IMPPAT Phytochemical information: 
Harmine, hydrochloride, dihydrate
Harmine, hydrochloride, dihydrate
Summary

SMILES: COc1ccc2-c3c([NH2+]c2c1)c(C)ncc3.[Cl-]
InChI: InChI=1S/C13H12N2O.ClH/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13;/h3-7,15H,1-2H3;1H
InChIKey: VNPLYCKZIUTKJM-UHFFFAOYSA-N
DeepSMILES: COcccc-cc[NH2+]c5c9)))cC)ncc6.[Cl-]
Scaffold Graph/Node/Bond level: c1ccc2c(c1)[NH2+]c1cnccc1-2
Scaffold Graph/Node level: C1CCC2C(C1)NC1CNCCC12
Scaffold Graph level: C1CCC2C(C1)CC1CCCCC12
Functional groups: [Cl-]; cOC; c[NH2+]c; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Harmala alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Nicotinic acid alkaloids
Synonymous chemical names:
7-methoxy-1-methyl-beta-carboline
External chemical identifiers:
CID:22382; ChEMBL:CHEMBL1593867; FDASRS:T89I34ODAA; SureChEMBL:SCHEMBL1469013
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Harmine, hydrochloride, dihydrate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 248.71
Log P RDKit -1.09
Topological polar surface area (Å2) RDKit 38.73
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 17
Number of heteroatoms RDKit 4
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 11
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3
Harmine, hydrochloride, dihydrate
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 1
Ghose filter RDKit Failed
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 0.5562
Harmine, hydrochloride, dihydrate
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.59
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
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
Harmine, hydrochloride, dihydrate
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000237612ABCG2800
ENSP00000262735PPARA800
ENSP00000269305TP53800
ENSP00000312789DYRK1B829
ENSP00000327850NFATC1786
ENSP00000340684MAOA977
ENSP00000342105DYRK2866
ENSP00000356076DYRK3708
ENSP00000369050CYP1A1700
ENSP00000381932DYRK1A996
ENSP00000394734CLK1798
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.