IMPPAT Phytochemical information: 
Isotrilobine

Isotrilobine
Summary

SMILES: COc1ccc2cc1Oc1ccc(cc1)C[C@@H]1N(C)CCc3c1c1Oc4cc5[C@H](C2)N(C)CCc5cc4Oc1c(c3)OC
InChI: InChI=1S/C36H36N2O5/c1-37-13-11-23-18-31-32-20-26(23)27(37)16-22-7-10-29(39-3)30(17-22)41-25-8-5-21(6-9-25)15-28-34-24(12-14-38(28)2)19-33(40-4)35(42-31)36(34)43-32/h5-10,17-20,27-28H,11-16H2,1-4H3/t27-,28-/m0/s1
InChIKey: SVMNNRZZJAFEJM-NSOVKSMOSA-N
DeepSMILES: COcccccc6Occcccc6))C[C@@H]NC)CCcc6cOccc[C@H]C%22)NC)CCc6cc%10Oc%14cc%18)OC
Scaffold Graph/Node/Bond level: c1cc2cc(c1)Oc1ccc(cc1)CC1NCCc3ccc4c(c31)Oc1cc3c(cc1O4)CCNC3C2
Scaffold Graph/Node level: C1CC2CC(C1)OC1CCC(CC1)CC1NCCC3CCC4OC5CC6CCNC(C2)C6CC5OC4C31
Scaffold Graph level: C1CC2CC3CCC(CC3)CC3CCCC4CCC5CC6CC7CCCC(CC(C1)C2)C7CC6CC5C43
Functional groups: cOC; cOc; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
isotrilobine
External chemical identifiers:
CID:CID_12310578; ChEMBL:CHEMBL503241; ZINC:ZINC000042803773; FDASRS:WIB21F188O; SureChEMBL:SCHEMBL2996999
Chemical structure download


Isotrilobine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 576.69
Log P RDKit 7.25
Topological polar surface area (Å2) RDKit 52.63
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 9
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 9


Isotrilobine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.219415


Isotrilobine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.32
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No