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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:06 UTC
HMDB IDHMDB0014670
Secondary Accession Numbers
  • HMDB14670
Metabolite Identification
Common NameFoscarnet
DescriptionFoscarnet, also known as phosphonoformate or foscavir, belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. Foscarnet is a drug which is used for the treatment of cmv retinitis in patients with acquired immunodeficiency syndrome (aids) and for treatment of acyclovir-resistant mucocutaneous hsv infections in immunocompromised patients. Foscarnet is only found in individuals that have used or taken this drug. Foscarnet is an organic analogue of inorganic pyrophosphate that inhibits replication of herpes viruses in vitro including cytomegalovirus (CMV) and herpes simplex virus types 1 and 2 (HSV-1 and HSV-2). Foscarnet is an extremely strong acidic compound (based on its pKa). However, acyclovir or ganciclovir resistant mutants with alterations in the viral DNA polymerase may be resistant to foscarnet and may not respond to therapy with foscarnet. Foscarnet does not require activation (phosphorylation) by thymidine kinase or other kinases and therefore is active in vitro against HSV TK deficient mutants and CMV UL97 mutants. The combination of foscarnet and ganciclovir has been shown to have enhanced activity in vitro. Foscarnet also shows activity against human herpesviruses and HIV.
Structure
Data?1582753206
Synonyms
ValueSource
Carboxyphosphonic acidChEBI
FoscarmetChEBI
Phosphonomethanoic acidChEBI
CarboxyphosphonateGenerator
PhosphonomethanoateGenerator
Dihydroxyphosphinecarboxylic acid oxideHMDB
Phgosphonocarboxylic acidHMDB
PhosphonoformateHMDB
Phosphonoformic acidHMDB
Foscarnet barium (2:3) saltHMDB
Foscarnet sodium hexahydrateHMDB
Foscarnet trisodium saltHMDB
FoscavirHMDB
Foscarnet disodium saltHMDB
Hexahydrate, foscarnet sodiumHMDB
Trilithium salt, foscarnetHMDB
Tripotassium salt, foscarnetHMDB
Foscarnet calcium (2:3) saltHMDB
Foscarnet manganese (2+) (2:3) saltHMDB
Foscarnet sodiumHMDB
Foscarnet tripotassium saltHMDB
Phosphonoformate, trisodiumHMDB
Sodium hexahydrate, foscarnetHMDB
Sodium, foscarnetHMDB
Disodium salt, foscarnetHMDB
Foscarnet magnesium (2:3) saltHMDB
Foscarnet trilithium saltHMDB
Trisodium phosphonoformateHMDB
Trisodium salt, foscarnetHMDB
FOSCARNETChEBI
Chemical FormulaCH3O5P
Average Molecular Weight126.0053
Monoisotopic Molecular Weight125.971809718
IUPAC Namephosphonoformic acid
Traditional Namefoscarnet
CAS Registry Number63585-09-1
SMILES
OC(=O)P(O)(O)=O
InChI Identifier
InChI=1S/CH3O5P/c2-1(3)7(4,5)6/h(H,2,3)(H2,4,5,6)
InChI KeyZJAOAACCNHFJAH-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
  • Carbonic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point88.06 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility16.8 g/LNot Available
LogP-2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility16.8 g/LALOGPS
logP-1.6ALOGPS
logP-0.83ChemAxon
logS-0.88ALOGPS
pKa (Strongest Acidic)-0.096ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity19.07 m³·mol⁻¹ChemAxon
Polarizability7.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-9500000000-29e34b6d5b8cc1784edeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9400000000-9a00c96ad9c0d4c8c6e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-5900000000-d1fa15eab370c32d2fe7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-45d4c79e5cb632ac5f31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-ab711fe79e31c9cfd5c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-9400000000-1dede2e854977c49e9cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9300000000-4cc1233e47347e183583Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3900000000-9457754caf0649be24ceSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00529 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00529 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00529
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00000800
Chemspider ID3297
KEGG Compound IDC06456
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFoscarnet
METLIN IDNot Available
PubChem Compound3415
PDB IDPPF
ChEBI ID127780
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Transporters

General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
SLC16A1
Uniprot ID:
P53985
Molecular weight:
53957.7
References
  1. Tamai I, Sai Y, Ono A, Kido Y, Yabuuchi H, Takanaga H, Satoh E, Ogihara T, Amano O, Izeki S, Tsuji A: Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J Pharm Pharmacol. 1999 Oct;51(10):1113-21. [PubMed:10579682 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [PubMed:10945832 ]