IMPPAT Phytochemical information: 
methyl (1R,1'R,7'S,11'R,12R,13'R,16S,17S,22R,24'R,25'S)-24'-hydroxy-19'-methoxy-9'-oxospiro[15-oxa-8,19-diazahexacyclo[10.9.1.01,9.02,7.012,16.019,22]docosa-2,4,6,9-tetraene-17,15'-8-oxa-4,17-diazahep
methyl (1R,1'R,7'S,11'R,12R,13'R,16S,17S,22R,24'R,25'S)-24'-hydroxy-19'-methoxy-9'-oxospiro[15-oxa-8,19-diazahexacyclo[10.9.1.01,9.02,7.012,16.019,22]docosa-2,4,6,9-tetraene-17,15'-8-oxa-4,17-diazahep
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@]45CC(=O)O[C@H]4CCN4[C@@H]5[C@@]5([C@]2(N(C1)c1c(OC)cccc51)O)CC4)cccc3
InChI: InChI=1S/C43H48N4O7/c1-51-29-9-5-7-27-32(29)47-23-38(18-24-19-40-21-31(48)54-30(40)10-14-45-16-12-42(27,36(40)45)43(24,47)50)22-46-15-11-41-26-6-3-4-8-28(26)44-33(41)25(34(49)52-2)20-39(35(41)46)13-17-53-37(38)39/h3-9,24,30,35-37,44,50H,10-23H2,1-2H3/t24-,30+,35+,36+,37+,38+,39+,40+,41+,42-,43-/m1/s1
InChIKey: RWRDIJCXMDTYOZ-ODWBGNIOSA-N
DeepSMILES: COC=O)C=CNcc[C@]5[C@@H][C@@]C9)CCO[C@H]5[C@]CN9CC%12))))C[C@@H]C[C@]CC=O)O[C@H]5CCN[C@@H]9[C@@][C@]%13NC%17)ccOC))cccc96)))))))O))CC5)))))))))))))))))))))))cccc6
Scaffold Graph/Node/Bond level: O=C1CC23CC4CC5(CN6CCC78C(=CCC9(CCOC59)C67)Nc5ccccc58)CN5c6ccccc6C6(CCN(CCC2O1)C36)C45
Scaffold Graph/Node level: OC1CC23CC4CC5(CN6CCC78C(CCC9(CCOC59)C67)NC5CCCCC58)CN5C6CCCCC6C6(CCN(CCC2O1)C36)C45
Scaffold Graph level: CC1CC2CCC3CCC45C6CCCCC6C6CC7(CC(CC2(C1)C34)C65)CC1CCC23C(CCC4(CCCC74)C12)CC1CCCCC13
Functional groups: CC(=O)OC; 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:
vobtusine lactone
External chemical identifiers:
CID:21598364; ZINC:ZINC000255263670
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl (1R,1'R,7'S,11'R,12R,13'R,16S,17S,22R,24'R,25'S)-24'-hydroxy-19'-methoxy-9'-oxospiro[15-oxa-8,19-diazahexacyclo[10.9.1.01,9.02,7.012,16.019,22]docosa-2,4,6,9-tetraene-17,15'-8-oxa-4,17-diazahep
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 732.88
Log P RDKit 3.69
Topological polar surface area (Å2) RDKit 113.04
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 43
Number of heavy atoms RDKit 54
Number of heteroatoms RDKit 11
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 16
Number of sp3 hybridized carbon atoms RDKit 27
Shape complexity RDKit 0.63
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
methyl (1R,1'R,7'S,11'R,12R,13'R,16S,17S,22R,24'R,25'S)-24'-hydroxy-19'-methoxy-9'-oxospiro[15-oxa-8,19-diazahexacyclo[10.9.1.01,9.02,7.012,16.019,22]docosa-2,4,6,9-tetraene-17,15'-8-oxa-4,17-diazahep
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 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 0.4415
methyl (1R,1'R,7'S,11'R,12R,13'R,16S,17S,22R,24'R,25'S)-24'-hydroxy-19'-methoxy-9'-oxospiro[15-oxa-8,19-diazahexacyclo[10.9.1.01,9.02,7.012,16.019,22]docosa-2,4,6,9-tetraene-17,15'-8-oxa-4,17-diazahep
ADMET 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 High
Log Kp (Skin permeation, cm/s) SwissADME -8.19
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