| Record Information |
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| Version | 2.0 |
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| Created at | 2022-02-14 20:56:03 UTC |
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| Updated at | 2022-03-10 22:17:29 UTC |
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| NP-MRD ID | NP0044398 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 4-Hydroxybutyric acid |
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| Description | 4-Hydroxybutyric acid, also known as 4-hydroxybutanoate or gamma hydroxybutyrate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 4-Hydroxybutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Hydroxybutyric acid is a potentially toxic compound. 4-Hydroxybutyric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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| Structure | InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7) |
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| Synonyms | | Value | Source |
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| 3-Carboxypropoxy acid | ChEBI | | 4-Hydroxy-butyric acid | ChEBI | | 4-Hydroxyalkanoic acid | ChEBI | | 4-Hydroxybutanoate | ChEBI | | 4-Hydroxybutanoic acid | ChEBI | | 4-Hydroxycarboxylic acid | ChEBI | | Gamma Hydroxybutyric acid | ChEBI | | gamma-Hydroxybutyric acid | ChEBI | | GHB | ChEBI | | Oxy-N-butyric acid | ChEBI | | Xyrem | ChEBI | | 4-Hydroxy-butyrate | Generator | | 4-Hydroxyalkanoate | Generator | | 4-Hydroxycarboxylate | Generator | | g Hydroxybutyrate | Generator | | g Hydroxybutyric acid | Generator | | gamma Hydroxybutyrate | Generator | | Γ hydroxybutyrate | Generator | | Γ hydroxybutyric acid | Generator | | g-Hydroxybutyrate | Generator | | g-Hydroxybutyric acid | Generator | | gamma-Hydroxybutyrate | Generator | | Γ-hydroxybutyrate | Generator | | Γ-hydroxybutyric acid | Generator | | Oxy-N-butyrate | Generator | | 4-Hydroxybutyrate | Generator | | 4-Hydroxy-butanoate | HMDB | | 4-Hydroxy-butanoic acid | HMDB | | 4-Hydroxybutyrate sodium | HMDB | | 4-Hydroxybutyric acid monosodium salt | HMDB | | gamma-Hydroxy butyrate | HMDB | | gamma-Hydroxy sodium butyrate | HMDB | | gamma-Hydroxybutyrate sodium | HMDB | | Hydroxybutyric acid | HMDB |
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| Chemical Formula | C4H8O3 |
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| Average Mass | 104.1045 Da |
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| Monoisotopic Mass | 104.04734 Da |
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| IUPAC Name | 4-hydroxybutanoic acid |
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| Traditional Name | gamma hydroxybutyric acid |
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| CAS Registry Number | 591-81-1 |
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| SMILES | OCCCC(O)=O |
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| InChI Identifier | InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7) |
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| InChI Key | SJZRECIVHVDYJC-UHFFFAOYSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acids and conjugates |
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| Direct Parent | Hydroxy fatty acids |
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| Alternative Parents | |
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| Substituents | - Short-chain hydroxy acid
- Hydroxy fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- 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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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | 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 | |
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| General References | - Shinka T, Inoue Y, Ohse M, Ito A, Ohfu M, Hirose S, Kuhara T: Rapid and sensitive detection of urinary 4-hydroxybutyric acid and its related compounds by gas chromatography-mass spectrometry in a patient with succinic semialdehyde dehydrogenase deficiency. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Aug 25;776(1):57-63. doi: 10.1016/s1570-0232(02)00126-5. [PubMed:12127325 ]
- Chen W, Wu H, Hernandez RJ, Mehta AK, Ticku MK, France CP, Coop A: Ethers of 3-hydroxyphenylacetic acid as selective gamma-hydroxybutyric acid receptor ligands. Bioorg Med Chem Lett. 2005 Jul 1;15(13):3201-2. doi: 10.1016/j.bmcl.2005.05.011. [PubMed:15927467 ]
- Bourguignon JJ, Schoenfelder A, Schmitt M, Wermuth CG, Hechler V, Charlier B, Maitre M: Analogues of gamma-hydroxybutyric acid. Synthesis and binding studies. J Med Chem. 1988 May;31(5):893-7. doi: 10.1021/jm00400a001. [PubMed:3361576 ]
- Gibson KM, Baumann C, Ogier H, Rossier E, Vollmer B, Jakobs C: Pre- and postnatal diagnosis of succinic semialdehyde dehydrogenase deficiency using enzyme and metabolite assays. J Inherit Metab Dis. 1994;17(6):732-7. doi: 10.1007/BF00712016. [PubMed:7707697 ]
- Gibson KM, Aramaki S, Sweetman L, Nyhan WL, DeVivo DC, Hodson AK, Jakobs C: Stable isotope dilution analysis of 4-hydroxybutyric acid: an accurate method for quantification in physiological fluids and the prenatal diagnosis of 4-hydroxybutyric aciduria. Biomed Environ Mass Spectrom. 1990 Feb;19(2):89-93. doi: 10.1002/bms.1200190207. [PubMed:2407302 ]
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