Showing metabocard for O-Phosphohomoserine (MMDBc0029716)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:38:46 UTC
Update Date2024-04-30 19:41:07 UTC
Metabolite IDMMDBc0029716
Metabolite Identification
Common NameO-Phosphohomoserine
DescriptionO-phosphohomoserine is a naturally occurring analogue of phosphonate amino acids. It is an intermediate in glycine, serine and threonine metabolism. It is comverted to L-threonine via threonine synthase (EC:4.2.3.1). (KEGG)
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fecb1f630b0>


  Mrv1652309042000292D          

 12 11  0  0  1  0            999 V2000
   22.6899  -10.1774    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.4044   -9.7649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2774   -9.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9754  -10.5899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9768  -10.1774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1024  -10.8918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2623   -8.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5479  -11.0024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5479  -10.1774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.1189  -10.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8333   -9.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2623   -9.7649    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  1  0  0  0  0
  1  6  2  0  0  0  0
  2 10  1  0  0  0  0
  5 12  1  0  0  0  0
  7 12  2  0  0  0  0
  9  8  1  1  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fecb1f630b0>

HMDB0003484
     RDKit          3D
O-Phosphohomoserine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.7857    1.7584    0.0243 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8534    0.6299   -0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4747    1.1539    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    0.0553   -0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8480    0.5538    0.1373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8735   -0.7996   -0.0644 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.4409   -1.8567    0.9191 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412   -0.3338    0.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8145   -1.3587   -1.6520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2563   -0.4104    0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491   -0.1801    1.6960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7016   -1.6666    0.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3958    2.6104   -0.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6726    1.4886   -0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188    0.2648   -1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3879    1.6825    1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670    1.9487   -0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3518   -0.7726    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282   -0.3693   -1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785    0.3630    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9249   -2.3404   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -2.4213    0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  6
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  8 20  1  0
  9 21  1  0
 12 22  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fecb1f630b0>


  Mrv1652309042000292D          

 12 11  0  0  1  0            999 V2000
   22.6899  -10.1774    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.4044   -9.7649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2774   -9.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9754  -10.5899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9768  -10.1774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1024  -10.8918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2623   -8.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5479  -11.0024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5479  -10.1774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.1189  -10.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8333   -9.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2623   -9.7649    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  1  0  0  0  0
  1  6  2  0  0  0  0
  2 10  1  0  0  0  0
  5 12  1  0  0  0  0
  7 12  2  0  0  0  0
  9  8  1  1  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029716

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H](CCOP(O)(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H10NO6P/c5-3(4(6)7)1-2-11-12(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1

> <INCHI_KEY>
FXDNYOANAXWZHG-VKHMYHEASA-N

> <FORMULA>
C4H10NO6P

> <MOLECULAR_WEIGHT>
199.0991

> <EXACT_MASS>
199.024573569

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.862376851424528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-(phosphonooxy)butanoic acid

> <ALOGPS_LOGP>
-2.34

> <JCHEM_LOGP>
-3.160008943226651

> <ALOGPS_LOGS>
-1.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.279284969740528

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5192579618572903

> <JCHEM_PKA_STRONGEST_BASIC>
9.460891275706492

> <JCHEM_POLAR_SURFACE_AREA>
130.08

> <JCHEM_REFRACTIVITY>
37.779300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-phosphohomoserine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fecb1f630b0>

HMDB0003484
     RDKit          3D
O-Phosphohomoserine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.7857    1.7584    0.0243 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8534    0.6299   -0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4747    1.1539    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    0.0553   -0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8480    0.5538    0.1373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8735   -0.7996   -0.0644 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.4409   -1.8567    0.9191 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412   -0.3338    0.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8145   -1.3587   -1.6520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2563   -0.4104    0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491   -0.1801    1.6960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7016   -1.6666    0.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3958    2.6104   -0.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6726    1.4886   -0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188    0.2648   -1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3879    1.6825    1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670    1.9487   -0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3518   -0.7726    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282   -0.3693   -1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785    0.3630    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9249   -2.3404   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -2.4213    0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  6
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  8 20  1  0
  9 21  1  0
 12 22  1  0
M  END
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PDB for #<Metabolite:0x00007fecb1f630b0>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  P   UNK     0      42.354 -18.998   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      43.688 -18.228   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      41.584 -17.664   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      41.021 -19.768   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      50.357 -18.998   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      43.124 -20.331   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      49.023 -16.688   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      47.689 -20.538   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      47.689 -18.998   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      45.022 -18.998   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      46.355 -18.228   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.023 -18.228   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    6                                             
CONECT    2    1   10                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5   12                                                            
CONECT    6    1                                                            
CONECT    7   12                                                            
CONECT    8    9                                                            
CONECT    9    8   11   12                                                  
CONECT   10    2   11                                                       
CONECT   11    9   10                                                       
CONECT   12    5    7    9                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for #<Metabolite:0x00007fecb1f630b0>

COMPND    HMDB0003484
HETATM    1  N1  UNL     1      -2.786   1.758   0.024  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.853   0.630  -0.131  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.475   1.154   0.096  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.539   0.055  -0.055  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.848   0.554   0.137  1.00  0.00           O  
HETATM    6  P1  UNL     1       2.874  -0.800  -0.064  1.00  0.00           P  
HETATM    7  O2  UNL     1       2.441  -1.857   0.919  1.00  0.00           O  
HETATM    8  O3  UNL     1       4.441  -0.334   0.283  1.00  0.00           O  
HETATM    9  O4  UNL     1       2.815  -1.359  -1.652  1.00  0.00           O  
HETATM   10  C4  UNL     1      -2.256  -0.410   0.830  1.00  0.00           C  
HETATM   11  O5  UNL     1      -3.149  -0.180   1.696  1.00  0.00           O  
HETATM   12  O6  UNL     1      -1.702  -1.667   0.841  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.396   2.610  -0.405  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.673   1.489  -0.461  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.019   0.265  -1.163  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.388   1.683   1.067  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.267   1.949  -0.677  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.352  -0.773   0.663  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.428  -0.369  -1.073  1.00  0.00           H  
HETATM   20  H8  UNL     1       4.479   0.363   0.959  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.925  -2.340  -1.684  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.178  -2.421   0.350  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3   10   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6
CONECT    6    7    7    8    9
CONECT    8   20
CONECT    9   21
CONECT   10   11   11   12
CONECT   12   22
END
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SMILES for #<Metabolite:0x00007fecb1f630b0>

N[C@@H](CCOP(O)(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fecb1f630b0>

InChI=1S/C4H10NO6P/c5-3(4(6)7)1-2-11-12(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1
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Synonyms
ValueSource
Homoserine phosphateChEBI
L-Homoserine, dihydrogen phosphate (ester)ChEBI
Homoserine phosphoric acidGenerator
L-Homoserine, dihydrogen phosphoric acid (ester)Generator
2-amino-4-Hydroxy-butyric acid phosphateHMDB
L-2-amino-4-Hydroxy-butyric acid dihydrogen phosphate (ester)HMDB
O-phospho-HomoserineHMDB
O-phospho-L-HomoserineHMDB
O-Phosphohomoserine, (DL)-isomerMeSH, HMDB
Molecular FormulaC4H10NO6P
Average Mass199.0991
Monoisotopic Mass199.024573569
IUPAC Name(2S)-2-amino-4-(phosphonooxy)butanoic acid
Traditional NameO-phosphohomoserine
CAS Registry Number4210-66-6
SMILES
N[C@@H](CCOP(O)(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H10NO6P/c5-3(4(6)7)1-2-11-12(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1
InChI KeyFXDNYOANAXWZHG-VKHMYHEASA-N