MiMeDB: Showing metabocard for Glycyl-Phenylalanine (MMDBc0000308)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-28 18:28:37 UTC

Update Date

2024-04-30 19:31:46 UTC

Metabolite ID

MMDBc0000308

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>
MMDBc0000308

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₁H₁₄N₂O₃

Average Mass

222.2405

Monoisotopic Mass

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.7 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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/Eubacteria	Firmicutes	347	Human ; Human feces; Human stool; Human pleural fluid plaque; Pig ; Human subgingival plaque; Cattle ; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	166	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	12	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	107	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	116	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria	Proteobacteria	7	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	24	Human ; Human feces; Human stool; Human pleural fluid plaque; Pig ; Human subgingival plaque; Cattle ; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050

External Links

HMDB ID

HMDB0253015

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

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1016/0378-1119(95)00369-h. [PubMed:7557412 ]
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. doi: 10.1016/s0041-0101(97)00134-7. [PubMed:9655632 ]
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. doi: 10.1002/jms.527. [PubMed:14595859 ]
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. doi: 10.1021/jf0305276. [PubMed:15137808 ]
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 ]
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. doi: 10.1042/BJ20050168. [PubMed:15847604 ]
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. doi: 10.1111/j.1600-0854.2006.00432.x. [PubMed:16787398 ]
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 ]
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 ]

Showing metabocard for Glycyl-Phenylalanine (MMDBc0000308)

MOL for #<Metabolite:0x00007f923283a560>

3D MOL for #<Metabolite:0x00007f923283a560>

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3D-SDF for #<Metabolite:0x00007f923283a560>

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Structure for #<Metabolite:0x00007f923283a560>

3D Structure for #<Metabolite:0x00007f923283a560>