IMPPAT Phytochemical information: 
(10S,22R,23R,24S)-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14,16,18-tetraene-12,20-dione
(10S,22R,23R,24S)-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14,16,18-tetraene-12,20-dione
Summary

SMILES: CN1CC[C@]23C(=O)C[C@H]4C(=CCO[C@@H]5[C@H]4[C@@H]3N(c3c2cccc3)C(=O)C5)C1
InChI: InChI=1S/C22H24N2O3/c1-23-8-7-22-15-4-2-3-5-16(15)24-19(26)11-17-20(21(22)24)14(10-18(22)25)13(12-23)6-9-27-17/h2-6,14,17,20-21H,7-12H2,1H3/t14-,17-,20-,21-,22+/m0/s1
InChIKey: RNZRHJNFQWMXHB-ZXXLSYNSSA-N
DeepSMILES: CNCC[C@@]C=O)C[C@H]C=CCO[C@@H][C@H]7[C@@H]%11Ncc%14cccc6))))))C=O)C6)))))))))C9
Scaffold Graph/Node/Bond level: O=C1CC2OCC=C3CNCCC45C(=O)CC3C2C4N1c1ccccc15
Scaffold Graph/Node level: OC1CC2OCCC3CNCCC45C(O)CC3C2C4N1C1CCCCC15
Scaffold Graph level: CC1CC2CCCC3CCCCC45C(C)CC3C2C4C1C1CCCCC15
Functional groups: CN(C)C; CC(=O)C; CC=C(C)C; COC; cN(C)C(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Carbazoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma-Iboga hybrid type (Vinca alkaloids)
Synonymous chemical names:
(10S,22R,23R,24S)-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14,16,18-tetraene-12,20-dione, icajine
External chemical identifiers:
CID:CID_3083907; ChEMBL:CHEMBL2164624; ChEBI:CHEBI:132668; ZINC:ZINC000001716562; SureChEMBL:SCHEMBL1445138
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(10S,22R,23R,24S)-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14,16,18-tetraene-12,20-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 364.45
Log P RDKit 1.91
Topological polar surface area (Å2) RDKit 49.85
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
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 10
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
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 7
(10S,22R,23R,24S)-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14,16,18-tetraene-12,20-dione
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 0.66
(10S,22R,23R,24S)-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14,16,18-tetraene-12,20-dione
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.32
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 No