IMPPAT Phytochemical information: 
N,N-Dimethyl-5-methoxytryptamine
N,N-Dimethyl-5-methoxytryptamine
Summary

SMILES: COc1ccc2c(c1)c(CCN(C)C)c[nH]2
InChI: InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3
InChIKey: ZSTKHSQDNIGFLM-UHFFFAOYSA-N
DeepSMILES: COcccccc6)cCCNC)C))))c[nH]5
Scaffold Graph/Node/Bond level: c1ccc2[nH]ccc2c1
Scaffold Graph/Node level: C1CCC2NCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: cOC; CN(C)C; 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:
n,n-dimethyl-5-methoxytryptamine, 5-methoxy-n,n-dimethyltryptamin, 5-methoxy-n,n-dimethyltryptamine
External chemical identifiers:
CID:CID_1832; ChEMBL:CHEMBL7257; ChEBI:CHEBI:2086; ZINC:ZINC000000057152; FDASRS:X0MKX3GWU9; SureChEMBL:SCHEMBL132733
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
N,N-Dimethyl-5-methoxytryptamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 218.3
Log P RDKit 2.28
Topological polar surface area (Å2) RDKit 28.26
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 3
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 5
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 4
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
N,N-Dimethyl-5-methoxytryptamine
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 0.852417
N,N-Dimethyl-5-methoxytryptamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.65
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
N,N-Dimethyl-5-methoxytryptamine
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_001518ENSG00000103546SLC6A26530BindingDB
TAR_EXP_001002ENSG00000082556OPRK14986BindingDB
TAR_EXP_000915ENSG00000134640MTNR1B4544BindingDB, ChEMBL, NPASS
TAR_EXP_000249ENSG00000274286ADRA2B151BindingDB
TAR_EXP_000739ENSG00000148680HTR73363BindingDB, ChEMBL, NPASS
TAR_EXP_000243ENSG00000150594ADRA2A150BindingDB
TAR_EXP_001519ENSG00000142319SLC6A36531BindingDB
TAR_EXP_000255ENSG00000184160ADRA2C152BindingDB
TAR_EXP_000258ENSG00000043591ADRB1153BindingDB
TAR_EXP_000914ENSG00000168412MTNR1A4543BindingDB, ChEMBL, NPASS
TAR_EXP_001520ENSG00000108576SLC6A46532BindingDB
TAR_EXP_000187ENSG00000118432CNR11268BindingDB
TAR_EXP_000236ENSG00000170214ADRA1B147BindingDB
TAR_EXP_000206ENSG00000157184CPT21376BindingDB
TAR_EXP_001700ENSG00000153956CACNA2D1781BindingDB
TAR_EXP_001880ENSG00000149305HTR3B9177ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134BindingDB
TAR_EXP_000188ENSG00000188822CNR21269BindingDB
TAR_EXP_000137ENSG00000184984CHRM51133BindingDB
TAR_EXP_000134ENSG00000180720CHRM41132BindingDB
TAR_EXP_000133ENSG00000133019CHRM31131BindingDB
TAR_EXP_000130ENSG00000181072CHRM21129BindingDB
TAR_EXP_000127ENSG00000168539CHRM11128BindingDB
TAR_EXP_000116ENSG00000010322NISCH11188BindingDB
TAR_EXP_000041ENSG00000147955SIGMAR110280BindingDB
TAR_EXP_000239ENSG00000120907ADRA1A148BindingDB
TAR_EXP_000261ENSG00000169252ADRB2154BindingDB
TAR_EXP_000738ENSG00000158748HTR63362BindingDB, ChEMBL, NPASS
TAR_EXP_000736ENSG00000164270HTR43360ChEMBL
TAR_EXP_000730ENSG00000168830HTR1E3354BindingDB, ChEMBL
TAR_EXP_000729ENSG00000179546HTR1D3352BindingDB, ChEMBL, NPASS
TAR_EXP_000728ENSG00000135312HTR1B3351BindingDB, ChEMBL, NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350BindingDB, ChEMBL, NPASS
TAR_EXP_000704ENSG00000113749HRH23274BindingDB
TAR_EXP_000624ENSG00000186038HTR3E285242ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812BindingDB
TAR_EXP_000559ENSG00000185513L3MBTL126013NPASS
TAR_EXP_000521ENSG00000022355GABRA12554BindingDB
TAR_EXP_000362ENSG00000186090HTR3D200909ChEMBL
TAR_EXP_000737ENSG00000157219HTR5A3361BindingDB, ChEMBL
TAR_EXP_000338ENSG00000213694S1PR31903BindingDB
TAR_EXP_000328ENSG00000169676DRD51816BindingDB
TAR_EXP_000327ENSG00000069696DRD41815BindingDB
TAR_EXP_000325ENSG00000149295DRD21813BindingDB
TAR_EXP_000731ENSG00000179097HTR1F3355BindingDB, ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356BindingDB, ChEMBL, NPASS
TAR_EXP_000600ENSG00000109084TMEM9727346BindingDB
TAR_EXP_000735ENSG00000166736HTR3A3359BindingDB, ChEMBL
TAR_EXP_000308ENSG00000178084HTR3C170572ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000734ENSG00000147246HTR2C3358BindingDB, ChEMBL, NPASS
TAR_EXP_000733ENSG00000135914HTR2B3357BindingDB, ChEMBL, NPASS