IMPPAT Phytochemical information: 
Aphelandrine
Aphelandrine
Summary

SMILES: Oc1ccc(cc1)[C@H]1Oc2c3[C@@H]1C(=O)N1CCCCNCCCN[C@H](c(c3)cc2)CC(=O)NCCC1
InChI: InChI=1S/C28H36N4O4/c33-21-8-5-19(6-9-21)27-26-22-17-20(7-10-24(22)36-27)23-18-25(34)31-14-4-16-32(28(26)35)15-2-1-11-29-12-3-13-30-23/h5-10,17,23,26-27,29-30,33H,1-4,11-16,18H2,(H,31,34)/t23-,26-,27+/m0/s1
InChIKey: ASCIWXOCZAWSON-MSLLRLGPSA-N
DeepSMILES: Occcccc6))[C@H]Occ[C@@H]5C=O)NCCCCNCCCN[C@H]cc%16)cc%18)))CC=O)NCCC%17
Scaffold Graph/Node/Bond level: O=C1CC2NCCCNCCCCN(CCCN1)C(=O)C1c3cc2ccc3OC1c1ccccc1
Scaffold Graph/Node level: OC1CC2NCCCNCCCCN(CCCN1)C(O)C1C3CC2CCC3OC1C1CCCCC1
Scaffold Graph level: CC1CCCCC2CCCCCCCCCC(C1)C1CCC3CC(C4CCCCC4)C(C2C)C3C1
Functional groups: cO; CNC(=O)C; cOC; CN(C)C(=O)C; CNC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: 2-arylbenzofuran flavonoids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Polyamines
Synonymous chemical names:
aphelandrine
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Aphelandrine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 492.62
Log P RDKit 2.75
Topological polar surface area (Å2) RDKit 102.93
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5
Aphelandrine
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 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.49
Aphelandrine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.26
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