Np mrd loader

Showing NP-Card for Tryptamine (NP0000058)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:32 UTC
NP-MRD IDNP0000058
Secondary Accession NumbersNone
Natural Product Identification
Common NameTryptamine
DescriptionTryptamine is a monoamine compound that is common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine in turn acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000058 (Tryptamine)


  Mrv1652309042000002D          

 12 13  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 N   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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0000058 (Tryptamine)

HMDB0000303
     RDKit          3D
Tryptamine
 24 25  0  0  0  0  0  0  0  0999 V2000
    2.9094    0.2659   -0.6145 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089    0.5611    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046   -0.6539    1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.8578    0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415   -1.7663   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -1.5473   -1.4165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -0.5189   -0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7315    0.0765   -1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    1.1296   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2923    1.5532    0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703    0.9913    0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652   -0.0794    0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563    0.9571   -1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291   -0.7222   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    1.4571    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.7845    1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611   -0.4813    2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2408   -1.5471    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -2.5146   -1.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423   -2.0749   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3317   -0.3197   -1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0955    1.6133   -0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169    2.3792    1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117    1.3145    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
Download

3D SDF for NP0000058 (Tryptamine)


  Mrv1652309042000002D          

 12 13  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 N   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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000058

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2

> <INCHI_KEY>
APJYDQYYACXCRM-UHFFFAOYSA-N

> <FORMULA>
C10H12N2

> <MOLECULAR_WEIGHT>
160.2157

> <EXACT_MASS>
160.100048394

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.336363890057264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
1.48643745

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.170311785836876

> <JCHEM_PKA_STRONGEST_BASIC>
9.733973681017083

> <JCHEM_POLAR_SURFACE_AREA>
41.81

> <JCHEM_REFRACTIVITY>
50.37290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tryptamine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000058 (Tryptamine)

HMDB0000303
     RDKit          3D
Tryptamine
 24 25  0  0  0  0  0  0  0  0999 V2000
    2.9094    0.2659   -0.6145 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089    0.5611    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046   -0.6539    1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.8578    0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415   -1.7663   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -1.5473   -1.4165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -0.5189   -0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7315    0.0765   -1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    1.1296   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2923    1.5532    0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703    0.9913    0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652   -0.0794    0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563    0.9571   -1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291   -0.7222   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    1.4571    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.7845    1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611   -0.4813    2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2408   -1.5471    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -2.5146   -1.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423   -2.0749   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3317   -0.3197   -1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0955    1.6133   -0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169    2.3792    1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117    1.3145    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
Download

PDB for NP0000058 (Tryptamine)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8669.1548664.625   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
Download

3D PDB for NP0000058 (Tryptamine)

COMPND    HMDB0000303
HETATM    1  N1  UNL     1       2.909   0.266  -0.614  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.409   0.561   0.707  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.605  -0.654   1.155  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.483  -0.858   0.184  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.341  -1.766  -0.828  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.842  -1.547  -1.417  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.491  -0.519  -0.824  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.731   0.076  -1.071  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.134   1.130  -0.281  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.292   1.553   0.722  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.070   0.991   0.988  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.665  -0.079   0.183  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.556   0.957  -1.002  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.229  -0.722  -0.711  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.742   1.457   0.595  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.159   0.784   1.461  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.161  -0.481   2.133  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.241  -1.547   1.138  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.088  -2.515  -1.070  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.242  -2.075  -2.220  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.332  -0.320  -1.877  1.00  0.00           H  
HETATM   22  H10 UNL     1      -4.096   1.613  -0.450  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.617   2.379   1.336  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.412   1.314   1.764  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5    5   12
CONECT    5    6   19
CONECT    6    7   20
CONECT    7    8    8   12
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   11   23
CONECT   11   12   12   24
END
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SMILES for NP0000058 (Tryptamine)

NCCC1=CNC2=C1C=CC=C2
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INCHI for NP0000058 (Tryptamine)

InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
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View in JSmol
Synonyms
ValueSource
1H-Indole-3-ethanamineChEBI
2-(1H-indol-3-yl)ETHANAMINEChEBI
2-(3-Indolyl)ethylamineChEBI
3-(2-Aminoethyl)indoleChEBI
(3-Indolyl)ethylamineHMDB
2-(1H-indol-3-yl)EthylamineHMDB
2-indol-3-yl-AethylaminHMDB
2-indol-3-yl-EthylamineHMDB
3-(2-Aminoethyl)-1H-indoleHMDB
3-IndoleethanamineHMDB
3-IndoleethylamineHMDB
TryptaminHMDB
2-(1H-indol-3-yl)Ethan-1-amineHMDB
beta-(3-Indolyl)ethylamineHMDB
Β-(3-indolyl)ethylamineHMDB
TRPNHMDB
TryptamineHMDB
Chemical FormulaC10H12N2
Average Mass160.2157 Da
Monoisotopic Mass160.10005 Da
IUPAC Name2-(1H-indol-3-yl)ethan-1-amine
Traditional Nametryptamine
CAS Registry Number61-54-1
SMILES
NCCC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
InChI KeyAPJYDQYYACXCRM-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
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Aloe velaKNApSAcK Database
Aloysia triphyllaFooDB
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Andrographis paniculatusKNApSAcK Database
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Annona cherimolaFooDB
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Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Arnebia euchromaKNApSAcK Database
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artemisis anna-
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Babreum coscluea-
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisKNApSAcK Database
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papayaKNApSAcK Database
Carica papaya L.Plant
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Catharanthus roseusKNApSAcK Database
Centaurea montanaLOTUS Database
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chenopodium rubrumKNApSAcK Database
Chimonanthus praecoxLOTUS Database
Chlamydomonas reinhardtiiLOTUS Database
Chrysanthemum coronariumFooDB
Chrysanthemum x morifoliumPlant
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
Cinchona calisayaLOTUS Database
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Cistanche deserticolaKNApSAcK Database
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Coptis chinensisKNApSAcK Database
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
Coruns officinalis-
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativusKNApSAcK Database
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma aeruginosaKNApSAcK Database
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dendranthema morifoliumKNApSAcK Database
Desmodium elegansKNApSAcK Database
Desmodium styracifoliumKNApSAcK Database
Dicorynia guianensisKNApSAcK Database
Didymosphaeria mori-albae-
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Epimedium brevicornumKNApSAcK Database
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Ervatamia coronariaLOTUS Database
Eucommia ulmoidesKNApSAcK Database
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Forsythia suspensaKNApSAcK Database
Fragaria x ananassaFooDB
Galdenia jasminoides-
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Gentiana macrophyllaKNApSAcK Database
Gentiana scabraKNApSAcK Database
Ginkgo bilobaFooDB
Glycine maxFooDB
Glycyrrhiza uralensisKNApSAcK Database
GossypiumFooDB
Grifola frondosaFooDB
Grona styracifoliaPlant
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareKNApSAcK Database
Hypericum perforatumKNApSAcK Database
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
Ipomoea nilPlant
Isatis indigoticaKNApSAcK Database
Isatis tinctoriaPlant
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisKNApSAcK Database
Lens esculentaKNApSAcK Database
Lentinus edodesFooDB
Leonurus japonicusKNApSAcK Database
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lobelia chinensisKNApSAcK Database
Lonicera japonicaKNApSAcK Database
Lophartherum gracile-
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusKNApSAcK Database
Lycium barbarumKNApSAcK Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Mahonia bealeiKNApSAcK Database
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Mimosa scabrellaKNApSAcK Database
Mimosa somniansKNApSAcK Database
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus albaKNApSAcK Database
Morus nigraFooDB
Mucuna pruriensKNApSAcK Database
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa spp.KNApSAcK Database
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Nicotiana tabacumKNApSAcK Database
Nicotiana tobacumKNApSAcK Database
Nitraria komaroviiLOTUS Database
Nitraria schoberiLOTUS Database
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Ophiopogon japonicusKNApSAcK Database
Ophiorrhiza pumilaKNApSAcK Database
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panaeolus semiovatusLOTUS Database
Panax ginsengFooDB
Panax notoginsnegKNApSAcK Database
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Patrinia scabiosifoliaKNApSAcK Database
Pediomelum esculentumFooDB
Pentaceras australisKNApSAcK Database
Pereskia aculeataLOTUS Database
Perideridia oreganaFooDB
Persea americanaFooDB
Petalostylis labicheoidesKNApSAcK Database
Petasites japonicusFooDB
Petroselinum crispumFooDB
Petunia hybridaLOTUS Database
Pharbitis nilKNApSAcK Database
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phellodendron amurenseKNApSAcK Database
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Piptadenia peregrinaKNApSAcK Database
Pirola decorata-
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Polygala tenuifoliaKNApSAcK Database
Polygonatum sibiricumKNApSAcK Database
Polygonum alpinumFooDB
Polygonum multiflorumKNApSAcK Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prosopis albaKNApSAcK Database
Prosopis alpatacoLOTUS Database
Prosopis glandulosaLOTUS Database
Prosopis nigraKNApSAcK Database
Prunella vulgarisKNApSAcK Database
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusKNApSAcK Database
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Pueraria lobataKNApSAcK Database
Punica granatumKNApSAcK Database
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusKNApSAcK Database
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rauvolfia serpentinaLOTUS Database
Rehmannia glutinosaKNApSAcK Database
Rheum palmatumKNApSAcK Database
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus chingiiKNApSAcK Database
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia miltiorrhizaKNApSAcK Database
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Saposhmikovia divaricata-
Satureja hortensis L.FooDB
Satureja montanaFooDB
Schisondra chinensis-
Scorzonera hispanicaFooDB
Scrophularia ningpoensisKNApSAcK Database
Scutellaria amoenaKNApSAcK Database
Scutellaria baicalensisKNApSAcK Database
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumKNApSAcK Database
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumKNApSAcK Database
Sophora flavescensKNApSAcK Database
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Stichodactyla giganteaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumKNApSAcK Database
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tabernaemontana elegansLOTUS Database
Tachigali paniculataKNApSAcK Database
Tamarindus indicaFooDB
Tanacetum partheniumKNApSAcK Database
Taraxacum officinaleFooDB
Taxillus chinensisKNApSAcK Database
Tecoma stansLOTUS Database
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Theobroma cacaoFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
Uncaria rhynchophyllaKNApSAcK Database
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Vachellia rigidulaLOTUS Database
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Viola philipicaKNApSAcK Database
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Wolfiporia cocos-
Xanthoselinum alsaticumLOTUS Database
Xanthosoma sagittifoliumFooDB
Zea maysKNApSAcK Database
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus jujubaKNApSAcK Database
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Coprinus micaceusKNApSAcK Database
Penicillium expansumKNApSAcK Database
Psilocybe arcanaKNApSAcK Database
Psilocybe bohemicaKNApSAcK Database
Psilocybe semilanceataKNApSAcK 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
  • 2-arylethylamine
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point114 - 119 °Chttps://en.wikipedia.org/wiki/Tryptamine
Boiling Point137 °Chttps://en.wikipedia.org/wiki/Tryptamine
Water Solubility1 mg/mLhttps://www.sigmaaldrich.com/CA/en/product/aldrich/193747
LogP1.55Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP1.21ALOGPS
logP1.49ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)17.17ChemAxon
pKa (Strongest Basic)9.73ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.81 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.37 m³·mol⁻¹ChemAxon
Polarizability18.34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000303
DrugBank IDDB08653
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000917
KNApSAcK IDC00001434
Chemspider ID1118
KEGG Compound IDC00398
BioCyc IDTRYPTAMINE
BiGG IDNot Available
Wikipedia LinkTryptamine
METLIN IDNot Available
PubChem Compound1150
PDB IDNot Available
ChEBI ID16765
Good Scents IDrw1295851
References
General References
  1. Radulovacki P, Djuricic-Nedelson M, Chen EH, Radulovacki M: Human tryptamine metabolism decreases during night sleep. Brain Res Bull. 1983 Jan;10(1):43-5. [PubMed:6186344 ]
  2. Mathew RJ, Ho BT, Kralik P, Weinman M, Claghorn JL: Anxiety and platelet MAO levels after relaxation training. Am J Psychiatry. 1981 Mar;138(3):371-3. [PubMed:7008633 ]
  3. Gilboa-Garber N, Katz-Bergman Y, Pinsky A: Comparative study of the sensitivity of acetylcholinesterases and cholinesterases from animal and bacterial sources to inhibition by serotonin and its derivatives. Experientia. 1978 Aug 15;34(8):992-3. [PubMed:100343 ]
  4. Tsuchiya H, Ohtani S, Yamada K, Tajima K, Sato M: Formation of tetrahydro-beta-carbolines in human saliva. Biochem Pharmacol. 1995 Dec 22;50(12):2109-12. [PubMed:8849340 ]
  5. Tam WY, Chan MY, Lee PH: The menstrual cycle and platelet 5-HT uptake. Psychosom Med. 1985 Jul-Aug;47(4):352-62. [PubMed:4023163 ]
  6. Friedl W, Kruger J, Propping P: Intraindividual stability and extent of genetic determination of platelet monoamine oxidase activity. Pharmacopsychiatria. 1981 May;14(3):83-6. [PubMed:7196052 ]
  7. Sullivan JP, McDonnell L, Hardiman OM, Farrell MA, Phillips JP, Tipton KF: The oxidation of tryptamine by the two forms of monoamine oxidase in human tissues. Biochem Pharmacol. 1986 Oct 1;35(19):3255-60. [PubMed:3094536 ]
  8. al Mardini H, Harrison EJ, Ince PG, Bartlett K, Record CO: Brain indoles in human hepatic encephalopathy. Hepatology. 1993 Jun;17(6):1033-40. [PubMed:7685732 ]
  9. Young SN, Gauthier S: Effect of tryptophan administration on tryptophan, 5-hydroxyindoleacetic acid and indoleacetic acid in human lumbar and cisternal cerebrospinal fluid. J Neurol Neurosurg Psychiatry. 1981 Apr;44(4):323-8. [PubMed:6165809 ]
  10. Siwers B, Ringberger VA, Tuck JR, Sjoqvist F: Initial clinical trial based on biochemical methodology of zimelidine (a serotonin uptake inhibitor) in depressed patients. Clin Pharmacol Ther. 1977 Feb;21(2):194-200. [PubMed:837638 ]
  11. Sullivan JL, Coffey CE, Basuk B, Cavenar JO, Maltbie AA, Zung WW: Urinary tryptamine excretion in chronic schizophrenics with low platelet MAO activity. Biol Psychiatry. 1980 Feb;15(1):113-20. [PubMed:7357050 ]
  12. Tsuchiya H, Hayashi T, Tatsumi M, Hoshino Y, Ohtani S, Takagi N: High-performance liquid-chromatographic analysis for serotonin and tryptamine excreted in urine after oral loading with L-tryptophan. Clin Chem. 1989 Jan;35(1):43-7. [PubMed:2910580 ]
  13. Anderson GM, Gerner RH, Cohen DJ, Fairbanks L: Central tryptamine turnover in depression, schizophrenia, and anorexia: measurement of indoleacetic acid in cerebrospinal fluid. Biol Psychiatry. 1984 Oct;19(10):1427-35. [PubMed:6518200 ]
  14. Gaszner P, Miklya I: The use of the synthetic enhancer substances (-)-deprenyl and (-)-BPAP in major depression. Neuropsychopharmacol Hung. 2004 Dec;6(4):210-20. [PubMed:15825677 ]
  15. Dolusic E, Kowalczyk M, Magnus V, Sandberg G, Normanly J: Biotinylated indoles as probes for indole-binding proteins. Bioconjug Chem. 2001 Mar-Apr;12(2):152-62. [PubMed:11312675 ]
  16. Demisch L, von der Muhlen H, Bochnik HJ, Seiler N: Substrate-typic changes of platelet monoamine oxidase activity in sub-types of schizophrenia. Arch Psychiatr Nervenkr (1970). 1977 Dec 28;224(4):319-29. [PubMed:606205 ]
  17. Gaszner P, Miklya I: Major depression and the synthetic enhancer substances, (-)-deprenyl and R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane. Prog Neuropsychopharmacol Biol Psychiatry. 2006 Jan;30(1):5-14. Epub 2005 Jul 14. [PubMed:16023777 ]
  18. Mousseau DD, Layrargues GP, Butterworth RF: Region-selective decreases in densities of [3H]tryptamine binding sites in autopsied brain tissue from cirrhotic patients with hepatic encephalopathy. J Neurochem. 1994 Feb;62(2):621-5. [PubMed:8294925 ]
  19. Anthenelli RM, Tipp J, Li TK, Magnes L, Schuckit MA, Rice J, Daw W, Nurnberger JI Jr: Platelet monoamine oxidase activity in subgroups of alcoholics and controls: results from the Collaborative Study on the Genetics of Alcoholism. Alcohol Clin Exp Res. 1998 May;22(3):598-604. [PubMed:9622437 ]
  20. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]