phosphonoformic acid (CHEBI:127780)

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ChEBI Name	phosphonoformic acid

ChEBI ID	CHEBI:127780

Definition	Phosphoric acid in which one of the hydroxy groups is replaced by a carboxylic acid group. It is used as the trisodium salt as an antiviral agent in the treatment of cytomegalovirus retinitis (CMV retinitis, an inflamation of the retina that can lead to blindness) and as an alternative to ganciclovir for AIDS patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45085, CHEBI:8158

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Formula

CH3O5P

Net Charge

Average Mass

126.00530

Monoisotopic Mass

125.97181

InChI

InChI=1S/CH3O5P/c2-1(3)7(4,5)6/h(H,2,3)(H2,4,5,6)

InChIKey

ZJAOAACCNHFJAH-UHFFFAOYSA-N

SMILES

OC(=O)P(O)(O)=O

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	antiviral drug A substance used in the prophylaxis or therapy of virus diseases. HIV-1 reverse transcriptase inhibitor An entity which inhibits the activity of HIV-1 reverse transcriptase. sodium-dependent Pi-transporter inhibitor Any substance that inhibits the action of sodium-dependent Pi-transporters.

Application(s):	antiviral drug A substance used in the prophylaxis or therapy of virus diseases. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

ChEBI Ontology
Outgoing	phosphonoformic acid (CHEBI:127780) has functional parent formic acid (CHEBI:30751) phosphonoformic acid (CHEBI:127780) has functional parent phosphonic acid (CHEBI:44976) phosphonoformic acid (CHEBI:127780) has role antiviral drug (CHEBI:36044) phosphonoformic acid (CHEBI:127780) has role geroprotector (CHEBI:176497) phosphonoformic acid (CHEBI:127780) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756) phosphonoformic acid (CHEBI:127780) has role sodium-dependent Pi-transporter inhibitor (CHEBI:63330) phosphonoformic acid (CHEBI:127780) is a carboxylic acid (CHEBI:33575) phosphonoformic acid (CHEBI:127780) is a one-carbon compound (CHEBI:64708) phosphonoformic acid (CHEBI:127780) is a phosphonic acids (CHEBI:26069) phosphonoformic acid (CHEBI:127780) is conjugate acid of phosphonatoformate (CHEBI:60268) phosphonoformic acid (CHEBI:127780) is conjugate acid of phosphonoformate(2−) (CHEBI:91254)

Incoming	CMP-5'-phosphonoformic acid (CHEBI:131759) has functional parent phosphonoformic acid (CHEBI:127780) phosphonatoformate (CHEBI:60268) is conjugate base of phosphonoformic acid (CHEBI:127780) phosphonoformate(2−) (CHEBI:91254) is conjugate base of phosphonoformic acid (CHEBI:127780)

IUPAC Name

dihydroxyphosphanecarboxylic acid oxide

Last Modified

28 October 2021