Np mrd loader

Showing NP-Card for Hydroxymethylphosphonic acid (NP0050521)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-27 21:47:07 UTC
Updated at2022-04-27 21:47:07 UTC
NP-MRD IDNP0050521
Secondary Accession NumbersNone
Natural Product Identification
Common NameHydroxymethylphosphonic acid
DescriptionHydroxymethylphosphonic acid, also known as methanehydroxyphosphonate, belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. A phosphonic acid having a hydroxymethyl group attached to the phosphorus. Hydroxymethylphosphonic acid is found in Streptomyces hygroscopicus. Hydroxymethylphosphonic acid was first documented in 1984 (PMID: 6239850). Hydroxymethylphosphonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 12697754) (PMID: 3009455).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050521 (Hydroxymethylphosphonic acid)


  Mrv0541 09041212382D          

  6  5  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
M  END
Download

3D MOL for NP0050521 (Hydroxymethylphosphonic acid)

Download
3D SDF for NP0050521 (Hydroxymethylphosphonic acid)

  Mrv0541 09041212382D          

  6  5  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050521

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/CH5O4P/c2-1-6(3,4)5/h2H,1H2,(H2,3,4,5)

> <INCHI_KEY>
GTTBQSNGUYHPNK-UHFFFAOYSA-N

> <FORMULA>
CH5O4P

> <MOLECULAR_WEIGHT>
112.0218

> <EXACT_MASS>
111.99254516

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
7.752614827282029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(hydroxymethyl)phosphonic acid

> <ALOGPS_LOGP>
-1.46

> <JCHEM_LOGP>
-1.619979677

> <ALOGPS_LOGS>
-0.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.909005396478078

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.355552725773551

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7378066504674843

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
18.838

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxymethylphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050521 (Hydroxymethylphosphonic acid)
Download
PDB for NP0050521 (Hydroxymethylphosphonic acid)
HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
CONECT    1    2    6                                                       
CONECT    2    1                                                            
CONECT    3    6                                                            
CONECT    4    6                                                            
CONECT    5    6                                                            
CONECT    6    1    3    4    5                                             
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

Download
3D PDB for NP0050521 (Hydroxymethylphosphonic acid)
Download
SMILES for NP0050521 (Hydroxymethylphosphonic acid)
OCP(O)(O)=O
Download
INCHI for NP0050521 (Hydroxymethylphosphonic acid)
InChI=1S/CH5O4P/c2-1-6(3,4)5/h2H,1H2,(H2,3,4,5)
Download
View in JSmol
Synonyms
ValueSource
(Hydroxymethyl)phosphonic acidChEBI
Hydroxymethanephosphonic acidChEBI
Methanehydroxyphosphonic acidChEBI
p-(Hydroxymethyl)phosphonic acidChEBI
p-(Hydroxymethyl)-phosphonic acidKegg
(Hydroxymethyl)phosphonateGenerator
HydroxymethanephosphonateGenerator
MethanehydroxyphosphonateGenerator
p-(Hydroxymethyl)phosphonateGenerator
p-(Hydroxymethyl)-phosphonateGenerator
HydroxymethylphosphonateGenerator
Chemical FormulaCH5O4P
Average Mass112.0218 Da
Monoisotopic Mass111.99255 Da
IUPAC Name(hydroxymethyl)phosphonic acid
Traditional Namehydroxymethylphosphonate
CAS Registry NumberNot Available
SMILES
OCP(O)(O)=O
InChI Identifier
InChI=1S/CH5O4P/c2-1-6(3,4)5/h2H,1H2,(H2,3,4,5)
InChI KeyGTTBQSNGUYHPNK-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
    • 

  • 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-1.5ALOGPS
logP-1.6ChemAxon
logS-0.65ALOGPS
pKa (Strongest Acidic)1.36ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.84 m³·mol⁻¹ChemAxon
Polarizability7.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000791  
Chemspider IDNot Available
KEGG Compound IDC06455  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75795  
PDB IDNot Available
ChEBI ID5810  
Good Scents IDNot Available
References
General References
  1. Kulakova AN, Wisdom GB, Kulakov LA, Quinn JP: The purification and characterization of phosphonopyruvate hydrolase, a novel carbon-phosphorus bond cleavage enzyme from Variovorax sp Pal2. J Biol Chem. 2003 Jun 27;278(26):23426-31. doi: 10.1074/jbc.M301871200. Epub 2003 Apr 15. [PubMed:12697754  ] 
  2. Szczepanska-Konkel M, Yusufi AN, VanScoy M, Webster SK, Dousa TP: Phosphonocarboxylic acids as specific inhibitors of Na+-dependent transport of phosphate across renal brush border membrane. J Biol Chem. 1986 May 15;261(14):6375-83. [PubMed:3009455  ] 
  3. Imai S, Seto H, Sasaki T, Tsuruoka T, Ogawa H, Satoh A, Inouye S, Niida T, Otake N: Studies on the biosynthesis of bialaphos (SF-1293). 4. Production of phosphonic acid derivatives, 2-hydroxyethylphosphonic acid, hydroxymethylphosphonic acid and phosphonoformic acid by blocked mutants of Streptomyces hygroscopicus SF-1293 and their roles in the biosynthesis of bialaphos. J Antibiot (Tokyo). 1984 Nov;37(11):1505-8. doi: 10.7164/antibiotics.37.1505. [PubMed:6239850  ]