IMPPAT Phytochemical information: 
Heterophyllisine
Heterophyllisine
Summary

SMILES: CO[C@H]1CC[C@@]2([C@@H]3[C@]41[C@H](N(C2)CC)[C@H](C3)[C@@]1([C@@H]2[C@H]4C[C@H](CC1)OC2=O)O)C
InChI: InChI=1S/C22H33NO4/c1-4-23-11-20(2)7-6-16(26-3)22-13-9-12-5-8-21(25,17(13)19(24)27-12)14(18(22)23)10-15(20)22/h12-18,25H,4-11H2,1-3H3/t12?,13-,14+,15-,16+,17-,18?,20+,21+,22-/m1/s1
InChIKey: FYWKVUJEFHOLFV-KHCXGHQWSA-N
DeepSMILES: CO[C@H]CC[C@@][C@@H][C@@]6[C@H]NC6)CC)))[C@H]C5)[C@@][C@@H][C@H]6C[C@H]CC7))OC6=O)))))))O))))))C
Scaffold Graph/Node/Bond level: O=C1OC2CCC3C4CC5C6CCCC5(C(C2)C13)C4NC6
Scaffold Graph/Node level: OC1OC2CCC3C4CC5C6CCCC5(C(C2)C13)C4NC6
Scaffold Graph level: CC1CC2CCC3C4CC5C6CCCC5(C4CC6)C(C2)C13
Functional groups: COC; CN(C)C; COC(=O)C; CO
Chemical classification

NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Terpenoid alkaloids
Synonymous chemical names:
heterophyllisine, Heterophyllisine
External chemical identifiers:
CID:CID_177507120
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Heterophyllisine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 375.51
Log P RDKit 2.21
Topological polar surface area (Å2) RDKit 59
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 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.95
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Heterophyllisine
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 0.750199
Heterophyllisine
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 -7.12
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 Yes