IMPPAT Phytochemical information: 
Methyl (1r,9r,10s,13z,14r)-13-ethylidene-17-methoxy-11-oxido-18-oxa-8-aza-11-azoniapentacyclo[7.6.3.110,14.01,9.02,7]nonadeca-2,4,6,11-tetraene-15-carboxylate
Methyl (1r,9r,10s,13z,14r)-13-ethylidene-17-methoxy-11-oxido-18-oxa-8-aza-11-azoniapentacyclo[7.6.3.110,14.01,9.02,7]nonadeca-2,4,6,11-tetraene-15-carboxylate
Summary

SMILES: CO[C@H]1OC23C(C1)(C(C(=O)OC)C1CC3[N+](=C/C/1=C\C)[O-])c1c(N2)cccc1
InChI: InChI=1S/C21H24N2O5/c1-4-12-11-23(25)16-9-13(12)18(19(24)27-3)20-10-17(26-2)28-21(16,20)22-15-8-6-5-7-14(15)20/h4-8,11,13,16-18,22H,9-10H2,1-3H3/b12-4+/t13?,16?,17-,18?,20?,21?/m0/s1
InChIKey: WHAYYXYTINYKPT-XWEYRWPWSA-N
DeepSMILES: CO[C@H]OCCC5)CC=O)OC)))CCC6[N+]=C/C/6=C\C))))[O-]))))))ccN5)cccc6
Scaffold Graph/Node/Bond level: C=C1C=[NH+]C2CC1CC13CCOC21Nc1ccccc13
Scaffold Graph/Node level: CC1CNC2CC1CC13CCOC21NC1CCCCC13
Scaffold Graph level: CC1CCC2CC1CC13CCCC21CC1CCCCC13
Functional groups: cNC1(C)CC[C@@H](OC)O1; COC(C)=O; C/C=C(/C)C=[N+]([O-])C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Carbazoles
Synonymous chemical names:
alschomine, methyl (1R,9R,10S,13Z,14R)-13-ethylidene-17-methoxy-11-oxido-18-oxa-8-aza-11-azoniapentacyclo[7.6.3.110,14.01,9.02,7]nonadeca-2,4,6,11-tetraene-15-carboxylate
External chemical identifiers:
CID:CID_11969856
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Methyl (1r,9r,10s,13z,14r)-13-ethylidene-17-methoxy-11-oxido-18-oxa-8-aza-11-azoniapentacyclo[7.6.3.110,14.01,9.02,7]nonadeca-2,4,6,11-tetraene-15-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 384.43
Log P RDKit 2.16
Topological polar surface area (Å2) RDKit 82.86
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.29
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 3
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 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Methyl (1r,9r,10s,13z,14r)-13-ethylidene-17-methoxy-11-oxido-18-oxa-8-aza-11-azoniapentacyclo[7.6.3.110,14.01,9.02,7]nonadeca-2,4,6,11-tetraene-15-carboxylate
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.478004
Methyl (1r,9r,10s,13z,14r)-13-ethylidene-17-methoxy-11-oxido-18-oxa-8-aza-11-azoniapentacyclo[7.6.3.110,14.01,9.02,7]nonadeca-2,4,6,11-tetraene-15-carboxylate
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 -8.22
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes