Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:39:02 UTC |
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Updated at | 2021-08-12 19:51:59 UTC |
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NP-MRD ID | NP0002731 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Acetylenedicarboxylic acid |
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Provided By | BMRB![BMRB logo](/attributions/logo_bmrb.svg) |
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Description | Acetylenedicarboxylic acid, also known as 2-butynedioic acid, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Acetylenedicarboxylic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 1952 (PMID: 12978816). Based on a literature review a significant number of articles have been published on Acetylenedicarboxylic acid (PMID: 17984079) (PMID: 10843633) (PMID: 33403487) (PMID: 20795634) (PMID: 17585766) (PMID: 27980849). |
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Structure | InChI=1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8) |
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Synonyms | Value | Source |
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2-Butynedioic acid | ChEBI | 2-Butynedioate | Generator | Acetylenedicarboxylate | Generator | Butynedioate | HMDB | 2-Butynedioic acid, potassium salt | HMDB | Acetylenedicarboxylic acid | ChEBI |
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Chemical Formula | C4H2O4 |
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Average Mass | 114.0560 Da |
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Monoisotopic Mass | 113.99531 Da |
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IUPAC Name | but-2-ynedioic acid |
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Traditional Name | acetylenedicarboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | OC(=O)C#CC(O)=O |
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InChI Identifier | InChI=1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8) |
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InChI Key | YTIVTFGABIZHHX-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. |
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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 | Dicarboxylic acids and derivatives |
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Direct Parent | Dicarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Fatty acyl
- Fatty acid
- Unsaturated fatty acid
- Dicarboxylic 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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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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External Links |
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HMDB ID | HMDB0247933 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 362 |
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KEGG Compound ID | C03248 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Acetylenedicarboxylic_acid |
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METLIN ID | Not Available |
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PubChem Compound | 371 |
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PDB ID | Not Available |
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ChEBI ID | 30781 |
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Good Scents ID | Not Available |
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References |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Domingo LR, Picher MT, Andres J: Toward an understanding of the selectivity in domino reactions. A DFT study of the reaction between acetylenedicarboxylic acid and 1, 3-Bis(2-furyl)propane J Org Chem. 2000 Jun 2;65(11):3473-7. doi: 10.1021/jo000030k. [PubMed:10843633 ]
- ROLLIER R, PELBOIS F: [Improvement in two cases of Kaposi's disease by butynedioic acid]. Bull Soc Fr Dermatol Syphiligr. 1952 Mar-Apr;59(2):144-5. [PubMed:12978816 ]
- Pahlavan Yali M, Hajmalek M: Interactions Between Brassicae napus and Pseudomonas putida (Strain ATCC12633) and Characterization of Volatile Organic Compounds Produced by the Bacterium. Curr Microbiol. 2021 Feb;78(2):679-687. doi: 10.1007/s00284-020-02335-2. Epub 2021 Jan 5. [PubMed:33403487 ]
- Park K, Bae G, Moon J, Choe J, Song KH, Lee S: Synthesis of symmetrical and unsymmetrical diarylalkynes from propiolic acid using palladium-catalyzed decarboxylative coupling. J Org Chem. 2010 Sep 17;75(18):6244-51. doi: 10.1021/jo101398a. [PubMed:20795634 ]
- Agenet N, Gandon V, Vollhardt KP, Malacria M, Aubert C: Cobalt-catalyzed cyclotrimerization of alkynes: the answer to the puzzle of parallel reaction pathways. J Am Chem Soc. 2007 Jul 18;129(28):8860-71. doi: 10.1021/ja072208r. Epub 2007 Jun 22. [PubMed:17585766 ]
- Tantardini C, Arkhipov SG, Cherkashina KA, Kil'met'ev AS, Boldyreva EV: Crystal structure of a 2:1 co-crystal of meloxicam with acetyl-endi-carb-oxy-lic acid. Acta Crystallogr E Crystallogr Commun. 2016 Nov 29;72(Pt 12):1856-1859. doi: 10.1107/S2056989016018909. eCollection 2016 Dec 1. [PubMed:27980849 ]
- Edwin Raja GC, Irudayanathan FM, Kim HS, Kim J, Lee S: Nickel-Catalyzed Hiyama-type Decarboxylative Coupling of Propiolic Acids and Organosilanes. J Org Chem. 2016 Jun 17;81(12):5244-9. doi: 10.1021/acs.joc.6b00883. Epub 2016 Jun 2. [PubMed:27188502 ]
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