Showing metabocard for Phenylphosphonate (MMDBc0030145)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:55:38 UTC
Update Date2022-08-31 17:40:07 UTC
Metabolite IDMMDBc0030145
Metabolite Identification
Common NamePhenylphosphonate
DescriptionPhenylphosphonate is a member of the chemical class known as Phenylphosphines and Derivatives. These are compounds containing a phenylphosphine, which consists of phosphine substituent bound to a phenyl group. . Phosphonates (Pn) are a large class of organophosphorus molecules that have direct carbon-phosphorus (C-P) bonds in place of the carbon-oxygen-phosphorus ester bond. In bacteria two pathways exist for Pn breakdown for use as a P source: the phosphonatase and C-P lyase pathways. These pathways differ both in regard to their substrate specificity and their cleavage mechanism. The phosphonatase pathway acts on the natural Pn alpha-aminoethylphosphonate (AEPn). In a two-step process it leads to cleavage of the C-P bond by a hydrolysis reaction requiring an adjacent carbonyl group. In contrast the C-P lyase pathway has a broad substrate specificity. It leads to cleavage of substituted Pn (such as AEPn) as well as unsubstituted Pn by a mechanism involving redox or radical chemistry. Due to its broad substrate specificity, the C-P lyase pathway is generally thought to be responsible for the breakdown of Pn herbicides (such as glyphosate) by bacteria.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x0000559cffcce128>

Structure #1
  Mrv0541 02241207112D          

 10 10  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
  6 10  1  0  0  0  0
  7 10  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  2  0  0  0  0
M  CHG  2   7  -1   8  -1
M  END
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3D MOL for #<Metabolite:0x0000559cffcce128>

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3D SDF for #<Metabolite:0x0000559cffcce128>
Structure #1
  Mrv0541 02241207112D          

 10 10  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
  6 10  1  0  0  0  0
  7 10  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  2  0  0  0  0
M  CHG  2   7  -1   8  -1
M  END
> <DATABASE_ID>
MMDBc0030145

> <DATABASE_NAME>
MIME

> <SMILES>
[O-]P([O-])(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H7O3P/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)/p-2

> <INCHI_KEY>
QLZHNIAADXEJJP-UHFFFAOYSA-L

> <FORMULA>
C6H5O3P

> <MOLECULAR_WEIGHT>
156.0759

> <EXACT_MASS>
155.997630538

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
12.922543520292686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
phenylphosphonate

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
0.47840000000000027

> <ALOGPS_LOGS>
-1.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.240607835561069

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8492216587743582

> <JCHEM_POLAR_SURFACE_AREA>
63.19

> <JCHEM_REFRACTIVITY>
35.00300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x0000559cffcce128>
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PDB for #<Metabolite:0x0000559cffcce128>
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O-1
HETATM    8  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0      -0.206   3.850   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0       1.334   3.850   0.000  0.00  0.00           P+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   10                                                  
CONECT    7   10                                                            
CONECT    8   10                                                            
CONECT    9   10                                                            
CONECT   10    6    7    8    9                                             
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for #<Metabolite:0x0000559cffcce128>
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SMILES for #<Metabolite:0x0000559cffcce128>
[O-]P([O-])(=O)C1=CC=CC=C1
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INCHI for #<Metabolite:0x0000559cffcce128>
InChI=1S/C6H7O3P/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)/p-2
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Synonyms
ValueSource
Phenylphosphonic acidGenerator
Phenylphosphonic acid, disodium saltMeSH
Phenylphosphonic acid, dysposium (3+) saltMeSH
Phenylphosphonic acid, erbium (3+) salt (3:2)MeSH
Phenylphosphonic acid, erbium (3+) salt (3:2), dihydrateMeSH
Phenylphosphonic acid, neodymium (3+) salt (3:2)MeSH
Phenylphosphonic acid, thulium (3+) salt (3:2)MeSH
Phenylphosphonic acid, aluminum saltMeSH
Phenylphosphonic acid, cerium (3+) salt (3:2)MeSH
Phenylphosphonic acid, dysposium (3+) salt (3:2), dihydrateMeSH
Phenylphosphonic acid, monocalcium saltMeSH
Phenylphosphonic acid, monosodium saltMeSH
Phenylphosphonic acid, potassium saltMeSH
Phenylphosphonic acid, terbium (3+) salt (3:2)MeSH
Phenylphosphonic acid, zinc saltMeSH
Phenylphosphonic acid, calcium saltMeSH
Phenylphosphonic acid, copper saltMeSH
Phenylphosphonic acid, holmium (3+) salt (3:2)MeSH
Phenylphosphonic acid, lanthanum (3+) salt (3:2)MeSH
Phenylphosphonic acid, monomagnesium saltMeSH
Phenylphosphonic acid, praseodymium (3+) salt (3:2), dihydrateMeSH
Phenylphosphonic acid, samarium (3+) salt (3:2), dihydrateMeSH
Phenylphosphonic acid, ytterbium (3+) salt (3:2)MeSH
Phenylphosphonic acid, yttrium (3+) salt (3:2)MeSH
Phenylphosphonic acid, zirconium (1+) salt (2:1)MeSH
Benzenephosphonic acidMeSH
Phenylphosphonic acid, dipotassium saltMeSH
Phenylphosphonic acid, europium (3+) salt (3:2)MeSH
Phenylphosphonic acid, gadolinium (3+) salt (3:2)MeSH
Phenylphosphonic acid, lutetium (3+) salt (3:2)MeSH
Phenylphosphonic acid, magnesium saltMeSH
Phenylphosphonic acid, monolead (2+) saltMeSH
Phenylphosphonic acid, neodymium (3+) salt (3:2), monohydrateMeSH
Phenylphosphonic acid, praseodymium (3+) salt (3:2)MeSH
Phenylphosphonic acid, samarium (3+) salt (3:2)MeSH
Phenylphosphonic acid, sodium saltMeSH
Molecular FormulaC6H5O3P
Average Mass156.0759
Monoisotopic Mass155.997630538
IUPAC Namephenylphosphonate
Traditional Namephenylphosphonate
CAS Registry Number1571-33-1
SMILES
[O-]P([O-])(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C6H7O3P/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)/p-2
InChI KeyQLZHNIAADXEJJP-UHFFFAOYSA-L