Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:43:25 UTC |
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Updated at | 2024-04-19 09:49:08 UTC |
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NP-MRD ID | NP0002910 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Salicylhydroxamic Acid |
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Provided By | BMRB |
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Description | Salicylhydroxamic acid, also known as 2-hydroxybenzhydroxamate or SHAM, belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid. It was first documented in 1990 (PMID: 16667326). Based on a literature review a significant number of articles have been published on Salicylhydroxamic acid (PMID: 17984079) (PMID: 1847381) (PMID: 22554042) (PMID: 23416493). |
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Structure | InChI=1S/C7H7NO3/c9-6-4-2-1-3-5(6)7(10)8-11/h1-4,9,11H,(H,8,10) |
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Synonyms | Value | Source |
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2-Hydroxybenzhydroxamic acid | ChEBI | 2-Hydroxybenzohydroxamic acid | ChEBI | O-Hydroxybenzohydroxamic acid | ChEBI | Salicylohydroximic acid | ChEBI | SHAM | ChEBI | 2-Hydroxybenzhydroxamate | Generator | 2-Hydroxybenzohydroxamate | Generator | O-Hydroxybenzohydroxamate | Generator | Salicylohydroximate | Generator | Salicylhydroxamate | Generator |
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Chemical Formula | C7H7NO3 |
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Average Mass | 153.1354 Da |
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Monoisotopic Mass | 153.04259 Da |
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IUPAC Name | N,2-dihydroxybenzamide |
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Traditional Name | salicylhydroxamic acid |
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CAS Registry Number | Not Available |
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SMILES | ONC(=O)C1=CC=CC=C1O |
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InChI Identifier | InChI=1S/C7H7NO3/c9-6-4-2-1-3-5(6)7(10)8-11/h1-4,9,11H,(H,8,10) |
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InChI Key | HBROZNQEVUILML-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 | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Not Available | Not Available | 2023-07-04 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Not Available | Not Available | 2023-07-04 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, methanol, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, methanol, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, methanol, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, methanol, 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 salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | Salicylamides |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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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 | 46600 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
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Predicted Properties | |
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External Links |
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HMDB ID | HMDB0257460 |
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DrugBank ID | DB03819 |
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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 | 60011 |
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KEGG Compound ID | C11343 |
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BioCyc ID | CPD-6543 |
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BiGG ID | Not Available |
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Wikipedia Link | Salicylhydroxamic_acid |
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METLIN ID | Not Available |
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PubChem Compound | 66644 |
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PDB ID | Not Available |
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ChEBI ID | 45615 |
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Good Scents ID | rw1281521 |
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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 ]
- Goyal A, Tolbert NE: Salicylhydroxamic Acid (SHAM) Inhibition of the Dissolved Inorganic Carbon Concentrating Process in Unicellular Green Algae. Plant Physiol. 1990 Mar;92(3):630-6. doi: 10.1104/pp.92.3.630. [PubMed:16667326 ]
- Ikeda-Saito M, Shelley DA, Lu L, Booth KS, Caughey WS, Kimura S: Salicylhydroxamic acid inhibits myeloperoxidase activity. J Biol Chem. 1991 Feb 25;266(6):3611-6. [PubMed:1847381 ]
- Xu F, Zhang DW, Zhu F, Tang H, Lv X, Cheng J, Xie HF, Lin HH: A novel role for cyanide in the control of cucumber (Cucumis sativus L.) seedlings response to environmental stress. Plant Cell Environ. 2012 Nov;35(11):1983-97. doi: 10.1111/j.1365-3040.2012.02531.x. Epub 2012 May 28. [PubMed:22554042 ]
- Gao J, Wang N, Wang GX: Saccharomyces cerevisiae-induced stomatal closure mainly mediated by salicylhydroxamic acid-sensitive peroxidases in Vicia faba. Plant Physiol Biochem. 2013 Apr;65:27-31. doi: 10.1016/j.plaphy.2013.01.008. Epub 2013 Jan 28. [PubMed:23416493 ]
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