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Showing NP-Card for 5-Methoxytryptophol (NP0001005)

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Record Information
Version2.0
Created at2006-03-08 14:40:32 UTC
Updated at2020-11-24 22:20:03 UTC
NP-MRD IDNP0001005
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Methoxytryptophol
Description5-Methoxytryptophol is synthesized by the pineal gland. Daily rhythms in pineal methoxyindole metabolism have been described in rodents and humans (5-Methoxytryptophol levels are coincident with serotonin levels in rodents pineal) and 5-Methoxytryptophol at its highest during the daylight hours and fall markedly soon after the onset of darkness, coincident with increases in the levels of pineal melatonin and the activities of pineal serotonin-N-acetyltransferase (EC 2.3.1.87, SNAT) and hydroxyindole-O-methyltransferase (EC 2.1.1.4, HIOMT). The fact that the levels of 5-methoxytryptophol and melatonin vary in parallel suggests that the major factor generating the methoxyindole rhythms is not SNAT activity, but perhaps a change in the availability (for metabolism) of "stored" serotonin. When the onset of darkness is delayed by 12 hours, human 5-methoxytryptophol (and melatonin) rhythms usually require 3 or 4 days to adjust to the new lighting regimen. Environmental factors, other than light, that activate the sympathetic nervous system or cause epinephrine to be secreted from the adrenal medulla (e.G., The stress of immobilization; insulin-induced hypoglycemia) can override the inhibitory effects of light and accelerate melatonin synthesis. Rhythms in 5-methoxytryptophol (and melatonin) synthesis apparently persist among animals placed in environments of continuous darkness; the source of the cyclic signal (mediated by the pineal sympathetic nerves) has not yet been identified. Preliminary evidence suggests that levels of a peptide hormone, arginine vasotocin, in rat pineal and sera also exhibit daily rhythms and are increased by norepinephrine. The circadian rhythm of melatonin secretion is generated in the suprachiasmatic nucleus. Sleep disruption, nightly restlessness, sundowning, and other circadian disturbances are frequently seen in Alzheimer's disease patients. Changes in the suprachiasmatic nucleus and pineal gland are thought to be the biological basis for these behavioral disturbances. (PMID 288858 , 2245336 ).
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001005 (5-Methoxytryptophol)


  Mrv1652305271900002D          

 14 15  0  0  0  0            999 V2000
   13.1808  -10.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1808  -11.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8952  -11.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6097  -11.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6097  -10.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8952   -9.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3943  -11.4141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8793  -10.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3943  -10.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6493   -9.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4562   -9.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7112   -8.3383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4664   -9.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4664   -9.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  5  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
Download

3D MOL for NP0001005 (5-Methoxytryptophol)

HMDB0001896
     RDKit          3D
5-Methoxytryptophol
 27 28  0  0  0  0  0  0  0  0999 V2000
    4.4654    1.1316    0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    1.4836    0.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1558    0.4696    0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -0.8572    0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581   -1.8676   -0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214   -1.5499   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7876   -2.3172   -0.2575 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8892   -1.5515   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5260   -0.2472   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248    0.9764    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8060    0.7146   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5353    1.8924    0.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1415   -0.2540    0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8072    0.7270    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1069    1.9837    0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292    0.3048    1.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8483    0.7580   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6317   -1.0817    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0277   -2.8700   -0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536   -3.3472   -0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9109   -1.8691   -0.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331    1.4121    1.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0609    1.7431   -0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0542    0.2802   -1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1923    0.0160    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6846    2.1475    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    1.7719    0.4061 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
 14 27  1  0
M  END
Download

3D SDF for NP0001005 (5-Methoxytryptophol)


  Mrv1652305271900002D          

 14 15  0  0  0  0            999 V2000
   13.1808  -10.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1808  -11.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8952  -11.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6097  -11.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6097  -10.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8952   -9.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3943  -11.4141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8793  -10.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3943  -10.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6493   -9.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4562   -9.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7112   -8.3383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4664   -9.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4664   -9.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  5  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001005

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2NC=C(CCO)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3

> <INCHI_KEY>
QLWKTGDEPLRFAT-UHFFFAOYSA-N

> <FORMULA>
C11H13NO2

> <MOLECULAR_WEIGHT>
191.2264

> <EXACT_MASS>
191.094628665

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.8621175575064

> <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-ol

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
1.4356479810000002

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.65783223206696

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.83195417589852

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4284988407908514

> <JCHEM_POLAR_SURFACE_AREA>
45.25

> <JCHEM_REFRACTIVITY>
55.17860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methoxytryptophol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001005 (5-Methoxytryptophol)

HMDB0001896
     RDKit          3D
5-Methoxytryptophol
 27 28  0  0  0  0  0  0  0  0999 V2000
    4.4654    1.1316    0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    1.4836    0.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1558    0.4696    0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -0.8572    0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581   -1.8676   -0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214   -1.5499   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7876   -2.3172   -0.2575 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8892   -1.5515   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5260   -0.2472   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248    0.9764    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8060    0.7146   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5353    1.8924    0.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1415   -0.2540    0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8072    0.7270    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1069    1.9837    0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292    0.3048    1.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8483    0.7580   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6317   -1.0817    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0277   -2.8700   -0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536   -3.3472   -0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9109   -1.8691   -0.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331    1.4121    1.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0609    1.7431   -0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0542    0.2802   -1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1923    0.0160    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6846    2.1475    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    1.7719    0.4061 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
 14 27  1  0
M  END
Download

PDB for NP0001005 (5-Methoxytryptophol)

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  C   UNK     0      24.604 -19.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.604 -20.830   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.938 -21.600   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.271 -20.830   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.271 -19.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.938 -18.520   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      28.736 -21.306   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      29.641 -20.060   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.736 -18.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.212 -17.350   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.718 -17.030   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      31.194 -15.565   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      23.271 -18.520   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      23.271 -16.980   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    1   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
Download

3D PDB for NP0001005 (5-Methoxytryptophol)

COMPND    HMDB0001896
HETATM    1  C1  UNL     1       4.465   1.132   0.594  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.098   1.484   0.548  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.156   0.470   0.340  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.565  -0.857   0.182  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.658  -1.868  -0.024  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.321  -1.550  -0.072  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.788  -2.317  -0.257  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.889  -1.551  -0.227  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.526  -0.247  -0.018  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.325   0.976   0.098  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.806   0.715  -0.042  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.535   1.892   0.073  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.142  -0.254   0.078  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.807   0.727   0.282  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.107   1.984   0.882  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.629   0.305   1.338  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.848   0.758  -0.375  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.632  -1.082   0.224  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.028  -2.870  -0.139  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.754  -3.347  -0.400  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.911  -1.869  -0.342  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.133   1.412   1.101  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.061   1.743  -0.674  1.00  0.00           H  
HETATM   24  H10 UNL     1      -4.054   0.280  -1.031  1.00  0.00           H  
HETATM   25  H11 UNL     1      -4.192   0.016   0.716  1.00  0.00           H  
HETATM   26  H12 UNL     1      -4.685   2.147   1.024  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.485   1.772   0.406  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
CONECT   13   14   14
CONECT   14   27
END
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SMILES for NP0001005 (5-Methoxytryptophol)

COC1=CC=C2NC=C(CCO)C2=C1
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INCHI for NP0001005 (5-Methoxytryptophol)

InChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3
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Synonyms
ValueSource
MethoxytryptopholHMDB
5-Methoxy-1H-indole-3-ethanolHMDB
5-Methoxyindole-3-ethanolHMDB
5-MethoxytryptopholMeSH
Chemical FormulaC11H13NO2
Average Mass191.2264 Da
Monoisotopic Mass191.09463 Da
IUPAC Name2-(5-methoxy-1H-indol-3-yl)ethan-1-ol
Traditional Namemethoxytryptophol
CAS Registry Number712-09-4
SMILES
COC1=CC=C2NC=C(CCO)C2=C1
InChI Identifier
InChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3
InChI KeyQLWKTGDEPLRFAT-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Anisole
  • Alkyl aryl ether
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Ether
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.64 g/LALOGPS
logP1.84ALOGPS
logP1.44ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)15.83ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area45.25 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity55.18 m³·mol⁻¹ChemAxon
Polarizability20.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001896
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022726
KNApSAcK IDNot Available
Chemspider ID12305
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTryptophol
METLIN IDNot Available
PubChem Compound12835
PDB IDNot Available
ChEBI ID114833
Good Scents IDNot Available
References
General References
  1. Wurtman RJ, Ozaki Y: Physiological control of melatonin synthesis and secretion: mechanisms, generating rhythms in melatonin, methoxytryptophol, and arginine vasotocin levels and effects on the pineal of endogenous catecholamines, the estrous cycle, and environmental lighting. J Neural Transm Suppl. 1978;(13):59-70. [PubMed:288858 ]
  2. Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]
  3. Skene DJ, Vivien-Roels B, Sparks DL, Hunsaker JC, Pevet P, Ravid D, Swaab DF: Daily variation in the concentration of melatonin and 5-methoxytryptophol in the human pineal gland: effect of age and Alzheimer's disease. Brain Res. 1990 Sep 24;528(1):170-4. [PubMed:2245336 ]
  4. Kermeoglu F, Aksoy U, Sebai A, Savtekin G, Ozkayalar H, Sayiner S, Sehirli AO: Anti-Inflammatory Effects of Melatonin and 5-Methoxytryptophol on Lipopolysaccharide-Induced Acute Pulpitis in Rats. Biomed Res Int. 2021 Feb 12;2021:8884041. doi: 10.1155/2021/8884041. eCollection 2021. [PubMed:33628825 ]
  5. Sehirli AO, Sayiner S: Daylight is critical to preserve 5-methoxytryptophol levels in suspected and confirmed COVID-19 patients. Med Hypotheses. 2021 Feb;147:110504. doi: 10.1016/j.mehy.2021.110504. Epub 2021 Jan 19. [PubMed:33485026 ]