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
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
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000728ENSG00000135312HTR1B3351BindingDB, ChEMBL, NPASS
TAR_EXP_000730ENSG00000168830HTR1E3354BindingDB
TAR_EXP_000731ENSG00000179097HTR1F3355BindingDB
TAR_EXP_000324ENSG00000184845DRD11812NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565NPASS
TAR_EXP_000269ENSG00000197838CYP2A131553BindingDB, ChEMBL, NPASS
TAR_EXP_000265ENSG00000255974CYP2A61548BindingDB, ChEMBL, NPASS
TAR_EXP_000729ENSG00000179546HTR1D3352BindingDB, ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000202ENSG00000146399TAAR1134864BindingDB, ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL, NPASS
TAR_EXP_000733ENSG00000135914HTR2B3357BindingDB
TAR_EXP_000860ENSG00000152601MBNL14154NPASS
TAR_EXP_000896ENSG00000005381MPO4353BindingDB, ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_000251ENSG00000143387CTSK1513BindingDB, ChEMBL, NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000846ENSG00000100299ARSA410NPASS
TAR_EXP_000766ENSG00000131203IDO13620BindingDB, ChEMBL, NPASS
TAR_EXP_000734ENSG00000147246HTR2C3358BindingDB, ChEMBL, NPASS
TAR_EXP_000738ENSG00000158748HTR63362BindingDB, ChEMBL, NPASS
TAR_EXP_000739ENSG00000148680HTR73363BindingDB, ChEMBL, NPASS
TAR_EXP_000968ENSG00000109320NFKB14790ChEMBL, NPASS