IMPPAT Phytochemical information: 
[(2R,3R,4bR,8R,8aR,9S)-9-hydroxy-2,3-dimethyl-3-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,4,4a,4b,5,6,7,9,10,10a-decahydro-1H-phenanthrene-8,2'-oxirane]-8a-yl]methyl acetate
[(2R,3R,4bR,8R,8aR,9S)-9-hydroxy-2,3-dimethyl-3-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,4,4a,4b,5,6,7,9,10,10a-decahydro-1H-phenanthrene-8,2'-oxirane]-8a-yl]methyl acetate
Summary

SMILES: CC(=O)OC[C@@]12[C@@H](O)CC3C([C@H]1CCC[C@@]12CO1)C[C@@]([C@@H](C3)C)(C)CCC1=CC(=O)OC1
InChI: InChI=1S/C26H38O6/c1-16-9-19-11-22(28)26(15-31-17(2)27)21(5-4-7-25(26)14-32-25)20(19)12-24(16,3)8-6-18-10-23(29)30-13-18/h10,16,19-22,28H,4-9,11-15H2,1-3H3/t16-,19?,20?,21-,22+,24-,25+,26+/m1/s1
InChIKey: PNWZOPZSXKKETE-XIUSWLETSA-N
DeepSMILES: CC=O)OC[C@@][C@@H]O)CCC[C@H]6CCC[C@]%10CO3)))))))C[C@@][C@@H]C6)C))C)CCC=CC=O)OC5
Scaffold Graph/Node/Bond level: O=C1C=C(CCC2CCC3CCC4C(CCCC45CO5)C3C2)CO1
Scaffold Graph/Node level: OC1CC(CCC2CCC3CCC4C(CCCC45CO5)C3C2)CO1
Scaffold Graph level: CC1CCC(CCC2CCC3CCC4C(CCCC45CC5)C3C2)C1
Functional groups: COC(C)=O; CO; C[C@@]1(C)CO1; CC1=CC(=O)OC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids
Synonymous chemical names:
ajugarin-i
External chemical identifiers:
CID:CID_481707
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(2R,3R,4bR,8R,8aR,9S)-9-hydroxy-2,3-dimethyl-3-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,4,4a,4b,5,6,7,9,10,10a-decahydro-1H-phenanthrene-8,2'-oxirane]-8a-yl]methyl acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 446.58
Log P RDKit 3.8
Topological polar surface area (Å2) RDKit 85.36
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.85
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
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 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
[(2R,3R,4bR,8R,8aR,9S)-9-hydroxy-2,3-dimethyl-3-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,4,4a,4b,5,6,7,9,10,10a-decahydro-1H-phenanthrene-8,2'-oxirane]-8a-yl]methyl acetate
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.510712
[(2R,3R,4bR,8R,8aR,9S)-9-hydroxy-2,3-dimethyl-3-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,4,4a,4b,5,6,7,9,10,10a-decahydro-1H-phenanthrene-8,2'-oxirane]-8a-yl]methyl acetate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.39
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 Yes
P-glycoprotein substrate SwissADME No