IMPPAT Phytochemical information: 
[(13Z,14S,16S)-13-ethylidene-11-methyl-1-aza-11-azoniapentacyclo[12.3.1.02,7.08,17.011,16]octadeca-2,4,6,8(17)-tetraen-18-yl]methanol
[(13Z,14S,16S)-13-ethylidene-11-methyl-1-aza-11-azoniapentacyclo[12.3.1.02,7.08,17.011,16]octadeca-2,4,6,8(17)-tetraen-18-yl]methanol
Summary

SMILES: OCC1[C@H]2C[C@H]3c4n1c1ccccc1c4CC[N+]3(C/C/2=C\C)C
InChI: InChI=1S/C20H25N2O/c1-3-13-11-22(2)9-8-15-14-6-4-5-7-17(14)21-18(12-23)16(13)10-19(22)20(15)21/h3-7,16,18-19,23H,8-12H2,1-2H3/q+1/b13-3+/t16-,18?,19-,22?/m0/s1
InChIKey: HFLUPWJGJPYITM-ILIQZIPWSA-N
DeepSMILES: OCC[C@H]C[C@H]cn6cccccc6c9CC[N+]%13C/C/%17=C\C))))C
Scaffold Graph/Node/Bond level: C=C1C[NH+]2CCc3c4n(c5ccccc35)CC1CC42
Scaffold Graph/Node level: CC1CN2CCC3C4CCCCC4N4CC1CC2C34
Scaffold Graph level: CC1CC2CCC3C4CCCCC4C4CC1CC2C34
Functional groups: CO; cn(c)C; C[N+](C)(C)C; C/C=C(\C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Pleiocarpaman alkaloids
Synonymous chemical names:
c-mavacurine
External chemical identifiers:
CID:CID_101289829
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(13Z,14S,16S)-13-ethylidene-11-methyl-1-aza-11-azoniapentacyclo[12.3.1.02,7.08,17.011,16]octadeca-2,4,6,8(17)-tetraen-18-yl]methanol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 309.43
Log P RDKit 3.2
Topological polar surface area (Å2) RDKit 25.16
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
[(13Z,14S,16S)-13-ethylidene-11-methyl-1-aza-11-azoniapentacyclo[12.3.1.02,7.08,17.011,16]octadeca-2,4,6,8(17)-tetraen-18-yl]methanol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.63
[(13Z,14S,16S)-13-ethylidene-11-methyl-1-aza-11-azoniapentacyclo[12.3.1.02,7.08,17.011,16]octadeca-2,4,6,8(17)-tetraen-18-yl]methanol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.98
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes