NP-MRD: Showing NP-Card for 5-Methoxytryptophan (NP0001120)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2006-05-22 14:17:48 UTC

Updated at

2021-06-29 00:47:33 UTC

NP-MRD ID

NP0001120

Secondary Accession Numbers

None

Natural Product 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>
NP0001120

> <DATABASE_NAME>
NP-MRD

> <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

Synonyms

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

Chemical Formula

C₁₂H₁₄N₂O₃

Average Mass

234.2512 Da

Monoisotopic Mass

234.10044 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0002339

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
Cheng HH, Kuo CC, Yan JL, Chen HL, Lin WC, Wang KH, Tsai KK, Guven H, Flaberg E, Szekely L, Klein G, Wu KK: Control of cyclooxygenase-2 expression and tumorigenesis by endogenous 5-methoxytryptophan. Proc Natl Acad Sci U S A. 2012 Aug 14;109(33):13231-6. doi: 10.1073/pnas.1209919109. Epub 2012 Jul 31. [PubMed:22851770 ]

Showing NP-Card for 5-Methoxytryptophan (NP0001120)

MOL for NP0001120 (5-Methoxytryptophan)

3D MOL for NP0001120 (5-Methoxytryptophan)

3D SDF for NP0001120 (5-Methoxytryptophan)

3D-SDF for NP0001120 (5-Methoxytryptophan)

PDB for NP0001120 (5-Methoxytryptophan)

3D PDB for NP0001120 (5-Methoxytryptophan)

SMILES for NP0001120 (5-Methoxytryptophan)

INCHI for NP0001120 (5-Methoxytryptophan)

Structure for NP0001120 (5-Methoxytryptophan)

3D Structure for NP0001120 (5-Methoxytryptophan)