| Record Information |
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| Version | 2.0 |
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| Creation Date | 2012-05-31 14:39:38 -0600 |
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| Update Date | 2015-06-03 17:19:48 -0600 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | Phenylphosphonate |
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| Description | Phenylphosphonate is a member of the chemical class known as Phenylphosphines and Derivatives. These are compounds containing a phenylphosphine, which consists of phosphine substituent bound to a phenyl group. . Phosphonates (Pn) are a large class of organophosphorus molecules that have direct carbon-phosphorus (C-P) bonds in place of the carbon-oxygen-phosphorus ester bond. In bacteria two pathways exist for Pn breakdown for use as a P source: the phosphonatase and C-P lyase pathways. These pathways differ both in regard to their substrate specificity and their cleavage mechanism. The phosphonatase pathway acts on the natural Pn alpha-aminoethylphosphonate (AEPn). In a two-step process it leads to cleavage of the C-P bond by a hydrolysis reaction requiring an adjacent carbonyl group. In contrast the C-P lyase pathway has a broad substrate specificity. It leads to cleavage of substituted Pn (such as AEPn) as well as unsubstituted Pn by a mechanism involving redox or radical chemistry. Due to its broad substrate specificity, the C-P lyase pathway is generally thought to be responsible for the breakdown of Pn herbicides (such as glyphosate) by bacteria. |
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| Structure | |
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| Synonyms: | - Benzenephosphonate
- Benzenephosphonic acid
- Phenyl-Phosphonate
- Phenyl-Phosphonic acid
- Phenylphosphonic acid
- PHPN
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| Chemical Formula: | C6H5O3P |
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| Weight: | Average: 156.0759
Monoisotopic: 155.997630538 |
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| InChI Key: | QLZHNIAADXEJJP-UHFFFAOYSA-L |
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| InChI: | InChI=1S/C6H7O3P/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)/p-2 |
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| CAS number: | 1571-33-1 |
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| IUPAC Name: | phenylphosphonate |
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| Traditional IUPAC Name: | phenylphosphonate |
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| SMILES: | [O-]P([O-])(=O)C1=CC=CC=C1 |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. |
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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 | Not Available |
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| Direct Parent | Benzene and substituted derivatives |
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| Alternative Parents | |
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| Substituents | - Monocyclic benzene moiety
- Organophosphonic acid derivative
- Organophosphonic acid
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organophosphorus compound
- Organic anion
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State: | Solid |
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| Charge: | -1 |
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| Melting point: | 163-166 °C |
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| Experimental Properties: | | Property | Value | Source |
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| Water Solubility: | 190 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations: | Cytoplasm |
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| Reactions: | |
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| SMPDB Pathways: | Not Available |
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| KEGG Pathways: | Not Available |
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| EcoCyc Pathways: | Not Available |
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| Concentrations |
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| Not Available |
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| Spectra |
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| Spectra: | |
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| References |
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| References: | - Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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| Synthesis Reference: | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| Links |
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| External Links: | | Resource | Link |
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| CHEBI ID | Not Available | | HMDB ID | Not Available | | Pubchem Compound ID | 5194779 | | Kegg ID | Not Available | | ChemSpider ID | 4366324 | | Wikipedia ID | Not Available | | BioCyc ID | CPD0-1078 | | EcoCyc ID | CPD0-1078 |
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