| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:48:27 UTC |
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| Update Date | 2020-06-04 21:13:48 UTC |
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| BMDB ID | BMDB0001873 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Isobutyric acid |
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| Description | Isobutanoic acid, also known as isobutyrate or 2,2-dimethylacetate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Isobutanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Isobutanoic acid exists in all living species, ranging from bacteria to humans. Isobutanoic acid has been found to be associated with several diseases known as nonalcoholic fatty liver disease, eosinophilic esophagitis, crohn's disease, and early preeclampsia; also isobutanoic acid has been linked to the inborn metabolic disorders including celiac disease. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2,2-Dimethylacetic acid | ChEBI | | 2-METHYL-propionIC ACID | ChEBI | | 2-Methylpropanoate | ChEBI | | 2-Methylpropanoic acid | ChEBI | | 2-Methylpropionsaeure | ChEBI | | alpha-Isobutyric acid | ChEBI | | alpha-Methylpropanoic acid | ChEBI | | alpha-Methylpropionic acid | ChEBI | | Dimethylacetic acid | ChEBI | | Iso-butyric acid | ChEBI | | Iso-C3H7COOH | ChEBI | | Isobutanoate | ChEBI | | Isobutanoic acid | ChEBI | | Isobuttersaeure | ChEBI | | Isobutyrate | ChEBI | | Isopropylformic acid | ChEBI | | 2,2-Dimethylacetate | Generator | | 2-METHYL-propionate | Generator | | a-Isobutyrate | Generator | | a-Isobutyric acid | Generator | | alpha-Isobutyrate | Generator | | Α-isobutyrate | Generator | | Α-isobutyric acid | Generator | | a-Methylpropanoate | Generator | | a-Methylpropanoic acid | Generator | | alpha-Methylpropanoate | Generator | | Α-methylpropanoate | Generator | | Α-methylpropanoic acid | Generator | | a-Methylpropionate | Generator | | a-Methylpropionic acid | Generator | | alpha-Methylpropionate | Generator | | Α-methylpropionate | Generator | | Α-methylpropionic acid | Generator | | Dimethylacetate | Generator | | Iso-butyrate | Generator | | Isopropylformate | Generator | | 2-Methylpropionate | HMDB | | 2-Methylpropionic acid | HMDB | | I-butyrate | HMDB | | I-butyric acid | HMDB | | Ammonium isobutyrate | HMDB | | Isobutyric acid, ammonium salt | HMDB | | Isobutyric acid, sodium salt | HMDB | | 2-Methpropanoic acid | HMDB | | Isobutyric acid, hemiammoniate | HMDB | | Sodium isobutyrate | HMDB | | Isobutyric acid, calcium salt | HMDB | | Isobutyric acid, nickel salt | HMDB | | Isobutyric acid, potassium salt | HMDB | | Isobutyric acid, sodium salt, 11C-labeled | HMDB | | Isobutyric acid, sodium salt, 14C-labeled | HMDB | | Isobutyric acid | KEGG |
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| Chemical Formula | C4H8O2 |
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| Average Molecular Weight | 88.1051 |
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| Monoisotopic Molecular Weight | 88.0524295 |
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| IUPAC Name | 2-methylpropanoic acid |
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| Traditional Name | isobutyric acid |
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| CAS Registry Number | 79-31-2 |
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| SMILES | CC(C)C(O)=O |
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| InChI Identifier | InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6) |
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| InChI Key | KQNPFQTWMSNSAP-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Carboxylic acids |
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| Direct Parent | Carboxylic acids |
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| Alternative Parents | |
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| Substituents | - Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | Not Available |
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -46 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 167 mg/mL at 20 °C | Not Available | | LogP | 0.94 | SANGSTER (1993) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | Not Available |
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| Biospecimen Locations | - Blood
- Fibroblasts
- Milk
- Ruminal Fluid
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 15.87 +/- 20.47 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1.3 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1.0 +/- 0.4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1.3 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1.2 +/- 0.4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.10 +/- 4.79 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 14.45 +/- 15.29 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1420 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 719 +/- 226 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1100-4100 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1429.07 +/- 228.2 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 708-1100 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1283 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1216 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1430 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 590 +/- 50 uM | Not Specified | Both | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1280 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1450 +/- 180 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1670 +/- 530 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1815 +/- 194 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1430 +/- 228 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1450 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1670 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1810 uM | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Mycobacterium avium subsp. paratuberculosis infection | | details | | Ruminal Fluid | Detected and Quantified | 1815.2 +/- 187.74 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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| External Links |
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| HMDB ID | HMDB0001873 |
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| DrugBank ID | DB02531 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB003277 |
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| KNApSAcK ID | C00029462 |
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| Chemspider ID | 6341 |
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| KEGG Compound ID | C02632 |
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| BioCyc ID | ISOBUTYRATE |
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| BiGG ID | Not Available |
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| Wikipedia Link | Isobutyric_acid |
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| METLIN ID | 106 |
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| PubChem Compound | 6590 |
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| PDB ID | Not Available |
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| ChEBI ID | 16135 |
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| References |
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| Synthesis Reference | Wang, Hengxiu; Chen, Weibin; Zhao, Dehua; Zhang, Jianbin. Preparation of isobutyric acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 5 pp. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. [PubMed:25599412 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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