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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-30 15:51:35 UTC

Update Date

2021-09-14 15:46:19 UTC

HMDB ID

HMDB0013243

Secondary Accession Numbers

HMDB0028936
HMDB13243
HMDB28936

Metabolite Identification

Common Name

Leucylphenylalanine

Description

Leucylphenylalanine, also known as L-F or L-leu-L-phe, 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. Leucylphenylalanine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make leucylphenylalanine a potential biomarker for the consumption of these foods. Leucylphenylalanine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Leucylphenylalanine.

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>
HMDB0013243

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₁₅H₂₂N₂O₃

Average Molecular Weight

278.352

Monoisotopic Molecular Weight

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

3063-05-6

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 )

Ontology

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	170.847	30932474
DeepCCS	[M-H]-	168.489	30932474
DeepCCS	[M-2H]-	201.375	30932474
DeepCCS	[M+Na]+	176.941	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	164.2	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.0	32859911
AllCCS	[M-H]-	167.2	32859911
AllCCS	[M+Na-2H]-	167.7	32859911
AllCCS	[M+HCOO]-	168.3	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.	2.89 minutes	32390414
Predicted by Siyang on May 30, 2022	11.506 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.91 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	109.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1562.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	246.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	106.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	410.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	399.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	194.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	896.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	422.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1179.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	241.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	280.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	279.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	35.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Leucylphenylalanine	CC(C)C[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	3544.0	Standard polar	33892256
Leucylphenylalanine	CC(C)C[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	2177.0	Standard non polar	33892256
Leucylphenylalanine	CC(C)C[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	2289.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leucylphenylalanine,1TMS,isomer #1	CC(C)C[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2230.7	Semi standard non polar	33892256
Leucylphenylalanine,1TMS,isomer #2	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2278.1	Semi standard non polar	33892256
Leucylphenylalanine,1TMS,isomer #3	CC(C)C[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2227.0	Semi standard non polar	33892256
Leucylphenylalanine,2TMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2240.1	Semi standard non polar	33892256
Leucylphenylalanine,2TMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2273.3	Standard non polar	33892256
Leucylphenylalanine,2TMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2890.6	Standard polar	33892256
Leucylphenylalanine,2TMS,isomer #2	CC(C)C[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2190.2	Semi standard non polar	33892256
Leucylphenylalanine,2TMS,isomer #2	CC(C)C[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2276.8	Standard non polar	33892256
Leucylphenylalanine,2TMS,isomer #2	CC(C)C[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3091.5	Standard polar	33892256
Leucylphenylalanine,2TMS,isomer #3	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2395.3	Semi standard non polar	33892256
Leucylphenylalanine,2TMS,isomer #3	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2329.5	Standard non polar	33892256
Leucylphenylalanine,2TMS,isomer #3	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	3039.4	Standard polar	33892256
Leucylphenylalanine,2TMS,isomer #4	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2262.5	Semi standard non polar	33892256
Leucylphenylalanine,2TMS,isomer #4	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2317.6	Standard non polar	33892256
Leucylphenylalanine,2TMS,isomer #4	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2926.0	Standard polar	33892256
Leucylphenylalanine,3TMS,isomer #1	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2365.9	Semi standard non polar	33892256
Leucylphenylalanine,3TMS,isomer #1	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2405.7	Standard non polar	33892256
Leucylphenylalanine,3TMS,isomer #1	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2755.0	Standard polar	33892256
Leucylphenylalanine,3TMS,isomer #2	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2234.8	Semi standard non polar	33892256
Leucylphenylalanine,3TMS,isomer #2	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2359.8	Standard non polar	33892256
Leucylphenylalanine,3TMS,isomer #2	CC(C)C[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2689.6	Standard polar	33892256
Leucylphenylalanine,3TMS,isomer #3	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2368.9	Semi standard non polar	33892256
Leucylphenylalanine,3TMS,isomer #3	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2449.0	Standard non polar	33892256
Leucylphenylalanine,3TMS,isomer #3	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2813.2	Standard polar	33892256
Leucylphenylalanine,4TMS,isomer #1	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2419.6	Semi standard non polar	33892256
Leucylphenylalanine,4TMS,isomer #1	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2501.3	Standard non polar	33892256
Leucylphenylalanine,4TMS,isomer #1	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2608.1	Standard polar	33892256
Leucylphenylalanine,1TBDMS,isomer #1	CC(C)C[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2494.6	Semi standard non polar	33892256
Leucylphenylalanine,1TBDMS,isomer #2	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2504.4	Semi standard non polar	33892256
Leucylphenylalanine,1TBDMS,isomer #3	CC(C)C[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2475.6	Semi standard non polar	33892256
Leucylphenylalanine,2TBDMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2710.7	Semi standard non polar	33892256
Leucylphenylalanine,2TBDMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2654.1	Standard non polar	33892256
Leucylphenylalanine,2TBDMS,isomer #1	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3075.4	Standard polar	33892256
Leucylphenylalanine,2TBDMS,isomer #2	CC(C)C[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2701.1	Semi standard non polar	33892256
Leucylphenylalanine,2TBDMS,isomer #2	CC(C)C[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2654.6	Standard non polar	33892256
Leucylphenylalanine,2TBDMS,isomer #2	CC(C)C[C@H](N)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3237.1	Standard polar	33892256
Leucylphenylalanine,2TBDMS,isomer #3	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2862.8	Semi standard non polar	33892256
Leucylphenylalanine,2TBDMS,isomer #3	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2693.5	Standard non polar	33892256
Leucylphenylalanine,2TBDMS,isomer #3	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3145.2	Standard polar	33892256
Leucylphenylalanine,2TBDMS,isomer #4	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2739.0	Semi standard non polar	33892256
Leucylphenylalanine,2TBDMS,isomer #4	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2676.6	Standard non polar	33892256
Leucylphenylalanine,2TBDMS,isomer #4	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3097.6	Standard polar	33892256
Leucylphenylalanine,3TBDMS,isomer #1	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3078.7	Semi standard non polar	33892256
Leucylphenylalanine,3TBDMS,isomer #1	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2929.1	Standard non polar	33892256
Leucylphenylalanine,3TBDMS,isomer #1	CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3009.8	Standard polar	33892256
Leucylphenylalanine,3TBDMS,isomer #2	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2924.9	Semi standard non polar	33892256
Leucylphenylalanine,3TBDMS,isomer #2	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2889.9	Standard non polar	33892256
Leucylphenylalanine,3TBDMS,isomer #2	CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3006.8	Standard polar	33892256
Leucylphenylalanine,3TBDMS,isomer #3	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3077.6	Semi standard non polar	33892256
Leucylphenylalanine,3TBDMS,isomer #3	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2954.2	Standard non polar	33892256
Leucylphenylalanine,3TBDMS,isomer #3	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3053.6	Standard polar	33892256
Leucylphenylalanine,4TBDMS,isomer #1	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3290.4	Semi standard non polar	33892256
Leucylphenylalanine,4TBDMS,isomer #1	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3167.3	Standard non polar	33892256
Leucylphenylalanine,4TBDMS,isomer #1	CC(C)C[C@@H](C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2973.2	Standard polar	33892256

Spectra

GC-MS Spectra

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

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylphenylalanine 10V, Positive-QTOF	splash10-004i-2290000000-f9bca613c3c1be686d24	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylphenylalanine 20V, Positive-QTOF	splash10-01b9-9500000000-16f4fa13fb6fd1c29466	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylphenylalanine 40V, Positive-QTOF	splash10-00r6-9300000000-5405f9dacb771654c6e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylphenylalanine 10V, Negative-QTOF	splash10-004i-0490000000-7cc05c14e81ff1ef01bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylphenylalanine 20V, Negative-QTOF	splash10-01ow-3900000000-9d5faab5a1caafb3e88f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucylphenylalanine 40V, Negative-QTOF	splash10-0006-9800000000-22caa12917c8a9286006	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	0.02 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details

Abnormal Concentrations

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

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

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

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

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 ]
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 ]
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 ]
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 (HMDB0013243)

MOL for HMDB0013243 (Leucylphenylalanine)

3D MOL for HMDB0013243 (Leucylphenylalanine)

3D SDF for HMDB0013243 (Leucylphenylalanine)

3D-SDF for HMDB0013243 (Leucylphenylalanine)

PDB for HMDB0013243 (Leucylphenylalanine)

3D PDB for HMDB0013243 (Leucylphenylalanine)

SMILES for HMDB0013243 (Leucylphenylalanine)

INCHI for HMDB0013243 (Leucylphenylalanine)

Structure for HMDB0013243 (Leucylphenylalanine)

3D Structure for HMDB0013243 (Leucylphenylalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra