Showing metabocard for Phosphoserine (MMDBc0029488)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:24:20 UTC
Update Date2024-10-15 20:11:49 UTC
Metabolite IDMMDBc0029488
Metabolite Identification
Common NamePhosphoserine
DescriptionPhosphoserine is phosphoric acid ester of serine. As a constituent (residue) of proteins, its side chain can undergo O-linked glycosylation. It is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling. Phosphorylated serine residues are often referred to as phosphoserine.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f46c1976468>


  Mrv1652309032023592D          

 11 10  0  0  1  0            999 V2000
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  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
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f46c1976468>

HMDB0000272
     RDKit          3D
Phosphoserine
 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.6079   -0.7593   -0.8790 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1320   -0.4959    0.4617 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1563    0.2782    0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0460   -0.5377   -0.3731 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5394    0.1877   -0.5892 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.9514    1.0253    0.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.0179   -0.7853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5025    1.1030   -1.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1524    0.1811    1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9567    0.5067    2.4584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3757    0.4736    0.6886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137   -1.4090   -0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105    0.1569   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9252   -1.4996    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764    1.1884   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    0.6016    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784   -1.8513   -0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368    2.0509   -1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1311   -0.1826    0.5843 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  2  0
  5  7  1  0
  5  8  1  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  0
  3 16  1  0
  7 17  1  0
  8 18  1  0
 11 19  1  0
M  END
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3D SDF for #<Metabolite:0x00007f46c1976468>


  Mrv1652309032023592D          

 11 10  0  0  1  0            999 V2000
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  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
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029488

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1

> <INCHI_KEY>
BZQFBWGGLXLEPQ-REOHCLBHSA-N

> <FORMULA>
C3H8NO6P

> <MOLECULAR_WEIGHT>
185.0725

> <EXACT_MASS>
185.008923505

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.968826440672615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(phosphonooxy)propanoic acid

> <ALOGPS_LOGP>
-2.32

> <JCHEM_LOGP>
-3.180275047030002

> <ALOGPS_LOGS>
-0.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.066741968210883

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1985006020847058

> <JCHEM_PKA_STRONGEST_BASIC>
9.39423622748354

> <JCHEM_POLAR_SURFACE_AREA>
130.08

> <JCHEM_REFRACTIVITY>
32.9139

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosphoserine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f46c1976468>

HMDB0000272
     RDKit          3D
Phosphoserine
 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.6079   -0.7593   -0.8790 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1320   -0.4959    0.4617 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1563    0.2782    0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0460   -0.5377   -0.3731 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5394    0.1877   -0.5892 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.9514    1.0253    0.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.0179   -0.7853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5025    1.1030   -1.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1524    0.1811    1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9567    0.5067    2.4584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3757    0.4736    0.6886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137   -1.4090   -0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105    0.1569   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9252   -1.4996    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764    1.1884   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    0.6016    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784   -1.8513   -0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368    2.0509   -1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1311   -0.1826    0.5843 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  2  0
  5  7  1  0
  5  8  1  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  0
  3 16  1  0
  7 17  1  0
  8 18  1  0
 11 19  1  0
M  END
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PDB for #<Metabolite:0x00007f46c1976468>

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  N   UNK     0       8.621   4.977   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.954   3.437   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0       4.620   2.667   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0       3.286   1.897   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.390   1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007f46c1976468>

COMPND    HMDB0000272
HETATM    1  N1  UNL     1      -1.608  -0.759  -0.879  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.132  -0.496   0.462  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.156   0.278   0.345  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.046  -0.538  -0.373  1.00  0.00           O  
HETATM    5  P1  UNL     1       2.539   0.188  -0.589  1.00  0.00           P  
HETATM    6  O2  UNL     1       2.951   1.025   0.590  1.00  0.00           O  
HETATM    7  O3  UNL     1       3.709  -1.018  -0.785  1.00  0.00           O  
HETATM    8  O4  UNL     1       2.503   1.103  -1.991  1.00  0.00           O  
HETATM    9  C3  UNL     1      -2.152   0.181   1.264  1.00  0.00           C  
HETATM   10  O5  UNL     1      -1.957   0.507   2.458  1.00  0.00           O  
HETATM   11  O6  UNL     1      -3.376   0.474   0.689  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.414  -1.409  -0.873  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.811   0.157  -1.339  1.00  0.00           H  
HETATM   14  H3  UNL     1      -0.925  -1.500   0.929  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.076   1.188  -0.277  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.562   0.602   1.310  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.478  -1.851  -0.316  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.637   2.051  -1.749  1.00  0.00           H  
HETATM   19  H8  UNL     1      -4.131  -0.183   0.584  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    9   14
CONECT    3    4   15   16
CONECT    4    5
CONECT    5    6    6    7    8
CONECT    7   17
CONECT    8   18
CONECT    9   10   10   11
CONECT   11   19
END
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SMILES for #<Metabolite:0x00007f46c1976468>

N[C@@H](COP(O)(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007f46c1976468>

InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1
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Synonyms
ValueSource
(+)-L-Serine dihydrogen phosphate (ester)ChEBI
(2S)-2-Amino-3-(phosphonooxy)propanoic acidChEBI
(S)-2-Amino-3-hydroxypropanoic acid 3-phosphateChEBI
3-PhosphoserineChEBI
DexfosfoserineChEBI
L-O-PhosphoserineChEBI
O-PhosphoserineChEBI
3-Phospho-L-serineKegg
(+)-L-Serine dihydrogen phosphoric acid (ester)Generator
(2S)-2-Amino-3-(phosphonooxy)propanoateGenerator
(S)-2-Amino-3-hydroxypropanoate 3-phosphateGenerator
(S)-2-Amino-3-hydroxypropanoic acid 3-phosphoric acidGenerator
3-O-PhosphoserineHMDB
FosforinaHMDB
L-3-PhosphoserineHMDB
L-O-Serine phosphateHMDB
L-PhosphoserineHMDB
L-Serine dihydrogen phosphate (ester)HMDB
L-Serine phosphateHMDB
L-SerinephosphorateHMDB
L-Serinephosphoric acidHMDB
L-Seryl phosphateHMDB
PlasmenylserineHMDB
Molecular FormulaC3H8NO6P
Average Mass185.0725
Monoisotopic Mass185.008923505
IUPAC Name(2S)-2-amino-3-(phosphonooxy)propanoic acid
Traditional Namephosphoserine
CAS Registry Number407-41-0
SMILES
N[C@@H](COP(O)(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1
InChI KeyBZQFBWGGLXLEPQ-REOHCLBHSA-N