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Record Information
Version3.6
Creation Date2006-08-13 11:11:24 UTC
Update Date2016-02-11 01:06:34 UTC
HMDB IDHMDB04110
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhosphonoacetate
DescriptionPhosphonoacetate is a simple organophosphorus compound that inhibits DNA polymerase, especially in viruses and is used as an antiviral agent.
Structure
Thumb
Synonyms
ValueSource
Phosphonoacetic acidKegg
FosfonetKegg
CarboxymethanephosphonateHMDB
Carboxymethanephosphonic acidHMDB
Disodium carboxymethylphosphonateHMDB
Disodium phosphonoacetateHMDB
Disodium phosphonoacetate monohydrateHMDB
Fosfonet sodiumHMDB
FosfonoacetateHMDB
Fosfonoacetic acidHMDB
Lopac-P-6909HMDB
PAEHMDB
PhosphonacetateHMDB
Phosphonacetic acidHMDB
PPAHMDB
Chemical FormulaC2H5O5P
Average Molecular Weight140.0319
Monoisotopic Molecular Weight139.987459782
IUPAC Name2-phosphonoacetic acid
Traditional Namephosphonoacetic acid
CAS Registry Number4408-78-0
SMILES
OC(=O)CP(O)(O)=O
InChI Identifier
InChI=1S/C2H5O5P/c3-2(4)1-8(5,6)7/h1H2,(H,3,4)(H2,5,6,7)
InChI KeyInChIKey=XUYJLQHKOGNDPB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphonic acids and derivatives
Sub ClassOrganic phosphonic acids
Direct ParentOrganic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • DNA component
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point143 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility392 mg/mL at 0 °CNot Available
LogPNot AvailableNot Available
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
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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023313
KNApSAcK IDNot Available
Chemspider ID531
KEGG Compound IDC05682
BioCyc IDCPD-764
BiGG IDNot Available
Wikipedia LinkPAE
NuGOwiki LinkHMDB04110
Metagene LinkHMDB04110
METLIN ID7018
PubChem Compound546
PDB IDPAE
ChEBI ID15732
References
Synthesis ReferenceDellinger 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)
General References
  1. 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. [11312359 ]
  2. 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. [202665 ]