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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:02:44 UTC

Update Date

2022-09-22 18:34:22 UTC

HMDB ID

HMDB0028848

Secondary Accession Numbers

HMDB28848

Metabolite Identification

Common Name

Glycyl-Phenylalanine

Description

Glycyl-Phenylalanine is a dipeptide composed of glycine and phenylalanine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite.

Structure

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

HMDB0252883
     RDKit          3D
Glycyl-L-phenylalanine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.9924    0.4858   -0.3427 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0544   -0.6207   -0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959   -0.1305   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4197    0.4217   -1.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7907   -0.2205    0.3827 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4263    0.2212    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432   -0.9013    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537   -0.4880   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -0.2229   -1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8257    0.1541   -1.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463    0.2817   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1394    0.0301    0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8008   -0.3512    1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    1.1060    1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    1.6938    1.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0087    1.3316    2.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4780    0.6859    0.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    0.2923   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3697   -1.4344   -0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -0.9774    0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6328   -0.0099   -2.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3677    0.8163   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465   -1.5899    0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -1.5368   -0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8681   -0.3246   -2.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505    0.3581   -2.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6868    0.5790   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7957    0.1342    1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4450   -0.5452    2.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.7615    3.2316 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
  3  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END


  Mrv1652304032018442D          

 16 16  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  4  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0028848

> <DATABASE_NAME>
hmdb

> <SMILES>
NCC(O)=NC(CC1=CC=CC=C1)C(O)=O

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

> <INCHI_KEY>
JBCLFWXMTIKCCB-UHFFFAOYSA-N

> <FORMULA>
C11H14N2O3

> <MOLECULAR_WEIGHT>
222.2405

> <EXACT_MASS>
222.100442324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.583167885483448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-amino-1-hydroxyethylidene)amino]-3-phenylpropanoic acid

> <ALOGPS_LOGP>
-2.13

> <JCHEM_LOGP>
-1.693454433568854

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.386802894261972

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.567675554409829

> <JCHEM_PKA_STRONGEST_BASIC>
9.334327004475691

> <JCHEM_POLAR_SURFACE_AREA>
95.91000000000001

> <JCHEM_REFRACTIVITY>
58.441500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2-amino-1-hydroxyethylidene)amino]-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252883
     RDKit          3D
Glycyl-L-phenylalanine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.9924    0.4858   -0.3427 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0544   -0.6207   -0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959   -0.1305   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4197    0.4217   -1.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7907   -0.2205    0.3827 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4263    0.2212    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432   -0.9013    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537   -0.4880   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -0.2229   -1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8257    0.1541   -1.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463    0.2817   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1394    0.0301    0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8008   -0.3512    1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    1.1060    1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    1.6938    1.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0087    1.3316    2.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4780    0.6859    0.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    0.2923   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3697   -1.4344   -0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -0.9774    0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6328   -0.0099   -2.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3677    0.8163   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465   -1.5899    0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -1.5368   -0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8681   -0.3246   -2.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505    0.3581   -2.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6868    0.5790   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7957    0.1342    1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4450   -0.5452    2.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.7615    3.2316 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
  3  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.667   9.240   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       2.667   6.160   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    8    9                                                       
CONECT    7   10   12                                                       
CONECT    8    4    5    6                                                  
CONECT    9    6   11   13                                                  
CONECT   10    7   13   14                                                  
CONECT   11    9   15   16                                                  
CONECT   12    7                                                            
CONECT   13    9   10                                                       
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0253015
HETATM    1  N1  UNL     1       2.401   1.442   2.436  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.094   0.013   2.430  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.829  -0.359   1.011  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.879  -0.144   0.115  1.00  0.00           O  
HETATM    5  N2  UNL     1       0.692  -0.850   0.650  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.528  -1.181  -0.745  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.926  -1.295  -1.149  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.657  -0.048  -0.930  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.743   0.909  -1.897  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.431   2.090  -1.701  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.041   2.291  -0.488  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.988   1.350   0.538  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.284   0.189   0.278  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.265  -2.417  -1.069  1.00  0.00           C  
HETATM   15  O2  UNL     1       1.236  -2.859  -2.246  1.00  0.00           O  
HETATM   16  O3  UNL     1       2.006  -3.150  -0.154  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.394   1.624   2.697  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.085   1.926   1.586  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.257  -0.240   3.101  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.045  -0.519   2.707  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.812   0.481  -0.668  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.937  -0.307  -1.322  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.923  -1.500  -2.250  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.425  -2.152  -0.680  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.250   0.721  -2.845  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.483   2.841  -2.496  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.583   3.206  -0.315  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.471   1.509   1.497  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.238  -0.556   1.080  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.982  -3.015   0.829  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   19   20
CONECT    3    4    5    5
CONECT    4   21
CONECT    5    6
CONECT    6    7   14   22
CONECT    7    8   23   24
CONECT    8    9    9   13
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   29
CONECT   14   15   15   16
CONECT   16   30
END

HMDB0252883
     RDKit          3D
Glycyl-L-phenylalanine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.9924    0.4858   -0.3427 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0544   -0.6207   -0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959   -0.1305   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4197    0.4217   -1.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7907   -0.2205    0.3827 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4263    0.2212    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432   -0.9013    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537   -0.4880   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -0.2229   -1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8257    0.1541   -1.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463    0.2817   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1394    0.0301    0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8008   -0.3512    1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    1.1060    1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    1.6938    1.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0087    1.3316    2.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4780    0.6859    0.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    0.2923   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3697   -1.4344   -0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -0.9774    0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6328   -0.0099   -2.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3677    0.8163   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465   -1.5899    0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -1.5368   -0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8681   -0.3246   -2.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2505    0.3581   -2.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6868    0.5790   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7957    0.1342    1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4450   -0.5452    2.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.7615    3.2316 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
  3  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Gly-phe	MeSH
Gly-D-phenylalanine	MeSH
Gly-L-phenylalanine	MeSH
Glycyl-D-phenylalanine	MeSH
Glycyl-L-phenylalanine	MeSH
Glycylphenylalanine	MeSH
Glycylphenylalanine monobrosylate, (L)-isomer	MeSH
Glycylphenylalanine monohydrochloride, monohydrate, (L)-isomer	MeSH
Glycylphenylalanine monotosylate, (L)-isomer	MeSH
Glycylphenylalanine, (D)-isomer	MeSH
Glycylphenylalanine, (L)-isomer	MeSH
g-F Dipeptide	HMDB
GF Dipeptide	HMDB
Glycine phenylalanine dipeptide	HMDB
Glycine-phenylalanine dipeptide	HMDB
L-Glycyl-L-phenylalanine	HMDB
2-[(2-Amino-1-hydroxyethylidene)amino]-3-phenylpropanoate	Generator, HMDB

Chemical Formula

C₁₁H₁₄N₂O₃

Average Molecular Weight

222.2405

Monoisotopic Molecular Weight

222.100442324

IUPAC Name

2-[(2-amino-1-hydroxyethylidene)amino]-3-phenylpropanoic acid

Traditional Name

2-[(2-amino-1-hydroxyethylidene)amino]-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

NCC(O)=NC(CC1=CC=CC=C1)C(O)=O

InChI Identifier

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

InChI Key

JBCLFWXMTIKCCB-UHFFFAOYSA-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 or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Amino acid
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	-2.29	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.21 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-1.7	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.44 m³·mol⁻¹	ChemAxon
Polarizability	22.58 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
DarkChem	[M+H]+	152.053	31661259
DarkChem	[M-H]-	149.883	31661259
DeepCCS	[M+H]+	144.093	30932474
DeepCCS	[M-H]-	141.152	30932474
DeepCCS	[M-2H]-	177.35	30932474
DeepCCS	[M+Na]+	152.889	30932474
AllCCS	[M+H]+	150.0	32859911
AllCCS	[M+H-H2O]+	146.2	32859911
AllCCS	[M+NH4]+	153.6	32859911
AllCCS	[M+Na]+	154.6	32859911
AllCCS	[M-H]-	150.3	32859911
AllCCS	[M+Na-2H]-	150.8	32859911
AllCCS	[M+HCOO]-	151.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.56 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0049 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.49 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	269.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycyl-Phenylalanine	NCC(O)=NC(CC1=CC=CC=C1)C(O)=O	3032.9	Standard polar	33892256
Glycyl-Phenylalanine	NCC(O)=NC(CC1=CC=CC=C1)C(O)=O	2002.5	Standard non polar	33892256
Glycyl-Phenylalanine	NCC(O)=NC(CC1=CC=CC=C1)C(O)=O	2158.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycyl-Phenylalanine,1TMS,isomer #1	C[Si](C)(C)OC(CN)=NC(CC1=CC=CC=C1)C(=O)O	2039.8	Semi standard non polar	33892256
Glycyl-Phenylalanine,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(O)CN	2058.6	Semi standard non polar	33892256
Glycyl-Phenylalanine,1TMS,isomer #3	C[Si](C)(C)NCC(O)=NC(CC1=CC=CC=C1)C(=O)O	2171.9	Semi standard non polar	33892256
Glycyl-Phenylalanine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(CN)O[Si](C)(C)C	2047.6	Semi standard non polar	33892256
Glycyl-Phenylalanine,2TMS,isomer #2	C[Si](C)(C)NCC(=NC(CC1=CC=CC=C1)C(=O)O)O[Si](C)(C)C	2101.7	Semi standard non polar	33892256
Glycyl-Phenylalanine,2TMS,isomer #3	C[Si](C)(C)NCC(O)=NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2145.0	Semi standard non polar	33892256
Glycyl-Phenylalanine,2TMS,isomer #4	C[Si](C)(C)N(CC(O)=NC(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2266.8	Semi standard non polar	33892256
Glycyl-Phenylalanine,3TMS,isomer #1	C[Si](C)(C)NCC(=NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2074.8	Semi standard non polar	33892256
Glycyl-Phenylalanine,3TMS,isomer #1	C[Si](C)(C)NCC(=NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2118.8	Standard non polar	33892256
Glycyl-Phenylalanine,3TMS,isomer #2	C[Si](C)(C)OC(CN([Si](C)(C)C)[Si](C)(C)C)=NC(CC1=CC=CC=C1)C(=O)O	2255.5	Semi standard non polar	33892256
Glycyl-Phenylalanine,3TMS,isomer #2	C[Si](C)(C)OC(CN([Si](C)(C)C)[Si](C)(C)C)=NC(CC1=CC=CC=C1)C(=O)O	2252.9	Standard non polar	33892256
Glycyl-Phenylalanine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(O)CN([Si](C)(C)C)[Si](C)(C)C	2266.3	Semi standard non polar	33892256
Glycyl-Phenylalanine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(O)CN([Si](C)(C)C)[Si](C)(C)C	2231.0	Standard non polar	33892256
Glycyl-Phenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2276.3	Semi standard non polar	33892256
Glycyl-Phenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2247.6	Standard non polar	33892256
Glycyl-Phenylalanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN)=NC(CC1=CC=CC=C1)C(=O)O	2269.7	Semi standard non polar	33892256
Glycyl-Phenylalanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(O)CN	2282.1	Semi standard non polar	33892256
Glycyl-Phenylalanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCC(O)=NC(CC1=CC=CC=C1)C(=O)O	2370.6	Semi standard non polar	33892256
Glycyl-Phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(CN)O[Si](C)(C)C(C)(C)C	2472.4	Semi standard non polar	33892256
Glycyl-Phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC(=NC(CC1=CC=CC=C1)C(=O)O)O[Si](C)(C)C(C)(C)C	2521.4	Semi standard non polar	33892256
Glycyl-Phenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCC(O)=NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2534.6	Semi standard non polar	33892256
Glycyl-Phenylalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CC(O)=NC(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2646.1	Semi standard non polar	33892256
Glycyl-Phenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2686.2	Semi standard non polar	33892256
Glycyl-Phenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2656.0	Standard non polar	33892256
Glycyl-Phenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC(CC1=CC=CC=C1)C(=O)O	2904.2	Semi standard non polar	33892256
Glycyl-Phenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC(CC1=CC=CC=C1)C(=O)O	2758.8	Standard non polar	33892256
Glycyl-Phenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2859.1	Semi standard non polar	33892256
Glycyl-Phenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2806.8	Standard non polar	33892256
Glycyl-Phenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3089.1	Semi standard non polar	33892256
Glycyl-Phenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2933.4	Standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva
Urine

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
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	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

FDB098201

KNApSAcK ID

Not Available

Chemspider ID

87926

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

97415

PDB ID

Not Available

ChEBI ID

Not Available

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

Rai DK, Mooney A, Kenny PT: A tandem mass spectrometric investigation of N-(3-ferrocenyl-2-naphthoyl) dipeptide ethyl esters and N-(6-ferrocenyl-2-naphthoyl) dipeptide ethyl esters. Rapid Commun Mass Spectrom. 2011 Oct 15;25(19):2905-10. doi: 10.1002/rcm.5184. [PubMed:21913269 ]
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. [PubMed:15762588 ]
Girelli AM, Mattei E, Messina A, Tarola AM: Inhibition of polyphenol oxidases activity by various dipeptides. J Agric Food Chem. 2004 May 19;52(10):2741-5. [PubMed:15137808 ]
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. [PubMed:19441281 ]
Turecek F, Syrstad EA, Seymour JL, Chen X, Yao C: Peptide cation-radicals. A computational study of the competition between peptide N-Calpha bond cleavage and loss of the side chain in the [GlyPhe-NH2 + 2H]+. cation-radical. J Mass Spectrom. 2003 Oct;38(10):1093-104. [PubMed:14595859 ]
Anderson L, Bussler B, Martins H, Dufton M: Enkephalin-processing oligopeptidases in cobra venom: inhibition by thiorphan and bestatin reveals co-operative actions. Toxicon. 1998 May;36(5):719-28. [PubMed:9655632 ]
Duman JG, Chen L, Palmer AE, Hille B: Contributions of intracellular compartments to calcium dynamics: implicating an acidic store. Traffic. 2006 Jul;7(7):859-72. [PubMed:16787398 ]
Epand RM: Virus replication inhibitory peptide inhibits the conversion of phospholipid bilayers to the hexagonal phase. Biosci Rep. 1986 Jul;6(7):647-53. [PubMed:3779040 ]
Lopez JJ, Camello-Almaraz C, Pariente JA, Salido GM, Rosado JA: Ca2+ accumulation into acidic organelles mediated by Ca2+- and vacuolar H+-ATPases in human platelets. Biochem J. 2005 Aug 15;390(Pt 1):243-52. [PubMed:15847604 ]
Tobin MB, Cole SC, Miller JR, Baldwin JE, Sutherland JD: Amino-acid substitutions in the cleavage site of acyl-coenzyme A:isopenicillin N acyltransferase from Penicillium chrysogenum: effect on proenzyme cleavage and activity. Gene. 1995 Aug 30;162(1):29-35. [PubMed:7557412 ]

Showing metabocard for Glycyl-Phenylalanine (HMDB0028848)

MOL for HMDB0028848 (Glycyl-Phenylalanine)

3D MOL for HMDB0028848 (Glycyl-Phenylalanine)

3D SDF for HMDB0028848 (Glycyl-Phenylalanine)

3D-SDF for HMDB0028848 (Glycyl-Phenylalanine)

PDB for HMDB0028848 (Glycyl-Phenylalanine)

3D PDB for HMDB0028848 (Glycyl-Phenylalanine)

SMILES for HMDB0028848 (Glycyl-Phenylalanine)

INCHI for HMDB0028848 (Glycyl-Phenylalanine)

Structure for HMDB0028848 (Glycyl-Phenylalanine)

3D Structure for HMDB0028848 (Glycyl-Phenylalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized