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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 09:38:27 UTC

Update Date

2021-09-24 09:38:27 UTC

HMDB ID

HMDB0304419

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N,N-dihydroxy-L-tryptophan

Description

N,n-dihydroxy-l-tryptophan belongs to indolyl carboxylic acids and derivatives class of compounds. Those are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. N,n-dihydroxy-l-tryptophan is slightly soluble (in water) and a weakly acidic compound (based on its pKa). N,n-dihydroxy-l-tryptophan can be found in a number of food items such as abalone, flaxseed, fig, and bamboo shoots, which makes n,n-dihydroxy-l-tryptophan a potential biomarker for the consumption of these food products.

Structure

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

HMDB0304419
     RDKit          3D
N,N-dihydroxy-L-tryptophan
 28 29  0  0  0  0  0  0  0  0999 V2000
    2.5693    2.0671    1.3988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9076    0.9656    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840    0.5667    2.2579 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.1172    0.2699    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2163   -0.7857   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1790   -0.3792   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401    0.2638   -1.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9237    0.5648   -1.7418 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3600    0.1611   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5812    0.2065    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274   -0.3323    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686   -0.9248    2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591   -0.9613    1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2778   -0.4254    0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5268   -0.1899   -0.0070 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    0.9402    0.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387   -0.7336   -1.2398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1061    1.0967   -0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114   -1.6310    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446   -1.2963   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    0.4340   -2.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5365    1.0407   -2.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4121    0.6795   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6966   -0.2832    1.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -1.3600    3.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4425    1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373    1.6011   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376   -0.1126   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 15 17  1  0
 14  6  1  0
 14  9  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  8 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 16 27  1  0
 17 28  1  0
M  CHG  1   3  -1
M  END

  Mrv1652303082008162D          

 17 18  0  0  0  0            999 V2000
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  1  9  2  0  0  0  0
M  CHG  1  17  -1
M  END
> <DATABASE_ID>
HMDB0304419

> <DATABASE_NAME>
hmdb

> <SMILES>
ON(O)C(CC1=CNC2=C1C=CC=C2)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O4/c14-11(15)10(13(16)17)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,10,12,16-17H,5H2,(H,14,15)/p-1

> <INCHI_KEY>
FKJQZUQEYSGYFZ-UHFFFAOYSA-M

> <FORMULA>
C11H11N2O4

> <MOLECULAR_WEIGHT>
235.22

> <EXACT_MASS>
235.072430422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.45638752169267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(N,N-dihydroxyamino)-3-(1H-indol-3-yl)propanoate

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
0.5558638060000002

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.03888274268682

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.090035575443535

> <JCHEM_PKA_STRONGEST_BASIC>
-2.66635721507899

> <JCHEM_POLAR_SURFACE_AREA>
99.62

> <JCHEM_REFRACTIVITY>
70.9479

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(N,N-dihydroxyamino)-3-(1H-indol-3-yl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304419
     RDKit          3D
N,N-dihydroxy-L-tryptophan
 28 29  0  0  0  0  0  0  0  0999 V2000
    2.5693    2.0671    1.3988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9076    0.9656    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840    0.5667    2.2579 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.1172    0.2699    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2163   -0.7857   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1790   -0.3792   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401    0.2638   -1.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9237    0.5648   -1.7418 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3600    0.1611   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5812    0.2065    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274   -0.3323    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686   -0.9248    2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591   -0.9613    1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2778   -0.4254    0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5268   -0.1899   -0.0070 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    0.9402    0.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387   -0.7336   -1.2398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1061    1.0967   -0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114   -1.6310    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446   -1.2963   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    0.4340   -2.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5365    1.0407   -2.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4121    0.6795   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6966   -0.2832    1.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -1.3600    3.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4425    1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373    1.6011   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376   -0.1126   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 15 17  1  0
 14  6  1  0
 14  9  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  8 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 16 27  1  0
 17 28  1  0
M  CHG  1   3  -1
M  END

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.143  -4.333   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.332  -5.798   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.839  -6.118   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.393  -3.509   0.000  0.00  0.00           O-1
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10    1                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0304419
HETATM    1  O1  UNL     1       2.569   2.067   1.399  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.908   0.966   1.244  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.084   0.567   2.258  1.00  0.00           O1-
HETATM    4  C2  UNL     1       2.117   0.270   0.004  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.216  -0.786  -0.482  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.179  -0.379  -0.721  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.640   0.264  -1.895  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.924   0.565  -1.742  1.00  0.00           N  
HETATM    9  C6  UNL     1      -2.360   0.161  -0.532  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.581   0.206   0.105  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.727  -0.332   1.364  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.669  -0.925   2.014  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.459  -0.961   1.367  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.278  -0.425   0.099  1.00  0.00           C  
HETATM   15  N2  UNL     1       3.527  -0.190  -0.007  1.00  0.00           N  
HETATM   16  O3  UNL     1       4.276   0.940   0.077  1.00  0.00           O  
HETATM   17  O4  UNL     1       3.739  -0.734  -1.240  1.00  0.00           O  
HETATM   18  H1  UNL     1       2.106   1.097  -0.821  1.00  0.00           H  
HETATM   19  H2  UNL     1       1.211  -1.631   0.283  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.645  -1.296  -1.384  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.028   0.434  -2.726  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.536   1.041  -2.431  1.00  0.00           H  
HETATM   23  H6  UNL     1      -4.412   0.680  -0.421  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.697  -0.283   1.845  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.754  -1.360   3.005  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.584  -1.443   1.833  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.837   1.601  -0.529  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.538  -0.113  -1.968  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5   15   18
CONECT    5    6   19   20
CONECT    6    7    7   14
CONECT    7    8   21
CONECT    8    9   22
CONECT    9   10   10   14
CONECT   10   11   23
CONECT   11   12   12   24
CONECT   12   13   25
CONECT   13   14   14   26
CONECT   15   16   17
CONECT   16   27
CONECT   17   28
END

HMDB0304419
     RDKit          3D
N,N-dihydroxy-L-tryptophan
 28 29  0  0  0  0  0  0  0  0999 V2000
    2.5693    2.0671    1.3988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9076    0.9656    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840    0.5667    2.2579 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.1172    0.2699    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2163   -0.7857   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1790   -0.3792   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401    0.2638   -1.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9237    0.5648   -1.7418 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3600    0.1611   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5812    0.2065    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274   -0.3323    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686   -0.9248    2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591   -0.9613    1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2778   -0.4254    0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5268   -0.1899   -0.0070 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    0.9402    0.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387   -0.7336   -1.2398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1061    1.0967   -0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114   -1.6310    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446   -1.2963   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    0.4340   -2.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5365    1.0407   -2.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4121    0.6795   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6966   -0.2832    1.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -1.3600    3.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4425    1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373    1.6011   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376   -0.1126   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 15 17  1  0
 14  6  1  0
 14  9  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  8 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 16 27  1  0
 17 28  1  0
M  CHG  1   3  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₁N₂O₄

Average Molecular Weight

235.22

Monoisotopic Molecular Weight

235.072430422

IUPAC Name

2-(N,N-dihydroxyamino)-3-(1H-indol-3-yl)propanoate

Traditional Name

2-(N,N-dihydroxyamino)-3-(1H-indol-3-yl)propanoate

CAS Registry Number

Not Available

SMILES

ON(O)C(CC1=CNC2=C1C=CC=C2)C([O-])=O

InChI Identifier

InChI=1S/C11H12N2O4/c14-11(15)10(13(16)17)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,10,12,16-17H,5H2,(H,14,15)/p-1

InChI Key

FKJQZUQEYSGYFZ-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
N-hydroxyl-alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
N-organohydroxylamine
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

an N-substituted amino acid (CPD-13027 )

Ontology

Not Available

Exogenous (HMDB: HMDB0304419)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0002445)
Camalexin Biosynthesis (PathBank: SMP0121212)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.31	ALOGPS
logP	0.56	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.95 m³·mol⁻¹	ChemAxon
Polarizability	22.46 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
AllCCS	[M+H]+	153.141	32859911
AllCCS	[M+H-H2O]+	149.236	32859911
AllCCS	[M+Na]+	157.816	32859911
AllCCS	[M+NH4]+	156.771	32859911
AllCCS	[M-H]-	149.914	32859911
AllCCS	[M+Na-2H]-	149.775	32859911
AllCCS	[M+HCOO]-	149.726	32859911
DeepCCS	[M+H]+	139.483	30932474
DeepCCS	[M-H]-	136.621	30932474
DeepCCS	[M-2H]-	172.204	30932474
DeepCCS	[M+Na]+	147.966	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N,N-dihydroxy-L-tryptophan,1TMS,isomer #1	C[Si](C)(C)N1C=C(CC(C(=O)[O-])N(O)O)C2=CC=CC=C21	2262.2	Semi standard non polar	33892256
N,N-dihydroxy-L-tryptophan,1TMS,isomer #1	C[Si](C)(C)N1C=C(CC(C(=O)[O-])N(O)O)C2=CC=CC=C21	2334.4	Standard non polar	33892256
N,N-dihydroxy-L-tryptophan,1TMS,isomer #1	C[Si](C)(C)N1C=C(CC(C(=O)[O-])N(O)O)C2=CC=CC=C21	3238.5	Standard polar	33892256
N,N-dihydroxy-L-tryptophan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(CC(C(=O)[O-])N(O)O)C2=CC=CC=C21	2535.5	Semi standard non polar	33892256
N,N-dihydroxy-L-tryptophan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(CC(C(=O)[O-])N(O)O)C2=CC=CC=C21	2524.3	Standard non polar	33892256
N,N-dihydroxy-L-tryptophan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(CC(C(=O)[O-])N(O)O)C2=CC=CC=C21	3233.5	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-dihydroxy-L-tryptophan 10V, Negative-QTOF	splash10-000i-1290000000-415281380081d2ef302e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-dihydroxy-L-tryptophan 20V, Negative-QTOF	splash10-00kr-5960000000-178e09ada11bf579c495	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N-dihydroxy-L-tryptophan 40V, Negative-QTOF	splash10-01ca-1910000000-c98b5be6c6c6abbee1c7	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031013

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75107009

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

Not Available

Showing metabocard for N,N-dihydroxy-L-tryptophan (HMDB0304419)

MOL for HMDB0304419 (N,N-dihydroxy-L-tryptophan)

3D MOL for HMDB0304419 (N,N-dihydroxy-L-tryptophan)

3D SDF for HMDB0304419 (N,N-dihydroxy-L-tryptophan)

3D-SDF for HMDB0304419 (N,N-dihydroxy-L-tryptophan)

PDB for HMDB0304419 (N,N-dihydroxy-L-tryptophan)

3D PDB for HMDB0304419 (N,N-dihydroxy-L-tryptophan)

SMILES for HMDB0304419 (N,N-dihydroxy-L-tryptophan)

INCHI for HMDB0304419 (N,N-dihydroxy-L-tryptophan)

Structure for HMDB0304419 (N,N-dihydroxy-L-tryptophan)

3D Structure for HMDB0304419 (N,N-dihydroxy-L-tryptophan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra