IMPPAT Phytochemical information: 
Epistephanine
Epistephanine
Summary

SMILES: COc1cc2CCN([C@H]3c2cc1Oc1c2C(=NCCc2cc(c1OC)OC)Cc1ccc(Oc2cc(C3)ccc2OC)cc1)C
InChI: InChI=1S/C37H38N2O6/c1-39-15-13-24-19-31(41-3)33-21-27(24)29(39)17-23-8-11-30(40-2)32(18-23)44-26-9-6-22(7-10-26)16-28-35-25(12-14-38-28)20-34(42-4)36(43-5)37(35)45-33/h6-11,18-21,29H,12-17H2,1-5H3/t29-/m1/s1
InChIKey: ZKHQJCUUEXSGCM-GDLZYMKVSA-N
DeepSMILES: COcccCCN[C@H]c6cc%10OccC=NCCc6ccc%10OC)))OC))))))))CccccOcccC%18)ccc6OC)))))))))cc6)))))))))))))))C
Scaffold Graph/Node/Bond level: c1cc2cc(c1)Oc1ccc(cc1)CC1=NCCc3cccc(c31)Oc1ccc3c(c1)C(C2)NCC3
Scaffold Graph/Node level: C1CC2CC(C1)OC1CCC(CC1)CC1NCCC3CCCC(OC4CCC5CCNC(C2)C5C4)C31
Scaffold Graph level: C1CC2CC3CCC(CC3)CC3CCCC4CCCC(CC5CCC6CCCC(CC(C1)C2)C6C5)C43
Functional groups: cOc; cOC; CN(C)C; cC(=NC)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|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
epistephanine, Epistephanine
External chemical identifiers:
CID:CID_5317122; ChEMBL:CHEMBL2063775; ZINC:ZINC000070454481
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Epistephanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 606.72
Log P RDKit 6.98
Topological polar surface area (Å2) RDKit 70.98
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.03
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 25
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 8
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 8
Epistephanine
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 0.248317
Epistephanine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -5.66
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