Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

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)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

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 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

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Valyltryptophan 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 - Valyltryptophan 10V, Negative-QTOF	splash10-0udi-0019000000-1682cfc6dc304047b1e4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valyltryptophan 20V, Negative-QTOF	splash10-0udi-4839000000-5fdd16d4e1fcb6897906	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valyltryptophan 40V, Negative-QTOF	splash10-014i-1900000000-0301ca78f06d1ca5cc0e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valyltryptophan 10V, Positive-QTOF	splash10-0k9i-0795000000-b7bf3519cb156656a35c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valyltryptophan 20V, Positive-QTOF	splash10-052r-3910000000-66d835ca54bd2106b94d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valyltryptophan 40V, Positive-QTOF	splash10-0a4i-9800000000-568451122d5316a74583	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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	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 Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra