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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:02:53 UTC

Update Date

2021-09-14 15:37:01 UTC

HMDB ID

HMDB0028892

Secondary Accession Numbers

HMDB28892

Metabolite Identification

Common Name

Histidylphenylalanine

Description

Histidylphenylalanine is a dipeptide composed of histidine and phenylalanine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Structure

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

HMDB0028892
     RDKit          3D
Histidylphenylalanine
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.7213   -1.4734   -0.0444 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5474   -0.2998    0.7740 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1717    0.9305    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138    0.7596   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1999    0.2468   -1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5357    0.2641   -0.9677 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7992    0.7669    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    1.0663    0.7824 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0981    0.0128    0.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946    1.0107    1.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -0.7884    0.3987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2976   -0.4392    0.6241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9609   -0.0667   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3770    0.2919   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7756    1.5939   -0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0941    1.9437    0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0795    0.9884   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6872   -0.3041   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3749   -0.6658   -0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -1.5011    1.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2874   -2.5240    1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2808   -1.4968    1.7982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670   -2.3290    0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431   -1.4333   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0127   -0.4926    1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250    1.1760   -0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792    1.7793    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6977   -0.1051   -2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2614   -0.0618   -1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7354    0.9322    0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -1.6158   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3484    0.4865    1.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276   -0.8589   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146    0.8247   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876    2.3238   -0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3823    2.9573    0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1300    1.2182    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4655   -1.0616   -0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962   -1.7035   -0.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184   -2.3527    1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  2  0
 20 22  1  0
  8  4  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  1
  3 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 12 32  1  1
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
M  END


  Mrv1652304062013492D          

 22 23  0  0  0  0            999 V2000
 9998.880610000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5954 9999.7892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.309310000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0248 9999.7892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.742510000.2013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.4560 9999.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.171610000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.309310001.0261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5954 9998.9638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.494910000.2836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8275 9999.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0824 9999.0140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9074 9999.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1623 9999.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.743510001.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.458510001.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.029610001.4397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.8860 9999.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.600610000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.600610001.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.886110001.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.171610001.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  1  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
 13 14  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 11  2  0  0  0  0
 10 14  1  0  0  0  0
  1 14  1  0  0  0  0
  5 15  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  6  7  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  7 18  2  0  0  0  0
 22  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0028892

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18N4O3/c16-12(7-11-8-17-9-18-11)14(20)19-13(15(21)22)6-10-4-2-1-3-5-10/h1-5,8-9,12-13H,6-7,16H2,(H,17,18)(H,19,20)(H,21,22)/t12-,13-/m0/s1

> <INCHI_KEY>
XMAUFHMAAVTODF-STQMWFEESA-N

> <FORMULA>
C15H18N4O3

> <MOLECULAR_WEIGHT>
302.334

> <EXACT_MASS>
302.137890456

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.793938264173978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanoic acid

> <ALOGPS_LOGP>
-1.55

> <JCHEM_LOGP>
-2.0969537745986293

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.885547920058201

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5285138458335306

> <JCHEM_PKA_STRONGEST_BASIC>
7.83852709152786

> <JCHEM_POLAR_SURFACE_AREA>
121.10000000000002

> <JCHEM_REFRACTIVITY>
79.40970000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0028892
     RDKit          3D
Histidylphenylalanine
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.7213   -1.4734   -0.0444 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5474   -0.2998    0.7740 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1717    0.9305    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138    0.7596   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1999    0.2468   -1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5357    0.2641   -0.9677 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7992    0.7669    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    1.0663    0.7824 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0981    0.0128    0.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946    1.0107    1.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -0.7884    0.3987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2976   -0.4392    0.6241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9609   -0.0667   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3770    0.2919   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7756    1.5939   -0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0941    1.9437    0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0795    0.9884   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6872   -0.3041   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3749   -0.6658   -0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -1.5011    1.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2874   -2.5240    1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2808   -1.4968    1.7982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670   -2.3290    0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431   -1.4333   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0127   -0.4926    1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250    1.1760   -0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792    1.7793    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6977   -0.1051   -2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2614   -0.0618   -1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7354    0.9322    0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -1.6158   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3484    0.4865    1.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276   -0.8589   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146    0.8247   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876    2.3238   -0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3823    2.9573    0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1300    1.2182    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4655   -1.0616   -0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962   -1.7035   -0.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184   -2.3527    1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  2  0
 20 22  1  0
  8  4  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  1
  3 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 12 32  1  1
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    8664.5778667.042   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.9118666.273   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.2448667.042   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8668.5808666.273   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8669.9198667.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.2518666.273   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8672.5878667.042   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8667.2448668.582   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8665.9118664.732   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0    8661.9908667.196   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8660.7458666.291   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8661.2208664.826   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8662.7608664.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.2368666.291   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.9218668.582   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8671.2568669.351   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8668.5898669.354   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8673.9218666.272   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8675.2548667.042   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8675.2548668.582   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8673.9218669.352   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8672.5878668.582   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6   18   22                                                  
CONECT    8    3                                                            
CONECT    9    2                                                            
CONECT   10   11   14                                                       
CONECT   11   12   10                                                       
CONECT   12   11   13                                                       
CONECT   13   14   12                                                       
CONECT   14   13   10    1                                                  
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   19    7                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    7                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0028892
HETATM    1  N1  UNL     1       2.721  -1.473  -0.044  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.547  -0.300   0.774  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.172   0.931   0.141  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.614   0.760  -0.066  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.200   0.247  -1.187  1.00  0.00           C  
HETATM    6  N2  UNL     1       6.536   0.264  -0.968  1.00  0.00           N  
HETATM    7  C5  UNL     1       6.799   0.767   0.244  1.00  0.00           C  
HETATM    8  N3  UNL     1       5.588   1.066   0.782  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.098   0.013   0.973  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.795   1.011   1.667  1.00  0.00           O  
HETATM   11  N4  UNL     1       0.088  -0.788   0.399  1.00  0.00           N  
HETATM   12  C7  UNL     1      -1.298  -0.439   0.624  1.00  0.00           C  
HETATM   13  C8  UNL     1      -1.961  -0.067  -0.670  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.377   0.292  -0.463  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.776   1.594  -0.162  1.00  0.00           C  
HETATM   16  C11 UNL     1      -5.094   1.944   0.024  1.00  0.00           C  
HETATM   17  C12 UNL     1      -6.080   0.988  -0.085  1.00  0.00           C  
HETATM   18  C13 UNL     1      -5.687  -0.304  -0.384  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.375  -0.666  -0.572  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.959  -1.501   1.384  1.00  0.00           C  
HETATM   21  O2  UNL     1      -1.287  -2.524   1.705  1.00  0.00           O  
HETATM   22  O3  UNL     1      -3.281  -1.497   1.798  1.00  0.00           O  
HETATM   23  H1  UNL     1       2.567  -2.329   0.510  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.243  -1.433  -0.954  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.013  -0.493   1.751  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.625   1.176  -0.801  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.979   1.779   0.831  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.698  -0.105  -2.078  1.00  0.00           H  
HETATM   29  H7  UNL     1       7.261  -0.062  -1.633  1.00  0.00           H  
HETATM   30  H8  UNL     1       7.735   0.932   0.756  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.366  -1.616  -0.176  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.348   0.486   1.271  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.828  -0.859  -1.449  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.415   0.825  -1.062  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.988   2.324  -0.081  1.00  0.00           H  
HETATM   36  H14 UNL     1      -5.382   2.957   0.257  1.00  0.00           H  
HETATM   37  H15 UNL     1      -7.130   1.218   0.053  1.00  0.00           H  
HETATM   38  H16 UNL     1      -6.466  -1.062  -0.472  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.096  -1.703  -0.811  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.818  -2.353   1.851  1.00  0.00           H  
CONECT    1    2   23   24
CONECT    2    3    9   25
CONECT    3    4   26   27
CONECT    4    5    5    8
CONECT    5    6   28
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    9   10   10   11
CONECT   11   12   31
CONECT   12   13   20   32
CONECT   13   14   33   34
CONECT   14   15   15   19
CONECT   15   16   35
CONECT   16   17   17   36
CONECT   17   18   37
CONECT   18   19   19   38
CONECT   19   39
CONECT   20   21   21   22
CONECT   22   40
END

HMDB0028892
     RDKit          3D
Histidylphenylalanine
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.7213   -1.4734   -0.0444 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5474   -0.2998    0.7740 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1717    0.9305    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138    0.7596   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1999    0.2468   -1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5357    0.2641   -0.9677 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7992    0.7669    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879    1.0663    0.7824 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0981    0.0128    0.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946    1.0107    1.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -0.7884    0.3987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2976   -0.4392    0.6241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9609   -0.0667   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3770    0.2919   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7756    1.5939   -0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0941    1.9437    0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0795    0.9884   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6872   -0.3041   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3749   -0.6658   -0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -1.5011    1.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2874   -2.5240    1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2808   -1.4968    1.7982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670   -2.3290    0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431   -1.4333   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0127   -0.4926    1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250    1.1760   -0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792    1.7793    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6977   -0.1051   -2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2614   -0.0618   -1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7354    0.9322    0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -1.6158   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3484    0.4865    1.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276   -0.8589   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146    0.8247   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876    2.3238   -0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3823    2.9573    0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1300    1.2182    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4655   -1.0616   -0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962   -1.7035   -0.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184   -2.3527    1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  2  0
 20 22  1  0
  8  4  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  1
  3 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 12 32  1  1
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S)-2-{[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino}-3-phenylpropanoic acid	ChEBI
H-F	ChEBI
H-F Dipeptide	ChEBI
HF	ChEBI
HF Dipeptide	ChEBI
Histidine phenylalanine dipeptide	ChEBI
N-Histidyl-phenylalanine	ChEBI
N-L-Histidyl-L-phenylalanine	ChEBI
(2S)-2-{[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino}-3-phenylpropanoate	Generator
Phenylalanylhistidine	HMDB
Phe-his	HMDB
His-phe	HMDB
Histidine-phenylalanine dipeptide	HMDB
Histidinyl-phenylalanine	HMDB
Histidinylphenylalanine	HMDB
Histidyl-phenylalanine	HMDB
L-His-L-phe	HMDB
L-Histidinyl-L-phenylalanine	HMDB
L-Histidyl-L-phenylalanine	HMDB
N-Histidinylphenylalanine	HMDB
N-Histidylphenylalanine	HMDB
N-L-Histidinyl-L-phenylalanine	HMDB
Histidylphenylalanine	ChEBI

Chemical Formula

C₁₅H₁₈N₄O₃

Average Molecular Weight

302.334

Monoisotopic Molecular Weight

302.137890456

IUPAC Name

(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanoic acid

CAS Registry Number

16874-81-0

SMILES

N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C15H18N4O3/c16-12(7-11-8-17-9-18-11)14(20)19-13(15(21)22)6-10-4-2-1-3-5-10/h1-5,8-9,12-13H,6-7,16H2,(H,17,18)(H,19,20)(H,21,22)/t12-,13-/m0/s1

InChI Key

XMAUFHMAAVTODF-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
Histidine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Imidazolyl carboxylic acid derivative
Aralkylamine
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Heteroaromatic compound
Imidazole
Azole
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid
Primary aliphatic amine
Hydrocarbon derivative
Amine
Carbonyl group
Organic oxygen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Primary amine
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	-2.3	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	7.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.1 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	79.41 m³·mol⁻¹	ChemAxon
Polarizability	30.79 Å³	ChemAxon
Number of Rings	2	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]+	167.423	30932474
DeepCCS	[M-H]-	165.065	30932474
DeepCCS	[M-2H]-	198.85	30932474
DeepCCS	[M+Na]+	174.077	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Histidylphenylalanine	N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	3818.6	Standard polar	33892256
Histidylphenylalanine	N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	2331.7	Standard non polar	33892256
Histidylphenylalanine	N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	3003.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Histidylphenylalanine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC1=C[NH]C=N1	2766.7	Semi standard non polar	33892256
Histidylphenylalanine,1TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2847.7	Semi standard non polar	33892256
Histidylphenylalanine,1TMS,isomer #3	C[Si](C)(C)N1C=NC(C[C@H](N)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O)=C1	2931.3	Semi standard non polar	33892256
Histidylphenylalanine,1TMS,isomer #4	C[Si](C)(C)N(C(=O)[C@@H](N)CC1=C[NH]C=N1)[C@@H](CC1=CC=CC=C1)C(=O)O	2756.0	Semi standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2781.6	Semi standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2750.3	Standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=C[NH]C=N1)[Si](C)(C)C	2712.0	Semi standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=C[NH]C=N1)[Si](C)(C)C	2678.8	Standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C=N1	2884.1	Semi standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C=N1	2622.9	Standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=C[NH]C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2913.4	Semi standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=C[NH]C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2892.0	Standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #5	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2941.3	Semi standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #5	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	2764.6	Standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2774.4	Semi standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2805.5	Standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #7	C[Si](C)(C)N(C(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C=N1)[C@@H](CC1=CC=CC=C1)C(=O)O	2828.5	Semi standard non polar	33892256
Histidylphenylalanine,2TMS,isomer #7	C[Si](C)(C)N(C(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C=N1)[C@@H](CC1=CC=CC=C1)C(=O)O	2750.1	Standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C)[Si](C)(C)C	2861.5	Semi standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C)[Si](C)(C)C	2837.1	Standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2895.9	Semi standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	2708.2	Standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2743.1	Semi standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2774.8	Standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C=N1)[Si](C)(C)C	2796.2	Semi standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C=N1)[Si](C)(C)C	2700.4	Standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #5	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3033.7	Semi standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #5	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2874.8	Standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #6	C[Si](C)(C)N(C(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	2869.9	Semi standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #6	C[Si](C)(C)N(C(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	2894.8	Standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #7	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2871.1	Semi standard non polar	33892256
Histidylphenylalanine,3TMS,isomer #7	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2794.7	Standard non polar	33892256
Histidylphenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2908.7	Semi standard non polar	33892256
Histidylphenylalanine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2873.9	Standard non polar	33892256
Histidylphenylalanine,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CN([Si](C)(C)C)C=N1)N([Si](C)(C)C)[Si](C)(C)C	3004.0	Semi standard non polar	33892256
Histidylphenylalanine,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CN([Si](C)(C)C)C=N1)N([Si](C)(C)C)[Si](C)(C)C	2840.6	Standard non polar	33892256
Histidylphenylalanine,4TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2854.4	Semi standard non polar	33892256
Histidylphenylalanine,4TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2765.4	Standard non polar	33892256
Histidylphenylalanine,4TMS,isomer #4	C[Si](C)(C)N(C(=O)[C@H](CC1=CN([Si](C)(C)C)C=N1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	2988.6	Semi standard non polar	33892256
Histidylphenylalanine,4TMS,isomer #4	C[Si](C)(C)N(C(=O)[C@H](CC1=CN([Si](C)(C)C)C=N1)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	2918.0	Standard non polar	33892256
Histidylphenylalanine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=CN([Si](C)(C)C)C=N1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3027.0	Semi standard non polar	33892256
Histidylphenylalanine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=CN([Si](C)(C)C)C=N1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2905.3	Standard non polar	33892256
Histidylphenylalanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC1=C[NH]C=N1	3023.9	Semi standard non polar	33892256
Histidylphenylalanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	3054.3	Semi standard non polar	33892256
Histidylphenylalanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC(C[C@H](N)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O)=C1	3164.2	Semi standard non polar	33892256
Histidylphenylalanine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)[C@@H](N)CC1=C[NH]C=N1)[C@@H](CC1=CC=CC=C1)C(=O)O	3011.1	Semi standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3215.1	Semi standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3124.9	Standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=C[NH]C=N1)[Si](C)(C)C(C)(C)C	3222.2	Semi standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=C[NH]C=N1)[Si](C)(C)C(C)(C)C	3059.9	Standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C=N1	3347.1	Semi standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C=N1	2979.7	Standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3376.0	Semi standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3220.8	Standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	3373.8	Semi standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O	3090.7	Standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3217.7	Semi standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3152.6	Standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C=N1)[C@@H](CC1=CC=CC=C1)C(=O)O	3304.3	Semi standard non polar	33892256
Histidylphenylalanine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C=N1)[C@@H](CC1=CC=CC=C1)C(=O)O	3077.5	Standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3567.1	Semi standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3336.0	Standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3529.5	Semi standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3235.3	Standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)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	3397.4	Semi standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C=N1)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	3273.2	Standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	3486.5	Semi standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	3201.4	Standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3706.7	Semi standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3348.9	Standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3539.4	Semi standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3377.7	Standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3514.0	Semi standard non polar	33892256
Histidylphenylalanine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3283.2	Standard non polar	33892256
Histidylphenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3726.4	Semi standard non polar	33892256
Histidylphenylalanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=C[NH]C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3506.0	Standard non polar	33892256
Histidylphenylalanine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3868.0	Semi standard non polar	33892256
Histidylphenylalanine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3491.2	Standard non polar	33892256
Histidylphenylalanine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)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	3667.1	Semi standard non polar	33892256
Histidylphenylalanine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)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	3436.1	Standard non polar	33892256
Histidylphenylalanine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3847.0	Semi standard non polar	33892256
Histidylphenylalanine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](CC1=CC=CC=C1)C(=O)O	3549.5	Standard non polar	33892256
Histidylphenylalanine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4013.4	Semi standard non polar	33892256
Histidylphenylalanine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C=N1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3691.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Histidylphenylalanine 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 - Histidylphenylalanine 10V, Positive-QTOF	splash10-0udi-0439000000-3b905649af5f2ba66d5f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylphenylalanine 20V, Positive-QTOF	splash10-03di-4910000000-e382cf10ab40fef2173d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylphenylalanine 40V, Positive-QTOF	splash10-03ec-9500000000-11f361f0c8850c4678a8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylphenylalanine 10V, Negative-QTOF	splash10-0udi-0529000000-6df0ed16df95042c1a5b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylphenylalanine 20V, Negative-QTOF	splash10-0ir1-4921000000-dce0eb4ef3e5e9c0b2c7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylphenylalanine 40V, Negative-QTOF	splash10-00kf-9700000000-0fff46a6aab844d14c60	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

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

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 ]
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 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111921

KNApSAcK ID

Not Available

Chemspider ID

134148

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

152198

PDB ID

Not Available

ChEBI ID

141438

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

Reddy PR, Mohan SK, Rao KS: Ternary zinc(II)-dipeptide complexes for the hydrolytic cleavage of DNA at physiological pH. Chem Biodivers. 2005 May;2(5):672-83. [PubMed:17192010 ]
Sigman JA, Kim HK, Zhao X, Carey JR, Lu Y: The role of copper and protons in heme-copper oxidases: kinetic study of an engineered heme-copper center in myoglobin. Proc Natl Acad Sci U S A. 2003 Apr 1;100(7):3629-34. Epub 2003 Mar 24. [PubMed:12655052 ]
Osz K, Varnagy K, Suli-Vargha H, Csampay A, Sanna D, Micera G, Sovago I: Acid-base properties and copper(II) complexes of dipeptides containing histidine and additional chelating bis(imidazol-2-yl) residues. J Inorg Biochem. 2004 Jan;98(1):24-32. [PubMed:14659629 ]

Showing metabocard for Histidylphenylalanine (HMDB0028892)

MOL for HMDB0028892 (Histidylphenylalanine)

3D MOL for HMDB0028892 (Histidylphenylalanine)

3D SDF for HMDB0028892 (Histidylphenylalanine)

3D-SDF for HMDB0028892 (Histidylphenylalanine)

PDB for HMDB0028892 (Histidylphenylalanine)

3D PDB for HMDB0028892 (Histidylphenylalanine)

SMILES for HMDB0028892 (Histidylphenylalanine)

INCHI for HMDB0028892 (Histidylphenylalanine)

Structure for HMDB0028892 (Histidylphenylalanine)

3D Structure for HMDB0028892 (Histidylphenylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra