Ethylphosphonate (PAMDB001161)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001161
Identification
Name: Ethylphosphonate
Description:Ethylphosphonate is a member of the chemical class known as Organic Phosphonic Acids and Derivatives. These are organic compounds containing phosphonic acid or a derivative thereof. phosphonoacetaldehyde is catalyzed by phosphonoacetaldehyde hydrolase. This is the first nucleic sequence report of the phosphonoacetaldehyde hydrolase, an enzyme involved in the carbon-phosphorus bond cleavage. (PMID 9332393). 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.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Phosphonoacetaldehyde
  • EPN
  • Ethylphosphonic acid
  • Phosphonoacetaldehyde
Chemical Formula: C2H6O3P
Average Molecular Weight: 109.041
Monoisotopic Molecular Weight: 109.00545557
InChI Key: GATNOFPXSDHULC-UHFFFAOYSA-M
InChI:InChI=1S/C2H7O3P/c1-2-6(3,4)5/h2H2,1H3,(H2,3,4,5)/p-1
CAS number: 6779-09-5
IUPAC Name:hydrogen ethylphosphonate
Traditional IUPAC Name: hydrogen ethylphosphonate
SMILES:CCP(O)([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
Kingdom Organic compounds
Super ClassOrganophosphorus compounds
Class Organic phosphonic acids and derivatives
Sub ClassOrganic phosphonic acids
Direct Parent Organic phosphonic acids
Alternative Parents
Substituents
  • Organophosphonic acid
  • Hydrocarbon derivative
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility43.4 mg/mLALOGPS
logP-0.78ALOGPS
logP-0.83ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.36 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.93 m3·mol-1ChemAxon
Polarizability8.48 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
  • Microbial metabolism in diverse environments pae01120
  • Phosphonate and phosphinate metabolism pae00440
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-2e07ccb842a16139b65aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-9a17a10d5011ef535accView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02e9-9200000000-41801a9e8519ed41e1e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3900000000-3b66e7da80377eea9a76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5c-9400000000-306d993c640e3f67918bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003u-9000000000-166311a7f9eb0294c879View in MoNA
References
References:
  • Dumora, C., Marche, M., Doignon, F., Aigle, M., Cassaigne, A., Crouzet, M. (1997). "First characterization of the phosphonoacetaldehyde hydrolase gene of Pseudomonas aeruginosa." Gene 197:405-412. Pubmed: 9332393
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID18124
HMDB IDNot Available
Pubchem Compound ID21680364
Kegg IDNot Available
ChemSpider ID10297570
Wikipedia IDNot Available
BioCyc IDCPD0-1075
EcoCyc IDCPD0-1075

Transporters

Protein Details
• Putative phosphonates transport system permease protein phnE
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for phosphonates; probably responsible for the translocation of the substrate across the membrane
Gene Name:
phnE
Locus Tag:
PA3382
Molecular weight:
28.4 kDa