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Showing NP-Card for Phosphonoformic acid (NP0050531)

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Record Information
Version2.0
Created at2022-04-27 21:56:00 UTC
Updated at2022-04-27 21:56:00 UTC
NP-MRD IDNP0050531
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhosphonoformic acid
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. Phosphonoformic acid is found in Streptomyces hygroscopicus. Phosphonoformic acid was first documented in 2001 (PMID: 11576919). Foscarnet is an extremely strong acidic compound (based on its pKa) (PMID: 15182735) (PMID: 16858125) (PMID: 19213941) (PMID: 19288498).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050531 (Phosphonoformic acid)


  Mrv0541 02231214452D          

  7  6  0  0  0  0            999 V2000
    2.8075   -0.2615    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950    0.4529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  7  1  0  0  0  0
  5  7  1  0  0  0  0
  6  7  2  0  0  0  0
M  END
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3D MOL for NP0050531 (Phosphonoformic acid)

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3D SDF for NP0050531 (Phosphonoformic acid)

  Mrv0541 02231214452D          

  7  6  0  0  0  0            999 V2000
    2.8075   -0.2615    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950    0.4529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  7  1  0  0  0  0
  5  7  1  0  0  0  0
  6  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050531

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
CH3O5P

> <MOLECULAR_WEIGHT>
126.0053

> <EXACT_MASS>
125.971809718

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
7.888062129212226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
phosphonoformic acid

> <ALOGPS_LOGP>
-1.63

> <JCHEM_LOGP>
-0.8303841046666666

> <ALOGPS_LOGS>
-0.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.497768602888783

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.09567521963130154

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
19.0731

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
foscarnet

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050531 (Phosphonoformic acid)
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PDB for NP0050531 (Phosphonoformic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0       5.241  -0.488   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0       3.907  -1.258   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.471   0.845   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.011  -1.822   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.908  -0.488   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.574   1.822   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.574   0.282   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    7                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    7                                                            
CONECT    6    7                                                            
CONECT    7    1    5    6                                                  
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0050531 (Phosphonoformic acid)
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SMILES for NP0050531 (Phosphonoformic acid)
OC(=O)P(O)(O)=O
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INCHI for NP0050531 (Phosphonoformic acid)
InChI=1S/CH3O5P/c2-1(3)7(4,5)6/h(H,2,3)(H2,4,5,6)
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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 Mass126.0053 Da
Monoisotopic Mass125.97181 Da
IUPAC Namephosphonoformic acid
Traditional Namefoscarnet
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces hygroscopicusBacteria
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0014670  
DrugBank IDDB00529  
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. Giachelli CM, Jono S, Shioi A, Nishizawa Y, Mori K, Morii H: Vascular calcification and inorganic phosphate. Am J Kidney Dis. 2001 Oct;38(4 Suppl 1):S34-7. doi: 10.1053/ajkd.2001.27394. [PubMed:11576919  ] 
  2. Kim KS, Choi YH, Kim KH, Lee YC, Kim CH, Moon SH, Kang SG, Park YG: Protective and anti-arthritic effects of deer antler aqua-acupuncture (DAA), inhibiting dihydroorotate dehydrogenase, on phosphate ions-mediated chondrocyte apoptosis and rat collagen-induced arthritis. Int Immunopharmacol. 2004 Jul;4(7):963-73. doi: 10.1016/j.intimp.2004.04.010. [PubMed:15182735  ] 
  3. Eto N, Tomita M, Hayashi M: NaPi-mediated transcellular permeation is the dominant route in intestinal inorganic phosphate absorption in rats. Drug Metab Pharmacokinet. 2006 Jun;21(3):217-21. doi: 10.2133/dmpk.21.217. [PubMed:16858125  ] 
  4. Villa-Bellosta R, Sorribas V: Phosphonoformic acid prevents vascular smooth muscle cell calcification by inhibiting calcium-phosphate deposition. Arterioscler Thromb Vasc Biol. 2009 May;29(5):761-6. doi: 10.1161/ATVBAHA.108.183384. Epub 2009 Feb 12. [PubMed:19213941  ] 
  5. Denison TA, Koch CF, Shapiro IM, Schwartz Z, Boyan BD: Inorganic phosphate modulates responsiveness to 24,25(OH)2D3 in chondrogenic ATDC5 cells. J Cell Biochem. 2009 May 1;107(1):155-62. doi: 10.1002/jcb.22111. [PubMed:19288498  ]