Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2008-08-12 13:25:57 UTC |
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Update Date | 2023-02-21 17:17:21 UTC |
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HMDB ID | HMDB0006804 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Propynoic acid |
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Description | Propynoic acid, also known as propiolic acid, is involved in propanoate metabolism and is interconverted into 2-propyn-1-al by mitochondrial aldehyde dehydrogenase. Propynoic acid is an unsaturated organic acid and it can be prepared by boiling acetylene dicarboxylic acid. It is chemically obtained by the action of alcoholic potash on dibromosuccinic acid, or its acid potassium salt with water. It forms silky crystals which melt at 6°C and boil at about 144°C with decomposition. It is soluble in water and possesses an odour resembling that of acetic acid. Exposure to sunlight converts it into trimesic acid (benzene-1,3,5-tricarboxylic acid). It undergoes bromination to give dibromoacrylic acid. With hydrogen chloride it forms chloroacrylic acid. Its ethyl ester condenses with hydrazine to form pyrazolone. Propynoic acid forms a characteristic explosive silver salt upon the addition of ammoniacal silver nitrate to its aqueous solution, and an amorphous precipitate which explodes upon warming with ammoniacal cuprous chloride. Its ethyl ester condenses with hydrazine to form pyrazolone (Wikipedia ). |
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Structure | InChI=1S/C3H2O2/c1-2-3(4)5/h1H,(H,4,5) |
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Synonyms | Value | Source |
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2-Propynoic acid | ChEBI | Acetylenecarboxylic acid | ChEBI | Acetylenic acid | ChEBI | Carboxyacetylene | ChEBI | HC#ccooh | ChEBI | Propargylic acid | ChEBI | Propinic acid | ChEBI | Propinsaeure | ChEBI | Propiolic acid | ChEBI | Propiolsaeure | ChEBI | Acetylenemonocarboxylate | Kegg | 2-Propynoate | Generator | Acetylenecarboxylate | Generator | Acetylenate | Generator | Propargylate | Generator | Propinate | Generator | Propiolate | Generator | Acetylenemonocarboxylic acid | Generator | Propynoate | Generator | Propiolic acid, monosodium salt | HMDB |
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Chemical Formula | C3H2O2 |
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Average Molecular Weight | 70.0468 |
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Monoisotopic Molecular Weight | 70.005479308 |
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IUPAC Name | prop-2-ynoic acid |
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Traditional Name | propiolic acid |
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CAS Registry Number | 471-25-0 |
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SMILES | OC(=O)C#C |
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InChI Identifier | InChI=1S/C3H2O2/c1-2-3(4)5/h1H,(H,4,5) |
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InChI Key | UORVCLMRJXCDCP-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 | - Acetylide
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Propynoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9000000000-4fe50bf7867f36e6b60b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Propynoic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00fr-9200000000-11dc3ec87a0f5813dfb2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Propynoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Propynoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Propynoic acid LC-ESI-QQ , negative-QTOF | splash10-014i-9000000000-f647da344adbdf7bfb1b | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 10V, Positive-QTOF | splash10-0udi-9000000000-aba6a2cb7cc1d727c528 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 20V, Positive-QTOF | splash10-0udi-9000000000-ac8e6e47367ea0619a46 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 40V, Positive-QTOF | splash10-0ufr-9000000000-8dd4db44558079fb672f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 10V, Negative-QTOF | splash10-014i-9000000000-e10d8d809cd357e5fa45 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 20V, Negative-QTOF | splash10-014i-9000000000-5272016322c64eb3692a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 40V, Negative-QTOF | splash10-014i-9000000000-85636846b0be925cb6da | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 10V, Negative-QTOF | splash10-014i-9000000000-7ead964aa3fde51fb5d0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 20V, Negative-QTOF | splash10-014i-9000000000-7ead964aa3fde51fb5d0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 40V, Negative-QTOF | splash10-014i-9000000000-7ead964aa3fde51fb5d0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 10V, Positive-QTOF | splash10-0udi-9000000000-4b05fbfee0b3c72773db | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 20V, Positive-QTOF | splash10-0udi-9000000000-4b05fbfee0b3c72773db | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Propynoic acid 40V, Positive-QTOF | splash10-0udi-9000000000-4b05fbfee0b3c72773db | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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