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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 11:11:24 UTC
Update Date2021-09-07 16:45:36 UTC
HMDB IDHMDB0004110
Secondary Accession Numbers
  • HMDB04110
Metabolite Identification
Common NamePhosphonoacetate
DescriptionPhosphonoacetate, also known as fosfonet, belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. Phosphonoacetate exists in all living organisms, ranging from bacteria to humans. Phosphonoacetate has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make phosphonoacetate a potential biomarker for the consumption of these foods. Phosphonoacetate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Phosphonoacetate.
Structure
Data?1582752298
Synonyms
ValueSource
FosfonetChEBI
Phosphonoacetic acidKegg
CarboxymethanephosphonateHMDB
Carboxymethanephosphonic acidHMDB
Disodium carboxymethylphosphonateHMDB
Disodium phosphonoacetateHMDB, MeSH
Disodium phosphonoacetate monohydrateHMDB
Fosfonet sodiumHMDB, MeSH
FosfonoacetateHMDB
Fosfonoacetic acidHMDB
Lopac-P-6909HMDB
PAEHMDB
PhosphonacetateHMDB
Phosphonacetic acidHMDB, MeSH
PPAHMDB
Acid, phosphonoaceticMeSH, HMDB
Phosphonoacetate, disodiumMeSH, HMDB
Sodium, fosfonetMeSH, HMDB
Acid, phosphonaceticMeSH, HMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point143 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility392 mg/mL at 0 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.36331661259
DarkChem[M-H]-120.031661259
DeepCCS[M+H]+118.93430932474
DeepCCS[M-H]-116.13330932474
DeepCCS[M-2H]-152.6630932474
DeepCCS[M+Na]+127.34330932474
AllCCS[M+H]+131.632859911
AllCCS[M+H-H2O]+127.532859911
AllCCS[M+NH4]+135.432859911
AllCCS[M+Na]+136.532859911
AllCCS[M-H]-123.632859911
AllCCS[M+Na-2H]-126.932859911
AllCCS[M+HCOO]-130.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhosphonoacetateOC(=O)CP(O)(O)=O2528.4Standard polar33892256
PhosphonoacetateOC(=O)CP(O)(O)=O1216.7Standard non polar33892256
PhosphonoacetateOC(=O)CP(O)(O)=O1378.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phosphonoacetate,1TMS,isomer #1C[Si](C)(C)OC(=O)CP(=O)(O)O1398.9Semi standard non polar33892256
Phosphonoacetate,1TMS,isomer #2C[Si](C)(C)OP(=O)(O)CC(=O)O1402.2Semi standard non polar33892256
Phosphonoacetate,2TMS,isomer #1C[Si](C)(C)OC(=O)CP(=O)(O)O[Si](C)(C)C1432.0Semi standard non polar33892256
Phosphonoacetate,2TMS,isomer #1C[Si](C)(C)OC(=O)CP(=O)(O)O[Si](C)(C)C1461.7Standard non polar33892256
Phosphonoacetate,2TMS,isomer #1C[Si](C)(C)OC(=O)CP(=O)(O)O[Si](C)(C)C1773.5Standard polar33892256
Phosphonoacetate,2TMS,isomer #2C[Si](C)(C)OP(=O)(CC(=O)O)O[Si](C)(C)C1482.8Semi standard non polar33892256
Phosphonoacetate,2TMS,isomer #2C[Si](C)(C)OP(=O)(CC(=O)O)O[Si](C)(C)C1497.0Standard non polar33892256
Phosphonoacetate,2TMS,isomer #2C[Si](C)(C)OP(=O)(CC(=O)O)O[Si](C)(C)C1680.7Standard polar33892256
Phosphonoacetate,3TMS,isomer #1C[Si](C)(C)OC(=O)CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1497.2Semi standard non polar33892256
Phosphonoacetate,3TMS,isomer #1C[Si](C)(C)OC(=O)CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1534.8Standard non polar33892256
Phosphonoacetate,3TMS,isomer #1C[Si](C)(C)OC(=O)CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1556.5Standard polar33892256
Phosphonoacetate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CP(=O)(O)O1653.7Semi standard non polar33892256
Phosphonoacetate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(O)CC(=O)O1676.3Semi standard non polar33892256
Phosphonoacetate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CP(=O)(O)O[Si](C)(C)C(C)(C)C1868.7Semi standard non polar33892256
Phosphonoacetate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CP(=O)(O)O[Si](C)(C)C(C)(C)C1905.9Standard non polar33892256
Phosphonoacetate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CP(=O)(O)O[Si](C)(C)C(C)(C)C2028.2Standard polar33892256
Phosphonoacetate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(CC(=O)O)O[Si](C)(C)C(C)(C)C1930.4Semi standard non polar33892256
Phosphonoacetate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(CC(=O)O)O[Si](C)(C)C(C)(C)C1901.9Standard non polar33892256
Phosphonoacetate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(CC(=O)O)O[Si](C)(C)C(C)(C)C1996.6Standard polar33892256
Phosphonoacetate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2116.6Semi standard non polar33892256
Phosphonoacetate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2149.2Standard non polar33892256
Phosphonoacetate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1943.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Phosphonoacetate GC-MS (3 TMS)splash10-0w5l-2974000000-382a946b6e8fb2405c6e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phosphonoacetate GC-MS (Non-derivatized)splash10-0w5l-2974000000-382a946b6e8fb2405c6e2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphonoacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00el-9400000000-765dac511198c32f95962017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphonoacetate GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9400000000-337da4930ff4e1d3f5092017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphonoacetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphonoacetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-0900000000-70f5ce5df0fbc8549eee2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a59-9500000000-dcce9b8fbef9f60ac1be2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-01q9-9000000000-acc3e10ed8fce033ef292012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-00di-0900000000-4693e243c6ff991b1db92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-00di-0900000000-ebabe051a2a75b2ef1692012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0089-9400000000-c316b0398040a3e683e12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-001i-9000000000-b51e69389ed95c7146172012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-003r-9000000000-fecadf6fba072e864e732012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate LC-ESI-QQ , positive-QTOFsplash10-00di-0900000000-4693e243c6ff991b1db92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate LC-ESI-QQ , positive-QTOFsplash10-00di-0900000000-ebabe051a2a75b2ef1692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate LC-ESI-QQ , positive-QTOFsplash10-0089-9400000000-4318b1a531b3db6338bc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate LC-ESI-QQ , positive-QTOFsplash10-001i-9000000000-b51e69389ed95c7146172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate LC-ESI-QQ , positive-QTOFsplash10-003r-9000000000-fecadf6fba072e864e732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate 10V, Negative-QTOFsplash10-004l-9000000000-9fd80c506c1deef72e7e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate 20V, Negative-QTOFsplash10-004i-9000000000-59d16e54cb52694084e92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phosphonoacetate 40V, Negative-QTOFsplash10-004i-9000000000-ae466fdb612535fbd3032021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphonoacetate 10V, Positive-QTOFsplash10-00di-0900000000-1ff082847f737c786ce82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphonoacetate 20V, Positive-QTOFsplash10-008d-9400000000-33b7754bc017297ff2ce2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphonoacetate 40V, Positive-QTOFsplash10-008c-9300000000-19778449412743bcf27a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphonoacetate 10V, Negative-QTOFsplash10-000i-4900000000-3cbdc72a15207691e1a32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphonoacetate 20V, Negative-QTOFsplash10-00di-3900000000-0bb2806fe2867dce38c32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphonoacetate 40V, Negative-QTOFsplash10-004i-9400000000-e1f4ab0fd240af6be33c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphonoacetate 10V, Positive-QTOFsplash10-008c-5900000000-a5e29b0fe44acda9a7392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphonoacetate 20V, Positive-QTOFsplash10-001i-9200000000-56a811594dfa7f4466a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphonoacetate 40V, Positive-QTOFsplash10-001i-9000000000-ae92e3f3907029fb2ab22021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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 ]