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Showing NP-Card for Phosphonoacetate (NP0000432)

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Record Information
Version1.0
Created at2006-08-13 11:11:24 UTC
Updated at2021-06-29 00:47:52 UTC
NP-MRD IDNP0000432
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhosphonoacetate
DescriptionPhosphonoacetate, also known as fosfonet or phosphonacetic acid, belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. Phosphonoacetate exists in all living organisms, ranging from bacteria to humans.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000432 (Phosphonoacetate)


  Mrv1652305271900262D          

  8  7  0  0  0  0            999 V2000
    0.1105   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
M  END
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3D MOL for NP0000432 (Phosphonoacetate)

HMDB0004110
     RDKit          3D
Phosphonoacetate
 13 12  0  0  0  0  0  0  0  0999 V2000
    1.6175    0.4155   -1.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6641    0.0100   -0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9001   -0.1905    0.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4662   -0.2785    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0754    0.0073   -0.4693 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.9185    0.2949   -1.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1255   -1.3382   -0.3399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9278    1.3210    0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057    0.0750    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5135    0.4201    1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5305   -1.3065    0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0629   -1.0333   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875    1.3397    1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  3  9  1  0
  4 10  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
M  END
Download

3D SDF for NP0000432 (Phosphonoacetate)


  Mrv1652305271900262D          

  8  7  0  0  0  0            999 V2000
    0.1105   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CP(O)(O)=O

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

> <INCHI_KEY>
XUYJLQHKOGNDPB-UHFFFAOYSA-N

> <FORMULA>
C2H5O5P

> <MOLECULAR_WEIGHT>
140.0319

> <EXACT_MASS>
139.987459782

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.62935134077581

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-phosphonoacetic acid

> <ALOGPS_LOGP>
-2.58

> <JCHEM_LOGP>
-1.6011253753333332

> <ALOGPS_LOGS>
-0.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.175716720456989

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6377235892899562

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
23.634

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosphonoacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0000432 (Phosphonoacetate)

HMDB0004110
     RDKit          3D
Phosphonoacetate
 13 12  0  0  0  0  0  0  0  0999 V2000
    1.6175    0.4155   -1.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6641    0.0100   -0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9001   -0.1905    0.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4662   -0.2785    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0754    0.0073   -0.4693 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.9185    0.2949   -1.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1255   -1.3382   -0.3399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9278    1.3210    0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057    0.0750    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5135    0.4201    1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5305   -1.3065    0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0629   -1.0333   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875    1.3397    1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  3  9  1  0
  4 10  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
M  END
Download

PDB for NP0000432 (Phosphonoacetate)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       0.206  -3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.206  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.127  -1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    5  P   UNK     0       1.540   0.000   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0       1.540   1.540   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.080   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for NP0000432 (Phosphonoacetate)

COMPND    HMDB0004110
HETATM    1  O1  UNL     1       1.617   0.415  -1.621  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.664   0.010  -0.439  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.900  -0.191   0.163  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.466  -0.278   0.385  1.00  0.00           C  
HETATM    5  P1  UNL     1      -1.075   0.007  -0.469  1.00  0.00           P  
HETATM    6  O3  UNL     1      -0.918   0.295  -1.930  1.00  0.00           O  
HETATM    7  O4  UNL     1      -2.126  -1.338  -0.340  1.00  0.00           O  
HETATM    8  O5  UNL     1      -1.928   1.321   0.215  1.00  0.00           O  
HETATM    9  H1  UNL     1       3.106   0.075   1.116  1.00  0.00           H  
HETATM   10  H2  UNL     1       0.514   0.420   1.259  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.531  -1.307   0.834  1.00  0.00           H  
HETATM   12  H4  UNL     1      -3.063  -1.033  -0.361  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.688   1.340   1.188  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5   10   11
CONECT    5    6    6    7    8
CONECT    7   12
CONECT    8   13
END
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SMILES for NP0000432 (Phosphonoacetate)

OC(=O)CP(O)(O)=O
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INCHI for NP0000432 (Phosphonoacetate)

InChI=1S/C2H5O5P/c3-2(4)1-8(5,6)7/h1H2,(H,3,4)(H2,5,6,7)
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View in JSmol
Synonyms
ValueSource
FosfonetChEBI
Phosphonoacetic acidKegg
CarboxymethanephosphonateHMDB
Carboxymethanephosphonic acidHMDB
Disodium carboxymethylphosphonateHMDB
Disodium phosphonoacetateHMDB
Disodium phosphonoacetate monohydrateHMDB
Fosfonet sodiumHMDB
FosfonoacetateHMDB
Fosfonoacetic acidHMDB
Lopac-p-6909HMDB
PAEHMDB
PhosphonacetateHMDB
Phosphonacetic acidHMDB
PPAHMDB
Acid, phosphonoaceticHMDB
Phosphonoacetate, disodiumHMDB
Sodium, fosfonetHMDB
Acid, phosphonaceticHMDB
PhosphonoacetateChEBI
Chemical FormulaC2H5O5P
Average Mass140.0319 Da
Monoisotopic Mass139.98746 Da
IUPAC Name2-phosphonoacetic acid
Traditional Namephosphonoacetic acid
CAS Registry Number4408-78-0
SMILES
OC(=O)CP(O)(O)=O
InChI Identifier
InChI=1S/C2H5O5P/c3-2(4)1-8(5,6)7/h1H2,(H,3,4)(H2,5,6,7)
InChI KeyXUYJLQHKOGNDPB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)V.dorna832021-09-06View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point143 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility392 mg/mL at 0 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility25.1 g/LALOGPS
logP-2.6ALOGPS
logP-1.6ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)1.64ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.63 m³·mol⁻¹ChemAxon
Polarizability9.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004110
DrugBank IDDB02823
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023313
KNApSAcK IDNot Available
Chemspider ID531
KEGG Compound IDC05682
BioCyc IDCPD-764
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7018
PubChem Compound546
PDB IDPAE
ChEBI ID15732
Good Scents IDNot Available
References
General References
  1. Abendroth A, Lin I, Slobedman B, Ploegh H, Arvin AM: Varicella-zoster virus retains major histocompatibility complex class I proteins in the Golgi compartment of infected cells. J Virol. 2001 May;75(10):4878-88. [PubMed:11312359 ]
  2. Sairenji T, Hinuma Y, Sekizawa T, Yoshida M: Appearance of early and late components of Epstein-Barr virus-associated membrane antigen in Daudi cells superinfected with P3HR-1 virus. J Gen Virol. 1978 Jan;38(1):111-20. [PubMed:202665 ]
  3. Dittmer A, Drach JC, Townsend LB, Fischer A, Bogner E: Interaction of the putative human cytomegalovirus portal protein pUL104 with the large terminase subunit pUL56 and its inhibition by benzimidazole-D-ribonucleosides. J Virol. 2005 Dec;79(23):14660-7. doi: 10.1128/JVI.79.23.14660-14667.2005. [PubMed:16282466 ]
  4. E X, Savidis G, Chin CR, Wang S, Lu S, Brass AL, Kowalik TF: A novel DDB2-ATM feedback loop regulates human cytomegalovirus replication. J Virol. 2014 Feb;88(4):2279-90. doi: 10.1128/JVI.03423-13. Epub 2013 Dec 11. [PubMed:24335308 ]
  5. Klimek-Ochab M: Phosphate-independent utilization of phosphonoacetic acid as sole phosphorus source by a psychrophilic strain of Geomyces pannorum P15. Folia Microbiol (Praha). 2014 Sep;59(5):375-80. doi: 10.1007/s12223-014-0309-3. Epub 2014 Feb 26. [PubMed:24570323 ]