IMPPAT Phytochemical information: 
(1S,13S,14Z,19S,21S)-14-(2-hydroxyethylidene)-4,5-dimethoxy-16-oxido-8-aza-16-azoniahexacyclo[11.5.2.11,8.02,7.016,19.012,21]henicosa-2,4,6,11-tetraen-9-one
(1S,13S,14Z,19S,21S)-14-(2-hydroxyethylidene)-4,5-dimethoxy-16-oxido-8-aza-16-azoniahexacyclo[11.5.2.11,8.02,7.016,19.012,21]henicosa-2,4,6,11-tetraen-9-one
Summary

SMILES: OC/C=C\1/C[N+]2([O-])CC[C@@]34C2C[C@@H]1C1=CCC(=O)N([C@H]31)c1c4cc(c(c1)OC)OC
InChI: InChI=1S/C23H26N2O5/c1-29-18-10-16-17(11-19(18)30-2)24-21(27)4-3-14-15-9-20-23(16,22(14)24)6-7-25(20,28)12-13(15)5-8-26/h3,5,10-11,15,20,22,26H,4,6-9,12H2,1-2H3/b13-5-/t15-,20?,22-,23+,25?/m0/s1
InChIKey: ICEFLCNOUJCINW-DLOVHLCKSA-N
DeepSMILES: OC/C=C/C[N+][O-])CC[C@@]C5C[C@@H]/9C=CCC=O)N[C@H]%106)cc%11cccc6)OC)))OC
Scaffold Graph/Node/Bond level: C=C1C[NH+]2CCC34c5ccccc5N5C(=O)CC=C(C1CC23)C54
Scaffold Graph/Node level: CC1CN2CCC34C5CCCCC5N5C(O)CCC(C1CC23)C54
Scaffold Graph level: CC1CC2CCC34C2CC1C1CCC(C)C(C2CCCCC23)C14
Functional groups: CO; C/C=C(/C)C; C[N+]([O-])(C)C; CC=C(C)C; cN(C)C(=O)C; cOC
Chemical classification
Synonymous chemical names:
Isobrucine N-oxide, isobrucine n-oxide, isobrucine-n-oxide, (1S,13S,14Z,19S,21S)-14-(2-hydroxyethylidene)-4,5-dimethoxy-16-oxido-8-aza-16-azoniahexacyclo[11.5.2.11,8.02,7.016,19.012,21]henicosa-2,4,6,11-tetraen-9-one
External chemical identifiers:
CID:CID_124079392
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,13S,14Z,19S,21S)-14-(2-hydroxyethylidene)-4,5-dimethoxy-16-oxido-8-aza-16-azoniahexacyclo[11.5.2.11,8.02,7.016,19.012,21]henicosa-2,4,6,11-tetraen-9-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 410.47
Log P RDKit 2.03
Topological polar surface area (Å2) RDKit 82.06
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
(1S,13S,14Z,19S,21S)-14-(2-hydroxyethylidene)-4,5-dimethoxy-16-oxido-8-aza-16-azoniahexacyclo[11.5.2.11,8.02,7.016,19.012,21]henicosa-2,4,6,11-tetraen-9-one
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 Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.47
(1S,13S,14Z,19S,21S)-14-(2-hydroxyethylidene)-4,5-dimethoxy-16-oxido-8-aza-16-azoniahexacyclo[11.5.2.11,8.02,7.016,19.012,21]henicosa-2,4,6,11-tetraen-9-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.87
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes