IMPPAT Phytochemical information: 
Isovoacristine

Isovoacristine
Summary

SMILES: COC(=O)[C@@]12C[C@H]3CN([C@H]1[C@H](C3)[C@@H](O)C)CCc1c2[nH]c2c1ccc(c2)OC
InChI: InChI=1S/C22H28N2O4/c1-12(25)17-8-13-10-22(21(26)28-3)19-16(6-7-24(11-13)20(17)22)15-5-4-14(27-2)9-18(15)23-19/h4-5,9,12-13,17,20,23,25H,6-8,10-11H2,1-3H3/t12-,13-,17+,20-,22+/m0/s1
InChIKey: XGWIRMWTCWJZPG-ZHBRIVESSA-N
DeepSMILES: COC=O)[C@@]C[C@H]CN[C@H]6[C@H]C6)[C@@H]O)C))))CCcc9[nH]cc5cccc6)OC
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2CCC1N(CC3)C2
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCN2CC3CCC2C1C3
Scaffold Graph level: C1CCC2C(C1)CC1C2CCC2CC3CCC2C1C3
Functional groups: COC(C)=O; CN(C)C; CO; c[nH]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:
Isovoacristine, isovoacristine
External chemical identifiers:
CID:CID_12304498; ChEMBL:CHEMBL360973; ZINC:ZINC000101354151
Chemical structure download


Isovoacristine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 384.48
Log P RDKit 2.23
Topological polar surface area (Å2) RDKit 74.79
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.59
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Isovoacristine
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 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 0.794167


Isovoacristine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.03
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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