IMPPAT Phytochemical information: 
(1S,2R,3S,6R,9S,10R,14R,17S,18R,19S)-12-ethyl-9,19-dihydroxy-17-methoxy-14-methyl-5-oxa-12-azahexacyclo[8.7.2.12,6.01,11.03,9.014,18]icosan-4-one
(1S,2R,3S,6R,9S,10R,14R,17S,18R,19S)-12-ethyl-9,19-dihydroxy-17-methoxy-14-methyl-5-oxa-12-azahexacyclo[8.7.2.12,6.01,11.03,9.014,18]icosan-4-one
Summary

SMILES: CO[C@H]1CC[C@@]2([C@@H]3[C@]41C(N(C2)CC)[C@H]([C@H]3O)[C@@]1([C@@H]2[C@H]4C[C@@H](CC1)OC2=O)O)C
InChI: InChI=1S/C22H33NO5/c1-4-23-10-20(2)7-6-13(27-3)22-12-9-11-5-8-21(26,14(12)19(25)28-11)15(18(22)23)16(24)17(20)22/h11-18,24,26H,4-10H2,1-3H3/t11-,12-,13+,14-,15+,16-,17-,18?,20+,21-,22+/m1/s1
InChIKey: YPSAOPXJHSESSR-ATENDURSSA-N
DeepSMILES: CO[C@H]CC[C@@][C@@H][C@@]6CNC6)CC)))[C@H][C@H]5O))[C@@][C@@H][C@H]6C[C@@H]CC7))OC6=O)))))))O))))))C
Scaffold Graph/Node/Bond level: O=C1OC2CCC3C4CC5C6CCCC5(C(C2)C13)C4NC6
Scaffold Graph/Node level: OC1OC2CCC3C4CC5C6CCCC5(C(C2)C13)C4NC6
Scaffold Graph level: CC1CC2CCC3C4CC5C6CCCC5(C4CC6)C(C2)C13
Functional groups: COC; CN(C)C; CO; COC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolidines
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Terpenoid alkaloids
Synonymous chemical names:
heteratisine
External chemical identifiers:
CID:CID_441735
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,2R,3S,6R,9S,10R,14R,17S,18R,19S)-12-ethyl-9,19-dihydroxy-17-methoxy-14-methyl-5-oxa-12-azahexacyclo[8.7.2.12,6.01,11.03,9.014,18]icosan-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 391.51
Log P RDKit 1.19
Topological polar surface area (Å2) RDKit 79.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.95
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
(1S,2R,3S,6R,9S,10R,14R,17S,18R,19S)-12-ethyl-9,19-dihydroxy-17-methoxy-14-methyl-5-oxa-12-azahexacyclo[8.7.2.12,6.01,11.03,9.014,18]icosan-4-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 Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.69
(1S,2R,3S,6R,9S,10R,14R,17S,18R,19S)-12-ethyl-9,19-dihydroxy-17-methoxy-14-methyl-5-oxa-12-azahexacyclo[8.7.2.12,6.01,11.03,9.014,18]icosan-4-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 -6.20
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