Showing metabocard for Phosphonoacetaldehyde (MMDBc0048262)

Pharmaceutical
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-04-29 21:54:59 UTC
Update Date2025-10-07 16:04:13 UTC
Metabolite IDMMDBc0048262
Metabolite Identification
Common NamePhosphonoacetaldehyde
DescriptionPhosphonoacetaldehyde is a phosphonate compound that serves as a significant metabolite in various biochemical pathways. Its chemical structure features a phosphonate group attached to an acetaldehyde moiety, making it a key intermediate in the degradation of organophosphonates. In microbial metabolism, phosphonoacetaldehyde is produced from R-HAEP by the enzyme PbfA, which can then be further processed by other enzymes (PMID:40384479 ). Additionally, it plays a role in the biosynthesis of rhizocticin, where the RhiE and RhiF proteins function together to generate phosphonoacetaldehyde via a thiamine pyrophosphate-dependent decarboxylation process (PMID:39586109 ). The presence of specific genes, such as phnX, which encodes phosphonoacetaldehyde hydrolase, indicates its involvement in pathways that mineralize organic phosphorus, as seen in certain bacterial species that utilize glyphosate as a phosphorus source (PMID:38928116 ). Furthermore, phosphonoacetaldehyde can be generated through hydrolytic pathways that involve the transaminase PhnW, highlighting its importance in microbial phosphorus cycling (PMID:37876809 ). Overall, phosphonoacetaldehyde is integral to various metabolic processes involving phosphonates and organic phosphorus compounds.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f2e264fcbe8>


  Mrv0541 02231216452D          

  7  6  0  0  0  0            999 V2000
    2.8875   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   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  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f2e264fcbe8>

HMDB0256485
     RDKit          3D
phosphonoacetaldehyde
 12 11  0  0  0  0  0  0  0  0999 V2000
    2.3079   -1.0473   -0.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487   -0.1008   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7282   -0.1680    0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -0.2410   -0.3264 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4590   -1.1683   -1.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0679    1.3431   -0.8436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018   -0.7922    0.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    0.8602   -0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344   -1.0350    1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6651    0.7941    1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2611    1.8672   -0.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066   -0.3119    0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  4  7  1  0
  2  8  1  0
  3  9  1  0
  3 10  1  0
  6 11  1  0
  7 12  1  0
M  END
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3D SDF for #<Metabolite:0x00007f2e264fcbe8>


  Mrv0541 02231216452D          

  7  6  0  0  0  0            999 V2000
    2.8875   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   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  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048262

> <DATABASE_NAME>
MIME

> <SMILES>
OP(O)(=O)CC=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H5O4P/c3-1-2-7(4,5)6/h1H,2H2,(H2,4,5,6)

> <INCHI_KEY>
YEMKIGUKNDOZEG-UHFFFAOYSA-N

> <FORMULA>
C2H5O4P

> <MOLECULAR_WEIGHT>
124.0325

> <EXACT_MASS>
123.99254516

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
8.748391812249178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-oxoethyl)phosphonic acid

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-1.8696854596666668

> <ALOGPS_LOGS>
-0.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.191054447993116

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.688364318878702

> <JCHEM_PKA_STRONGEST_BASIC>
-7.255448610798288

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
22.7086

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosphonoacetaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f2e264fcbe8>

HMDB0256485
     RDKit          3D
phosphonoacetaldehyde
 12 11  0  0  0  0  0  0  0  0999 V2000
    2.3079   -1.0473   -0.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487   -0.1008   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7282   -0.1680    0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -0.2410   -0.3264 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4590   -1.1683   -1.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0679    1.3431   -0.8436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018   -0.7922    0.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    0.8602   -0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344   -1.0350    1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6651    0.7941    1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2611    1.8672   -0.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066   -0.3119    0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  4  7  1  0
  2  8  1  0
  3  9  1  0
  3 10  1  0
  6 11  1  0
  7 12  1  0
M  END
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PDB for #<Metabolite:0x00007f2e264fcbe8>

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  O   UNK     0       5.390  -1.334   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0       3.850  -1.334   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0       3.850   0.206   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.850  -2.874   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for #<Metabolite:0x00007f2e264fcbe8>

COMPND    HMDB0256485
HETATM    1  O1  UNL     1       2.308  -1.047  -0.833  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.849  -0.101  -0.232  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.728  -0.168   0.724  1.00  0.00           C  
HETATM    4  P1  UNL     1      -0.799  -0.241  -0.326  1.00  0.00           P  
HETATM    5  O2  UNL     1      -0.459  -1.168  -1.496  1.00  0.00           O  
HETATM    6  O3  UNL     1      -1.068   1.343  -0.844  1.00  0.00           O  
HETATM    7  O4  UNL     1      -2.102  -0.792   0.559  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.311   0.860  -0.441  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.734  -1.035   1.390  1.00  0.00           H  
HETATM   10  H3  UNL     1       0.665   0.794   1.283  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.261   1.867  -0.028  1.00  0.00           H  
HETATM   12  H5  UNL     1      -2.907  -0.312   0.243  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4    9   10
CONECT    4    5    5    6    7
CONECT    6   11
CONECT    7   12
END
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SMILES for #<Metabolite:0x00007f2e264fcbe8>

OP(O)(=O)CC=O
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INCHI for #<Metabolite:0x00007f2e264fcbe8>

InChI=1S/C2H5O4P/c3-1-2-7(4,5)6/h1H,2H2,(H2,4,5,6)
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Synonyms
ValueSource
2-OxoethylphosphonateChEBI
2-PhosphonoacetaldehydeChEBI
2-Oxoethylphosphonic acidGenerator
AcetylphosphonateMeSH
Molecular FormulaC2H5O4P
Average Mass124.0325
Monoisotopic Mass123.99254516
IUPAC Name(2-oxoethyl)phosphonic acid
Traditional Namephosphonoacetaldehyde
CAS Registry NumberNot Available
SMILES
OP(O)(=O)CC=O
InChI Identifier
InChI=1S/C2H5O4P/c3-1-2-7(4,5)6/h1H,2H2,(H2,4,5,6)
InChI KeyYEMKIGUKNDOZEG-UHFFFAOYSA-N