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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:03:50 UTC

Update Date

2021-09-14 15:45:33 UTC

HMDB ID

HMDB0029138

Secondary Accession Numbers

HMDB29138

Metabolite Identification

Common Name

Valyltryptophan

Description

Valyltryptophan is a dipeptide composed of valine and tryptophan. 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

HMDB0029138
     RDKit          3D
Valyltryptophan
 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.5911    2.1212    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865    1.1242    0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2709    1.2302   -0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2293   -0.2751    0.7168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7493   -0.4290    2.0561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2240   -0.7773   -0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4032   -0.6309   -1.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0382   -1.4355    0.1769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0559   -1.9262   -0.7652 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3532   -1.6123   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6836   -0.1788   -0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    0.9498   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593    2.0245   -0.3342 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670    1.6062    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090    2.3262    0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2220    1.6219    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2472    0.2410    0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1104   -0.4340    0.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9530    0.2501    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1468   -3.4414   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9905   -4.0739   -0.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6878   -4.1672   -1.6567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879    1.8134    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0634    3.0915    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242    2.2509   -0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5263    1.3942    1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649    1.4371   -1.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    2.0763   -0.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8543    0.3120   -1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1394   -0.9487    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681   -1.4562    2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7943   -0.0546    2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662   -1.5728    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -1.5534   -1.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9968   -2.0589   -1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5889   -2.1272    0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637    0.9889   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031    3.0043   -0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0868    3.4040    0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283    2.1508    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409   -0.3054    1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1285   -1.5111    0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329   -4.4487   -1.3536 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  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
  9 20  1  0
 20 21  2  0
 20 22  1  0
 19 11  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  1
  5 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  6
 10 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 22 43  1  0
M  END


  Mrv1652304062014272D          

 22 23  0  0  0  0            999 V2000
10000.516910000.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.232210001.1006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.945010000.6897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.657810001.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.370510000.6897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.657810001.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.805110001.1006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.091310000.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.379610001.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0913 9999.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.805110001.9235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.5169 9999.8666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.9450 9999.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6596 9999.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.7459 9998.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5528 9998.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.9654 9999.1766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.4133 9999.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1937 9998.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4485 9997.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2556 9997.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8078 9997.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 12  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 18  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 15 19  2  0  0  0  0
 22 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029138

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)[C@H](N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H21N3O3/c1-9(2)14(17)15(20)19-13(16(21)22)7-10-8-18-12-6-4-3-5-11(10)12/h3-6,8-9,13-14,18H,7,17H2,1-2H3,(H,19,20)(H,21,22)/t13-,14-/m0/s1

> <INCHI_KEY>
LZDNBBYBDGBADK-KBPBESRZSA-N

> <FORMULA>
C16H21N3O3

> <MOLECULAR_WEIGHT>
303.362

> <EXACT_MASS>
303.158291548

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.625111056160712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-0.7375271924689719

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.73023194531827

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.952647781653769

> <JCHEM_PKA_STRONGEST_BASIC>
8.514467306959524

> <JCHEM_POLAR_SURFACE_AREA>
108.20999999999998

> <JCHEM_REFRACTIVITY>
82.49580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(1H-indol-3-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029138
     RDKit          3D
Valyltryptophan
 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.5911    2.1212    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865    1.1242    0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2709    1.2302   -0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2293   -0.2751    0.7168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7493   -0.4290    2.0561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2240   -0.7773   -0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4032   -0.6309   -1.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0382   -1.4355    0.1769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0559   -1.9262   -0.7652 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3532   -1.6123   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6836   -0.1788   -0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    0.9498   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593    2.0245   -0.3342 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670    1.6062    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090    2.3262    0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2220    1.6219    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2472    0.2410    0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1104   -0.4340    0.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9530    0.2501    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1468   -3.4414   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9905   -4.0739   -0.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6878   -4.1672   -1.6567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879    1.8134    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0634    3.0915    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242    2.2509   -0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5263    1.3942    1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649    1.4371   -1.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    2.0763   -0.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8543    0.3120   -1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1394   -0.9487    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681   -1.4562    2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7943   -0.0546    2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662   -1.5728    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -1.5534   -1.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9968   -2.0589   -1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5889   -2.1272    0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637    0.9889   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031    3.0043   -0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0868    3.4040    0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283    2.1508    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409   -0.3054    1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1285   -1.5111    0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329   -4.4487   -1.3536 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  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
  9 20  1  0
 20 21  2  0
 20 22  1  0
 19 11  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  1
  5 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  6
 10 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 22 43  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    8667.6328667.954   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8668.9678668.721   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8670.2978667.954   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8671.6288668.721   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8672.9588667.954   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8671.6288670.257   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8666.3038668.721   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.9708667.954   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.6428668.721   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.9708666.418   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8666.3038670.257   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    8667.6328666.418   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8670.2978666.418   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8671.6318665.648   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8671.7928664.116   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8673.2998663.796   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    8674.0698665.130   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0    8673.0388666.274   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.7628662.971   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.2378661.507   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.7448661.186   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8673.7758662.331   0.000  0.00  0.00           C+0
CONECT    1    2    7   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    1                                                            
CONECT   13    3   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   22   17                                                  
CONECT   17   16   18                                                       
CONECT   18   14   17                                                       
CONECT   19   20   15                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0029138
HETATM    1  C1  UNL     1      -2.591   2.121   0.622  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.687   1.124   0.447  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.271   1.230  -0.968  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.229  -0.275   0.717  1.00  0.00           C  
HETATM    5  N1  UNL     1      -2.749  -0.429   2.056  1.00  0.00           N  
HETATM    6  C5  UNL     1      -2.224  -0.777  -0.254  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.403  -0.631  -1.493  1.00  0.00           O  
HETATM    8  N2  UNL     1      -1.038  -1.436   0.177  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.056  -1.926  -0.765  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.353  -1.612  -0.429  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.684  -0.179  -0.336  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.954   0.950  -0.569  1.00  0.00           C  
HETATM   13  N3  UNL     1       1.759   2.024  -0.334  1.00  0.00           N  
HETATM   14  C10 UNL     1       2.967   1.606   0.037  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.109   2.326   0.376  1.00  0.00           C  
HETATM   16  C12 UNL     1       5.222   1.622   0.720  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.247   0.241   0.740  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.110  -0.434   0.402  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.953   0.250   0.045  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.147  -3.441  -0.835  1.00  0.00           C  
HETATM   21  O2  UNL     1      -0.990  -4.074  -0.142  1.00  0.00           O  
HETATM   22  O3  UNL     1       0.688  -4.167  -1.657  1.00  0.00           O  
HETATM   23  H1  UNL     1      -1.888   1.813   1.417  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.063   3.092   0.893  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.024   2.251  -0.341  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.526   1.394   1.126  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.465   1.437  -1.674  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.968   2.076  -0.966  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.854   0.312  -1.191  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.139  -0.949   0.599  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.768  -1.456   2.324  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.794  -0.055   2.145  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.866  -1.573   1.185  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.346  -1.553  -1.775  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.997  -2.059  -1.226  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.589  -2.127   0.551  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.064   0.989  -0.883  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.403   3.004  -0.452  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.087   3.404   0.359  1.00  0.00           H  
HETATM   40  H18 UNL     1       6.128   2.151   0.990  1.00  0.00           H  
HETATM   41  H19 UNL     1       6.141  -0.305   1.015  1.00  0.00           H  
HETATM   42  H20 UNL     1       4.128  -1.511   0.418  1.00  0.00           H  
HETATM   43  H21 UNL     1       1.633  -4.449  -1.354  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4   26
CONECT    3   27   28   29
CONECT    4    5    6   30
CONECT    5   31   32
CONECT    6    7    7    8
CONECT    8    9   33
CONECT    9   10   20   34
CONECT   10   11   35   36
CONECT   11   12   12   19
CONECT   12   13   37
CONECT   13   14   38
CONECT   14   15   15   19
CONECT   15   16   39
CONECT   16   17   17   40
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   20   21   21   22
CONECT   22   43
END

HMDB0029138
     RDKit          3D
Valyltryptophan
 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.5911    2.1212    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865    1.1242    0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2709    1.2302   -0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2293   -0.2751    0.7168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7493   -0.4290    2.0561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2240   -0.7773   -0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4032   -0.6309   -1.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0382   -1.4355    0.1769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0559   -1.9262   -0.7652 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3532   -1.6123   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6836   -0.1788   -0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    0.9498   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593    2.0245   -0.3342 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670    1.6062    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090    2.3262    0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2220    1.6219    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2472    0.2410    0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1104   -0.4340    0.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9530    0.2501    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1468   -3.4414   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9905   -4.0739   -0.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6878   -4.1672   -1.6567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879    1.8134    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0634    3.0915    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242    2.2509   -0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5263    1.3942    1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649    1.4371   -1.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    2.0763   -0.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8543    0.3120   -1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1394   -0.9487    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681   -1.4562    2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7943   -0.0546    2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662   -1.5728    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -1.5534   -1.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9968   -2.0589   -1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5889   -2.1272    0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637    0.9889   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031    3.0043   -0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0868    3.4040    0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283    2.1508    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409   -0.3054    1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1285   -1.5111    0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329   -4.4487   -1.3536 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  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
  9 20  1  0
 20 21  2  0
 20 22  1  0
 19 11  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  1
  5 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  6
 10 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 22 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-Valyltryptophan	HMDB
N-Valyltryptophan, (DL)-isomer	HMDB
N-L-Valyl-L-tryptophan	HMDB
L-Valyl-L-tryptophan	HMDB
L-Val-L-TRP	HMDB
V-W Dipeptide	HMDB
VW Dipeptide	HMDB
Val-TRP	HMDB
Valine tryptophan dipeptide	HMDB
Valine-tryptophan dipeptide	HMDB
Valyl-tryptophan	HMDB
Valyltryptophan	HMDB

Chemical Formula

C₁₆H₂₁N₃O₃

Average Molecular Weight

303.362

Monoisotopic Molecular Weight

303.158291548

IUPAC Name

(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(1H-indol-3-yl)propanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(1H-indol-3-yl)propanoic acid

CAS Registry Number

24587-37-9

SMILES

CC(C)[C@H](N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C16H21N3O3/c1-9(2)14(17)15(20)19-13(16(21)22)7-10-8-18-12-6-4-3-5-11(10)12/h3-6,8-9,13-14,18H,7,17H2,1-2H3,(H,19,20)(H,21,22)/t13-,14-/m0/s1

InChI Key

LZDNBBYBDGBADK-KBPBESRZSA-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
Valine or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Indolyl carboxylic acid derivative
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Carboxylic acid
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organopnictogen compound
Primary amine
Organonitrogen compound
Carbonyl group
Primary aliphatic amine
Amine
Organic nitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Feces (PMID: 27015276)

Source

Endogenous

Endogenous (HMDB: HMDB0029138)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-0.74	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	-0.64	ALOGPS
logP	-0.74	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	8.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	108.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.5 m³·mol⁻¹	ChemAxon
Polarizability	31.63 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-2H]-	204.198	30932474
DeepCCS	[M+Na]+	179.425	30932474
AllCCS	[M+H]+	171.9	32859911
AllCCS	[M+H-H2O]+	169.0	32859911
AllCCS	[M+NH4]+	174.6	32859911
AllCCS	[M+Na]+	175.4	32859911
AllCCS	[M-H]-	172.0	32859911
AllCCS	[M+Na-2H]-	172.1	32859911
AllCCS	[M+HCOO]-	172.4	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.	3.21 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6586 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.84 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	151.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1456.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	218.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	114.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	116.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	319.4 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	317.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	314.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	740.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	386.4 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	1069.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	238.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	253.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	324.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	325.5 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	120.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valyltryptophan	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O	3933.2	Standard polar	33892256
Valyltryptophan	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O	2465.1	Standard non polar	33892256
Valyltryptophan	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O	2868.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valyltryptophan,1TMS,isomer #1	CC(C)[C@H](N)C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2763.1	Semi standard non polar	33892256
Valyltryptophan,1TMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O	2798.8	Semi standard non polar	33892256
Valyltryptophan,1TMS,isomer #3	CC(C)[C@H](N)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2793.7	Semi standard non polar	33892256
Valyltryptophan,1TMS,isomer #4	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O	2803.4	Semi standard non polar	33892256
Valyltryptophan,2TMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2750.0	Semi standard non polar	33892256
Valyltryptophan,2TMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2708.0	Standard non polar	33892256
Valyltryptophan,2TMS,isomer #2	CC(C)[C@H](N)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2766.9	Semi standard non polar	33892256
Valyltryptophan,2TMS,isomer #2	CC(C)[C@H](N)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2740.0	Standard non polar	33892256
Valyltryptophan,2TMS,isomer #3	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2767.9	Semi standard non polar	33892256
Valyltryptophan,2TMS,isomer #3	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2664.8	Standard non polar	33892256
Valyltryptophan,2TMS,isomer #4	CC(C)[C@@H](C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2927.8	Semi standard non polar	33892256
Valyltryptophan,2TMS,isomer #4	CC(C)[C@@H](C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2817.3	Standard non polar	33892256
Valyltryptophan,2TMS,isomer #5	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2787.8	Semi standard non polar	33892256
Valyltryptophan,2TMS,isomer #5	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2735.0	Standard non polar	33892256
Valyltryptophan,2TMS,isomer #6	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O	2784.1	Semi standard non polar	33892256
Valyltryptophan,2TMS,isomer #6	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O	2732.8	Standard non polar	33892256
Valyltryptophan,2TMS,isomer #7	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2767.0	Semi standard non polar	33892256
Valyltryptophan,2TMS,isomer #7	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2754.4	Standard non polar	33892256
Valyltryptophan,3TMS,isomer #1	CC(C)[C@@H](C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2878.9	Semi standard non polar	33892256
Valyltryptophan,3TMS,isomer #1	CC(C)[C@@H](C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2835.3	Standard non polar	33892256
Valyltryptophan,3TMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2786.4	Semi standard non polar	33892256
Valyltryptophan,3TMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2763.2	Standard non polar	33892256
Valyltryptophan,3TMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2775.0	Semi standard non polar	33892256
Valyltryptophan,3TMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2724.0	Standard non polar	33892256
Valyltryptophan,3TMS,isomer #4	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2768.5	Semi standard non polar	33892256
Valyltryptophan,3TMS,isomer #4	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2794.8	Standard non polar	33892256
Valyltryptophan,3TMS,isomer #5	CC(C)[C@@H](C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2924.4	Semi standard non polar	33892256
Valyltryptophan,3TMS,isomer #5	CC(C)[C@@H](C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2887.0	Standard non polar	33892256
Valyltryptophan,3TMS,isomer #6	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2943.2	Semi standard non polar	33892256
Valyltryptophan,3TMS,isomer #6	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2838.5	Standard non polar	33892256
Valyltryptophan,3TMS,isomer #7	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2780.1	Semi standard non polar	33892256
Valyltryptophan,3TMS,isomer #7	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2775.0	Standard non polar	33892256
Valyltryptophan,4TMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2953.3	Semi standard non polar	33892256
Valyltryptophan,4TMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2920.5	Standard non polar	33892256
Valyltryptophan,4TMS,isomer #2	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2928.8	Semi standard non polar	33892256
Valyltryptophan,4TMS,isomer #2	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2859.9	Standard non polar	33892256
Valyltryptophan,4TMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2798.7	Semi standard non polar	33892256
Valyltryptophan,4TMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2790.4	Standard non polar	33892256
Valyltryptophan,4TMS,isomer #4	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2967.6	Semi standard non polar	33892256
Valyltryptophan,4TMS,isomer #4	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2927.3	Standard non polar	33892256
Valyltryptophan,5TMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3001.4	Semi standard non polar	33892256
Valyltryptophan,5TMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2954.6	Standard non polar	33892256
Valyltryptophan,1TBDMS,isomer #1	CC(C)[C@H](N)C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	3050.7	Semi standard non polar	33892256
Valyltryptophan,1TBDMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O	3041.5	Semi standard non polar	33892256
Valyltryptophan,1TBDMS,isomer #3	CC(C)[C@H](N)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3072.0	Semi standard non polar	33892256
Valyltryptophan,1TBDMS,isomer #4	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O	3050.5	Semi standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	3248.7	Semi standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #1	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	3137.6	Standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #2	CC(C)[C@H](N)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3278.8	Semi standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #2	CC(C)[C@H](N)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3159.3	Standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #3	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	3232.5	Semi standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #3	CC(C)[C@H](N)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	3078.1	Standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #4	CC(C)[C@@H](C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3437.1	Semi standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #4	CC(C)[C@@H](C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3207.8	Standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #5	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3288.2	Semi standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #5	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3152.4	Standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #6	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O	3242.1	Semi standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #6	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O	3114.5	Standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #7	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3252.9	Semi standard non polar	33892256
Valyltryptophan,2TBDMS,isomer #7	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3131.0	Standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #1	CC(C)[C@@H](C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)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	3599.4	Semi standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #1	CC(C)[C@@H](C(=O)N[C@@H](CC1=C[NH]C2=CC=CC=C12)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	3400.4	Standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3471.5	Semi standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #2	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3365.5	Standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	3380.3	Semi standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	3295.2	Standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #4	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3388.6	Semi standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #4	CC(C)[C@H](N)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3351.0	Standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #5	CC(C)[C@@H](C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)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	3622.2	Semi standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #5	CC(C)[C@@H](C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)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	3447.1	Standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #6	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3631.1	Semi standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #6	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3351.0	Standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #7	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3431.6	Semi standard non polar	33892256
Valyltryptophan,3TBDMS,isomer #7	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3303.1	Standard non polar	33892256
Valyltryptophan,4TBDMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)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	3822.4	Semi standard non polar	33892256
Valyltryptophan,4TBDMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=C[NH]C2=CC=CC=C12)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	3643.7	Standard non polar	33892256
Valyltryptophan,4TBDMS,isomer #2	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)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	3738.4	Semi standard non polar	33892256
Valyltryptophan,4TBDMS,isomer #2	CC(C)[C@@H](C(=O)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)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	3526.9	Standard non polar	33892256
Valyltryptophan,4TBDMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3572.8	Semi standard non polar	33892256
Valyltryptophan,4TBDMS,isomer #3	CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3494.5	Standard non polar	33892256
Valyltryptophan,4TBDMS,isomer #4	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)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	3797.2	Semi standard non polar	33892256
Valyltryptophan,4TBDMS,isomer #4	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)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	3566.2	Standard non polar	33892256
Valyltryptophan,5TBDMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)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	3971.1	Semi standard non polar	33892256
Valyltryptophan,5TBDMS,isomer #1	CC(C)[C@@H](C(=O)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)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	3771.4	Standard non polar	33892256

Spectra

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	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

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

FDB112139

KNApSAcK ID

Not Available

Chemspider ID

147114

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

168182

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kano K, Hasegawa H, Miyamura M: Chiral recognition of dipeptide methyl esters by an anionic beta-cyclodextrin. Chirality. 2001 Aug;13(8):474-82. [PubMed:11466771 ]
Galardy RE: Inhibition of angiotensin converting enzyme by phosphoramidates and polyphosphates. Biochemistry. 1982 Nov 9;21(23):5777-81. [PubMed:6295438 ]

Showing metabocard for Valyltryptophan (HMDB0029138)

MOL for HMDB0029138 (Valyltryptophan)

3D MOL for HMDB0029138 (Valyltryptophan)

3D SDF for HMDB0029138 (Valyltryptophan)

3D-SDF for HMDB0029138 (Valyltryptophan)

PDB for HMDB0029138 (Valyltryptophan)

3D PDB for HMDB0029138 (Valyltryptophan)

SMILES for HMDB0029138 (Valyltryptophan)

INCHI for HMDB0029138 (Valyltryptophan)

Structure for HMDB0029138 (Valyltryptophan)

3D Structure for HMDB0029138 (Valyltryptophan)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized