IMPPAT Phytochemical information: 
dimethyl (2R,6R,13R,22S,23S,24S,35R,38R,39S)-13,24-diethyl-23,32-dihydroxy-30,31-dimethoxy-21-oxa-1,9,17,28-tetrazaundecacyclo[22.13.1.16,9.02,22.03,20.05,18.06,16.027,35.029,34.035,38.013,39]nonatriaconta-3,5(18),11,15,19,26,29,31,33-nonaene-15,26-dicarboxylate
dimethyl (2R,6R,13R,22S,23S,24S,35R,38R,39S)-13,24-diethyl-23,32-dihydroxy-30,31-dimethoxy-21-oxa-1,9,17,28-tetrazaundecacyclo[22.13.1.16,9.02,22.03,20.05,18.06,16.027,35.029,34.035,38.013,39]nonatriaconta-3,5(18),11,15,19,26,29,31,33-nonaene-15,26-dicarboxylate
Summary

SMILES: COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@@](C1)(CC)[C@H](O)[C@H]1Oc5c([C@H]1N2CC4)cc1c(c5)NC2=C(C[C@]4([C@H]5[C@@]12CCN5CC=C4)CC)C(=O)OC)cc(c(c3OC)OC)O
InChI: InChI=1S/C44H50N4O9/c1-7-41-10-9-13-47-14-11-43(39(41)47)24-16-21-28(18-26(24)45-34(43)22(19-41)37(51)55-5)57-33-30(21)48-15-12-44-25-17-27(49)31(53-3)32(54-4)29(25)46-35(44)23(38(52)56-6)20-42(8-2,36(33)50)40(44)48/h9-10,16-18,30,33,36,39-40,45-46,49-50H,7-8,11-15,19-20H2,1-6H3/t30-,33+,36-,39+,40+,41+,42-,43+,44+/m1/s1
InChIKey: XVLKCTCGGIJHCK-BFENJZFZSA-N
DeepSMILES: COC=O)C=CNcc[C@]5[C@@H][C@@]C9)CC))[C@H]O)[C@H]Occ[C@H]5N9CC%12))))cccc6)NC=CC[C@][C@H][C@@]96CCN5CC=C9))))))))CC))))C=O)OC)))))))))))))))))cccc6OC)))OC)))O
Scaffold Graph/Node/Bond level: C1=CC2CC=C3Nc4cc5c(cc4C34CCN(C1)C24)C1C(CC2CC=C3Nc4ccccc4C34CCN1C24)O5
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC3CC4OC5CC6NC7CCC8CCCN9CCC7(C6CC5C4N4CCC12C34)C89
Scaffold Graph level: C1CCC2C(C1)CC1CCC3CC4CC5CC6CC7CCC8CCCC9CCC7(C6CC5C4C4CCC12C34)C89
Functional groups: cNC(=C(C(=O)OC)C)C; CO; cOC; CN(C)C; CC=CC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aspidospermatan-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
conophyllidine
External chemical identifiers:
CID:CID_16663648; ChEMBL:CHEMBL220132
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
dimethyl (2R,6R,13R,22S,23S,24S,35R,38R,39S)-13,24-diethyl-23,32-dihydroxy-30,31-dimethoxy-21-oxa-1,9,17,28-tetrazaundecacyclo[22.13.1.16,9.02,22.03,20.05,18.06,16.027,35.029,34.035,38.013,39]nonatriaconta-3,5(18),11,15,19,26,29,31,33-nonaene-15,26-dicarboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 778.9
Log P RDKit 4.79
Topological polar surface area (Å2) RDKit 151.29
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 44
Number of heavy atoms RDKit 57
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 7
Number of aliphatic rings RDKit 9
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 11
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 11
dimethyl (2R,6R,13R,22S,23S,24S,35R,38R,39S)-13,24-diethyl-23,32-dihydroxy-30,31-dimethoxy-21-oxa-1,9,17,28-tetrazaundecacyclo[22.13.1.16,9.02,22.03,20.05,18.06,16.027,35.029,34.035,38.013,39]nonatriaconta-3,5(18),11,15,19,26,29,31,33-nonaene-15,26-dicarboxylate
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 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
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 0.18
dimethyl (2R,6R,13R,22S,23S,24S,35R,38R,39S)-13,24-diethyl-23,32-dihydroxy-30,31-dimethoxy-21-oxa-1,9,17,28-tetrazaundecacyclo[22.13.1.16,9.02,22.03,20.05,18.06,16.027,35.029,34.035,38.013,39]nonatriaconta-3,5(18),11,15,19,26,29,31,33-nonaene-15,26-dicarboxylate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.83
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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