IMPPAT Phytochemical information: 
(1R,2R,3S,6R,7S,8S,10S)-2-ethyl-8-hydroxy-6-methyl-10-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.01,8.03,7]hexadecane-5,16-dione
(1R,2R,3S,6R,7S,8S,10S)-2-ethyl-8-hydroxy-6-methyl-10-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.01,8.03,7]hexadecane-5,16-dione
Summary

SMILES: CC[C@H]1[C@@H]2OC(=O)[C@@H]([C@@H]2[C@@]2([C@]31CCCCN(C3=O)[C@@H](C2)[C@@H]1C[C@@H](C(=O)O1)C)O)C
InChI: InChI=1S/C22H31NO6/c1-4-13-17-16(12(3)19(25)29-17)22(27)10-14(15-9-11(2)18(24)28-15)23-8-6-5-7-21(13,22)20(23)26/h11-17,27H,4-10H2,1-3H3/t11-,12+,13-,14-,15-,16-,17-,21-,22-/m0/s1
InChIKey: YOBIPOVYJKVGIS-QHSDLTJRSA-N
DeepSMILES: CC[C@H][C@@H]OC=O)[C@@H][C@@H]5[C@@][C@@]8CCCCNC7=O))[C@@H]C9)[C@@H]C[C@@H]C=O)O5))C)))))))))))O)))C
Scaffold Graph/Node/Bond level: O=C1CC2C(CC34CCCCN(C3=O)C(C3CCC(=O)O3)CC24)O1
Scaffold Graph/Node level: OC1CC2C(CC34CCCCN(C(C5CCC(O)O5)CC23)C4O)O1
Scaffold Graph level: CC1CCC(C2CC3C4CC(C)CC4CC34CCCCC2C4C)C1
Functional groups: COC(=O)C; CN(C)C(=O)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Lactams
ClassyFire Subclass: Caprolactams
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Stemona alkaloids
Synonymous chemical names:
tuberostemoninol
External chemical identifiers:
CID:CID_101670618; ZINC:ZINC000005822692
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2R,3S,6R,7S,8S,10S)-2-ethyl-8-hydroxy-6-methyl-10-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.01,8.03,7]hexadecane-5,16-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 405.49
Log P RDKit 1.66
Topological polar surface area (Å2) RDKit 93.14
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.86
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(1R,2R,3S,6R,7S,8S,10S)-2-ethyl-8-hydroxy-6-methyl-10-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.01,8.03,7]hexadecane-5,16-dione
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 0.7
(1R,2R,3S,6R,7S,8S,10S)-2-ethyl-8-hydroxy-6-methyl-10-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.01,8.03,7]hexadecane-5,16-dione
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 -7.52
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