IMPPAT Phytochemical information: 
Spirostane-3,6-dione
Spirostane-3,6-dione
Summary

SMILES: CC1CCC2(OC1)OC1C(C2C)C2(C(C1)C1CC(=O)C3C(C1CC2)(C)CCC(=O)C3)C
InChI: InChI=1S/C27H40O4/c1-15-5-10-27(30-14-15)16(2)24-23(31-27)13-20-18-12-22(29)21-11-17(28)6-8-25(21,3)19(18)7-9-26(20,24)4/h15-16,18-21,23-24H,5-14H2,1-4H3
InChIKey: CGXQJOWMWZPOPV-UHFFFAOYSA-N
DeepSMILES: CCCCCOC6))OCCC5C))CCC5)CCC=O)CCC6CC%10)))C)CCC=O)C6))))))))))C
Scaffold Graph/Node/Bond level: O=C1CCC2C(C1)C(=O)CC1C2CCC2C3CC4(CCCCO4)OC3CC21
Scaffold Graph/Node level: OC1CCC2C(C1)C(O)CC1C2CCC2C3CC4(CCCCO4)OC3CC21
Scaffold Graph level: CC1CCC2C(C1)C(C)CC1C2CCC2C3CC4(CCCCC4)CC3CC21
Functional groups: COC(C)(C)OC; CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Spirostane steroids
Synonymous chemical names:
25r-5α-spirostane-3,6-dione (chlorogenone), chlorogenone
External chemical identifiers:
CID:CID_13889197; ChEBI:CHEBI:175478
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Spirostane-3,6-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 428.61
Log P RDKit 5.18
Topological polar surface area (Å2) RDKit 52.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.93
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Spirostane-3,6-dione
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.53
Spirostane-3,6-dione
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.75
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No