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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-07-12 23:05:07 UTC

HMDB ID

HMDB0000472

Secondary Accession Numbers

HMDB0000504
HMDB0015571
HMDB00472
HMDB00504
HMDB15571

Metabolite Identification

Common Name

5-Hydroxy-L-tryptophan

Description

5-Hydroxy-L-tryptophan is an aromatic amino acid naturally produced by the body from the essential amino acid L-tryptophan. 5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. The conversion to serotonin is catalyzed by the enzyme aromatic L-amino acid decarboxylase (EC 4.1.1.28) (AADC1 also known as DOPA decarboxylase), an essential enzyme in the metabolism of the monoamine neurotransmitters. An accumulation of 5-hydroxy-L-tryptophan in cerebrospinal fluid occurs in aromatic L-amino acid decarboxylase deficiency (AADC deficiency) (OMIM: 608643 ) accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder but not specific. 5-Hydroxy-L-tryptophan is also increased in other disorders such as in Parkinson's patients with severe postural instability and gait disorders. The amount of endogenous 5-hydroxy-L-tryptophan available for serotonin synthesis depends on the availability of tryptophan and on the activity of various enzymes, especially tryptophan hydroxylase (EC 1.14.16.4), indoleamine 2,3-dioxygenase (EC 1.13.11.52), and tryptophan 2,3-dioxygenase (TDO) (EC 1.13.11.11). 5-Hydroxy-L-tryptophan has been used clinically for over 30 years. In addition to its use in the treatment of depression, the therapeutic administration of 5-hydroxy-L-tryptophan has been shown to be effective in treating a wide variety of conditions, including fibromyalgia, insomnia, binge eating associated with obesity, cerebellar ataxia, and chronic headaches. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system (CNS) synthesis of serotonin. Supplementation with 5-hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties (PMID: 9295177 , 17240182 , 16023217 ). When present in sufficiently high levels, 5-hydroxytryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells or tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Signs and symptoms of AADC deficiency generally appear in the first year of life. Affected infants may have severe developmental delay, weak muscle tone (hypotonia), muscle stiffness, difficulty moving, and involuntary writhing movements of the limbs (athetosis). They may be lacking in energy (lethargic), feed poorly, startle easily, and have sleep disturbances. Since 5-hydroxytryptophan is a precursor to serotonin, altered levels of serotonin can accumulate in the brain, which leads to abnormal neural signalling. Infants with AADC deficiency have very low levels of neural signalling molecules while individuals who consume high levels of 5-hydroxytryptophan will have very high levels of neural signalling molecules. Both conditions can lead to vomiting, nausea, extreme drowsiness, and lethargy. 5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN) is sold over-the-counter in the United Kingdom, the United States, and Canada as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid. It is also marketed in many European countries for the indication of major depression under trade names such as Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. Several double-blind placebo-controlled clinical trials have demonstrated the effectiveness of 5-HTP in the treatment of depression, though a lack of high-quality studies has been noted. More and larger studies are needed to determine if 5-HTP is truly effective in treating depression.

Structure

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

HMDB0000472
     RDKit          3D
5-Hydroxy-L-tryptophan
 28 29  0  0  0  0  0  0  0  0999 V2000
    3.2155    1.5153    0.4605 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1059    0.5861    0.5240 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4462    0.5976   -0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857   -0.3146   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311   -1.5456   -1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0044   -2.0426   -1.3705 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7541   -1.1771   -0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0766   -1.1782   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5851   -0.1159    0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746    0.9624    0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3118    2.0288    1.4892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4636    0.9911    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664   -0.0979   -0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -0.7248    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8874   -1.7522    1.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9527   -0.8941    1.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8052    2.4740    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094    1.3348   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3444    0.9560    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1756    0.3538   -1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1162    1.6425   -1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -2.0509   -2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3632   -2.9758   -1.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857   -2.0482   -0.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6196   -0.1403    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7460    2.7733    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8008    1.8419    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2480   -0.9992    2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
 13  4  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  3 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 16 28  1  0
M  END

  Mrv1652305271900002D          

 16 17  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9840    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8347    1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8045    0.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401    0.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6551    1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    2.2610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0  0  0  0
  3  1  1  1  0  0  0
  3 13  1  0  0  0  0
  2  4  1  0  0  0  0
  4  3  1  0  0  0  0
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 15  2  0  0  0  0
 10 11  2  0  0  0  0
 11 15  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000472

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1

> <INCHI_KEY>
LDCYZAJDBXYCGN-VIFPVBQESA-N

> <FORMULA>
C11H12N2O3

> <MOLECULAR_WEIGHT>
220.2246

> <EXACT_MASS>
220.08479226

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.03065870612876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-1.56

> <JCHEM_LOGP>
-1.3896984621581003

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.795366619375281

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.152663935897663

> <JCHEM_PKA_STRONGEST_BASIC>
9.18065085700301

> <JCHEM_POLAR_SURFACE_AREA>
99.34

> <JCHEM_REFRACTIVITY>
58.18370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxytryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000472
     RDKit          3D
5-Hydroxy-L-tryptophan
 28 29  0  0  0  0  0  0  0  0999 V2000
    3.2155    1.5153    0.4605 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1059    0.5861    0.5240 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4462    0.5976   -0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857   -0.3146   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311   -1.5456   -1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0044   -2.0426   -1.3705 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7541   -1.1771   -0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0766   -1.1782   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5851   -0.1159    0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746    0.9624    0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3118    2.0288    1.4892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4636    0.9911    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664   -0.0979   -0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -0.7248    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8874   -1.7522    1.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9527   -0.8941    1.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8052    2.4740    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094    1.3348   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3444    0.9560    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1756    0.3538   -1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1162    1.6425   -1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -2.0509   -2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3632   -2.9758   -1.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857   -2.0482   -0.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6196   -0.1403    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7460    2.7733    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8008    1.8419    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2480   -0.9992    2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
 13  4  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  3 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 16 28  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.798  -1.246   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -3.703   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.798   1.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.425   2.653   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.235   0.161   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.862   1.568   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.956   2.814   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.583   4.221   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    8    4    5                                                  
CONECT    3    1   13    4                                                  
CONECT    4    2    3                                                       
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    2    7    9                                                  
CONECT    9    8   15                                                       
CONECT   10    7   11                                                       
CONECT   11   10   15                                                       
CONECT   12   13                                                            
CONECT   13    3   12   14                                                  
CONECT   14   13                                                            
CONECT   15    9   11   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0000472
HETATM    1  N1  UNL     1       3.215   1.515   0.461  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.106   0.586   0.524  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.446   0.598  -0.833  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.286  -0.315  -0.914  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.231  -1.546  -1.528  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.004  -2.043  -1.370  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.754  -1.177  -0.676  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.077  -1.178  -0.235  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.585  -0.116   0.480  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.775   0.962   0.763  1.00  0.00           C  
HETATM   11  O1  UNL     1      -3.312   2.029   1.489  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.464   0.991   0.340  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.966  -0.098  -0.385  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.598  -0.725   0.927  1.00  0.00           C  
HETATM   15  O2  UNL     1       1.887  -1.752   1.078  1.00  0.00           O  
HETATM   16  O3  UNL     1       3.953  -0.894   1.171  1.00  0.00           O  
HETATM   17  H1  UNL     1       2.805   2.474   0.386  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.709   1.335  -0.451  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.344   0.956   1.244  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.176   0.354  -1.636  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.116   1.642  -1.018  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.030  -2.051  -2.052  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.363  -2.976  -1.730  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.686  -2.048  -0.477  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.620  -0.140   0.813  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.746   2.773   0.943  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.801   1.842   0.555  1.00  0.00           H  
HETATM   28  H12 UNL     1       4.248  -0.999   2.131  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   14   19
CONECT    3    4   20   21
CONECT    4    5    5   13
CONECT    5    6   22
CONECT    6    7   23
CONECT    7    8    8   13
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   12
CONECT   11   26
CONECT   12   13   13   27
CONECT   14   15   15   16
CONECT   16   28
END

HMDB0000472
     RDKit          3D
5-Hydroxy-L-tryptophan
 28 29  0  0  0  0  0  0  0  0999 V2000
    3.2155    1.5153    0.4605 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1059    0.5861    0.5240 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4462    0.5976   -0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857   -0.3146   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311   -1.5456   -1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0044   -2.0426   -1.3705 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7541   -1.1771   -0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0766   -1.1782   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5851   -0.1159    0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746    0.9624    0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3118    2.0288    1.4892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4636    0.9911    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664   -0.0979   -0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -0.7248    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8874   -1.7522    1.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9527   -0.8941    1.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8052    2.4740    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094    1.3348   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3444    0.9560    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1756    0.3538   -1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1162    1.6425   -1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -2.0509   -2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3632   -2.9758   -1.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857   -2.0482   -0.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6196   -0.1403    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7460    2.7733    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8008    1.8419    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2480   -0.9992    2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
 13  4  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  3 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 16 28  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Hydroxytryptophan L-form	ChEBI
Cincofarm	ChEBI
L-5-Hydroxytryptophan	ChEBI
Levothym	ChEBI
Oxitriptan	ChEBI
Tript-OH	ChEBI
Hydroxy-5 L-tryptophane	HMDB
5-HTP	HMDB
Hydroxytryptophan	HMDB
5-Hydroxytryptophan	HMDB
5 Hydroxytryptophan	HMDB
5-Hydroxy- tryptophan	HMDB
Oxytryptophan	HMDB
Tryptophan, 5 hydroxy	HMDB
(S)-5-Hydroxytryptophan	HMDB
5-Hydroxyl-L-tryptophan	HMDB
Levotonine	HMDB
Oxyfan	HMDB
Pretonine	HMDB
Quietim	HMDB
Serotonyl	HMDB
Telesol	HMDB
Triptene	HMDB
Triptum	HMDB
L-5-HTP	HMDB
5-Hydroxy-L-tryptophan	HMDB

Chemical Formula

C₁₁H₁₂N₂O₃

Average Molecular Weight

220.2246

Monoisotopic Molecular Weight

220.08479226

IUPAC Name

(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

Traditional Name

hydroxytryptophan

CAS Registry Number

4350-09-8

SMILES

N[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O

InChI Identifier

InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1

InChI Key

LDCYZAJDBXYCGN-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Serotonins

Alternative Parents

Substituents

Serotonin
Indolyl carboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
L-alpha-amino acid
Hydroxyindole
Indole
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid
Amino acid or derivatives
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Organopnictogen compound
Amine
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:17780 )
5-hydroxytryptophan (CHEBI:17780 )
hydroxy-L-tryptophan (CHEBI:17780 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0244288)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Biological role

Metabolite (HMDB: HMDB0244288)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	293 - 298 °C	Not Available
Boiling Point	520.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	31500 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-2.051	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	153.722	30932474
[M-H]-	MetCCS_train_neg	148.858	30932474
[M+H]+	Baker	157.877	30932474
[M-H]-	Not Available	153.722	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001799
[M+H]+	Not Available	157.877	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001799

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.63 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.15	ChemAxon
pKa (Strongest Basic)	9.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.34 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	58.18 m³·mol⁻¹	ChemAxon
Polarizability	22.03 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
DarkChem	[M+H]+	151.139	31661259
DarkChem	[M-H]-	149.643	31661259
AllCCS	[M+H]+	149.707	32859911
AllCCS	[M-H]-	149.195	32859911
DeepCCS	[M+H]+	149.425	30932474
DeepCCS	[M-H]-	147.03	30932474
DeepCCS	[M-2H]-	180.083	30932474
DeepCCS	[M+Na]+	155.378	30932474
AllCCS	[M+H]+	149.7	32859911
AllCCS	[M+H-H2O]+	145.7	32859911
AllCCS	[M+NH4]+	153.4	32859911
AllCCS	[M+Na]+	154.4	32859911
AllCCS	[M-H]-	149.2	32859911
AllCCS	[M+Na-2H]-	149.2	32859911
AllCCS	[M+HCOO]-	149.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-L-tryptophan	N[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O	3889.4	Standard polar	33892256
5-Hydroxy-L-tryptophan	N[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O	2240.5	Standard non polar	33892256
5-Hydroxy-L-tryptophan	N[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O	2669.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-L-tryptophan,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@H](N)C(=O)O)C2=C1	2494.7	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=C(O)C=C12	2426.4	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O	2476.1	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,1TMS,isomer #4	C[Si](C)(C)N1C=C(C[C@H](N)C(=O)O)C2=CC(O)=CC=C21	2497.4	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12	2455.3	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O	2473.2	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O)=CN2[Si](C)(C)C	2513.3	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C	2397.9	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12	2416.7	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #6	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C	2628.0	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #7	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O	2503.6	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C	2437.9	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C	2487.6	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C	2747.1	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2476.4	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2447.6	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2872.6	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	2594.1	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	2569.1	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	2883.0	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O	2499.0	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O	2488.6	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O	2879.3	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2563.5	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2597.2	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2829.6	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C	2412.7	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C	2519.8	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C	2779.6	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #7	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C	2629.0	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #7	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C	2628.3	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #7	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C	2925.0	Standard polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2619.8	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2605.9	Standard non polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2638.3	Standard polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C	2478.9	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C	2491.0	Standard non polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C	2615.3	Standard polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2653.1	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2609.8	Standard non polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2750.8	Standard polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2607.8	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2650.4	Standard non polar	33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2683.9	Standard polar	33892256
5-Hydroxy-L-tryptophan,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2698.4	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2619.4	Standard non polar	33892256
5-Hydroxy-L-tryptophan,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C	2563.7	Standard polar	33892256
5-Hydroxy-L-tryptophan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@H](N)C(=O)O)C2=C1	2790.8	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=C(O)C=C12	2733.2	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O	2741.8	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C=C(C[C@H](N)C(=O)O)C2=CC(O)=CC=C21	2769.7	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	3008.9	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O	3044.3	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O)=CN2[Si](C)(C)C(C)(C)C	3048.7	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	2947.0	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12	2944.0	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3076.2	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O	2999.7	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	3198.6	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	3139.3	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	3020.0	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	3216.2	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	3053.9	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	3084.6	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3370.5	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3196.8	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3085.9	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O	3265.6	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O	3104.5	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O	3095.0	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3275.0	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3227.7	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3035.3	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	3120.1	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	3156.5	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	3012.0	Standard polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3307.2	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3220.6	Standard non polar	33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3090.8	Standard polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3543.3	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3405.5	Standard non polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3003.7	Standard polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	3371.2	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	3268.7	Standard non polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C	2998.6	Standard polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3565.2	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3338.8	Standard non polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3040.2	Standard polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3451.7	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3402.0	Standard non polar	33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2995.8	Standard polar	33892256
5-Hydroxy-L-tryptophan,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3718.7	Semi standard non polar	33892256
5-Hydroxy-L-tryptophan,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3486.6	Standard non polar	33892256
5-Hydroxy-L-tryptophan,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3008.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (4 TMS)	splash10-0006-0390000000-d4e36a90b7591787e67b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (3 TMS)	splash10-0006-1390000000-b0af49def87c0211653c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (3 TMS)	splash10-014i-0390000000-8b7f6cc8f51c032dd86d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-EI-TOF (Non-derivatized)	splash10-014i-0390000000-88191cf8140abf0f3205	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-EI-TOF (Non-derivatized)	splash10-0006-0290000000-a30ea02ff8d4d14ba7a4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized)	splash10-0006-0390000000-d4e36a90b7591787e67b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized)	splash10-0006-1390000000-b0af49def87c0211653c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized)	splash10-014i-0390000000-8b7f6cc8f51c032dd86d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized) - 70eV, Positive	splash10-00bd-4920000000-c1f07beecfc6ada179c1	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9044000000-9dc0e361e3885451d81f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan LC-ESI-QTOF , positive-QTOF	splash10-0udi-0790000000-a699ed429ebd1609f995	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan LC-ESI-QTOF , positive-QTOF	splash10-03e9-0900000000-bbd302f8ff188f6cf93d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan LC-ESI-QTOF , positive-QTOF	splash10-053r-0900000000-6cc3ba396b1cfa8db1e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan , positive-QTOF	splash10-053r-2900000000-90a465428eacaced71e2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Positive-QTOF	splash10-0udi-0390000000-8d1a103c7fb1b7dfa685	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 20V, Positive-QTOF	splash10-03di-0900000000-25de1fda6182de338d15	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 30V, Positive-QTOF	splash10-053r-0900000000-e8cfeeeea0f83c87c0a3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Positive-QTOF	splash10-0w29-0790000000-61308573c0d4d1caee8a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 0V, Positive-QTOF	splash10-0w90-0590000000-9c6aa4b5a920add9f8ea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Positive-QTOF	splash10-03di-0930000000-074911d5bc17a486cbb0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 0V, Positive-QTOF	splash10-0uk9-0190000000-9d6cad9671c04310ac0c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 30V, Positive-QTOF	splash10-05ox-2900000000-08b2a2c24032d96597db	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 20V, Negative-QTOF	splash10-000x-1900000000-9c83828dc6df75a0e798	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 30V, Negative-QTOF	splash10-001l-1900000000-dc720fc8e93906bb0c67	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Negative-QTOF	splash10-014l-1970000000-6deb0cc19e89586090e6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 40V, Negative-QTOF	splash10-001l-0900000000-cab77201c86bda083dd0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 40V, Positive-QTOF	splash10-053r-1900000000-b1c220623de477b387ee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 30V, Positive-QTOF	splash10-053r-0900000000-f7c54dfcc55add0c83d6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Positive-QTOF	splash10-00b9-0950000000-e3f9fbda111b2109f630	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 20V, Positive-QTOF	splash10-004i-0900000000-b21f3fecc8ae15c125de	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 40V, Positive-QTOF	splash10-0002-0900000000-817e4d468ea1bf1a3bc3	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Negative-QTOF	splash10-014i-2190000000-65b1ee730ae09a2cd6a5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 20V, Negative-QTOF	splash10-00di-9650000000-68d73bfc7c9dd0f880e1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 40V, Negative-QTOF	splash10-00di-9600000000-c58badf19c5cbb2f4347	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Negative-QTOF	splash10-001i-1950000000-5df9078df2a62ba2dc7e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.018 +/- 0.0027 uM	Adult (>18 years old)	Both	Normal	11910264	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.005 (0.00-0.010) uM	Infant (0-1 year old)	Both	Normal	11486900	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.0100 uM	Children (1-13 years old)	Female	Normal	9686366	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0078 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.063 uM	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0970-0.136 uM	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Enthesitis-related arthritis	27786174	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details

Associated Disorders and Diseases

Disease References

Aromatic L-amino acid decarboxylase deficiency
Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]

Associated OMIM IDs

608643 (Aromatic L-amino acid decarboxylase deficiency)
266600 (Crohn's disease)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB02959

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

5-Hydroxytryptophan

METLIN ID

Not Available

PubChem Compound

439280

PDB ID

Not Available

ChEBI ID

17780

Food Biomarker Ontology

Not Available

VMH ID

5HTRP

MarkerDB ID

MDB00000169

Good Scents ID

rw1700141

References

Synthesis Reference

Boroda, E.; Rakowska, S.; Kanski, R.; Kanska, M. Enzymatic synthesis of L-tryptophan and 5'-hydroxy-L-tryptophan labeled with deuterium and tritium at the a-carbon position. Journal of Labelled Compounds & Radiopharmaceuticals (2003), 46(8), 691-698.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Magnussen I, Van Woert MH: Human pharmacokinetics of long term 5-hydroxytryptophan combined with decarboxylase inhibitors. Eur J Clin Pharmacol. 1982;23(1):81-6. [PubMed:6182005 ]
Li Kam Wa TC, Freestone S, Samson RR, Johnson NR, Lee MR: A comparison of the renal and neuroendocrine effects of two 5-hydroxytryptamine renal prodrugs in normal man. Clin Sci (Lond). 1993 Nov;85(5):607-14. [PubMed:8287650 ]
Li Kam Wa TC, Freestone S, Samson RR, Johnston NR, Lee MR: Renal metabolism and effects of the glutamyl derivatives of L-dopa and 5-hydroxytryptophan in man. Clin Sci (Lond). 1996 Aug;91(2):177-85. [PubMed:8795441 ]
Iacono RP, Kuniyoshi SM, Ahlman JR, Zimmerman GJ, Maeda G, Pearlstein RD: Concentrations of indoleamine metabolic intermediates in the ventricular cerebrospinal fluid of advanced Parkinson's patients with severe postural instability and gait disorders. J Neural Transm (Vienna). 1997;104(4-5):451-9. [PubMed:9295177 ]
Verbeek MM, Geurtz PB, Willemsen MA, Wevers RA: Aromatic L-amino acid decarboxylase enzyme activity in deficient patients and heterozygotes. Mol Genet Metab. 2007 Apr;90(4):363-9. Epub 2007 Jan 19. [PubMed:17240182 ]
Turner EH, Loftis JM, Blackwell AD: Serotonin a la carte: supplementation with the serotonin precursor 5-hydroxytryptophan. Pharmacol Ther. 2006 Mar;109(3):325-38. Epub 2005 Jul 14. [PubMed:16023217 ]
Bouchard S, Roberge AG: Biochemical properties and kinetic parameters of dihydroxyphenylalanine--5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat. Can J Biochem. 1979 Jul;57(7):1014-8. [PubMed:39668 ]
Amamoto T, Sarai K: On the tryptophan-serotonin metabolism in manic-depressive disorders. Changes in plasma 5-HT and 5-HIAA levels and urinary 5-HIAA excretion following oral loading of L-5HTP in patients with depression. Hiroshima J Med Sci. 1976 Sep;25(2-3):135-40. [PubMed:1088369 ]
Caruso I, Sarzi Puttini P, Cazzola M, Azzolini V: Double-blind study of 5-hydroxytryptophan versus placebo in the treatment of primary fibromyalgia syndrome. J Int Med Res. 1990 May-Jun;18(3):201-9. [PubMed:2193835 ]
De Benedittis G, Massei R: Serotonin precursors in chronic primary headache. A double-blind cross-over study with L-5-hydroxytryptophan vs. placebo. J Neurosurg Sci. 1985 Jul-Sep;29(3):239-48. [PubMed:3913752 ]
Magnussen I, Jensen TS, Rand JH, Van Woert MH: Plasma accumulation of metabolism of orally administered single dose L-5-hydroxytryptophan in man. Acta Pharmacol Toxicol (Copenh). 1981 Sep;49(3):184-9. [PubMed:6175178 ]
Rahman MK, Nagatsu T, Sakurai T, Hori S, Abe M, Matsuda M: Effect of pyridoxal phosphate deficiency on aromatic L-amino acid decarboxylase activity with L-DOPA and L-5-hydroxytryptophan as substrates in rats. Jpn J Pharmacol. 1982 Oct;32(5):803-11. [PubMed:6983619 ]
Sternberg EM, Van Woert MH, Young SN, Magnussen I, Baker H, Gauthier S, Osterland CK: Development of a scleroderma-like illness during therapy with L-5-hydroxytryptophan and carbidopa. N Engl J Med. 1980 Oct 2;303(14):782-7. [PubMed:6997735 ]
Trouillas P, Serratrice G, Laplane D, Rascol A, Augustin P, Barroche G, Clanet M, Degos CF, Desnuelle C, Dumas R, et al.: Levorotatory form of 5-hydroxytryptophan in Friedreich's ataxia. Results of a double-blind drug-placebo cooperative study. Arch Neurol. 1995 May;52(5):456-60. [PubMed:7733839 ]
Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. [PubMed:9727088 ]
Shaw K, Turner J, Del Mar C: Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. [PubMed:11869656 ]
Turner EH, Blackwell AD: 5-Hydroxytryptophan plus SSRIs for interferon-induced depression: synergistic mechanisms for normalizing synaptic serotonin. Med Hypotheses. 2005;65(1):138-44. [PubMed:15893130 ]
Nakatani Y, Sato-Suzuki I, Tsujino N, Nakasato A, Seki Y, Fumoto M, Arita H: Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat. Eur J Neurosci. 2008 May;27(9):2466-72. doi: 10.1111/j.1460-9568.2008.06201.x. [PubMed:18445233 ]

Enzymes

Enzyme Details

1. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Reactions

5-Hydroxy-L-tryptophan → Serotonin + CO(2)	details
5-Hydroxy-L-tryptophan → Serotonin + Carbon dioxide	details

Enzyme Details

2. Indoleamine 2,3-dioxygenase 1

General function:: Involved in heme binding
Specific function:: Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:: IDO1
Uniprot ID:: P14902
Molecular weight:: 45325.89

Reactions

5-Hydroxy-L-tryptophan + Oxygen → 5-Hydroxy-N-formylkynurenine	details

Enzyme Details

3. Tryptophan 5-hydroxylase 1

General function:: Involved in amino acid binding
Specific function:: Not Available
Gene Name:: TPH1
Uniprot ID:: P17752
Molecular weight:: 50984.725

Reactions

L-Tryptophan + Tetrahydrobiopterin + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Hydroxytetrahydrobiopterin	details
Tetrahydrobiopterin + L-Tryptophan + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Carbinolamine tetrahydrobiopterin + Water	details

Enzyme Details

4. Tryptophan 5-hydroxylase 2

General function:: Involved in amino acid binding
Specific function:: Not Available
Gene Name:: TPH2
Uniprot ID:: Q8IWU9
Molecular weight:: 56056.295

Reactions

L-Tryptophan + Tetrahydrobiopterin + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Hydroxytetrahydrobiopterin	details
Tetrahydrobiopterin + L-Tryptophan + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Carbinolamine tetrahydrobiopterin + Water	details

Enzyme Details

5. Aryl hydrocarbon receptor

General function:: Involved in transcription regulator activity
Specific function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:: AHR
Uniprot ID:: P35869
Molecular weight:: 96146.7

Enzyme Details

6. Indoleamine 2,3-dioxygenase 2

General function:: Involved in heme binding
Specific function:: Catalyzes the first and rate-limiting step in the kynurenine pathway of tryptophan catabolism.
Gene Name:: IDO2
Uniprot ID:: Q6ZQW0
Molecular weight:: 47074.745

Reactions

5-Hydroxy-L-tryptophan + Oxygen → 5-Hydroxy-N-formylkynurenine	details

Showing metabocard for 5-Hydroxy-L-tryptophan (HMDB0000472)

MOL for HMDB0000472 (5-Hydroxy-L-tryptophan)

3D MOL for HMDB0000472 (5-Hydroxy-L-tryptophan)

3D SDF for HMDB0000472 (5-Hydroxy-L-tryptophan)

3D-SDF for HMDB0000472 (5-Hydroxy-L-tryptophan)

PDB for HMDB0000472 (5-Hydroxy-L-tryptophan)

3D PDB for HMDB0000472 (5-Hydroxy-L-tryptophan)

SMILES for HMDB0000472 (5-Hydroxy-L-tryptophan)

INCHI for HMDB0000472 (5-Hydroxy-L-tryptophan)

Structure for HMDB0000472 (5-Hydroxy-L-tryptophan)

3D Structure for HMDB0000472 (5-Hydroxy-L-tryptophan)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions