MiMeDB: Showing metabocard for Leucylphenylalanine (MMDBc0000658)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:52:06 UTC

Update Date

2024-04-30 19:33:25 UTC

Metabolite ID

MMDBc0000658

Metabolite Identification

Common Name

Leucylphenylalanine

Description

Leucylphenylalanine is a dipeptide composed of leucine and phenylalanine. It is an incomplete breakdown product of protein digestion or protein catabolism. 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

HMDB0013243
     RDKit          3D
Leucylphenylalanine
 42 42  0  0  0  0  0  0  0  0999 V2000
    3.9587   -2.6265   -1.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3177   -1.3615   -1.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -0.3261   -2.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264   -1.6357   -0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3954   -0.2809   -0.2123 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2598    0.2975    0.7570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196   -0.4230    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8554   -0.9257   -0.3706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2293   -0.0096    1.6694 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878   -0.1089    2.3262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2222    1.1786    2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4573    1.4971    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898    2.2361    0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042    2.5894   -1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    2.2168   -2.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6778    1.4838   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5678    1.1226   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3197   -1.2780    2.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027   -2.2385    1.2912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5703   -1.3063    2.6890 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5045   -3.4769   -1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0382   -2.6060   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7901   -2.8100   -2.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9690   -0.9223   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9998   -0.4090   -3.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2312    0.6824   -1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1930   -0.4011   -2.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -2.2886    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -2.0383   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    0.3415   -1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    1.2800    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5661   -0.3161    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.4151    2.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -0.2119    3.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714    1.2450    2.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825    2.0156    2.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    2.5499    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097    3.1669   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8397    2.4723   -3.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5648    1.1661   -1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3354    0.5528    0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1621   -0.5087    2.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  1
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
M  END


  Mrv1652304062013002D          

 20 20  0  0  0  0            999 V2000
 9995.9486 9996.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6626 9996.5852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.6626 9995.7604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3869 9995.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1008 9995.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3869 9994.5355    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.6708 9994.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9569 9994.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2421 9994.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9569 9995.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1008 9994.1217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3786 9996.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0926 9996.5852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3786 9997.8233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2339 9996.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5198 9996.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8055 9996.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8054 9995.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5197 9995.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2340 9995.7604    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  1  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000658

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O3/c1-10(2)8-12(16)14(18)17-13(15(19)20)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9,16H2,1-2H3,(H,17,18)(H,19,20)/t12-,13-/m0/s1

> <INCHI_KEY>
KFKWRHQBZQICHA-STQMWFEESA-N

> <FORMULA>
C15H22N2O3

> <MOLECULAR_WEIGHT>
278.352

> <EXACT_MASS>
278.163042576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.42677125064617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-phenylpropanoic acid

> <ALOGPS_LOGP>
-0.62

> <JCHEM_LOGP>
-0.46947635194879256

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.737269551274156

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9469115952661666

> <JCHEM_PKA_STRONGEST_BASIC>
8.432596068138574

> <JCHEM_POLAR_SURFACE_AREA>
92.42000000000002

> <JCHEM_REFRACTIVITY>
76.08730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013243
     RDKit          3D
Leucylphenylalanine
 42 42  0  0  0  0  0  0  0  0999 V2000
    3.9587   -2.6265   -1.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3177   -1.3615   -1.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -0.3261   -2.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264   -1.6357   -0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3954   -0.2809   -0.2123 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2598    0.2975    0.7570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196   -0.4230    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8554   -0.9257   -0.3706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2293   -0.0096    1.6694 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878   -0.1089    2.3262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2222    1.1786    2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4573    1.4971    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898    2.2361    0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042    2.5894   -1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    2.2168   -2.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6778    1.4838   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5678    1.1226   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3197   -1.2780    2.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027   -2.2385    1.2912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5703   -1.3063    2.6890 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5045   -3.4769   -1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0382   -2.6060   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7901   -2.8100   -2.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9690   -0.9223   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9998   -0.4090   -3.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2312    0.6824   -1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1930   -0.4011   -2.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -2.2886    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -2.0383   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    0.3415   -1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    1.2800    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5661   -0.3161    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.4151    2.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -0.2119    3.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714    1.2450    2.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825    2.0156    2.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    2.5499    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097    3.1669   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8397    2.4723   -3.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5648    1.1661   -1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3354    0.5528    0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1621   -0.5087    2.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  1
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  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    8659.1048661.063   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.4378660.292   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8660.4378658.753   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8661.7898658.007   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8663.1218658.776   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8661.7898656.466   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8660.4528655.694   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.1208656.466   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8657.7858655.694   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8659.1208658.007   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8663.1218655.694   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0    8661.7738661.063   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8663.1068660.292   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8661.7738662.603   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8657.7708660.292   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8656.4378661.062   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8655.1048660.292   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8655.1038658.753   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8656.4378657.983   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8657.7708658.753   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6                                                            
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   16   20    1                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0013243
HETATM    1  C1  UNL     1       3.959  -2.626  -1.700  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.318  -1.362  -1.232  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.164  -0.326  -2.315  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.926  -1.636  -0.642  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.395  -0.281  -0.212  1.00  0.00           C  
HETATM    6  N1  UNL     1       2.260   0.297   0.757  1.00  0.00           N  
HETATM    7  C6  UNL     1       0.020  -0.423   0.374  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.855  -0.926  -0.371  1.00  0.00           O  
HETATM    9  N2  UNL     1      -0.229  -0.010   1.669  1.00  0.00           N  
HETATM   10  C7  UNL     1      -1.488  -0.109   2.326  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.222   1.179   2.129  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.457   1.497   0.707  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.490   2.236   0.022  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.604   2.589  -1.299  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.705   2.217  -2.010  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.678   1.484  -1.354  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.568   1.123  -0.015  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.320  -1.278   2.026  1.00  0.00           C  
HETATM   19  O2  UNL     1      -2.103  -2.238   1.291  1.00  0.00           O  
HETATM   20  O3  UNL     1      -3.570  -1.306   2.689  1.00  0.00           O  
HETATM   21  H1  UNL     1       3.504  -3.477  -1.136  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.038  -2.606  -1.478  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.790  -2.810  -2.790  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.969  -0.922  -0.431  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.000  -0.409  -3.039  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.231   0.682  -1.833  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.193  -0.401  -2.853  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.008  -2.289   0.241  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.255  -2.038  -1.408  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.348   0.342  -1.128  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.096   1.280   0.977  1.00  0.00           H  
HETATM   32  H12 UNL     1       2.566  -0.316   1.511  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.609   0.415   2.199  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.292  -0.212   3.466  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.171   1.245   2.698  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.582   2.016   2.547  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.602   2.550   0.552  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.810   3.167  -1.768  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.840   2.472  -3.055  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.565   1.166  -1.870  1.00  0.00           H  
HETATM   41  H21 UNL     1      -4.335   0.553   0.480  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.162  -0.509   2.598  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4   24
CONECT    3   25   26   27
CONECT    4    5   28   29
CONECT    5    6    7   30
CONECT    6   31   32
CONECT    7    8    8    9
CONECT    9   10   33
CONECT   10   11   18   34
CONECT   11   12   35   36
CONECT   12   13   13   17
CONECT   13   14   37
CONECT   14   15   15   38
CONECT   15   16   39
CONECT   16   17   17   40
CONECT   17   41
CONECT   18   19   19   20
CONECT   20   42
END

HMDB0013243
     RDKit          3D
Leucylphenylalanine
 42 42  0  0  0  0  0  0  0  0999 V2000
    3.9587   -2.6265   -1.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3177   -1.3615   -1.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -0.3261   -2.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264   -1.6357   -0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3954   -0.2809   -0.2123 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2598    0.2975    0.7570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196   -0.4230    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8554   -0.9257   -0.3706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2293   -0.0096    1.6694 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878   -0.1089    2.3262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2222    1.1786    2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4573    1.4971    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898    2.2361    0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042    2.5894   -1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    2.2168   -2.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6778    1.4838   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5678    1.1226   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3197   -1.2780    2.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027   -2.2385    1.2912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5703   -1.3063    2.6890 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5045   -3.4769   -1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0382   -2.6060   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7901   -2.8100   -2.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9690   -0.9223   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9998   -0.4090   -3.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2312    0.6824   -1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1930   -0.4011   -2.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -2.2886    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -2.0383   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    0.3415   -1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    1.2800    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5661   -0.3161    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.4151    2.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -0.2119    3.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714    1.2450    2.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825    2.0156    2.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    2.5499    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097    3.1669   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8397    2.4723   -3.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5648    1.1661   -1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3354    0.5528    0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1621   -0.5087    2.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  1
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
M  END

Synonyms

Value	Source
L-F	ChEBI
L-Leu-L-phe	ChEBI
LF	ChEBI
L-F Dipeptide	HMDB
L-Leucyl-L-phenylalanine	HMDB
LF Dipeptide	HMDB
Leu-phe	HMDB
Leucine phenylalanine dipeptide	HMDB
Leucine-phenylalanine dipeptide	HMDB
Leucyl-phenylalanine	HMDB
N-L-Leucyl-L-phenylalanine	HMDB
N-Leucyl-3-phenylalanine	HMDB
N-Leucylphenylalanine	HMDB
Leucylphenylalanine	ChEBI

Molecular Formula

C₁₅H₂₂N₂O₃

Average Mass

278.352

Monoisotopic Mass

278.163042576

IUPAC Name

(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-phenylpropanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H22N2O3/c1-10(2)8-12(16)14(18)17-13(15(19)20)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9,16H2,1-2H3,(H,17,18)(H,19,20)/t12-,13-/m0/s1

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:73585 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	-0.62	ALOGPS
logP	-0.47	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	8.43	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	7	ChemAxon
Refractivity	76.09 m³·mol⁻¹	ChemAxon
Polarizability	30.43 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	splash10-004i-2290000000-f9bca613c3c1be686d24	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01b9-9500000000-16f4fa13fb6fd1c29466	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00r6-9300000000-5405f9dacb771654c6e4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0490000000-7cc05c14e81ff1ef01bf	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ow-3900000000-9d5faab5a1caafb3e88f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9800000000-22caa12917c8a9286006	2021-09-22	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
Urine

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

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	2	Human ; Human stool; Human feces	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	Mean	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.02	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Feces	Detected but not Quantified			Not Specified	Both	Normal	HMDB	25486321
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	25037050

External Links

HMDB ID

HMDB0013243

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111642

KNApSAcK ID

Not Available

Chemspider ID

5360450

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6992309

PDB ID

Not Available

ChEBI ID

73585

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Khwaja A, Roberts PJ, Jones HM, Yong K, Jaswon MS, Linch DC: Isoquinolinesulfonamide protein kinase inhibitors H7 and H8 enhance the effects of granulocyte-macrophage colony-stimulating factor (GM-CSE) on neutrophil function and inhibit GM-CSF receptor internalization. Blood. 1990 Sep 1;76(5):996-1003. [PubMed:2168226 ]
Zigmond SH, Tranquillo AW: Chemotactic peptide binding by rabbit polymorphonuclear leukocytes. Presence of two compartments having similar affinities but different kinetics. J Biol Chem. 1986 Apr 25;261(12):5283-8. [PubMed:3957925 ]
Sjolinder M, Stenke L, Nasman-Glaser B, Widell S, Doucet J, Jakobsson PJ, Lindgren JA: Aberrant expression of active leukotriene C(4) synthase in CD16(+) neutrophils from patients with chronic myeloid leukemia. Blood. 2000 Feb 15;95(4):1456-64. [PubMed:10666225 ]
Folefoc AT, Fromme BJ, Katz AA, Flanagan CA: South African mutations of the CCR5 coreceptor for HIV modify interaction with chemokines and HIV Envelope protein. J Acquir Immune Defic Syndr. 2010 Aug;54(4):352-9. doi: 10.1097/QAI.0b013e3181e0c7b2. [PubMed:20442662 ]

Showing metabocard for Leucylphenylalanine (MMDBc0000658)

MOL for #<Metabolite:0x00007f55d87feb00>

3D MOL for #<Metabolite:0x00007f55d87feb00>

3D SDF for #<Metabolite:0x00007f55d87feb00>

3D-SDF for #<Metabolite:0x00007f55d87feb00>

PDB for #<Metabolite:0x00007f55d87feb00>

3D PDB for #<Metabolite:0x00007f55d87feb00>

SMILES for #<Metabolite:0x00007f55d87feb00>

INCHI for #<Metabolite:0x00007f55d87feb00>

Structure for #<Metabolite:0x00007f55d87feb00>

3D Structure for #<Metabolite:0x00007f55d87feb00>