IMPPAT Phytochemical information: 
N-Methoxyanhydrovobasinediol
N-Methoxyanhydrovobasinediol
Summary

SMILES: C/C=C/1\CN(C)[C@@H]2C3[C@@H]1C[C@H](OC3)c1c(C2)c2c(n1OC)cccc2
InChI: InChI=1S/C21H26N2O2/c1-4-13-11-22(2)19-9-16-14-7-5-6-8-18(14)23(24-3)21(16)20-10-15(13)17(19)12-25-20/h4-8,15,17,19-20H,9-12H2,1-3H3/b13-4+/t15-,17?,19+,20?/m1/s1
InChIKey: WZEYGSAJRPIRJA-BATDSJRDSA-N
DeepSMILES: C/C=C\CNC)[C@@H]C[C@@H]\6C[C@H]OC6))ccC8)ccn5OC)))cccc6
Scaffold Graph/Node/Bond level: C=C1CNC2Cc3c([nH]c4ccccc34)C3CC1C2CO3
Scaffold Graph/Node level: CC1CNC2CC3C4CCCCC4NC3C3CC1C2CO3
Scaffold Graph level: CC1CCC2CC3C4CCCCC4CC3C3CCC2C1C3
Functional groups: C/C=C(\C)C; CN(C)C; COC; cn(OC)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Vobasan alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
n-methoxyanhydrovobasinediol (n-methoxytaberpsychine)
External chemical identifiers:
CID:CID_102004539; MolPort-039-338-216
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
N-Methoxyanhydrovobasinediol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 338.45
Log P RDKit 3.21
Topological polar surface area (Å2) RDKit 26.63
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
N-Methoxyanhydrovobasinediol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.747186
N-Methoxyanhydrovobasinediol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.25
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No