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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:03:19 UTC

Update Date

2021-09-14 15:37:03 UTC

HMDB ID

HMDB0029004

Secondary Accession Numbers

HMDB29004

Metabolite Identification

Common Name

Phenylalanylserine

Description

Phenylalanylserine is a dipeptide composed of phenylalanine and serine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0029004
     RDKit          3D
Phenylalanylserine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -0.9303    1.9886   -1.3679 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3519    1.0905   -0.4211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9828   -0.2832   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4316   -0.2341   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087   -0.0917   -1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7400   -0.0532   -0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1177   -0.1565    0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1449   -0.2980    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8214   -0.3370    1.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0887    0.9212   -0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6101    1.5316   -1.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951    0.0759    0.0492 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3102   -0.0979   -0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1294    0.4424    0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8632   -0.2041    2.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828   -1.5171   -0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551   -2.3750   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8427   -1.9815   -0.8277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3243    1.5547   -2.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4347    2.7885   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4832    1.4805    0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -0.8894    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -0.7855   -1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424   -0.0096   -2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4919    0.0618   -1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1587   -0.1268    0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4422   -0.3791    2.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0734   -0.4499    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4900   -0.4236    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5641    0.5141   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    0.4681    0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308    1.5132    1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5615   -0.8258    2.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1756   -2.9124   -0.6865 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
  9  4  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  6
 14 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END


  Mrv1652304062014062D          

 18 18  0  0  0  0            999 V2000
10001.8001 9999.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.085410000.2157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3730 9999.8034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.659010000.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9455 9999.8034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.230210000.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9455 9998.9797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.659010001.0394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.085410001.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5187 9999.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.804210000.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0897 9999.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0896 9998.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8041 9998.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5187 9998.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.512010000.2149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.8005 9998.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.799910001.4519    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  9  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  1  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
  6 10  1  0  0  0  0
  1 17  2  0  0  0  0
  1 16  1  0  0  0  0
  9 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029004

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O4/c13-9(6-8-4-2-1-3-5-8)11(16)14-10(7-15)12(17)18/h1-5,9-10,15H,6-7,13H2,(H,14,16)(H,17,18)/t9-,10-/m0/s1

> <INCHI_KEY>
ROHDXJUFQVRDAV-UWVGGRQHSA-N

> <FORMULA>
C12H16N2O4

> <MOLECULAR_WEIGHT>
252.27

> <EXACT_MASS>
252.111007003

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.253175519661447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-hydroxypropanoic acid

> <ALOGPS_LOGP>
-2.08

> <JCHEM_LOGP>
-2.770914143970553

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.845032484974062

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.551884402674064

> <JCHEM_PKA_STRONGEST_BASIC>
8.009599951963539

> <JCHEM_POLAR_SURFACE_AREA>
112.64999999999999

> <JCHEM_REFRACTIVITY>
63.957400000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-hydroxypropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029004
     RDKit          3D
Phenylalanylserine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -0.9303    1.9886   -1.3679 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3519    1.0905   -0.4211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9828   -0.2832   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4316   -0.2341   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087   -0.0917   -1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7400   -0.0532   -0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1177   -0.1565    0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1449   -0.2980    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8214   -0.3370    1.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0887    0.9212   -0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6101    1.5316   -1.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951    0.0759    0.0492 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3102   -0.0979   -0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1294    0.4424    0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8632   -0.2041    2.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828   -1.5171   -0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551   -2.3750   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8427   -1.9815   -0.8277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3243    1.5547   -2.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4347    2.7885   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4832    1.4805    0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -0.8894    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -0.7855   -1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424   -0.0096   -2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4919    0.0618   -1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1587   -0.1268    0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4422   -0.3791    2.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0734   -0.4499    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4900   -0.4236    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5641    0.5141   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    0.4681    0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308    1.5132    1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5615   -0.8258    2.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1756   -2.9124   -0.6865 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
  9  4  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  6
 14 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    8670.0278666.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.6938667.069   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8667.3638666.300   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8666.0308667.069   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8664.6988666.300   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8663.3638667.069   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8664.6988664.762   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8666.0308668.607   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8668.6938668.607   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.0358666.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.7018667.071   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8659.3678666.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8659.3678664.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.7018663.991   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.0358664.761   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8671.3568667.068   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8670.0288664.760   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8670.0268669.377   0.000  0.00  0.00           O+0
CONECT    1    2   17   16                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   10                                                       
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    2   18                                                       
CONECT   10   11   15    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    9                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0029004
HETATM    1  N1  UNL     1      -0.930   1.989  -1.368  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.352   1.091  -0.421  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.983  -0.283  -0.430  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.432  -0.234  -0.113  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.409  -0.092  -1.068  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.740  -0.053  -0.706  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.118  -0.156   0.619  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.145  -0.298   1.568  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.821  -0.337   1.216  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.089   0.921  -0.743  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.610   1.532  -1.730  1.00  0.00           O  
HETATM   12  N2  UNL     1       1.895   0.076   0.049  1.00  0.00           N  
HETATM   13  C10 UNL     1       3.310  -0.098  -0.257  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.129   0.442   0.900  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.863  -0.204   2.088  1.00  0.00           O  
HETATM   16  C12 UNL     1       3.583  -1.517  -0.511  1.00  0.00           C  
HETATM   17  O3  UNL     1       2.655  -2.375  -0.447  1.00  0.00           O  
HETATM   18  O4  UNL     1       4.843  -1.981  -0.828  1.00  0.00           O  
HETATM   19  H1  UNL     1      -1.324   1.555  -2.206  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.435   2.788  -0.976  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.483   1.480   0.630  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.483  -0.889   0.350  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.842  -0.786  -1.415  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.142  -0.010  -2.102  1.00  0.00           H  
HETATM   25  H7  UNL     1      -5.492   0.062  -1.500  1.00  0.00           H  
HETATM   26  H8  UNL     1      -6.159  -0.127   0.906  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.442  -0.379   2.609  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.073  -0.450   1.988  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.490  -0.424   0.849  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.564   0.514  -1.146  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.206   0.468   0.650  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.831   1.513   1.043  1.00  0.00           H  
HETATM   33  H15 UNL     1       4.562  -0.826   2.375  1.00  0.00           H  
HETATM   34  H16 UNL     1       5.176  -2.912  -0.687  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3   10   21
CONECT    3    4   22   23
CONECT    4    5    5    9
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   28
CONECT   10   11   11   12
CONECT   12   13   29
CONECT   13   14   16   30
CONECT   14   15   31   32
CONECT   15   33
CONECT   16   17   17   18
CONECT   18   34
END

HMDB0029004
     RDKit          3D
Phenylalanylserine
 34 34  0  0  0  0  0  0  0  0999 V2000
   -0.9303    1.9886   -1.3679 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3519    1.0905   -0.4211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9828   -0.2832   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4316   -0.2341   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087   -0.0917   -1.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7400   -0.0532   -0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1177   -0.1565    0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1449   -0.2980    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8214   -0.3370    1.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0887    0.9212   -0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6101    1.5316   -1.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951    0.0759    0.0492 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3102   -0.0979   -0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1294    0.4424    0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8632   -0.2041    2.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828   -1.5171   -0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551   -2.3750   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8427   -1.9815   -0.8277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3243    1.5547   -2.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4347    2.7885   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4832    1.4805    0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -0.8894    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -0.7855   -1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424   -0.0096   -2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4919    0.0618   -1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1587   -0.1268    0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4422   -0.3791    2.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0734   -0.4499    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4900   -0.4236    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5641    0.5141   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    0.4681    0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308    1.5132    1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5615   -0.8258    2.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1756   -2.9124   -0.6865 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
  9  4  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  6
 14 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
FS	ChEBI
L-Phe-L-ser	ChEBI
F-S Dipeptide	HMDB
FS Dipeptide	HMDB
L-Phenylalanyl-L-serine	HMDB
N-L-Phenylalanyl-L-serine	HMDB
N-Phenylalanylserine	HMDB
Phe-ser	HMDB
Phenylalanine serine dipeptide	HMDB
Phenylalanine-serine dipeptide	HMDB
Phenylalanyl-serine	HMDB
Phenylalanylserine	HMDB, ChEBI

Chemical Formula

C₁₂H₁₆N₂O₄

Average Molecular Weight

252.27

Monoisotopic Molecular Weight

252.111007003

IUPAC Name

(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-hydroxypropanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-hydroxypropanoic acid

CAS Registry Number

16053-39-7

SMILES

N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(O)=O

InChI Identifier

InChI=1S/C12H16N2O4/c13-9(6-8-4-2-1-3-5-8)11(16)14-10(7-15)12(17)18/h1-5,9-10,15H,6-7,13H2,(H,14,16)(H,17,18)/t9-,10-/m0/s1

InChI Key

ROHDXJUFQVRDAV-UWVGGRQHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Serine or derivatives
Alpha-amino acid or derivatives
Amphetamine or derivatives
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Fatty amide
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:71032 )

Ontology

Not Available

Feces (PMID: 27275383)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-2.77	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.89 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-2.8	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	8.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.65 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.96 m³·mol⁻¹	ChemAxon
Polarizability	25.25 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	159.323	30932474
DeepCCS	[M-H]-	156.927	30932474
DeepCCS	[M-2H]-	189.941	30932474
DeepCCS	[M+Na]+	165.374	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylalanylserine	N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(O)=O	3571.5	Standard polar	33892256
Phenylalanylserine	N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(O)=O	2103.1	Standard non polar	33892256
Phenylalanylserine	N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(O)=O	2447.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylalanylserine,1TMS,isomer #1	C[Si](C)(C)OC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(=O)O	2314.5	Semi standard non polar	33892256
Phenylalanylserine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CO)NC(=O)[C@@H](N)CC1=CC=CC=C1	2265.8	Semi standard non polar	33892256
Phenylalanylserine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(=O)O	2314.5	Semi standard non polar	33892256
Phenylalanylserine,1TMS,isomer #4	C[Si](C)(C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[C@@H](CO)C(=O)O	2235.2	Semi standard non polar	33892256
Phenylalanylserine,2TMS,isomer #1	C[Si](C)(C)OC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2242.1	Semi standard non polar	33892256
Phenylalanylserine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO[Si](C)(C)C)C(=O)O	2315.7	Semi standard non polar	33892256
Phenylalanylserine,2TMS,isomer #3	C[Si](C)(C)OC[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C	2258.8	Semi standard non polar	33892256
Phenylalanylserine,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(=O)O[Si](C)(C)C	2281.3	Semi standard non polar	33892256
Phenylalanylserine,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CO)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C	2193.4	Semi standard non polar	33892256
Phenylalanylserine,2TMS,isomer #6	C[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(=O)O)[Si](C)(C)C	2465.1	Semi standard non polar	33892256
Phenylalanylserine,2TMS,isomer #7	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO)C(=O)O)[Si](C)(C)C	2284.4	Semi standard non polar	33892256
Phenylalanylserine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO[Si](C)(C)C)C(=O)O[Si](C)(C)C	2287.1	Semi standard non polar	33892256
Phenylalanylserine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO[Si](C)(C)C)C(=O)O[Si](C)(C)C	2332.2	Standard non polar	33892256
Phenylalanylserine,3TMS,isomer #2	C[Si](C)(C)OC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C	2226.1	Semi standard non polar	33892256
Phenylalanylserine,3TMS,isomer #2	C[Si](C)(C)OC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C	2289.8	Standard non polar	33892256
Phenylalanylserine,3TMS,isomer #3	C[Si](C)(C)OC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2450.2	Semi standard non polar	33892256
Phenylalanylserine,3TMS,isomer #3	C[Si](C)(C)OC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2409.6	Standard non polar	33892256
Phenylalanylserine,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2298.6	Semi standard non polar	33892256
Phenylalanylserine,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2378.1	Standard non polar	33892256
Phenylalanylserine,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2427.2	Semi standard non polar	33892256
Phenylalanylserine,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2376.7	Standard non polar	33892256
Phenylalanylserine,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2245.5	Semi standard non polar	33892256
Phenylalanylserine,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2335.0	Standard non polar	33892256
Phenylalanylserine,3TMS,isomer #7	C[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CO)C(=O)O	2379.9	Semi standard non polar	33892256
Phenylalanylserine,3TMS,isomer #7	C[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CO)C(=O)O	2426.0	Standard non polar	33892256
Phenylalanylserine,4TMS,isomer #1	C[Si](C)(C)OC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2414.0	Semi standard non polar	33892256
Phenylalanylserine,4TMS,isomer #1	C[Si](C)(C)OC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2450.6	Standard non polar	33892256
Phenylalanylserine,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2280.5	Semi standard non polar	33892256
Phenylalanylserine,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2396.8	Standard non polar	33892256
Phenylalanylserine,4TMS,isomer #3	C[Si](C)(C)OC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2440.9	Semi standard non polar	33892256
Phenylalanylserine,4TMS,isomer #3	C[Si](C)(C)OC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2495.7	Standard non polar	33892256
Phenylalanylserine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CO)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2407.6	Semi standard non polar	33892256
Phenylalanylserine,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CO)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2463.1	Standard non polar	33892256
Phenylalanylserine,5TMS,isomer #1	C[Si](C)(C)OC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2496.9	Semi standard non polar	33892256
Phenylalanylserine,5TMS,isomer #1	C[Si](C)(C)OC[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2519.0	Standard non polar	33892256
Phenylalanylserine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(=O)O	2557.2	Semi standard non polar	33892256
Phenylalanylserine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CO)NC(=O)[C@@H](N)CC1=CC=CC=C1	2530.6	Semi standard non polar	33892256
Phenylalanylserine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(=O)O	2540.8	Semi standard non polar	33892256
Phenylalanylserine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[C@@H](CO)C(=O)O	2506.5	Semi standard non polar	33892256
Phenylalanylserine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2727.2	Semi standard non polar	33892256
Phenylalanylserine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O	2763.7	Semi standard non polar	33892256
Phenylalanylserine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2760.1	Semi standard non polar	33892256
Phenylalanylserine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(=O)O[Si](C)(C)C(C)(C)C	2746.9	Semi standard non polar	33892256
Phenylalanylserine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CO)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2729.6	Semi standard non polar	33892256
Phenylalanylserine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(=O)O)[Si](C)(C)C(C)(C)C	2908.4	Semi standard non polar	33892256
Phenylalanylserine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO)C(=O)O)[Si](C)(C)C(C)(C)C	2755.3	Semi standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2947.9	Semi standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2898.8	Standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2959.5	Semi standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2860.0	Standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3133.3	Semi standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2942.1	Standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2982.5	Semi standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2919.4	Standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3120.9	Semi standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2925.2	Standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2943.1	Semi standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2898.9	Standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CO)C(=O)O	3097.9	Semi standard non polar	33892256
Phenylalanylserine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CO)C(=O)O	2952.6	Standard non polar	33892256
Phenylalanylserine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3331.5	Semi standard non polar	33892256
Phenylalanylserine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3127.9	Standard non polar	33892256
Phenylalanylserine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3166.9	Semi standard non polar	33892256
Phenylalanylserine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N([C@@H](CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3087.7	Standard non polar	33892256
Phenylalanylserine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3336.6	Semi standard non polar	33892256
Phenylalanylserine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](C(=O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3166.7	Standard non polar	33892256
Phenylalanylserine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CO)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3281.6	Semi standard non polar	33892256
Phenylalanylserine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CO)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3164.4	Standard non polar	33892256
Phenylalanylserine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3525.0	Semi standard non polar	33892256
Phenylalanylserine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3328.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylalanylserine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylserine 10V, Positive-QTOF	splash10-00di-2910000000-db44d0796e1521331e52	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylserine 20V, Positive-QTOF	splash10-006x-9600000000-09e69e3e9ba5165c1292	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylserine 40V, Positive-QTOF	splash10-002f-9700000000-4e244a22ea72055f4a66	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylserine 10V, Negative-QTOF	splash10-0udi-1290000000-144479db009b7d7fca19	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylserine 20V, Negative-QTOF	splash10-00dl-9430000000-1f15c13c8d07a176ef00	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanylserine 40V, Negative-QTOF	splash10-0006-9200000000-eaf9e5be498213e54191	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112020

KNApSAcK ID

Not Available

Chemspider ID

167923

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193508

PDB ID

Not Available

ChEBI ID

71032

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Mizuma T, Narasaka T, Awazu S: Uptake of cyclic dipeptide by PEPT1 in Caco-2 cells: phenolic hydroxyl group of substrate enhances affinity for PEPT1. J Pharm Pharmacol. 2002 Sep;54(9):1293-6. [PubMed:12356285 ]
Mizuma T, Narasaka T, Awazu S: Concentration-dependent atypical intestinal absorption of cyclic phenylalanylserine: small intestine acts as an interface between the body and ingested compounds. Biol Pharm Bull. 2003 Nov;26(11):1625-8. [PubMed:14600416 ]
Schwarz A, Steinke D, Kula MR, Wandrey C: Optimization of enzyme-mediated peptide bond formation. Biotechnol Appl Biochem. 1990 Apr;12(2):188-95. [PubMed:2109983 ]
Behling RA, Fischer AG: Formation of phenylalanylserine and cyclo-phenylalanylseryl by protoplasts of Gliocladium virens. Int J Biochem. 1980;11(5):457-8. [PubMed:6156101 ]
Bucevic-Popovic V, Pavela-Vrancic M, Dieckmann R, Von Dohren H: Relationship between activating and editing functions of the adenylation domain of apo-tyrocidin synthetase 1 (apo-TY1). Biochimie. 2006 Mar-Apr;88(3-4):265-70. Epub 2005 Sep 15. [PubMed:16182433 ]
Mizuma T, Narasaka T, Hiyoshi W, Awazu S: Concentration-dependent preferences of absorptive and excretive transport cause atypical intestinal absorption of cyclic phenylalanylserine: small intestine acts as an interface between the body and ingested compounds. Res Commun Mol Pathol Pharmacol. 2002;111(5-6):199-209. [PubMed:15244036 ]

Showing metabocard for Phenylalanylserine (HMDB0029004)

MOL for HMDB0029004 (Phenylalanylserine)

3D MOL for HMDB0029004 (Phenylalanylserine)

3D SDF for HMDB0029004 (Phenylalanylserine)

3D-SDF for HMDB0029004 (Phenylalanylserine)

PDB for HMDB0029004 (Phenylalanylserine)

3D PDB for HMDB0029004 (Phenylalanylserine)

SMILES for HMDB0029004 (Phenylalanylserine)

INCHI for HMDB0029004 (Phenylalanylserine)

Structure for HMDB0029004 (Phenylalanylserine)

3D Structure for HMDB0029004 (Phenylalanylserine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra