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Showing NP-Card for 5-Methoxytryptamine (NP0000622)

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Record Information
Version1.0
Created at2006-08-13 10:47:12 UTC
Updated at2021-06-29 00:47:52 UTC
NP-MRD IDNP0000622
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Methoxytryptamine
Description5-Methoxytryptamine, also known as mexamine or 5-MT, belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. It is biosynthesized via the deacetylation of melatonin in the pineal gland. 5-MT acts as a full agonist at the 5-HT1, 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors. 5-Methoxytryptamine exists in all living organisms, ranging from bacteria to humans. Its affinity for the 5-HT5A receptor is unknown. It has no affinity for the 5-HT3 receptor and is affinity for the 5-HT1E receptor is very weak in comparison to the other 5-HT1 receptors. 5-MT has been shown to occur naturally in the body in low levels.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000622 (5-Methoxytryptamine)


  Mrv1652305271900002D          

 14 15  0  0  0  0            999 V2000
   25.8762  -12.0742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1203  -10.4968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8003  -13.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8639  -11.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0566  -11.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1617  -12.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5908  -12.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0197  -13.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8003  -12.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0197  -12.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2818  -12.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3052  -12.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5908  -13.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3052  -13.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  4  1  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  5  9  1  0  0  0  0
  7 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 10  2  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
Download

3D MOL for NP0000622 (5-Methoxytryptamine)

HMDB0004095
     RDKit          3D
5-Methoxytryptamine
 28 29  0  0  0  0  0  0  0  0999 V2000
   -2.8135    2.3413    0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2149    1.0350    0.7334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3401   -0.0314    0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7577   -1.3181    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810   -2.3577    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030   -2.1410    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -2.9563    0.0193 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5052   -2.2586   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592   -0.9278   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460    0.2295   -0.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4494    1.0858    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    2.1844   -0.3558 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -0.8694   -0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    0.1736    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    2.6964    1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3025    2.3512   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049    3.0234    0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7752   -1.4258    1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -3.3551    0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -3.9863    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829   -2.6565   -0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689    0.8843   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421   -0.0968   -1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669    1.4749    0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0868    0.5672    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2274    2.0488   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8953    3.1119   -0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870    1.1732   -0.1541 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
  9 13  1  0
 13 14  2  0
 14  3  1  0
 13  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
M  END
Download

3D SDF for NP0000622 (5-Methoxytryptamine)


  Mrv1652305271900002D          

 14 15  0  0  0  0            999 V2000
   25.8762  -12.0742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1203  -10.4968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8003  -13.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8639  -11.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0566  -11.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1617  -12.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5908  -12.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0197  -13.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8003  -12.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0197  -12.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2818  -12.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3052  -12.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5908  -13.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3052  -13.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  4  1  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  5  9  1  0  0  0  0
  7 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 10  2  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000622

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(NC=C2CCN)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3

> <INCHI_KEY>
JTEJPPKMYBDEMY-UHFFFAOYSA-N

> <FORMULA>
C11H14N2O

> <MOLECULAR_WEIGHT>
190.2417

> <EXACT_MASS>
190.11061308

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.31855693693656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.3287661843333338

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.44662112135106

> <JCHEM_PKA_STRONGEST_BASIC>
9.760262342114133

> <JCHEM_POLAR_SURFACE_AREA>
51.04

> <JCHEM_REFRACTIVITY>
56.8361

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5 methoxytryptamine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000622 (5-Methoxytryptamine)

HMDB0004095
     RDKit          3D
5-Methoxytryptamine
 28 29  0  0  0  0  0  0  0  0999 V2000
   -2.8135    2.3413    0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2149    1.0350    0.7334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3401   -0.0314    0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7577   -1.3181    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810   -2.3577    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030   -2.1410    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -2.9563    0.0193 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5052   -2.2586   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592   -0.9278   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460    0.2295   -0.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4494    1.0858    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    2.1844   -0.3558 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -0.8694   -0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    0.1736    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    2.6964    1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3025    2.3512   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049    3.0234    0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7752   -1.4258    1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -3.3551    0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -3.9863    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829   -2.6565   -0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689    0.8843   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421   -0.0968   -1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669    1.4749    0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0868    0.5672    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2274    2.0488   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8953    3.1119   -0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870    1.1732   -0.1541 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
  9 13  1  0
 13 14  2  0
 14  3  1  0
 13  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
M  END
Download

PDB for NP0000622 (5-Methoxytryptamine)

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      48.302 -22.539   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      56.225 -19.594   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      53.761 -25.318   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      55.746 -21.058   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      54.239 -21.375   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      46.969 -23.309   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      49.636 -23.309   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      52.303 -24.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      53.761 -22.839   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      52.303 -23.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      54.659 -24.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      50.970 -22.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      49.636 -24.849   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      50.970 -25.619   0.000  0.00  0.00           C+0
CONECT    1    6    7                                                       
CONECT    2    4                                                            
CONECT    3    8   11                                                       
CONECT    4    2    5                                                       
CONECT    5    4    9                                                       
CONECT    6    1                                                            
CONECT    7    1   12   13                                                  
CONECT    8    3   10   14                                                  
CONECT    9    5   10   11                                                  
CONECT   10    8    9   12                                                  
CONECT   11    3    9                                                       
CONECT   12    7   10                                                       
CONECT   13    7   14                                                       
CONECT   14    8   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for NP0000622 (5-Methoxytryptamine)

COMPND    HMDB0004095
HETATM    1  C1  UNL     1      -2.814   2.341   0.417  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.215   1.035   0.733  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.340  -0.031   0.579  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.758  -1.318   0.898  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.881  -2.358   0.739  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.603  -2.141   0.270  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.451  -2.956   0.019  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.505  -2.259  -0.438  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.159  -0.928  -0.501  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.946   0.230  -0.930  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.449   1.086   0.189  1.00  0.00           C  
HETATM   12  N2  UNL     1       3.204   2.184  -0.356  1.00  0.00           N  
HETATM   13  C10 UNL     1      -0.158  -0.869  -0.057  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.060   0.174   0.111  1.00  0.00           C  
HETATM   15  H1  UNL     1      -2.074   2.696   1.178  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.302   2.351  -0.559  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.705   3.023   0.417  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.775  -1.426   1.263  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.201  -3.355   0.985  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.388  -3.986   0.182  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.483  -2.657  -0.720  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.369   0.884  -1.616  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.842  -0.097  -1.532  1.00  0.00           H  
HETATM   24  H10 UNL     1       1.567   1.475   0.769  1.00  0.00           H  
HETATM   25  H11 UNL     1       3.087   0.567   0.917  1.00  0.00           H  
HETATM   26  H12 UNL     1       4.227   2.049  -0.337  1.00  0.00           H  
HETATM   27  H13 UNL     1       2.895   3.112  -0.041  1.00  0.00           H  
HETATM   28  H14 UNL     1      -0.687   1.173  -0.154  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   18
CONECT    5    6    6   19
CONECT    6    7   13
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   13
CONECT   10   11   22   23
CONECT   11   12   24   25
CONECT   12   26   27
CONECT   13   14   14
CONECT   14   28
END
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SMILES for NP0000622 (5-Methoxytryptamine)

COC1=CC2=C(NC=C2CCN)C=C1
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INCHI for NP0000622 (5-Methoxytryptamine)

InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3
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Synonyms
ValueSource
2-(5-Methoxyindol-3-yl)ethylamineChEBI
3-(2-Aminoethyl)-5-methoxyindoleChEBI
5-MeOTChEBI
5-Methoxy-1H-indole-3-ethanamineChEBI
5-MotChEBI
5-MTChEBI
5MOTChEBI
MexamineChEBI
O-MethylserotoninChEBI
2-(5-Methoxy-1H-indol-3-yl)ethanamineHMDB
Lopac-m-6628HMDB
MeksaminHMDB
MethoxytryptamineHMDB
Mexamine baseHMDB
MeksamineHMDB
5 MethoxytryptamineHMDB
5-MethoxytryptamineChEBI
Chemical FormulaC11H14N2O
Average Mass190.2417 Da
Monoisotopic Mass190.11061 Da
IUPAC Name2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
Traditional Name5 methoxytryptamine
CAS Registry Number608-07-1
SMILES
COC1=CC2=C(NC=C2CCN)C=C1
InChI Identifier
InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3
InChI KeyJTEJPPKMYBDEMY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acetabularia acetabulumKNApSAcK Database
Agastaches rugosa-
Aloe velaKNApSAcK Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Andrographis paniculatusKNApSAcK Database
Angelica biserrataKNApSAcK Database
Angelica sinensisKNApSAcK Database
Anser anserFooDB
Arnebia euchromaKNApSAcK Database
Artemisis anna-
Babreum coscluea-
Beta vulgarisKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Ceratium horridum-
CervidaeFooDB
Cervus canadensisFooDB
Chenopodium rubrumKNApSAcK Database
Chlomydomonas spp.-
Chrysanthemum x morifoliumPlant
Cinchona calisayaLOTUS Database
Cistanche deseriocolaKNApSAcK Database
Citrus reticulataKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Coptis chinensisKNApSAcK Database
Coruns officinalis-
Cucumis sativusKNApSAcK Database
Cucumis sativus L.Plant
Curcuma aeruginosaKNApSAcK Database
Dendranthema morifoliumKNApSAcK Database
Desmodium styracifoliumKNApSAcK Database
Didymosphaeria mori-albae-
Dromaius novaehollandiaeFooDB
Dunaliella teriolectaKNApSAcK Database
Epimedium brevicornumKNApSAcK Database
Equus caballusFooDB
Eucommia ulmoidesKNApSAcK Database
Forsythia suspensaKNApSAcK Database
Galdenia jasminoides-
Gallus gallusFooDB
Gekko japanicus-
Gentiana macrophyllaKNApSAcK Database
Gentiana scabraKNApSAcK Database
Glycyrrhiza uralensisKNApSAcK Database
Gonyaulax polyedra-
Grona styracifoliaPlant
Hypericum perforatumKNApSAcK Database
Ipomoea nilPlant
Isatis indigoticaKNApSAcK Database
Isatis tinctoriaPlant
Lagopus mutaFooDB
Laminaria digitataKNApSAcK Database
Leonurus japonicusKNApSAcK Database
LeporidaeFooDB
Lepus timidusFooDB
Lobelia chinensisKNApSAcK Database
Lonicera japonicaKNApSAcK Database
Lophartherum gracile-
Lupinus albusKNApSAcK Database
Lycium barbarumKNApSAcK Database
Mahania bealei-
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mimosa somniansLOTUS Database
Morus albaKNApSAcK Database
Mus musculusLOTUS Database
Musa spp.KNApSAcK Database
Nicotiana tobacumKNApSAcK Database
Noctiluca scintillans-
Numida meleagrisFooDB
OdocoileusFooDB
Ophiopogon japonicusKNApSAcK Database
OryctolagusFooDB
Ovis ariesFooDB
Panax notoginsnegKNApSAcK Database
Patrinia scabiosifoliaKNApSAcK Database
Patriniae scabiosaefoliae-
Periostracum cicadae-
Petalonia fascia-
Pharbitis nilKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phellodendron amurenseKNApSAcK Database
Pheretima aspergillum-
Pirola decorata-
Polygala tenuifoliaKNApSAcK Database
Polygonatum sibiricumKNApSAcK Database
Polygonum multiflorumKNApSAcK Database
Prunella vulgarisKNApSAcK Database
Prunus cerasusKNApSAcK Database
Pterygophora californica-
Pueraria lobataKNApSAcK Database
Pyrocystis lunula-
Raphanus sativusKNApSAcK Database
Rehmannia glutinosaKNApSAcK Database
Rheum palmatumKNApSAcK Database
Rubus chingiiKNApSAcK Database
Salvia miltiorrhizaKNApSAcK Database
Saposhmikovia divaricata-
Schisondra chinensis-
Scrophularia ningpoensisKNApSAcK Database
Scutellaria amoenaKNApSAcK Database
Scutellaria baicalensisKNApSAcK Database
Solanum lycopersicumKNApSAcK Database
Sophora flavescensKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumKNApSAcK Database
Tanacetum partheniumKNApSAcK Database
Taxillus chinensisKNApSAcK Database
Trypanosoma cruzi-
Uncaria rhynchophyllaKNApSAcK Database
Viola philipicaKNApSAcK Database
Wolfiporia cocos-
Ziziphus jujubaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Alexandrium lusitanicumKNApSAcK Database
Amphidinium carteraeKNApSAcK Database
Bombyx batryticatusKNApSAcK Database
Chondrus crispusKNApSAcK Database
Erythrobacter longusKNApSAcK Database
Euglena gracilisKNApSAcK Database
Gracilaria tenustipitataKNApSAcK Database
Neurospora crassaKNApSAcK Database
Palmaria palmataKNApSAcK Database
Porphyra umbilicalisKNApSAcK Database
Rattus sp.KNApSAcK Database
Rhodospirillum rubrumKNApSAcK Database
Saccharomyces cerevisiaeKNApSAcK Database
Scolopendra subspinipesKNApSAcK Database
Tetrahymena thermophilaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • 3-alkylindole
  • Indole
  • Anisole
  • 2-arylethylamine
  • Alkyl aryl ether
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Ether
  • Azacycle
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point121.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP1.41ALOGPS
logP1.33ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)17.45ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area51.04 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.84 m³·mol⁻¹ChemAxon
Polarizability21.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004095
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023311
KNApSAcK IDC00051985
Chemspider ID1767
KEGG Compound IDC05659
BioCyc IDCPD-12018
BiGG IDNot Available
Wikipedia Link5-Methoxytryptamine
METLIN ID7015
PubChem Compound1833
PDB IDNot Available
ChEBI ID2089
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. Rom-Bugolavskaia ES, Shcherbakova VS, Komarova IV: [The effect of melatonin and mexamine on the human thyroid under in-vitro conditions]. Eksp Klin Farmakol. 1997 Jul-Aug;60(4):46-9. [PubMed:9376758 ]
  3. Kirchheiner J, Henckel HB, Franke L, Meineke I, Tzvetkov M, Uebelhack R, Roots I, Brockmoller J: Impact of the CYP2D6 ultra-rapid metabolizer genotype on doxepin pharmacokinetics and serotonin in platelets. Pharmacogenet Genomics. 2005 Aug;15(8):579-87. [PubMed:16007002 ]
  4. Romsing S, Bokman F, Bergqvist Y: Determination of melatonin in saliva using automated solid-phase extraction, high-performance liquid chromatography and fluorescence detection. Scand J Clin Lab Invest. 2006;66(3):181-90. [PubMed:16714247 ]
  5. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]