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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 11:11:24 UTC
Update Date2020-02-26 21:24:58 UTC
HMDB IDHMDB0004110
Secondary Accession Numbers
  • HMDB04110
Metabolite Identification
Common NamePhosphonoacetate
DescriptionPhosphonoacetate, also known as fosfonet or phosphonacetic acid, belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. Phosphonoacetate is a moderately acidic compound (based on its pKa). Phosphonoacetate exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1582752298
Synonyms
ValueSource
FosfonetChEBI
Phosphonoacetic acidKegg
Disodium phosphonoacetateHMDB
Fosfonet sodiumHMDB
Phosphonoacetate, disodiumHMDB
Phosphonacetic acidHMDB
CarboxymethanephosphonateHMDB
Carboxymethanephosphonic acidHMDB
Disodium carboxymethylphosphonateHMDB
Disodium phosphonoacetate monohydrateHMDB
FosfonoacetateHMDB
Fosfonoacetic acidHMDB
Lopac-p-6909HMDB
PAEHMDB
PhosphonacetateHMDB
PPAHMDB
Acid, phosphonoaceticHMDB
Sodium, fosfonetHMDB
Acid, phosphonaceticHMDB
PhosphonoacetateChEBI
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 KeyXUYJLQHKOGNDPB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
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
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.63 m³·mol⁻¹ChemAxon
Polarizability9.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0w5l-2974000000-382a946b6e8fb2405c6eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0w5l-2974000000-382a946b6e8fb2405c6eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00el-9400000000-765dac511198c32f9596Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9400000000-337da4930ff4e1d3f509Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-70f5ce5df0fbc8549eeeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-9500000000-dcce9b8fbef9f60ac1beSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01q9-9000000000-acc3e10ed8fce033ef29Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-4693e243c6ff991b1db9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-ebabe051a2a75b2ef169Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0089-9400000000-c316b0398040a3e683e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-b51e69389ed95c714617Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-003r-9000000000-fecadf6fba072e864e73Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-4693e243c6ff991b1db9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-ebabe051a2a75b2ef169Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0089-9400000000-4318b1a531b3db6338bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-b51e69389ed95c714617Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003r-9000000000-fecadf6fba072e864e73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-1ff082847f737c786ce8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008d-9400000000-33b7754bc017297ff2ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-008c-9300000000-19778449412743bcf27aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-4900000000-3cbdc72a15207691e1a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3900000000-0bb2806fe2867dce38c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-e1f4ab0fd240af6be33cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02823
Phenol Explorer Compound IDNot Available
FooDB IDFDB023313
KNApSAcK IDNot Available
Chemspider ID531
KEGG Compound IDC05682
BioCyc IDCPD-764
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7018
PubChem Compound546
PDB IDPAE
ChEBI ID15732
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. [PubMed: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. [PubMed:202665 ]