IMPPAT Phytochemical information: 
Otosenine
Otosenine
Summary

SMILES: CN1CC[C@H]2OC(=O)[C@]3(O[C@H]3C)C[C@H]([C@@](C(=O)OCC(=CC1)C2=O)(C)O)C
InChI: InChI=1S/C19H27NO7/c1-11-9-19(12(2)27-19)17(23)26-14-6-8-20(4)7-5-13(15(14)21)10-25-16(22)18(11,3)24/h5,11-12,14,24H,6-10H2,1-4H3/b13-5-/t11-,12+,14-,18-,19+/m1/s1
InChIKey: CZQLULNMKQAIQL-GZSSMBGUSA-N
DeepSMILES: CNCC[C@H]OC=O)[C@]O[C@H]3C)))C[C@H][C@@]C=O)OCC=CC%16))C%12=O))))))C)O))C
Scaffold Graph/Node/Bond level: O=C1CCCC2(CO2)C(=O)OC2CCNCC=C(CO1)C2=O
Scaffold Graph/Node level: OC1CCCC2(CO2)C(O)OC2CCNCCC(CO1)C2O
Scaffold Graph level: CC1CCCC2(CC2)C(C)CC2CCCCCC(CC1)C2C
Functional groups: CN(C)C; C[C@@H]1O[C@]1(C)C(=O)OC; COC(=O)C; CC=C(C)C(=O)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Azaspirodecane derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
otosenine, othosenine, tomentosine
External chemical identifiers:
CID:CID_6438142; ChEMBL:CHEMBL511627; ChEBI:CHEBI:136467; FDASRS:Z999A1E7I4; MolPort-002-527-385
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Otosenine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 381.43
Log P RDKit 0.22
Topological polar surface area (Å2) RDKit 105.67
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.74
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Otosenine
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 0.47
Otosenine
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 -8.18
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