MiMeDB: Showing metabocard for 5-Hydroxy-L-tryptophan (MMDBc0047911)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:14:34 UTC

Update Date

2022-09-01 02:01:24 UTC

Metabolite ID

MMDBc0047911

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>
MMDBc0047911

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₁H₁₂N₂O₃

Average Mass

220.2246

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0006-0390000000-d4e36a90b7591787e67b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0006-1390000000-b0af49def87c0211653c	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-014i-0390000000-8b7f6cc8f51c032dd86d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0390000000-88191cf8140abf0f3205	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0290000000-a30ea02ff8d4d14ba7a4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-0390000000-d4e36a90b7591787e67b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-1390000000-b0af49def87c0211653c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-0390000000-8b7f6cc8f51c032dd86d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00bd-4920000000-c1f07beecfc6ada179c1	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9044000000-9dc0e361e3885451d81f	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0790000000-a699ed429ebd1609f995	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03e9-0900000000-bbd302f8ff188f6cf93d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-053r-0900000000-6cc3ba396b1cfa8db1e6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-053r-2900000000-90a465428eacaced71e2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0390000000-8d1a103c7fb1b7dfa685	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-25de1fda6182de338d15	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-053r-0900000000-e8cfeeeea0f83c87c0a3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0w29-0790000000-61308573c0d4d1caee8a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0w90-0590000000-9c6aa4b5a920add9f8ea	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0930000000-074911d5bc17a486cbb0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0uk9-0190000000-9d6cad9671c04310ac0c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-05ox-2900000000-08b2a2c24032d96597db	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000x-1900000000-9c83828dc6df75a0e798	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001l-1900000000-dc720fc8e93906bb0c67	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014l-1970000000-6deb0cc19e89586090e6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001l-0900000000-cab77201c86bda083dd0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-053r-1900000000-b1c220623de477b387ee	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-053r-0900000000-f7c54dfcc55add0c83d6	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00b9-0950000000-e3f9fbda111b2109f630	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-b21f3fecc8ae15c125de	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0900000000-817e4d468ea1bf1a3bc3	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2190000000-65b1ee730ae09a2cd6a5	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9650000000-68d73bfc7c9dd0f880e1	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9600000000-c58badf19c5cbb2f4347	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1950000000-5df9078df2a62ba2dc7e	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Prostate
Urine

Tissue Locations

Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191948	Aromatic-L-amino-acid decarboxylase	Enzyme	P20711	Homo sapiens
MMDBp0192103	Indoleamine 2,3-dioxygenase 1	Unknown	P14902	Homo sapiens
MMDBp0192127	Tryptophan 5-hydroxylase 1	Enzyme	P17752	Homo sapiens
MMDBp0192129	Tryptophan 5-hydroxylase 2	Enzyme	Q8IWU9	Homo sapiens
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo sapiens
MMDBp0194191	Indoleamine 2,3-dioxygenase 2	Unknown	Q6ZQW0	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000114	5-Hydroxy-L-tryptophan	Carbon dioxide	Not Available	5-Hydroxy-L-Tryptophan Decarboxy-Lyase	VMH	1540578
MMDBr0000119	5-Hydroxy-L-tryptophan	5-Hydroxy-N-formylkynurenine	Indoleamine 2,3-dioxygenase 1	5-Hydroxy-L-Tryptophan:Oxygen 2, 3-Dioxygenase (Indole-Decyclizing)	VMH	10564724
MMDBr0000120	5-Hydroxy-L-tryptophan	5-Hydroxy-L-tryptophan	Solute carrier family 18 (vesicular monoamine transporter), member 1	5-Hydroxy-L-Tryptophan Secretion via Secretory Vesicle (ATP Driven)	VMH	12827358 15383652
MMDBr0002276	Oxygen	5-Hydroxy-L-tryptophan	Tryptophan hydroxylase 1	L-Tryptophan, Tetrahydrobiopterin:Oxygen Oxidoreductase (5-Hydroxylating)	VMH	10727395 12379098
MMDBr0002541	Oxygen	5-Hydroxy-L-tryptophan	Tryptophan hydroxylase 1	L-Tryptophan, Tetrahydrobiopterin:Oxygen Oxidoreductase (5-Hydroxylating)	VMH	30371894
MMDBr0012629	5-Hydroxy-L-tryptophan	5-Hydroxy-L-tryptophan	Not Available	L-Dopa transport in via proton symport	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Aromatic l-amino acid decarboxylase deficiency		Association	Human Cerebrospinal Fluid (CSF)	HMDB	9686366

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	89	Human feces; Pig ; Human ; Cattle	Metabolic reconstruction
Bacteria	Proteobacteria	207	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Bacteria	Actinobacteria	86	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	6	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Fusobacteria	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Plant	Plant	Musa x paradisiaca	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.063				uM	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.0970	0.136	uM	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Urine	Detected and Quantified	0.0078				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Cerebrospinal fluid (csf)	Detected and Quantified	<0.0100				uM	Children (1-13 years old)	Female	Normal	HMDB	9686366
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.005		0.00	0.010	uM	Infant (0-1 year old)	Both	Normal	HMDB	11486900
Human Blood	Detected and Quantified	0.018	0.0027			uM	Adult (>18 years old)	Both	Normal	HMDB	11910264
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000472

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1139/o79-126. [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. doi: 10.1177/030006059001800304. [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 ]
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Showing metabocard for 5-Hydroxy-L-tryptophan (MMDBc0047911)

MOL for #<Metabolite:0x00007fe273ac4100>

3D MOL for #<Metabolite:0x00007fe273ac4100>

3D SDF for #<Metabolite:0x00007fe273ac4100>

3D-SDF for #<Metabolite:0x00007fe273ac4100>

PDB for #<Metabolite:0x00007fe273ac4100>

3D PDB for #<Metabolite:0x00007fe273ac4100>

SMILES for #<Metabolite:0x00007fe273ac4100>

INCHI for #<Metabolite:0x00007fe273ac4100>

Structure for #<Metabolite:0x00007fe273ac4100>

3D Structure for #<Metabolite:0x00007fe273ac4100>