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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 | 2019-01-11 19:15:00 UTC |
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HMDB ID | HMDB0000729 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Alpha-Hydroxyisobutyric acid |
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Description | Alpha-Hydroxyisobutyric acid is a metabolite of methyl tert-butyl ether (MTBE). MTBE may be obtained through environmental exposure. MTBE is rapidly eliminated from the body, mainly through expired air as the unchanged compound. MTBE is to some extent metabolised to t-butyl alcohol (TBA) and formaldehyde and oxidised to 2-methyl-1,2-propanediol and a-hydroxy isobuturic acid. Alpha-Hydroxyisobutyric acid has been used as an arial bactericide. |
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Structure | |
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Synonyms | Value | Source |
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2-Hydroxy-2-methylpropionic acid | ChEBI | 2-Hydroxy-2-methylpropionsaeure | ChEBI | 2-Methyl-2-hydroxypropanoic acid | ChEBI | 2-Methyl-2-hydroxypropionsaeure | ChEBI | 2-Methyllactic acid | ChEBI | Acetonic acid | ChEBI | Acide 2-hydroxy-2-methylpropanoique | ChEBI | acido 2-Hidroxi-2-metilpropionico | ChEBI | alpha-Hydroxy-alpha-methylpropanoic acid | ChEBI | alpha-Hydroxy-alpha-methylpropionic acid | ChEBI | alpha-Hydroxyisobutanoic acid | ChEBI | HIBA | ChEBI | Hydroxydimethylacetic acid | ChEBI | 2-Hydroxy-2-methylpropionate | Generator | a-Hydroxyisobutyrate | Generator | a-Hydroxyisobutyric acid | Generator | alpha-Hydroxyisobutyrate | Generator | α-hydroxyisobutyrate | Generator | α-hydroxyisobutyric acid | Generator | 2-Methyl-2-hydroxypropanoate | Generator | 2-Methyllactate | Generator | Acetonate | Generator | a-Hydroxy-a-methylpropanoate | Generator | a-Hydroxy-a-methylpropanoic acid | Generator | alpha-Hydroxy-alpha-methylpropanoate | Generator | α-hydroxy-α-methylpropanoate | Generator | α-hydroxy-α-methylpropanoic acid | Generator | a-Hydroxy-a-methylpropionate | Generator | a-Hydroxy-a-methylpropionic acid | Generator | alpha-Hydroxy-alpha-methylpropionate | Generator | α-hydroxy-α-methylpropionate | Generator | α-hydroxy-α-methylpropionic acid | Generator | a-Hydroxyisobutanoate | Generator | a-Hydroxyisobutanoic acid | Generator | alpha-Hydroxyisobutanoate | Generator | α-hydroxyisobutanoate | Generator | α-hydroxyisobutanoic acid | Generator | Hydroxydimethylacetate | Generator | (CH3)2cohcooh | HMDB | 2-Hydroxy-2-methylpropanoate | HMDB | 2-Hydroxy-2-methylpropanoic acid | HMDB | 2-Hydroxyisobutyrate | HMDB | 2-Hydroxyisobutyric acid | HMDB | a-HIB | HMDB | alpha-HIB | HMDB | Hydroxyisobutyrate | HMDB | L-2-Methyllactate | HMDB | L-2-Methyllactic acid | HMDB | 2-Hydroxyisobutyric acid, lead salt | MeSH | Lead 2-hydroxyisobutyric acid | MeSH |
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Chemical Formula | C4H8O3 |
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Average Molecular Weight | 104.1045 |
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Monoisotopic Molecular Weight | 104.047344122 |
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IUPAC Name | 2-hydroxy-2-methylpropanoic acid |
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Traditional Name | acetonate |
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CAS Registry Number | 594-61-6 |
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SMILES | CC(C)(O)C(O)=O |
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InChI Identifier | InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6) |
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InChI Key | BWLBGMIXKSTLSX-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Hydroxy acids and derivatives |
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Sub Class | Alpha hydroxy acids and derivatives |
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Direct Parent | Alpha hydroxy acids and derivatives |
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Alternative Parents | |
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Substituents | - Alpha-hydroxy acid
- Tertiary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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Physiological effect | Health effect: |
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Disposition | Biological location: |
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Role | Environmental role: |
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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 | 82.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | -0.36 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00e9-8900000000-2d2298731d2c1ce975ff | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4l-9000000000-bb87a50521380a4f04c0 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00e9-8900000000-2d2298731d2c1ce975ff | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4l-9000000000-af78bdeb830f08b3a6a6 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00su-9610000000-cea13166d0c9b277d7d8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0zfr-8900000000-b51c12e744025b833f31 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-9100000000-0d72fcffff267d7bc980 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-0a4l-9000000000-bb87a50521380a4f04c0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0udi-0900000000-09121cf499d55d5656ac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0pb9-9600000000-3394a5ec4ff4ff576fcd | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0a4i-9000000000-5fc3362d72c467fb6197 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-052f-9000000000-3de5183bd97ccc5072c8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-d524fab140880c782425 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0a4i-0900000000-1aadb4e9ee70b665d435 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0udi-0900000000-591fd3d7ad484dd6f1ff | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-0udi-0900000000-69f23830b20d34978bed | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0udi-0900000000-09121cf499d55d5656ac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0pb9-9600000000-3394a5ec4ff4ff576fcd | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-5fc3362d72c467fb6197 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-052f-9000000000-3de5183bd97ccc5072c8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-d524fab140880c782425 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0900000000-591fd3d7ad484dd6f1ff | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0900000000-69f23830b20d34978bed | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-8900000000-f40f4783e4b817b45a70 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9100000000-28ad10690e6680bd4046 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-0a3b71647acebd936a7e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-1900000000-7f058188704b24bc8cee | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-2900000000-40bbfa4d36a4c19902c0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9100000000-237ae993c0cc1090dd96 | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in 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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Blood | Detected and Quantified | 8.2 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 7.0 (0.0-9.0) uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 9.00 +/- 2.95 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 2.9 (1.3-4.6) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 4.4-7.4 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 7.821 +/- 3.811 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 3.80 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.1 (0.1-3.8) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 6.2 (3.8-14.1) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 5.5 (2.9-10.3) umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | Urine | Detected and Quantified | <50 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 7.9 (3.7-19.5) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.1 (0.1-8.2) umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 4.4-7.6 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 3.8 (1.7-5.9) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 13.322 +/- 5.638 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | | Adult (>18 years old) | Both | Lung cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected and Quantified | 9.37 +/- 5.223 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 5.0 (0.0-8.0) umol/mmol creatinine | Not Specified | Both | Lung cancer | | details | Urine | Detected and Quantified | 11.83 +/- 4.351 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 12.057 +/- 6.013 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details |
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Associated Disorders and Diseases |
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Disease References | 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 ]
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- 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 ]
| Lung Cancer |
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- Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
- Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
| 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 | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB022207 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 11181 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 3750 |
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PubChem Compound | 11671 |
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PDB ID | Not Available |
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ChEBI ID | 50129 |
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References |
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Synthesis Reference | Vogl, O. Synthesis of a-hydroxyisobutyric acid from isobutylene. Journal of Organic Chemistry (1958), 23 1488-9. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- Benson JM, Barr EB, Krone JR: MTBE inhaled alone and in combination with gasoline vapor: uptake, distribution, metabolism, and excretion in rats. Res Rep Health Eff Inst. 2001 May;(102):73-94; discussion 95-109. [PubMed:11504149 ]
- Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Isobutene (CAS No. 115-11-7) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser. 1998 Dec;487:1-230. [PubMed:12563344 ]
- Shigematsu Y, Sudo M, Momoi T, Inoue Y, Suzuki Y, Kameyama J: Changing plasma and urinary organic acid levels in a patient with isovaleric acidemia during an attack. Pediatr Res. 1982 Sep;16(9):771-5. [PubMed:7133811 ]
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