IMPPAT Phytochemical information: 
Vobtusine
Vobtusine
Summary

SMILES: COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@@]5(C1)CCO[C@H]5[C@]1(CN2CC4)C[C@@H]2C[C@]45CCO[C@H]4CCN4[C@@H]5[C@@]5([C@]2(N(C1)c1c(OC)cccc51)O)CC4)cccc3
InChI: InChI=1S/C43H50N4O6/c1-50-30-9-5-7-28-32(30)47-24-38(20-25-21-39-13-18-52-31(39)10-15-45-17-12-42(28,36(39)45)43(25,47)49)23-46-16-11-41-27-6-3-4-8-29(27)44-33(41)26(34(48)51-2)22-40(35(41)46)14-19-53-37(38)40/h3-9,25,31,35-37,44,49H,10-24H2,1-2H3/t25-,31+,35+,36+,37+,38+,39-,40+,41+,42-,43-/m1/s1
InChIKey: IIMPGJMHQMBXKL-OPDPKHDKSA-N
DeepSMILES: COC=O)C=CNcc[C@]5[C@@H][C@@]C9)CCO[C@H]5[C@]CN9CC%12))))C[C@@H]C[C@]CCO[C@H]5CCN[C@@H]9[C@@][C@]%13NC%17)ccOC))cccc96)))))))O))CC5)))))))))))))))))))))))cccc6
Scaffold Graph/Node/Bond level: C1=C2Nc3ccccc3C23CCN2CC4(CC5CC67CCOC6CCN6CCC8(c9ccccc9N(C4)C58)C67)C4OCCC4(C1)C23
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC34CCOC3C3(CC5CC67CCOC6CCN6CCC8(C9CCCCC9N(C3)C58)C67)CN3CCC12C34
Scaffold Graph level: C1CCC2C(C1)CC1CCC34CCCC3C3(CC5CC67CCCC6CCC6CCC8(C9CCCCC9C(C3)C58)C67)CC3CCC12C34
Functional groups: CN(C)C; cNC(=C(C(=O)OC)C)C; cN(C)[C@@](O)(C)C; cOC; COC
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|Aspidosperma-Iboga hybrid type (Vinca alkaloids)
Synonymous chemical names:
vobtusine, vobtusin, Vobtusine
External chemical identifiers:
CID:CID_73534; ChEBI:CHEBI:10016; ZINC:ZINC000087496265; MolPort-006-123-032
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vobtusine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 718.9
Log P RDKit 4.16
Topological polar surface area (Å2) RDKit 95.97
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 43
Number of heavy atoms RDKit 53
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 28
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 9
Number of aliphatic rings RDKit 11
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 13
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 7
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 13
Vobtusine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
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 0.44139
Vobtusine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.39
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