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; COC; cN(C)[C@](C)(C)O; cNC(C)=C(C)C(=O)OC; 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:
vobtusin, vobtusine
External chemical identifiers:
CID:73534; 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 0.4414
Vobtusine
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.46
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
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