IMPPAT Phytochemical information: 
Methyl 10-hydroxy-17-(1-hydroxyethyl)-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2,4(9),5,7-tetraene-1-carboxylate
Methyl 10-hydroxy-17-(1-hydroxyethyl)-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2,4(9),5,7-tetraene-1-carboxylate
Summary

SMILES: COC(=O)C12CC3CN(C1C(C3)C(O)C)CCC1(C2=Nc2c1cc(cc2)OC)O
InChI: InChI=1S/C22H28N2O5/c1-12(25)15-8-13-10-21(20(26)29-3)18(15)24(11-13)7-6-22(27)16-9-14(28-2)4-5-17(16)23-19(21)22/h4-5,9,12-13,15,18,25,27H,6-8,10-11H2,1-3H3
InChIKey: MMANMJCGIGNJGH-UHFFFAOYSA-N
DeepSMILES: COC=O)CCCCNC6CC6)CO)C))))CCCC9=Ncc5cccc6))OC))))))))O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)N=C1C2CCN2CC3CCC2C1C3
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCN2CC3CCC2C1C3
Scaffold Graph level: C1CCC2C(C1)CC1C2CCC2CC3CCC2C1C3
Functional groups: COC(C)=O; CN(C)C; CO; cN=C(C)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Ibogan-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Iboga type
Synonymous chemical names:
Voacristine hydroxyindolenine, voacristine hydroxyindolenine, voacristinehydroxyindolenine
External chemical identifiers:
CID:CID_634039
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Methyl 10-hydroxy-17-(1-hydroxyethyl)-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2,4(9),5,7-tetraene-1-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 400.48
Log P RDKit 1.62
Topological polar surface area (Å2) RDKit 91.59
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.64
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Methyl 10-hydroxy-17-(1-hydroxyethyl)-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2,4(9),5,7-tetraene-1-carboxylate
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 Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.75
Methyl 10-hydroxy-17-(1-hydroxyethyl)-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2,4(9),5,7-tetraene-1-carboxylate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.87
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes