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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:48 UTC

Update Date

2021-09-14 14:57:58 UTC

HMDB ID

HMDB0002339

Secondary Accession Numbers

HMDB02339

Metabolite Identification

Common Name

5-Methoxytryptophan

Description

5-methoxytryptophan is an L-tryptophan derivative that is L-tryptophan with a methoxy substituent at position 5. It has a role as a metabolite. It derives from a L-tryptophan. It is a tautomer of a 5-methoxy-L-tryptophan zwitterion. 5-Methoxytryptophan 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. Outside of the human body, 5-Methoxytryptophan has been detected, but not quantified in cow milk. 5-Methoxytryptophan is reduced in the urine of patients with liver disease. 5-Methoxytryptophan is reduced in the urine of parients with liver disease.

Structure

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

HMDB0002339
     RDKit          3D
5-Methoxytryptophan
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.3119   -0.0787    2.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9812    0.1962    2.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3932    0.0853    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1458   -0.3309   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106   -0.4269   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756   -0.1131   -1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -0.1352   -2.7491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514    0.2635   -2.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8629    0.5450   -1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932    1.0085   -0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5702   -0.1207    0.6561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0412   -1.1436   -0.2689 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7375    0.4027    1.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167    1.3032    2.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0407    0.0117    1.2184 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311    0.3021   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    0.3991    0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334   -0.4269    3.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7973   -0.8383    1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608    0.8211    2.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1784   -0.5866   -0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1067   -0.7569   -2.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6402   -0.4040   -3.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7064    0.3500   -3.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242    1.3734   -0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    1.8515    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8061   -0.5374    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5780   -0.6873   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2563   -1.7190   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4076   -0.6565    0.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4496    0.7258    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  9 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  1
 12 28  1  0
 12 29  1  0
 15 30  1  0
 17 31  1  0
M  END


  Mrv1652305271900002D          

 17 18  0  0  1  0            999 V2000
   25.1962  -11.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2475   -9.5442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8892   -9.1003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7349  -11.1127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1203  -12.7808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1839  -10.4986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.3766  -10.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4817  -11.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4403   -9.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9108  -11.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3397  -12.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1203  -11.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3397  -11.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6018  -12.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6252  -11.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9108  -12.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6252  -12.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 10  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  2  0  0  0  0
  6  4  1  1  0  0  0
  5 11  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7 12  1  0  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 11 13  2  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002339

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC=C2C[C@H](N)C(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O3/c1-17-8-2-3-11-9(5-8)7(6-14-11)4-10(13)12(15)16/h2-3,5-6,10,14H,4,13H2,1H3,(H,15,16)/t10-/m0/s1

> <INCHI_KEY>
KVNPSKDDJARYKK-JTQLQIEISA-N

> <FORMULA>
C12H14N2O3

> <MOLECULAR_WEIGHT>
234.2512

> <EXACT_MASS>
234.100442324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.995668391019752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.03

> <JCHEM_LOGP>
-1.2436285774982447

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.48534979708527

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2158500009276234

> <JCHEM_PKA_STRONGEST_BASIC>
9.418194371105473

> <JCHEM_POLAR_SURFACE_AREA>
88.34

> <JCHEM_REFRACTIVITY>
62.66600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxytryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002339
     RDKit          3D
5-Methoxytryptophan
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.3119   -0.0787    2.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9812    0.1962    2.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3932    0.0853    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1458   -0.3309   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106   -0.4269   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756   -0.1131   -1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -0.1352   -2.7491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514    0.2635   -2.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8629    0.5450   -1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932    1.0085   -0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5702   -0.1207    0.6561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0412   -1.1436   -0.2689 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7375    0.4027    1.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167    1.3032    2.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0407    0.0117    1.2184 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311    0.3021   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    0.3991    0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334   -0.4269    3.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7973   -0.8383    1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608    0.8211    2.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1784   -0.5866   -0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1067   -0.7569   -2.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6402   -0.4040   -3.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7064    0.3500   -3.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242    1.3734   -0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    1.8515    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8061   -0.5374    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5780   -0.6873   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2563   -1.7190   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4076   -0.6565    0.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4496    0.7258    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  9 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  1
 12 28  1  0
 12 29  1  0
 15 30  1  0
 17 31  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  O   UNK     0      47.033 -21.078   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      56.462 -17.816   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      53.927 -16.987   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      55.505 -20.744   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      52.491 -23.857   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      54.477 -19.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      52.970 -19.915   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      45.699 -21.848   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      54.955 -18.133   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      48.367 -21.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      51.034 -23.388   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      52.491 -21.379   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.034 -21.848   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.390 -22.618   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      49.700 -21.078   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      48.367 -23.388   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      49.700 -24.158   0.000  0.00  0.00           C+0
CONECT    1    8   10                                                       
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    6                                                            
CONECT    5   11   14                                                       
CONECT    6    4    7    9                                                  
CONECT    7    6   12                                                       
CONECT    8    1                                                            
CONECT    9    2    3    6                                                  
CONECT   10    1   15   16                                                  
CONECT   11    5   13   17                                                  
CONECT   12    7   13   14                                                  
CONECT   13   11   12   15                                                  
CONECT   14    5   12                                                       
CONECT   15   10   13                                                       
CONECT   16   10   17                                                       
CONECT   17   11   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0002339
HETATM    1  C1  UNL     1       4.312  -0.079   2.346  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.981   0.196   2.036  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.393   0.085   0.786  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.146  -0.331  -0.285  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.511  -0.427  -1.528  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.176  -0.113  -1.663  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.395  -0.135  -2.749  1.00  0.00           N  
HETATM    8  C6  UNL     1      -0.851   0.263  -2.377  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.863   0.545  -1.030  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.993   1.009  -0.186  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.570  -0.121   0.656  1.00  0.00           C  
HETATM   12  N2  UNL     1      -3.041  -1.144  -0.269  1.00  0.00           N  
HETATM   13  C10 UNL     1      -3.737   0.403   1.395  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.517   1.303   2.278  1.00  0.00           O  
HETATM   15  O3  UNL     1      -5.041   0.012   1.218  1.00  0.00           O  
HETATM   16  C11 UNL     1       0.431   0.302  -0.585  1.00  0.00           C  
HETATM   17  C12 UNL     1       1.040   0.399   0.627  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.333  -0.427   3.417  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.797  -0.838   1.675  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.961   0.821   2.268  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.178  -0.587  -0.240  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.107  -0.757  -2.373  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.640  -0.404  -3.737  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.706   0.350  -3.032  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.824   1.373  -0.832  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.658   1.851   0.472  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.806  -0.537   1.348  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.578  -0.687  -1.039  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.256  -1.719  -0.660  1.00  0.00           H  
HETATM   30  H13 UNL     1      -5.408  -0.657   0.589  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.450   0.726   1.473  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   16
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   16
CONECT   10   11   25   26
CONECT   11   12   13   27
CONECT   12   28   29
CONECT   13   14   14   15
CONECT   15   30
CONECT   16   17   17
CONECT   17   31
END

HMDB0002339
     RDKit          3D
5-Methoxytryptophan
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.3119   -0.0787    2.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9812    0.1962    2.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3932    0.0853    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1458   -0.3309   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106   -0.4269   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756   -0.1131   -1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -0.1352   -2.7491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514    0.2635   -2.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8629    0.5450   -1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932    1.0085   -0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5702   -0.1207    0.6561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0412   -1.1436   -0.2689 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7375    0.4027    1.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167    1.3032    2.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0407    0.0117    1.2184 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311    0.3021   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    0.3991    0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334   -0.4269    3.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7973   -0.8383    1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608    0.8211    2.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1784   -0.5866   -0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1067   -0.7569   -2.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6402   -0.4040   -3.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7064    0.3500   -3.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242    1.3734   -0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    1.8515    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8061   -0.5374    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5780   -0.6873   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2563   -1.7190   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4076   -0.6565    0.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4496    0.7258    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  9 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  1
 12 28  1  0
 12 29  1  0
 15 30  1  0
 17 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Methoxytryptophan, (L)-isomer	HMDB
5-Methoxytryptophan, (DL)-isomer	HMDB

Chemical Formula

C₁₂H₁₄N₂O₃

Average Molecular Weight

234.2512

Monoisotopic Molecular Weight

234.100442324

IUPAC Name

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

Traditional Name

5-methoxytryptophan

CAS Registry Number

2504-22-5

SMILES

COC1=CC2=C(NC=C2C[C@H](N)C(O)=O)C=C1

InChI Identifier

InChI=1S/C12H14N2O3/c1-17-8-2-3-11-9(5-8)7(6-14-11)4-10(13)12(15)16/h2-3,5-6,10,14H,4,13H2,1H3,(H,15,16)/t10-/m0/s1

InChI Key

KVNPSKDDJARYKK-JTQLQIEISA-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
L-alpha-amino acid
3-alkylindole
Indole
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Ether
Azacycle
Monocarboxylic acid or derivatives
Amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Primary amine
Primary aliphatic amine
Organic oxide
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

L-tryptophan derivative (CHEBI:74049 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0002339)

Source

Endogenous

Endogenous (HMDB: HMDB0002339)

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	154.356	30932474
[M-H]-	Not Available	154.356	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000352

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.83 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1.2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.22	ChemAxon
pKa (Strongest Basic)	9.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.34 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.67 m³·mol⁻¹	ChemAxon
Polarizability	24 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]+	154.598	31661259
DarkChem	[M-H]-	154.327	31661259
DeepCCS	[M+H]+	155.409	30932474
DeepCCS	[M-H]-	153.051	30932474
DeepCCS	[M-2H]-	186.007	30932474
DeepCCS	[M+Na]+	161.502	30932474
AllCCS	[M+H]+	153.9	32859911
AllCCS	[M+H-H2O]+	150.0	32859911
AllCCS	[M+NH4]+	157.4	32859911
AllCCS	[M+Na]+	158.5	32859911
AllCCS	[M-H]-	154.9	32859911
AllCCS	[M+Na-2H]-	154.9	32859911
AllCCS	[M+HCOO]-	155.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.45 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9225 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.24 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	273.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	661.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	270.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	92.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	91.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	302.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	266.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	733.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	671.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	231.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	775.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	201.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	586.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	407.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	289.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxytryptophan	COC1=CC2=C(NC=C2C[C@H](N)C(O)=O)C=C1	3788.9	Standard polar	33892256
5-Methoxytryptophan	COC1=CC2=C(NC=C2C[C@H](N)C(O)=O)C=C1	2284.3	Standard non polar	33892256
5-Methoxytryptophan	COC1=CC2=C(NC=C2C[C@H](N)C(O)=O)C=C1	2487.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxytryptophan,1TMS,isomer #1	COC1=CC=C2[NH]C=C(C[C@H](N)C(=O)O[Si](C)(C)C)C2=C1	2398.5	Semi standard non polar	33892256
5-Methoxytryptophan,1TMS,isomer #2	COC1=CC=C2[NH]C=C(C[C@H](N[Si](C)(C)C)C(=O)O)C2=C1	2452.3	Semi standard non polar	33892256
5-Methoxytryptophan,1TMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O)=CN2[Si](C)(C)C	2487.8	Semi standard non polar	33892256
5-Methoxytryptophan,2TMS,isomer #1	COC1=CC=C2[NH]C=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C2=C1	2393.4	Semi standard non polar	33892256
5-Methoxytryptophan,2TMS,isomer #1	COC1=CC=C2[NH]C=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C2=C1	2406.7	Standard non polar	33892256
5-Methoxytryptophan,2TMS,isomer #1	COC1=CC=C2[NH]C=C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C2=C1	2967.4	Standard polar	33892256
5-Methoxytryptophan,2TMS,isomer #2	COC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C	2433.4	Semi standard non polar	33892256
5-Methoxytryptophan,2TMS,isomer #2	COC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C	2388.1	Standard non polar	33892256
5-Methoxytryptophan,2TMS,isomer #2	COC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C	3063.4	Standard polar	33892256
5-Methoxytryptophan,2TMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C)C(=O)O)=CN2[Si](C)(C)C	2477.7	Semi standard non polar	33892256
5-Methoxytryptophan,2TMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C)C(=O)O)=CN2[Si](C)(C)C	2442.9	Standard non polar	33892256
5-Methoxytryptophan,2TMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C)C(=O)O)=CN2[Si](C)(C)C	3100.1	Standard polar	33892256
5-Methoxytryptophan,2TMS,isomer #4	COC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	2546.7	Semi standard non polar	33892256
5-Methoxytryptophan,2TMS,isomer #4	COC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	2493.6	Standard non polar	33892256
5-Methoxytryptophan,2TMS,isomer #4	COC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	3147.5	Standard polar	33892256
5-Methoxytryptophan,3TMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C	2426.1	Semi standard non polar	33892256
5-Methoxytryptophan,3TMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C	2425.3	Standard non polar	33892256
5-Methoxytryptophan,3TMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C	2775.4	Standard polar	33892256
5-Methoxytryptophan,3TMS,isomer #2	COC1=CC=C2[NH]C=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	2522.5	Semi standard non polar	33892256
5-Methoxytryptophan,3TMS,isomer #2	COC1=CC=C2[NH]C=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	2543.8	Standard non polar	33892256
5-Methoxytryptophan,3TMS,isomer #2	COC1=CC=C2[NH]C=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	2823.9	Standard polar	33892256
5-Methoxytryptophan,3TMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2582.6	Semi standard non polar	33892256
5-Methoxytryptophan,3TMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2562.3	Standard non polar	33892256
5-Methoxytryptophan,3TMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2910.4	Standard polar	33892256
5-Methoxytryptophan,4TMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2597.8	Semi standard non polar	33892256
5-Methoxytryptophan,4TMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2553.6	Standard non polar	33892256
5-Methoxytryptophan,4TMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2699.4	Standard polar	33892256
5-Methoxytryptophan,1TBDMS,isomer #1	COC1=CC=C2[NH]C=C(C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C2=C1	2683.1	Semi standard non polar	33892256
5-Methoxytryptophan,1TBDMS,isomer #2	COC1=CC=C2[NH]C=C(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C2=C1	2725.2	Semi standard non polar	33892256
5-Methoxytryptophan,1TBDMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O)=CN2[Si](C)(C)C(C)(C)C	2748.2	Semi standard non polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #1	COC1=CC=C2[NH]C=C(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C2=C1	2907.1	Semi standard non polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #1	COC1=CC=C2[NH]C=C(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C2=C1	2863.0	Standard non polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #1	COC1=CC=C2[NH]C=C(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C2=C1	3095.3	Standard polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #2	COC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2924.7	Semi standard non polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #2	COC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2812.6	Standard non polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #2	COC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3149.3	Standard polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)=CN2[Si](C)(C)C(C)(C)C	2976.5	Semi standard non polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)=CN2[Si](C)(C)C(C)(C)C	2866.2	Standard non polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #3	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)=CN2[Si](C)(C)C(C)(C)C	3186.2	Standard polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #4	COC1=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	3060.9	Semi standard non polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #4	COC1=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	2931.6	Standard non polar	33892256
5-Methoxytryptophan,2TBDMS,isomer #4	COC1=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	3190.5	Standard polar	33892256
5-Methoxytryptophan,3TBDMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3098.8	Semi standard non polar	33892256
5-Methoxytryptophan,3TBDMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3063.5	Standard non polar	33892256
5-Methoxytryptophan,3TBDMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3042.4	Standard polar	33892256
5-Methoxytryptophan,3TBDMS,isomer #2	COC1=CC=C2[NH]C=C(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3258.1	Semi standard non polar	33892256
5-Methoxytryptophan,3TBDMS,isomer #2	COC1=CC=C2[NH]C=C(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3170.3	Standard non polar	33892256
5-Methoxytryptophan,3TBDMS,isomer #2	COC1=CC=C2[NH]C=C(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3061.2	Standard polar	33892256
5-Methoxytryptophan,3TBDMS,isomer #3	COC1=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	3272.6	Semi standard non polar	33892256
5-Methoxytryptophan,3TBDMS,isomer #3	COC1=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	3130.7	Standard non polar	33892256
5-Methoxytryptophan,3TBDMS,isomer #3	COC1=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	3111.8	Standard polar	33892256
5-Methoxytryptophan,4TBDMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3432.8	Semi standard non polar	33892256
5-Methoxytryptophan,4TBDMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3311.8	Standard non polar	33892256
5-Methoxytryptophan,4TBDMS,isomer #1	COC1=CC=C2C(=C1)C(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3031.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxytryptophan GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-5920000000-ffba36adb450cd195025	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxytryptophan GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9260000000-e578266deb11647b6038	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxytryptophan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxytryptophan Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014i-0090000000-98b67a871de8f6b734b7	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxytryptophan Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0002-0900000000-0b2e81c476982c3890ba	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxytryptophan Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0fur-0900000000-1d843566e7fb8915aa0e	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 10V, Positive-QTOF	splash10-000i-0970000000-acee09725ba82e4e72c7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 20V, Positive-QTOF	splash10-000i-0910000000-88d7862280a8ce1779d8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 40V, Positive-QTOF	splash10-01q9-0900000000-31129998c458c6c3c454	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 10V, Negative-QTOF	splash10-001i-2090000000-1663a625f71fa9a0d490	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 20V, Negative-QTOF	splash10-00di-9560000000-7fc44f90a890e8c82e55	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 40V, Negative-QTOF	splash10-00di-9600000000-ac4fab328618b00e6373	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 10V, Negative-QTOF	splash10-0089-1590000000-0810f437fce8f57d59d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 20V, Negative-QTOF	splash10-00e9-6970000000-0a0c9b0d1d20b9da1dd5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 40V, Negative-QTOF	splash10-008c-1900000000-a399bb78fbe6070b9a7e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 10V, Positive-QTOF	splash10-000i-0190000000-d84e219841879424e605	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 20V, Positive-QTOF	splash10-00kr-0890000000-147dc404892ce92bb5e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophan 40V, Positive-QTOF	splash10-03l1-0900000000-6c9279ea8fd7cacb8919	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022969

KNApSAcK ID

Not Available

Chemspider ID

133110

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6631

PubChem Compound

151018

PDB ID

Not Available

ChEBI ID

74049

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Geffard M, Dulluc J, Rock AM: Antisera against the indolealkylamines: tryptophan, 5-hydroxytryptophan, 5-hydroxytryptamine, 5-methoxytryptophan, and 5-methoxytryptamine tested by an enzyme-linked immunosorbent assay method. J Neurochem. 1985 Apr;44(4):1221-8. [PubMed:3919158 ]
HARTMANN F, FREIBERG E, RUGE W: [Indolepatterns in the urine of liver patients]. Klin Wochenschr. 1962 Jul 15;40:721-9. [PubMed:13905029 ]
Leino M, Airaksinen MM: Methoxyindoles of the retina. Med Biol. 1985;63(4):160-9. [PubMed:2419712 ]

Showing metabocard for 5-Methoxytryptophan (HMDB0002339)

MOL for HMDB0002339 (5-Methoxytryptophan)

3D MOL for HMDB0002339 (5-Methoxytryptophan)

3D SDF for HMDB0002339 (5-Methoxytryptophan)

3D-SDF for HMDB0002339 (5-Methoxytryptophan)

PDB for HMDB0002339 (5-Methoxytryptophan)

3D PDB for HMDB0002339 (5-Methoxytryptophan)

SMILES for HMDB0002339 (5-Methoxytryptophan)

INCHI for HMDB0002339 (5-Methoxytryptophan)

Structure for HMDB0002339 (5-Methoxytryptophan)

3D Structure for HMDB0002339 (5-Methoxytryptophan)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra