IMPPAT Phytochemical information: 
(+)-Isotylocrebrine

(+)-Isotylocrebrine
Summary

SMILES: COc1cc2c(cc1OC)c1CN3CCC[C@H]3Cc1c1c2c(OC)c(OC)cc1
InChI: InChI=1S/C24H27NO4/c1-26-20-8-7-15-16-10-14-6-5-9-25(14)13-19(16)17-11-21(27-2)22(28-3)12-18(17)23(15)24(20)29-4/h7-8,11-12,14H,5-6,9-10,13H2,1-4H3/t14-/m0/s1
InChIKey: ZRGRTHUWZSWRSQ-AWEZNQCLSA-N
DeepSMILES: COcccccc6OC))))cCNCCC[C@H]5Cc9cc%13cOC))cOC))cc6
Scaffold Graph/Node/Bond level: c1ccc2c(c1)c1c(c3ccccc32)CN2CCCC2C1
Scaffold Graph/Node level: C1CCC2C(C1)C1CCCCC1C1CN3CCCC3CC21
Scaffold Graph level: C1CC2CC3C4CCCCC4C4CCCCC4C3CC2C1
Functional groups: cOC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
ClassyFire Subclass: Phenanthroindolizidines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Indolizidine alkaloids
Synonymous chemical names:
(+)-isotylocrebrine
External chemical identifiers:
CID:CID_12304631; ChEMBL:CHEMBL520783; ZINC:ZINC000038796306
Chemical structure download


(+)-Isotylocrebrine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 393.48
Log P RDKit 4.55
Topological polar surface area (Å2) RDKit 40.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


(+)-Isotylocrebrine
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.61


(+)-Isotylocrebrine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.34
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes