IMPPAT Phytochemical information: 
Thalpindione
Thalpindione
Summary

SMILES: COc1cc2CCN([C@@H]3c2c(c1O)Oc1c2CCN([C@H](c2cc(c1OC)OC)Cc1ccc(Oc2cc(C3)ccc2OC)cc1)C)C=O
InChI: InChI=1S/C38H40N2O8/c1-39-14-13-26-27-20-33(45-4)37(46-5)36(26)48-38-34-24(19-32(44-3)35(38)42)12-15-40(21-41)29(34)17-23-8-11-30(43-2)31(18-23)47-25-9-6-22(7-10-25)16-28(27)39/h6-11,18-21,28-29,42H,12-17H2,1-5H3/t28-,29-/m0/s1
InChIKey: CRIBSGNDLYNZDL-VMPREFPWSA-N
DeepSMILES: COcccCCN[C@@H]c6cc%10O))OccCCN[C@H]c6ccc%10OC)))OC)))))CccccOcccC%20)ccc6OC)))))))))cc6))))))))C))))))))))C=O
Scaffold Graph/Node/Bond level: c1cc2cc(c1)Oc1ccc(cc1)CC1NCCc3c(cccc31)Oc1cccc3c1C(C2)NCC3
Scaffold Graph/Node level: C1CC2CC(C1)OC1CCC(CC1)CC1NCCC3C(CCCC13)OC1CCCC3CCNC(C2)C31
Scaffold Graph level: C1CC2CC3CCC(CC3)CC3CCCC4C(CCCC34)CC3CCCC4CCCC(CC(C1)C2)C43
Functional groups: cOC; cOc; CN(C=O)C; cO; 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|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
Thalpindione
External chemical identifiers:
CID:CID_156761; ZINC:ZINC000085985209
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Thalpindione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 652.74
Log P RDKit 6.39
Topological polar surface area (Å2) RDKit 99.16
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 38
Number of heavy atoms RDKit 48
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 25
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.34
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
Thalpindione
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.25
Thalpindione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly 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 -6.18
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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