IMPPAT Phytochemical information: 
14-Hydroxyicajine
14-Hydroxyicajine
Summary

SMILES: CN1CCC23C(=O)CC4(C(=CCOC5C4C3N(c3c2cccc3)C(=O)C5)C1)O
InChI: InChI=1S/C22H24N2O4/c1-23-8-7-21-14-4-2-3-5-15(14)24-18(26)10-16-19(20(21)24)22(27,11-17(21)25)13(12-23)6-9-28-16/h2-6,16,19-20,27H,7-12H2,1H3
InChIKey: AHOSVLHVFRDGQF-UHFFFAOYSA-N
DeepSMILES: CNCCCC=O)CCC=CCOCC7C%11Ncc%14cccc6))))))C=O)C6)))))))))C9))O
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; CO
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:
14-hydroxyicajine
External chemical identifiers:
CID:CID_210990
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
14-Hydroxyicajine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 380.44
Log P RDKit 1.02
Topological polar surface area (Å2) RDKit 70.08
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
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 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
14-Hydroxyicajine
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 0.680967
14-Hydroxyicajine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -9.19
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes