Phosphonoacetate (PAMDB001843)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001843
Identification
Name: Phosphonoacetate
Description:A simple organophosphorus compound that inhibits DNA polymerase, especially in viruses and is used as an antiviral agent.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Phosphonoacetic acid
Chemical Formula: C2H5O5P
Average Molecular Weight: 140.0319
Monoisotopic Molecular Weight: 139.987459782
InChI Key: XUYJLQHKOGNDPB-UHFFFAOYSA-N
InChI:InChI=1S/C2H5O5P/c3-2(4)1-8(5,6)7/h1H2,(H,3,4)(H2,5,6,7)
CAS number: 4408-78-0
IUPAC Name:2-phosphonoacetic acid
Traditional IUPAC Name: phosphonoacetic acid
SMILES:OC(=O)CP(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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 143-146 °C
Experimental Properties:
PropertyValueSource
Water Solubility:392 mg/mL at 0 oC [STEPHEN,H & STEPHEN,T (1963)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility25.1 mg/mLALOGPS
logP-2.6ALOGPS
logP-1.6ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)1.64ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.63 m3·mol-1ChemAxon
Polarizability9.63 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Phosphonoacetate + Water <> Acetic acid + Phosphate
Pathways:
  • Microbial metabolism in diverse environments pae01120
  • Phosphonate and phosphinate metabolism pae00440
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0w5l-2974000000-382a946b6e8fb2405c6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-70f5ce5df0fbc8549eeeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9500000000-dcce9b8fbef9f60ac1beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01q9-9000000000-acc3e10ed8fce033ef29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-4693e243c6ff991b1db9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-ebabe051a2a75b2ef169View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0089-9400000000-c316b0398040a3e683e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-b51e69389ed95c714617View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-003r-9000000000-fecadf6fba072e864e73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-1ff082847f737c786ce8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008d-9400000000-33b7754bc017297ff2ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-008c-9300000000-19778449412743bcf27aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-4900000000-3cbdc72a15207691e1a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3900000000-0bb2806fe2867dce38c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-e1f4ab0fd240af6be33cView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Abendroth A, Lin I, Slobedman B, Ploegh H, Arvin AM: Varicella-zoster virus retains major histocompatibility complex class I proteins in the Golgi compartment of infected cells. J Virol. 2001 May;75(10):4878-88. Pubmed: 11312359
  • Sairenji T, Hinuma Y, Sekizawa T, Yoshida M: Appearance of early and late components of Epstein-Barr virus-associated membrane antigen in Daudi cells superinfected with P3HR-1 virus. J Gen Virol. 1978 Jan;38(1):111-20. Pubmed: 202665
  • 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: Dellinger Douglas J; Sheehan David M; Christensen Nanna K; Lindberg James G; Caruthers Marvin H Solid-phase chemical synthesis of phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides. Journal of the American Chemical Society (2003), 125(4), 940-50.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID15732
HMDB IDHMDB04110
Pubchem Compound ID546
Kegg IDC05682
ChemSpider ID531
WikipediaPAE
BioCyc IDNot Available
Ligand ExpoPAE

Enzymes

Protein Details
• conserved protein
General function:
Not Available
Specific function:
Not Available
Gene Name:
yjdM
Locus Tag:
PA0128
Molecular weight:
12.1 kDa