IMPPAT Phytochemical information: 
(1S)-7-hydroxy-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,15,17,19-heptaen-14-one
(1S)-7-hydroxy-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,15,17,19-heptaen-14-one
Summary

SMILES: Oc1ccc2c(c1)c1CCN3[C@@H](c1[nH]2)N(C)c1c(C3=O)cccc1
InChI: InChI=1S/C19H17N3O2/c1-21-16-5-3-2-4-13(16)19(24)22-9-8-12-14-10-11(23)6-7-15(14)20-17(12)18(21)22/h2-7,10,18,20,23H,8-9H2,1H3/t18-/m0/s1
InChIKey: XYSMNZWLVJYABK-SFHVURJKSA-N
DeepSMILES: Occcccc6)cCCN[C@@H]c6[nH]9))NC)ccC6=O))cccc6
Scaffold Graph/Node/Bond level: O=C1c2ccccc2NC2c3[nH]c4ccccc4c3CCN12
Scaffold Graph/Node level: OC1C2CCCCC2NC2C3NC4CCCCC4C3CCN12
Scaffold Graph level: CC1C2CCCCC2CC2C1CCC1C3CCCCC3CC12
Functional groups: cO; c[C@H]1N(C)ccC(=O)N1C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyridoindoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
NP Classifier Class: Benzodiazepine alkaloids
Synonymous chemical names:
Evodiamine, hydroxy, hydroxyevodiamine
External chemical identifiers:
CID:CID_71307457; ZINC:ZINC000087493235
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S)-7-hydroxy-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,15,17,19-heptaen-14-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 319.36
Log P RDKit 3.02
Topological polar surface area (Å2) RDKit 59.57
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5
(1S)-7-hydroxy-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,15,17,19-heptaen-14-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.67
(1S)-7-hydroxy-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,15,17,19-heptaen-14-one
ADME 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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.30
Number of PAINS structural alerts SwissADME 1
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 Yes
P-glycoprotein substrate SwissADME Yes