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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References transporters (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2023-02-21 17:18:14 UTC

HMDB ID

HMDB0014670

Secondary Accession Numbers

HMDB14670

Metabolite Identification

Common Name

Foscarnet

Description

Foscarnet is only found in individuals that have used or taken this drug. It is an antiviral agent used in the treatment of cytomegalovirus retinitis. Foscarnet also shows activity against human herpesviruses and HIV. [PubChem]Foscarnet exerts its antiviral activity by a selective inhibition at the pyrophosphate binding site on virus-specific DNA polymerases at concentrations that do not affect cellular DNA polymerases.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
Carboxyphosphonic acid	ChEBI
Foscarmet	ChEBI
Phosphonomethanoic acid	ChEBI
Carboxyphosphonate	Generator
Phosphonomethanoate	Generator
Dihydroxyphosphinecarboxylic acid oxide	HMDB
Phgosphonocarboxylic acid	HMDB
Phosphonoformate	HMDB
Phosphonoformic acid	HMDB
Foscarnet barium (2:3) salt	HMDB
Foscarnet sodium hexahydrate	HMDB
Foscarnet trisodium salt	HMDB
Foscavir	HMDB
Foscarnet disodium salt	HMDB
Hexahydrate, foscarnet sodium	HMDB
Trilithium salt, foscarnet	HMDB
Tripotassium salt, foscarnet	HMDB
Foscarnet calcium (2:3) salt	HMDB
Foscarnet manganese (2+) (2:3) salt	HMDB
Foscarnet sodium	HMDB
Foscarnet tripotassium salt	HMDB
Phosphonoformate, trisodium	HMDB
Sodium hexahydrate, foscarnet	HMDB
Sodium, foscarnet	HMDB
Disodium salt, foscarnet	HMDB
Foscarnet magnesium (2:3) salt	HMDB
Foscarnet trilithium salt	HMDB
Trisodium phosphonoformate	HMDB
Trisodium salt, foscarnet	HMDB
FOSCARNET	ChEBI

Chemical Formula

CH₃O₅P

Average Molecular Weight

126.0053

Monoisotopic Molecular Weight

125.971809718

IUPAC Name

phosphonoformic acid

Traditional Name

foscarnet

CAS Registry Number

63585-09-1

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 Key

ZJAOAACCNHFJAH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Organic phosphonic acids

Direct Parent

Organic 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 Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:127780 )
phosphonic acids (CHEBI:127780 )
carboxylic acid (CHEBI:127780 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014670)
Membrane (HMDB: HMDB0014670)

Source

Exogenous

Exogenous (HMDB: HMDB0014670)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	88.06 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	16.8 g/L	Not Available
LogP	-2.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	16.8 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-0.83	ChemAxon
logS	-0.88	ALOGPS
pKa (Strongest Acidic)	-0.096	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	19.07 m³·mol⁻¹	ChemAxon
Polarizability	7.89 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	123.459	31661259
DarkChem	[M-H]-	116.755	31661259
DeepCCS	[M+H]+	118.655	30932474
DeepCCS	[M-H]-	115.855	30932474
DeepCCS	[M-2H]-	152.289	30932474
DeepCCS	[M+Na]+	126.909	30932474
AllCCS	[M+H]+	132.9	32859911
AllCCS	[M+H-H2O]+	128.9	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	123.0	32859911
AllCCS	[M+Na-2H]-	127.0	32859911
AllCCS	[M+HCOO]-	131.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.08 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0573 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.01 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	372.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	543.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	376.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	76.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	276.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	135.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	275.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	262.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	750.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	593.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	662.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	234.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	685.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	412.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	413.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Foscarnet	OC(=O)P(O)(O)=O	2179.5	Standard polar	33892256
Foscarnet	OC(=O)P(O)(O)=O	1312.1	Standard non polar	33892256
Foscarnet	OC(=O)P(O)(O)=O	1150.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Foscarnet,1TMS,isomer #1	C[Si](C)(C)OC(=O)P(=O)(O)O	1281.8	Semi standard non polar	33892256
Foscarnet,1TMS,isomer #2	C[Si](C)(C)OP(=O)(O)C(=O)O	1349.1	Semi standard non polar	33892256
Foscarnet,2TMS,isomer #1	C[Si](C)(C)OC(=O)P(=O)(O)O[Si](C)(C)C	1358.3	Semi standard non polar	33892256
Foscarnet,2TMS,isomer #1	C[Si](C)(C)OC(=O)P(=O)(O)O[Si](C)(C)C	1305.0	Standard non polar	33892256
Foscarnet,2TMS,isomer #1	C[Si](C)(C)OC(=O)P(=O)(O)O[Si](C)(C)C	1537.2	Standard polar	33892256
Foscarnet,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(=O)O	1415.9	Semi standard non polar	33892256
Foscarnet,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(=O)O	1334.5	Standard non polar	33892256
Foscarnet,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(=O)O	1497.4	Standard polar	33892256
Foscarnet,3TMS,isomer #1	C[Si](C)(C)OC(=O)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1455.1	Semi standard non polar	33892256
Foscarnet,3TMS,isomer #1	C[Si](C)(C)OC(=O)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1398.3	Standard non polar	33892256
Foscarnet,3TMS,isomer #1	C[Si](C)(C)OC(=O)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1410.9	Standard polar	33892256
Foscarnet,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)P(=O)(O)O	1548.0	Semi standard non polar	33892256
Foscarnet,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)C(=O)O	1615.7	Semi standard non polar	33892256
Foscarnet,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)P(=O)(O)O[Si](C)(C)C(C)(C)C	1816.4	Semi standard non polar	33892256
Foscarnet,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)P(=O)(O)O[Si](C)(C)C(C)(C)C	1718.3	Standard non polar	33892256
Foscarnet,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)P(=O)(O)O[Si](C)(C)C(C)(C)C	1828.7	Standard polar	33892256
Foscarnet,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(=O)O	1857.0	Semi standard non polar	33892256
Foscarnet,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(=O)O	1761.6	Standard non polar	33892256
Foscarnet,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(=O)O	1818.2	Standard polar	33892256
Foscarnet,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2042.6	Semi standard non polar	33892256
Foscarnet,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1976.8	Standard non polar	33892256
Foscarnet,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1819.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Foscarnet GC-MS (Non-derivatized) - 70eV, Positive	splash10-0059-9500000000-29e34b6d5b8cc1784ede	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Foscarnet GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9400000000-9a00c96ad9c0d4c8c6e4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Foscarnet GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 10V, Positive-QTOF	splash10-0059-5900000000-d1fa15eab370c32d2fe7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 20V, Positive-QTOF	splash10-001i-9000000000-45d4c79e5cb632ac5f31	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 40V, Positive-QTOF	splash10-001i-9000000000-ab711fe79e31c9cfd5c5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 10V, Negative-QTOF	splash10-0089-9400000000-1dede2e854977c49e9cd	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 20V, Negative-QTOF	splash10-001i-9300000000-4cc1233e47347e183583	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 40V, Negative-QTOF	splash10-0a4i-3900000000-9457754caf0649be24ce	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 10V, Negative-QTOF	splash10-024i-9400000000-2bed6358f65878a8187f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 20V, Negative-QTOF	splash10-03di-9000000000-a79bd10f4cdbb7efec47	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 40V, Negative-QTOF	splash10-03di-9000000000-5afa5d3cea1d23978ed6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 10V, Positive-QTOF	splash10-003r-9700000000-463993cb255207248399	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 20V, Positive-QTOF	splash10-001i-9000000000-9bf8d71fcf21f56edb86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Foscarnet 40V, Positive-QTOF	splash10-01q9-9000000000-0c8460c828950fec5438	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00529	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00529	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00529

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000800

Chemspider ID

3297

KEGG Compound ID

C06456

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Foscarnet

METLIN ID

Not Available

PubChem Compound

3415

PDB ID

PPF

ChEBI ID

127780

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Transporters

Enzyme Details

1. Monocarboxylate transporter 1

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

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 ]

Enzyme Details

2. Solute carrier family 22 member 6

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

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 ]

Showing metabocard for Foscarnet (HMDB0014670)

MOL for HMDB0014670 (Foscarnet)

3D MOL for HMDB0014670 (Foscarnet)

3D SDF for HMDB0014670 (Foscarnet)

3D-SDF for HMDB0014670 (Foscarnet)

PDB for HMDB0014670 (Foscarnet)

3D PDB for HMDB0014670 (Foscarnet)

SMILES for HMDB0014670 (Foscarnet)

INCHI for HMDB0014670 (Foscarnet)

Structure for HMDB0014670 (Foscarnet)

3D Structure for HMDB0014670 (Foscarnet)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Transporters

References

References