| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:27:11 UTC |
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| Update Date | 2020-06-04 22:29:10 UTC |
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| BMDB ID | BMDB0000237 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Propionic acid |
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| Description | Propionic acid, also known as propionate or acide propanoique, 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. Propionic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Propionic acid exists in all living species, ranging from bacteria to humans. Propionic acid is a potentially toxic compound. Propionic acid has been found to be associated with several diseases known as rheumatoid arthritis, irritable bowel syndrome, colorectal cancer, and ulcerative colitis; also propionic acid has been linked to the inborn metabolic disorders including propionic acidemia. |
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| Structure | |
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| Synonyms | | Value | Source |
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| Acide propanoique | ChEBI | | Acide propionique | ChEBI | | Carboxyethane | ChEBI | | CH3-CH2-COOH | ChEBI | | Ethanecarboxylic acid | ChEBI | | Ethylformic acid | ChEBI | | Metacetonic acid | ChEBI | | Methylacetic acid | ChEBI | | PA | ChEBI | | Propanoic acid | ChEBI | | Propioic acid | ChEBI | | Propionsaeure | ChEBI | | Propoic acid | ChEBI | | Pseudoacetic acid | ChEBI | | Propionate | Kegg | | Ethanecarboxylate | Generator | | Ethylformate | Generator | | Metacetonate | Generator | | Methylacetate | Generator | | Propanoate | Generator | | Propioate | Generator | | Propoate | Generator | | Pseudoacetate | Generator | | Adofeed | HMDB | | Antischim b | HMDB | | Luprosil | HMDB | | MonoProp | HMDB | | Propanate | HMDB | | Propcorn | HMDB | | Propkorn | HMDB | | Prozoin | HMDB | | Toxi-check | HMDB | | Propionic acid, zinc salt | HMDB | | Potassium propionate | HMDB | | Chromium propionate | HMDB | | Lithium propanoate | HMDB | | Zinc propionate | HMDB |
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| Chemical Formula | C3H6O2 |
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| Average Molecular Weight | 74.0785 |
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| Monoisotopic Molecular Weight | 74.036779436 |
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| IUPAC Name | propanoic acid |
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| Traditional Name | propanoic acid |
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| CAS Registry Number | 79-09-4 |
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| SMILES | CCC(O)=O |
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| InChI Identifier | InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5) |
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| InChI Key | XBDQKXXYIPTUBI-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 | |
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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 | -20.7 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 1000.0 mg/mL | Not Available | | LogP | 0.33 | HANSCH,C ET AL. (1995) |
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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 | |
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| Biospecimen Locations | - Adipose Tissue
- Blood
- Brain
- Colostrum
- Epidermis
- Fibroblasts
- Intestine
- Milk
- Muscle
- Neuron
- Platelet
- Ruminal Fluid
- Testis
- Urine
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1.0 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1.9 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.3 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.71 +/- 7.02 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.94 +/- 0.12 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.0 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.0 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 7.58 +/- 6.92 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.84 +/- 2.27 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.2 (0.1 - 0.6) uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.2 (0.1 - 0.4) uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.2 (0.1 - 0.5) uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.5 (0.7 - 2.7) uM | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 16103 +/- 4550 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1820 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 2260 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 3180 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1680 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 14000-17000 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 13196-21732 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 18210 +/- 3210 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 22630 +/- 8030 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 31835 +/- 6795 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 16860 +/- 5180 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 | 17900 uM | 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 | 18000 uM | 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 | 27600 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 15000 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 21340 +/- 2970 uM | Adult | Both | Normal | | details | | Ruminal Fluid | Detected and Quantified | 16855.86 +/- 5180.48 uM | Not Specified | Not Specified | Normal | | details | | Testis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | 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 | 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 | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | | Ruminal Fluid | Detected and Quantified | 31831.51 +/- 6577.68 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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| External Links |
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| HMDB ID | HMDB0000237 |
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| DrugBank ID | DB03766 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB031132 |
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| KNApSAcK ID | C00044287 |
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| Chemspider ID | 1005 |
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| KEGG Compound ID | C00163 |
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| BioCyc ID | PROPIONATE |
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| BiGG ID | 34098 |
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| Wikipedia Link | Propionic acid |
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| METLIN ID | 3215 |
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| PubChem Compound | 1032 |
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| PDB ID | Not Available |
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| ChEBI ID | 30768 |
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| References |
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| Synthesis Reference | Zhan, Jianghong; Meng, Wei; Gong, Tao; Huang, Fen-sheng. Preparation of propionic acid by propionaldehyde oxidation. Shihua Jishu Yu Yingyong (2005), 23(6), 421-423. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
- Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
- Brigitta Gaspardo, Giuseppe Procida, Saša Volarič, Sandy Sgorlon & Bruno Stefanon (2009). Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009. Italian Journal of Animal Science .
- 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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