dcb939c91e313be7889 | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 40V, Positive-QTOF | splash10-0006-9000000000-0ddbae5fe95cd5c2cc3a | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 10V, Negative-QTOF | splash10-0a4i-7900000000-483a2fcbaa1f9e4282f8 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 20V, Negative-QTOF | splash10-0a4i-9200000000-c37acde4cab84c418b98 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 40V, Negative-QTOF | splash10-0a4l-9000000000-c2110468981b90e60c2b | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 10V, Positive-QTOF | splash10-00du-9000000000-e4b00c30702ce3ea058c | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 20V, Positive-QTOF | splash10-006x-9000000000-88e9a7bbb2eae9f5a36b | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 40V, Positive-QTOF | splash10-0006-9000000000-cbe41726597364826475 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 10V, Negative-QTOF | splash10-0a6r-9700000000-e74837163c200bdac143 | 2021-09-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 20V, Negative-QTOF | splash10-0a6r-9000000000-3d8e20cb2f7b52d78388 | 2021-09-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Glyceric acid 40V, Negative-QTOF | splash10-052f-9000000000-54fe1ddd9f87bf26bf84 | 2021-09-23 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| 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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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 | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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| Biological Properties |
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| Cellular Locations | |
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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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| Blood | Detected and Quantified | 2.0 (0.0-5.0) uM | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 12.8-187.1 umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 20.3-121.6 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 0-205 umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 23.448-89.529 umol/mmol creatinine | Children (1-13 years old) | Male | Normal | | details | | Urine | Detected and Quantified | 39.436-197.178 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected and Quantified | 3.0 (0.0-5.0) uM | Adult (>18 years old) | Both | Glycolic aciduria | | details | | Urine | Detected and Quantified | >205 umol/mmol creatinine | Children (1-13 years old) | Both | Glycolic aciduria | | details | | Urine | Detected and Quantified | 430.594 umol/mmol creatinine | Children (1-13 years old) | Male | Glutaric acidemia type 2 | | details | | Urine | Detected and Quantified | 590.468-4130.0778 umol/mmol creatinine | Adult (>18 years old) | Female | Glutaric acidemia type 2 | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Glycolic aciduria |
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- Petrarulo M, Marangella M, Cosseddu D, Linari F: High-performance liquid chromatographic assay for L-glyceric acid in body fluids. Application in primary hyperoxaluria type 2. Clin Chim Acta. 1992 Oct 30;211(3):143-53. [PubMed:1458609 ]
- Coulter-Mackie MB, White CT, Lange D, et al. (2002). Primary Hyperoxaluria Type 1. 2002 Jun 19 [Updated 2014 Jul 17]. In: Adam MP, Ardinger HH, Pagon RA, et al., editors. GeneReviews® [Internet]. Seattle (WA): University of Washington, Seattle; 1993-2017. Available from: https://www.ncbi.nlm.nih.gov/books/NBK1283/. University of Washington, Seattle.
| | Glutaric acidemia type 2 |
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- Chlebeck PT, Milliner DS, Smith LH: Long-term prognosis in primary hyperoxaluria type II (L-glyceric aciduria). Am J Kidney Dis. 1994 Feb;23(2):255-9. [PubMed:8311084 ]
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| Associated OMIM IDs | - 259900 (Glycolic aciduria)
- 231680 (Glutaric acidemia type 2)
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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 | FDB023907 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 4885497 |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | 2226325 |
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| Wikipedia Link | Glyceric acid |
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| METLIN ID | Not Available |
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| PubChem Compound | 6326776 |
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| PDB ID | Not Available |
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| ChEBI ID | 74324 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | GLYC_S |
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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 | Lok, C. M.; Ward, J. P.; Van Dorp, D. A. The synthesis of chiral glycerides starting from D- and L-serine. Actes Congr. Mond. - Soc. Int. Etude Corps Gras, 13th (1976), Sect. E 15-20. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Booth MP, Conners R, Rumsby G, Brady RL: Structural basis of substrate specificity in human glyoxylate reductase/hydroxypyruvate reductase. J Mol Biol. 2006 Jun 30;360(1):178-89. Epub 2006 May 22. [PubMed:16756993 ]
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