PHOSPHONOACETIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C2H5O5P
Molecular Weight	140.0319
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CP(O)(O)=O

InChI

InChIKey=XUYJLQHKOGNDPB-UHFFFAOYSA-N

InChI=1S/C2H5O5P/c3-2(4)1-8(5,6)7/h1H2,(H,3,4)(H2,5,6,7)

HIDE SMILES / InChI

Molecular Formula	C2H5O5P
Molecular Weight	140.0319
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7069603 | https://www.ncbi.nlm.nih.gov/pubmed/212978

Fosfonet sodium (or phosphonoacetate sodium), an organophosphorus compound, was found to be a specific inhibitor of the virus-induced DNA polymerases and thus could inhibit specifically the replication of herpes-viruses.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA polymerase catalytic subunit 14 Target ID: P04293 Gene ID: 2703462.0 Gene Symbol: NA Target Organism: Human herpesvirus 1 (strain 17) (HHV-1) (Human herpes simplex virus\|\|\|1) Sources: https://www.ncbi.nlm.nih.gov/pubmed/189089 \| https://www.ncbi.nlm.nih.gov/pubmed/172657	Interacts 323

PubMed

Title	Date	PubMed
Autophagy suppresses tumor progression by limiting chromosomal instability.	2007-06-01	17510285
Glycosaminoglycan interactions in murine gammaherpesvirus-68 infection.	2007-04-04	17406671
Design, synthesis, and bioactivity of novel inhibitors of E. coli aspartate transcarbamoylase.	2007-04-01	17336518
Inhibition of gene amplification in telomerase deficient immortalized mouse embryonic fibroblasts.	2007-03	16973670
Enriching suicide gene bearing tumor cells for an increased bystander effect.	2007-01	17024230
Unique uptake and efflux systems of inorganic phosphate in osteoclast-like cells.	2007-01	16971494
Phosphonoacetic acid utilization by fungal isolates: occurrence and properties of a phosphonoacetate hydrolase in some penicillia.	2006-12	17123811
Imaging immediate-early and strict-late promoter activity during oncolytic herpes simplex virus type 1 infection and replication in tumors.	2006-12	16871231
Synergistic antiviral activity of acyclovir and vidarabine against herpes simplex virus types 1 and 2 and varicella-zoster virus.	2006-11	16797734
N-phosphonacetyl-L-isoasparagine a potent and specific inhibitor of Escherichia coli aspartate transcarbamoylase.	2006-10-05	17004708
Picosecond dynamics of T and R forms of aspartate transcarbamylase: a neutron scattering study.	2006-10	17008138
Selective excision of chain-terminating nucleotides by HIV-1 reverse transcriptase with phosphonoformate as substrate.	2006-09-22	16829515
Alpha-herpesvirus infection induces the formation of nuclear actin filaments.	2006-08	16933992
A role for carbon catabolite repression in the metabolism of phosphonoacetate by Agromyces fucosus Vs2.	2006-08	16842370
Development of a common fully stereocontrolled access to the medicinally important and promising prostacyclin analogues iloprost, 3-oxa-iloprost and cicaprost.	2006-07-17	16708414
Fully stereocontrolled syntheses of 3-oxacarbacyclin and carbacyclin by the conjugate addition-azoalkene-asymmetric olefination strategy.	2006-06-09	16749799
Bond strength to primed Ti-6Al-7Nb alloy of two acrylic resin adhesives.	2006-06	16916231
Detection of phosphonoacetate degradation and phnA genes in soil bacteria from distinct geographical origins suggest its possible biogenic origin.	2006-05	16623750
Functional annotation and kinetic characterization of PhnO from Salmonella enterica.	2006-03-07	16503658
Continued survival of more than ten years, without resection of metastatic disease, in patients with metastatic colorectal cancer treated with biomodulated fluorouracil: report of two cases.	2006-03	16475032
Phosphonoacetate hydrolase from Penicillium oxalicum: purification and properties, phosphate starvation-independent expression, and partial sequencing.	2006-03	16129582
Inhibition of adenosine kinase by phosphonate and bisphosphonate derivatives.	2006-02	16444581
Severe cytochrome c oxidase inhibition in vivo does not induce a pyrimidine deficiency; neuroprotective action of oral uridine prodrug PN401 requires supraphysiological levels of uridine.	2005-12-20	16330000
Antiviral activity of the marine alga Symphyocladia latiuscula against herpes simplex virus (HSV-1) in vitro and its therapeutic efficacy against HSV-1 infection in mice.	2005-12	16327161
Functional inaccessibility of quiescent herpes simplex virus genomes.	2005-11-21	16300675
Adenosine phosphonoacetic acid is slowly metabolized by NDP kinase.	2005-11	16787337
Synthesis of farnesol isomers via a modified Wittig procedure.	2005-10-27	16235893
Precursor decomposition and nucleation kinetics during platelike apatite synthesis.	2005-09-15	16853209
[Photodynamic inhibition of infection caused by herpes simplex virus type 1 in the cultured cells, by using 5-aminolevulinic acid-induced porphyrins].	2005-08-18	16104524
Efficient synthesis of fluorothiosparfosic acid analogues with potential antitumoral activity.	2005-08-15	15975800
Anion binding and controlled aggregation of human interleukin-1 receptor antagonist.	2005-07-26	16026159
Effect of ligand structure on the pathways for iron release from human serum transferrin.	2005-07-11	15998048
A single amino acid substitution in the active site of Escherichia coli aspartate transcarbamoylase prevents the allosteric transition.	2005-06-03	15890205
Aspartate transcarbamylase from the hyperthermophilic archaeon Pyrococcus abyssi. Insights into cooperative and allosteric mechanisms.	2005-06	15943802
Sensitivity to phosphonoacetic acid: a new phenotype to probe DNA polymerase delta in Saccharomyces cerevisiae.	2005-06	15802517
Genomic instability in Gadd45a-/- cells is coupled with S-phase checkpoint defects.	2005-05	15846075
The antiviral activity of the combinations of netropsin derivatives with modified nucleosides and phosphonoacetic acid as estimated in the model of herpesvirus type 1 in a vero cell culture.	2005-04-26	15846992
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides.	2005-03	15728906
The human cytomegalovirus UL78 gene is highly conserved among clinical isolates, but is dispensable for replication in fibroblasts and a renal artery organ-culture system.	2005-02	15659748
Phosphonate catabolism by Campylobacter spp.	2005-02	15647906
A facile synthesis of novel chiral phosphonoacetates bearing a stereogenic phosphorus atom.	2005-01	15635249
Cyclic sulfamidates as vehicles for the synthesis of substituted lactams.	2004-12-09	15575671
A phase II pilot study of high-dose 24-hour continuous infusion of 5-FU and leucovorin and low-dose PALA for patients with colorectal cancer: a Southwest Oncology Group study.	2004-11	15292717
Characterization and expression of the pseudorabies virus early gene UL54.	2004-08	15158594
Uncharged AZT and D4T derivatives of phosphonoformic and phosphonoacetic acids as anti-HIV pronucleosides.	2004-07-01	15214788
Tetrahedral intermediates in thiamin diphosphate-dependent decarboxylations exist as a 1',4'-imino tautomeric form of the coenzyme, unlike the michaelis complex or the free coenzyme.	2004-06-01	15157089
Aspartate transcarbamylase (ATCase) of Escherichia coli: a new crystalline R-state bound to PALA, or to product analogues citrate and phosphate.	2004-06-01	15157075
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir?	2004-03	15168799
In vitro antiviral activity of polyoxotungstate (PM-19) and other polyoxometalates against herpes simplex virus.	1991-12	1663733
Inhibition of herpes simplex virus replication by phosphonoacetic acid.	1974-09	15830487

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:23:47 GMT 2025` Edited by `admin` on `Mon Mar 31 18:23:47 GMT 2025`
Record UNII	N919E46723
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-18205

Preferred Name

English

PHOSPHONOACETIC ACID

Systematic Name

English

FOSFONET

Common Name

English

PHOSPHONOACETATE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

J05AD02