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| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:07:18 UTC |
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| Update Date | 2020-05-11 22:52:21 UTC |
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| BMDB ID | BMDB0000008 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 2-Hydroxybutyric acid |
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| Description | 2-Hydroxybutyric acid, also known as alpha-hydroxybutyrate or 2-hydroxybutanoate, 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. 2-Hydroxybutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 2-Hydroxybutyric acid is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (S)-2-Hydroxybutanoic acid | ChEBI | | 2-Hydroxybutyrate | ChEBI | | 2-Hydroxybutyric acid | ChEBI | | L-2-Hydroxybutanoic acid | ChEBI | | L-2-Hydroxybutyric acid | ChEBI | | L-alpha-Hydroxybutanoic acid | ChEBI | | L-alpha-Hydroxybutyric acid | ChEBI | | (S)-2-Hydroxybutanoate | Generator | | L-2-Hydroxybutanoate | Generator | | L-2-Hydroxybutyrate | Generator | | L-a-Hydroxybutanoate | Generator | | L-a-Hydroxybutanoic acid | Generator | | L-alpha-Hydroxybutanoate | Generator | | L-Α-hydroxybutanoate | Generator | | L-Α-hydroxybutanoic acid | Generator | | L-a-Hydroxybutyrate | Generator | | L-a-Hydroxybutyric acid | Generator | | L-alpha-Hydroxybutyrate | Generator | | L-Α-hydroxybutyrate | Generator | | L-Α-hydroxybutyric acid | Generator | | (S)-2-Hydroxybutyrate | Generator | | 2-Hydroxybutanoate | Generator | | (+)-2-Hydroxy-n-butyric acid | HMDB | | (+)-2-Hydroxybutanoic acid | HMDB | | (+)-2-Hydroxybutyric acid | HMDB | | (+)-alpha-Hydroxybutyric acid | HMDB | | (+)-α-Hydroxybutyric acid | HMDB | | (2S)-2-Hydroxybutanoic acid | HMDB | | (S)-(+)-2-Hydroxybutanoic acid | HMDB | | (S)-2-Hydroxybutyric acid | HMDB | | 2-Hydroxybutanoic acid | HMDB | | alpha-Hydroxy-n-butyric acid | HMDB | | alpha-Hydroxybutanoic acid | HMDB | | alpha-Hydroxybutyric acid | HMDB | | α-Hydroxy-n-butyric acid | HMDB | | α-Hydroxybutanoic acid | HMDB | | α-Hydroxybutyric acid | HMDB |
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| Chemical Formula | C4H8O3 |
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| Average Molecular Weight | 104.105 |
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| Monoisotopic Molecular Weight | 104.047344118 |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 600-15-7 |
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| SMILES | Not Available |
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| InChI Identifier | InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1 |
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| InChI Key | AFENDNXGAFYKQO-VKHMYHEASA-N |
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| Chemical Taxonomy |
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| Description | 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 | - Fatty acid
- Alpha-hydroxy acid
- Secondary 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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| Status | Detected but not 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 | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 44.2 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | Not Available |
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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 | - Liver
- Mammary Gland
- Milk
- Muscle
- Placenta
- Prostate Tissue
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| Pathways | |
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| Normal Concentrations |
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| Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0000008 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB021867 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 389701 |
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| KEGG Compound ID | C05984 |
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| BioCyc ID | CPD-3564 |
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| BiGG ID | Not Available |
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| Wikipedia Link | 2-Hydroxybutyric_acid |
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| METLIN ID | Not Available |
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| PubChem Compound | 440864 |
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| PDB ID | Not Available |
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| ChEBI ID | 50613 |
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| References |
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| Synthesis Reference | Carlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology (1997), 25(5), 371-374. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]
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