IMPPAT Phytochemical information: 
Tryptamine
Tryptamine
Summary

SMILES: NCCc1c[nH]c2c1cccc2
InChI: InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
InChIKey: APJYDQYYACXCRM-UHFFFAOYSA-N
DeepSMILES: NCCcc[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2[nH]ccc2c1
Scaffold Graph/Node level: C1CCC2NCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CN; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Tryptamines and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
tryptamine
External chemical identifiers:
CID:CID_1150; ChEMBL:CHEMBL6640; ChEBI:CHEBI:16765; ZINC:ZINC000000120144; FDASRS:422ZU9N5TV; SureChEMBL:SCHEMBL26725; MolPort-001-002-280
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Tryptamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 160.22
Log P RDKit 1.67
Topological polar surface area (Å2) RDKit 41.81
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Tryptamine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.689024
Tryptamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.78
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Tryptamine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000354193AOC1918
ENSP00000235521WARS2834
ENSP00000013222INMT834
ENSP00000316244HTR1A949
ENSP00000322924HTR1F913
ENSP00000337949HTR7977
ENSP00000340684MAOA945
ENSP00000347495WARS816
ENSP00000350616DDC966
ENSP00000356908TAAR2855
ENSP00000358963HTR1B951
ENSP00000367309MAOB942
ENSP00000367959HTR2A996
ENSP00000369050CYP1A1786
ENSP00000456039INMT-FAM188B900
ENSP00000342007CYP1A2815
ENSP00000301141CYP2A6938
ENSP00000307766HTR1E899
ENSP00000258400HTR2B950
ENSP00000275198TAAR6855
ENSP00000275200TAAR8855
ENSP00000313661HTR1D962
ENSP00000258034TAAR5863
ENSP00000276198HTR2C948
ENSP00000289753HTR6953
ENSP00000299964NNMT706
ENSP00000275216TAAR1982
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.