MiMeDB: Showing metabocard for Phenylalanylglycine (MMDBc0000472)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:38:32 UTC

Update Date

2024-04-30 19:32:33 UTC

Metabolite ID

MMDBc0000472

Metabolite Identification

Common Name

Phenylalanylglycine

Description

Phenylalanylglycine is a dipeptide composed of phenylalanine and glycine. 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

HMDB0028995
     RDKit          3D
Phenylalanylglycine
 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.2753   -2.4242   -0.2802 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080   -1.1285   -0.5242 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3541   -0.0228    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    0.2340    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -0.2295   -0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9446    0.1246   -0.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4627    1.0041   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6547    1.4934    0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3527    1.0997    1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -1.0395   -0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3672   -1.5855   -1.3444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3415   -0.3519    0.6692 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650   -0.3370    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3090    0.9863    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4492    1.2732    0.6597 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5926    1.8914   -0.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827   -2.6940    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -3.1693   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539   -0.9205   -1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2304    0.9088    0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2030   -0.3099    1.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1177   -0.9019   -1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5885   -0.2654   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4737    1.3417   -0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736    2.1742    1.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416    1.5106    1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808    0.1113    1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2204   -0.5586    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1957   -1.1037   -0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8751    2.8893   -0.4147 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  2  0
 14 16  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 16 30  1  0
M  END


  Mrv1652304062014052D          

 16 16  0  0  0  0            999 V2000
 9998.937910000.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6525 9999.9804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.366410000.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0818 9999.9804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.797210000.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5105 9999.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.225910000.3927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.5105 9999.1561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.366410001.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6525 9999.1561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2230 9999.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.508610000.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7941 9999.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7940 9999.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5085 9998.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2231 9999.1556    0.0000 C   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 10  1  1  0  0  0
  3  4  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  1 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000472

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O3/c12-9(11(16)13-7-10(14)15)6-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)/t9-/m0/s1

> <INCHI_KEY>
GLUBLISJVJFHQS-VIFPVBQESA-N

> <FORMULA>
C11H14N2O3

> <MOLECULAR_WEIGHT>
222.244

> <EXACT_MASS>
222.100442319

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.764249288715025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-2.292126300574983

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.399565245921018

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.709022259922749

> <JCHEM_PKA_STRONGEST_BASIC>
8.010007600994834

> <JCHEM_POLAR_SURFACE_AREA>
92.42

> <JCHEM_REFRACTIVITY>
57.91980000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.82e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0028995
     RDKit          3D
Phenylalanylglycine
 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.2753   -2.4242   -0.2802 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080   -1.1285   -0.5242 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3541   -0.0228    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    0.2340    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -0.2295   -0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9446    0.1246   -0.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4627    1.0041   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6547    1.4934    0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3527    1.0997    1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -1.0395   -0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3672   -1.5855   -1.3444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3415   -0.3519    0.6692 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650   -0.3370    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3090    0.9863    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4492    1.2732    0.6597 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5926    1.8914   -0.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827   -2.6940    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -3.1693   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539   -0.9205   -1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2304    0.9088    0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2030   -0.3099    1.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1177   -0.9019   -1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5885   -0.2654   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4737    1.3417   -0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736    2.1742    1.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416    1.5106    1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808    0.1113    1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2204   -0.5586    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1957   -1.1037   -0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8751    2.8893   -0.4147 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  2  0
 14 16  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 16 30  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    8664.6848667.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.0188666.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.3518667.400   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8668.6868666.630   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8670.0218667.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.3538666.630   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8672.6888667.400   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8671.3538665.091   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8667.3518668.939   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    8666.0188665.091   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8663.3508666.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.0168667.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.6828666.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.6828665.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.0168664.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.3508665.090   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3                                                            
CONECT   10    2                                                            
CONECT   11   12   16    1                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0028995
HETATM    1  N1  UNL     1      -0.275  -2.424  -0.280  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.208  -1.128  -0.524  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.354  -0.023   0.278  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.802   0.234   0.136  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.598  -0.229  -0.849  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.945   0.125  -0.989  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.463   1.004  -0.041  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.655   1.493   0.974  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.353   1.100   1.038  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.677  -1.039  -0.424  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.367  -1.586  -1.344  1.00  0.00           O  
HETATM   12  N2  UNL     1       2.342  -0.352   0.669  1.00  0.00           N  
HETATM   13  C10 UNL     1       3.765  -0.337   0.628  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.309   0.986   0.245  1.00  0.00           C  
HETATM   15  O2  UNL     1       5.449   1.273   0.660  1.00  0.00           O  
HETATM   16  O3  UNL     1       3.593   1.891  -0.519  1.00  0.00           O  
HETATM   17  H1  UNL     1      -0.283  -2.694   0.706  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.034  -3.169  -0.957  1.00  0.00           H  
HETATM   19  H3  UNL     1      -0.054  -0.920  -1.646  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.230   0.909   0.093  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.203  -0.310   1.367  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.118  -0.902  -1.572  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.588  -0.265  -1.727  1.00  0.00           H  
HETATM   24  H8  UNL     1      -5.474   1.342  -0.079  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.074   2.174   1.715  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.742   1.511   1.870  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.781   0.111   1.373  1.00  0.00           H  
HETATM   28  H12 UNL     1       4.220  -0.559   1.663  1.00  0.00           H  
HETATM   29  H13 UNL     1       4.196  -1.104  -0.029  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.875   2.889  -0.415  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   10   19
CONECT    3    4   20   21
CONECT    4    5    5    9
CONECT    5    6   22
CONECT    6    7    7   23
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   26
CONECT   10   11   11   12
CONECT   12   13   27
CONECT   13   14   28   29
CONECT   14   15   15   16
CONECT   16   30
END

HMDB0028995
     RDKit          3D
Phenylalanylglycine
 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.2753   -2.4242   -0.2802 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080   -1.1285   -0.5242 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3541   -0.0228    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    0.2340    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -0.2295   -0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9446    0.1246   -0.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4627    1.0041   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6547    1.4934    0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3527    1.0997    1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -1.0395   -0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3672   -1.5855   -1.3444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3415   -0.3519    0.6692 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650   -0.3370    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3090    0.9863    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4492    1.2732    0.6597 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5926    1.8914   -0.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827   -2.6940    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -3.1693   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539   -0.9205   -1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2304    0.9088    0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2030   -0.3099    1.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1177   -0.9019   -1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5885   -0.2654   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4737    1.3417   -0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736    2.1742    1.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416    1.5106    1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808    0.1113    1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2204   -0.5586    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1957   -1.1037   -0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8751    2.8893   -0.4147 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  2  0
 14 16  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 16 30  1  0
M  END

Synonyms

Value	Source
F-G	ChEBI
FG	ChEBI
L-Phe-gly	ChEBI
F-g Dipeptide	HMDB
FG Dipeptide	HMDB
L-Phenylalanylglycine	HMDB
N-L-Phenylalanylglycine	HMDB
N-Phenylalanylglycine	HMDB
Phe-gly	HMDB
Phenylalanine glycine dipeptide	HMDB
Phenylalanine-glycine dipeptide	HMDB
Phenylalanyl-glycine	HMDB
Phenylalanylglycine	ChEBI

Molecular Formula

C₁₁H₁₄N₂O₃

Average Mass

222.244

Monoisotopic Mass

222.100442319

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H14N2O3/c12-9(11(16)13-7-10(14)15)6-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)/t9-/m0/s1

InChI Key

GLUBLISJVJFHQS-VIFPVBQESA-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
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
Aralkylamine
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organic salt
Hydrocarbon derivative
Primary aliphatic amine
Organic nitrogen compound
Amine
Organic oxygen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Organic zwitterion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:73635 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.78 g/L	ALOGPS
logP	-0.9	ALOGPS
logP	-2.3	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	8.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.92 m³·mol⁻¹	ChemAxon
Polarizability	22.76 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1910000000-69f6b703e4914169a960	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9400000000-d2f0749424189385b61c	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9500000000-990725f616a852839088	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1190000000-d9cf02536a5a863769b3	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9810000000-3c953bf79faee88c837e	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05bf-9200000000-a42bc5f9b3b0a4113bf4	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human feces; Human stool; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0028995

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112015

KNApSAcK ID

Not Available

Chemspider ID

5360444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6992303

PDB ID

Not Available

ChEBI ID

73635

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Yeagle PL, Young J, Hui SW, Epand RM: On the mechanism of inhibition of viral and vesicle membrane fusion by carbobenzoxy-D-phenylalanyl-L-phenylalanylglycine. Biochemistry. 1992 Mar 31;31(12):3177-83. doi: 10.1021/bi00127a019. [PubMed:1554703 ]
Kelsey DR, Flanagan TD, Young JE, Yeagle PL: Inhibition of Sendai virus fusion with phospholipid vesicles and human erythrocyte membranes by hydrophobic peptides. Virology. 1991 Jun;182(2):690-702. doi: 10.1016/0042-6822(91)90610-n. [PubMed:1850923 ]
Kelsey DR, Flanagan TD, Young J, Yeagle PL: Peptide inhibitors of enveloped virus infection inhibit phospholipid vesicle fusion and Sendai virus fusion with phospholipid vesicles. J Biol Chem. 1990 Jul 25;265(21):12178-83. [PubMed:2165053 ]
Storer AC, Angus RH, Carey PR: Comparison of the kinetics of the papain-catalyzed hydrolysis of glycine- and alanine-based esters and thiono esters. Biochemistry. 1988 Jan 12;27(1):264-8. doi: 10.1021/bi00401a040. [PubMed:3349032 ]
Epand RM: Virus replication inhibitory peptide inhibits the conversion of phospholipid bilayers to the hexagonal phase. Biosci Rep. 1986 Jul;6(7):647-53. doi: 10.1007/BF01114759. [PubMed:3779040 ]
Li L, Zheng LX, Yang FY: Effect of propensity of hexagonal II phase formation on the activity of mitochondrial ubiquinol-cytochrome c reductase and H(+)-ATPase. Chem Phys Lipids. 1995 Jun 19;76(2):135-44. doi: 10.1016/0009-3084(95)02437-n. [PubMed:7634362 ]
Andersson LI, Muller R, Vlatakis G, Mosbach K: Mimics of the binding sites of opioid receptors obtained by molecular imprinting of enkephalin and morphine. Proc Natl Acad Sci U S A. 1995 May 23;92(11):4788-92. doi: 10.1073/pnas.92.11.4788. [PubMed:7761401 ]
Yeagle PL, Dentino AR, Smith FT, Spooner P, Watts A: The antiviral peptide carbobenzoxy-D-phenylalanyl-L-phenylalanylglycine changes the average conformation of phospholipids in membranes. Biochemistry. 1993 Nov 16;32(45):12197-202. doi: 10.1021/bi00096a032. [PubMed:8218297 ]
Varela AS, Bosco Lopez Saez JJ: Utility of serum activity of angiotensin-converting enzyme as a tumor marker. Oncology. 1993 Nov-Dec;50(6):430-5. doi: 10.1159/000227224. [PubMed:8233282 ]
Ram S, Buchsbaum DJ: Synthesis of a new class of isothiocyanatopeptide bifunctional chelating agents for coupling to monoclonal antibodies. Int J Pept Protein Res. 1996 Jul;48(1):79-86. doi: 10.1111/j.1399-3011.1996.tb01109.x. [PubMed:8844266 ]
Mizuma T, Masubuchi S, Awazu S: Intestinal absorption of stable cyclic glycylphenylalanine: comparison with the linear form. J Pharm Pharmacol. 1997 Nov;49(11):1067-71. doi: 10.1111/j.2042-7158.1997.tb06043.x. [PubMed:9401939 ]
Fujita T, Morishita Y, Ito H, Kuribayashi D, Yamamoto A, Muranishi S: Enhancement of the small intestinal uptake of phenylalanylglycine via a H+/oligopeptide transport system by chemical modification with fatty acids. Life Sci. 1997;61(25):2455-65. doi: 10.1016/s0024-3205(97)00980-6. [PubMed:9416764 ]
Kruger RG, Lu W, Oberthur M, Tao J, Kahne D, Walsh CT: Tailoring of glycopeptide scaffolds by the acyltransferases from the teicoplanin and A-40,926 biosynthetic operons. Chem Biol. 2005 Jan;12(1):131-40. doi: 10.1016/j.chembiol.2004.12.005. [PubMed:15664522 ]
Pingitore F, Wesdemiotis C: Characterization of dipeptide isomers by tandem mass spectrometry of their mono- versus dilithiated complexes. Anal Chem. 2005 Mar 15;77(6):1796-806. doi: 10.1021/ac048469q. [PubMed:15762588 ]
Wang P, Polce MJ, Ohanessian G, Wesdemiotis C: The sodium ion affinities of cytosine and its methylated derivatives. J Mass Spectrom. 2008 Apr;43(4):485-94. doi: 10.1002/jms.1336. [PubMed:17994645 ]
Thirumoorthy K, Soni K, Nandi N: The molecular recognition of dipeptide by oligoglycyl head group of amphiphile: a quantum chemical study. J Nanosci Nanotechnol. 2009 Jan;9(1):77-89. doi: 10.1166/jnn.2009.j077. [PubMed:19441281 ]
Makowski M, Lisowski M, Maciag A, Wiktor M, Szlachcic A, Lis T: Two pentadehydropeptides with different configurations of the DeltaPhe residues. Acta Crystallogr C. 2010 Mar;66(Pt 3):o119-23. doi: 10.1107/S0108270110003094. Epub 2010 Feb 3. [PubMed:20203407 ]
Ningsih F, Kitani S, Fukushima E, Nihira T: VisG is essential for biosynthesis of virginiamycin S, a streptogramin type B antibiotic, as a provider of the nonproteinogenic amino acid phenylglycine. Microbiology (Reading). 2011 Nov;157(Pt 11):3213-3220. doi: 10.1099/mic.0.050203-0. Epub 2011 Aug 4. [PubMed:21816878 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Phenylalanylglycine (MMDBc0000472)

MOL for #<Metabolite:0x00007fa50a86de70>

3D MOL for #<Metabolite:0x00007fa50a86de70>

3D SDF for #<Metabolite:0x00007fa50a86de70>

3D-SDF for #<Metabolite:0x00007fa50a86de70>

PDB for #<Metabolite:0x00007fa50a86de70>

3D PDB for #<Metabolite:0x00007fa50a86de70>

SMILES for #<Metabolite:0x00007fa50a86de70>

INCHI for #<Metabolite:0x00007fa50a86de70>

Structure for #<Metabolite:0x00007fa50a86de70>

3D Structure for #<Metabolite:0x00007fa50a86de70>