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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 | 2020-11-09 23:13:55 UTC |
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HMDB ID | HMDB0000625 |
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Secondary Accession Numbers | - HMDB0003373
- HMDB00625
- HMDB03373
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Metabolite Identification |
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Common Name | Gluconic acid |
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Description | Gluconic acid, also known as D-gluconate or D-glukonsaeure, 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. Gluconic acid is a drug which is used for use as part of electrolyte supplementation in total parenteral nutrition [fda label]. It is also used in cleaning products where it helps cleaning up mineral deposits. The salts of gluconic acid are known as "gluconates". Gluconic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gluconic acid or Gluconic acid is used to maintain the cation-anion balance on electrolyte solutions. Gluconic acid exists in all living species, ranging from bacteria to humans. In humans, gluconic acid is involved in the metabolic disorder called the transaldolase deficiency pathway. Outside of the human body, Gluconic acid has been detected, but not quantified in, milk (cow). This could make gluconic acid a potential biomarker for the consumption of these foods. Gluconic acid has been found to be a metabolite in Aspergillus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987). It chelates the anions of calcium, iron, aluminium, copper, and other heavy metals. Gluconic acid occurs naturally in fruit, honey, kombucha tea, and wine. |
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Structure | |
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Synonyms | Value | Source |
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(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid | ChEBI | D-Gluco-hexonic acid | ChEBI | D-Gluconsaeure | ChEBI | D-Glukonsaeure | ChEBI | Dextronic acid | ChEBI | Glycogenic acid | ChEBI | Hexonic acid | ChEBI | Maltonic acid | ChEBI | D-Gluconate | Kegg | (2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoate | Generator | D-Gluco-hexonate | Generator | Dextronate | Generator | Glycogenate | Generator | Hexonate | Generator | Maltonate | Generator | D-Gluconic acid | Generator | Gluconate | Generator | 2,3,4,5,6-Pentahydroxy-hexanoate | HMDB | 2,3,4,5,6-Pentahydroxy-hexanoic acid | HMDB | 2,3,4,5,6-Pentahydroxyhexanoate | HMDB | 2,3,4,5,6-Pentahydroxyhexanoic acid | HMDB | GCO | HMDB | Glosanto | HMDB | Glyconate | HMDB | Glyconic acid | HMDB | Pentahydroxycaproate | HMDB | Pentahydroxycaproic acid | HMDB | Boron gluconate | HMDB | Gluconic acid, (113)indium-labeled | HMDB | Gluconic acid, calcium salt | HMDB | Gluconic acid, cesium(+3) salt | HMDB | Gluconic acid, lanthanum(+3) salt | HMDB | Gluconic acid, sodium salt | HMDB | Gluconic acid, strontium (2:1) salt | HMDB | Magnerot | HMDB | Manganese gluconate | HMDB | Sodium gluconate | HMDB | Zinc gluconate | HMDB | Gluconic acid, (159)dysprosium-labeled salt | HMDB | Gluconic acid, aluminum (3:1) salt | HMDB | Gluconic acid, ammonium salt | HMDB | Gluconic acid, magnesium (2:1) salt | HMDB | Gluconic acid, (14)C-labeled | HMDB | Gluconic acid, 1-(14)C-labeled | HMDB | Gluconic acid, 6-(14)C-labeled | HMDB | Gluconic acid, cobalt (2:1) salt | HMDB | Gluconic acid, copper salt | HMDB | Gluconic acid, manganese (2:1) salt | HMDB | Gluconic acid, potassium salt | HMDB | Gluconic acid, tin(+2) salt | HMDB | Gluconic acid, zinc salt | HMDB | Lithium gluconate | HMDB | Magnesium gluconate | HMDB | Gluconic acid, (99)technecium (5+) salt | HMDB | Gluconic acid, fe(+2) salt, dihydrate | HMDB | Gluconic acid, monolithium salt | HMDB | Gluconic acid, monopotassium salt | HMDB | Gluconic acid, monosodium salt | HMDB |
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Chemical Formula | C6H12O7 |
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Average Molecular Weight | 196.1553 |
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Monoisotopic Molecular Weight | 196.058302738 |
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IUPAC Name | (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid |
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Traditional Name | gluconate |
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CAS Registry Number | 526-95-4 |
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SMILES | OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O |
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InChI Identifier | InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1 |
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InChI Key | RGHNJXZEOKUKBD-SQOUGZDYSA-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 | - Gluconic_acid
- Medium-chain hydroxy acid
- Medium-chain fatty acid
- Beta-hydroxy acid
- Hydroxy fatty acid
- Alpha-hydroxy acid
- Fatty acyl
- Fatty acid
- Hydroxy acid
- Monosaccharide
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Polyol
- Monocarboxylic acid or derivatives
- Alcohol
- Carbonyl group
- Primary alcohol
- Organic oxide
- 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 | Health effect: |
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Disposition | Source: Biological location: |
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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 | 113 - 118 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 316 mg/mL at 25 °C | MERCK INDEX (1996) | 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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0932000000-202af87cea2d1f7184ab | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-005a-0920000000-2308d9356bc5bb01420e | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-014j-0950000000-61ab7adf15e353df4ba2 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (6 TMS) | splash10-0le9-1964000000-5eb7d6777170e1ad5fa0 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0932000000-202af87cea2d1f7184ab | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0le9-1964000000-5eb7d6777170e1ad5fa0 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0931000000-b07fcc4ac1e6701d32c8 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fr2-0930000000-181f7b697b591cf8080b | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-06tu-9500000000-ebe398c88f74bb51e702 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positive | splash10-03fr-6121297000-698854fa2453487a1d69 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-06vj-1900000000-78e4a5d92be678c068e4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03ds-5900000000-f5d8284baa473ce9d77f | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014i-9500000000-7c5b20eef98d0e3d6cbb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0002-0900000000-b2632ca9154cc5e44438 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-002b-5900000000-4a3066f9dfd6653682fb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-9000000000-50f63dfd017a8380a47c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-056r-9000000000-91ccf7c8949c1c9d852a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a6r-9000000000-6e40f1cebd8b460016b3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-0900000000-b2632ca9154cc5e44438 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-002b-5900000000-cf9b480ac397acfebc71 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-eca61f6a9c0f1d06e84d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-056r-9000000000-91ccf7c8949c1c9d852a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a6r-9000000000-6e40f1cebd8b460016b3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004j-2900000000-42150530e3232b66059b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9500000000-763d7b03787732284c19 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0bvi-9100000000-040569af699927ca6859 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-05ic-9800000000-3571d4f2ff79bc0d7fa0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052r-9400000000-3cb207fadbe1fcae5cb7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9100000000-8c900935a94065d0938b | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | 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 and Quantified | <5 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 3.295 +/- 0.534 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Feces | 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 | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 45.49 +/- 24.12 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 13.3 (8.2-26.4) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 35.0+/-29.0 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 21.5 (8.1-38.8) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 63.463 +/- 28.036 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 3.732 +/- 0.687 uM | Adult (>18 years old) | Both | Schizophrenia | | details | Feces | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Cryptosporidium infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details | Urine | Detected and Quantified | 65.277 +/- 47.794 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details |
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Associated Disorders and Diseases |
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Disease References | Schizophrenia |
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- Koike S, Bundo M, Iwamoto K, Suga M, Kuwabara H, Ohashi Y, Shinoda K, Takano Y, Iwashiro N, Satomura Y, Nagai T, Natsubori T, Tada M, Yamasue H, Kasai K: A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study. Transl Psychiatry. 2014 Apr 8;4:e379. doi: 10.1038/tp.2014.19. [PubMed:24713860 ]
| Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB13180 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB001980 |
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KNApSAcK ID | C00007303 |
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Chemspider ID | 10240 |
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KEGG Compound ID | C00257 |
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BioCyc ID | GLUCONATE |
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BiGG ID | Not Available |
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Wikipedia Link | Gluconic_acid |
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METLIN ID | 345 |
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PubChem Compound | 10690 |
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PDB ID | Not Available |
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ChEBI ID | 33198 |
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Food Biomarker Ontology | Not Available |
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VMH ID | GLCN |
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MarkerDB ID | |
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References |
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Synthesis Reference | Anastassiadis, Savas; Morgunov, Igor G. Gluconic acid production. Recent Patents on Biotechnology (2007), 1(2), 167-180. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Harkness RA, Purkiss P, Duffy S, Chalmers RA, Jones M: The effects of fetal energy depletion on amniotic fluid concentrations of amino acids, organic acids and related metabolites. J Inherit Metab Dis. 1988;11(1):103-13. [PubMed:3128683 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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