IMPPAT Phytochemical information: 
(5aR,11bS,11cS)-9,10-dimethoxy-1-methyl-1-oxido-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-1-ium-7-one
(5aR,11bS,11cS)-9,10-dimethoxy-1-methyl-1-oxido-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-1-ium-7-one
Summary

SMILES: COc1cc2c(cc1OC)C(=O)O[C@H]1[C@@H]2[C@H]2C(=CC1)CC[N+]2([O-])C
InChI: InChI=1S/C18H21NO5/c1-19(21)7-6-10-4-5-13-16(17(10)19)11-8-14(22-2)15(23-3)9-12(11)18(20)24-13/h4,8-9,13,16-17H,5-7H2,1-3H3/t13-,16-,17-,19?/m1/s1
InChIKey: LAEQLQRWNDLBBU-KNFXUPHZSA-N
DeepSMILES: COcccccc6OC))))C=O)O[C@H][C@@H]6[C@H]C=CC6))CC[N+]5[O-])C
Scaffold Graph/Node/Bond level: O=C1OC2CC=C3CC[NH2+]C3C2c2ccccc21
Scaffold Graph/Node level: OC1OC2CCC3CCNC3C2C2CCCCC12
Scaffold Graph level: CC1CC2CCC3CCCC3C2C2CCCCC12
Functional groups: cOC; cC(=O)OC; CC=C(C)C; C[N+](C)([O-])C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Amaryllidaceae alkaloids
ClassyFire Subclass: Homolycorine-type amaryllidaceae alkaloids
Synonymous chemical names:
homolycorine n-oxide
External chemical identifiers:
CID:CID_14109783; ZINC:ZINC000014583801
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(5aR,11bS,11cS)-9,10-dimethoxy-1-methyl-1-oxido-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-1-ium-7-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 331.37
Log P RDKit 2.37
Topological polar surface area (Å2) RDKit 67.82
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
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 4
(5aR,11bS,11cS)-9,10-dimethoxy-1-methyl-1-oxido-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-1-ium-7-one
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 0.360144
(5aR,11bS,11cS)-9,10-dimethoxy-1-methyl-1-oxido-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-1-ium-7-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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.26
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