IMPPAT Phytochemical information: 
(1R,2R,4Z,9S)-2-hydroxy-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-3-one
(1R,2R,4Z,9S)-2-hydroxy-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-3-one
Summary

SMILES: C=C1CC/C=C(\C(=O)[C@@H]([C@@H]2[C@@H]1CC2(C)C)O)/C
InChI: InChI=1S/C15H22O2/c1-9-6-5-7-10(2)13(16)14(17)12-11(9)8-15(12,3)4/h7,11-12,14,17H,1,5-6,8H2,2-4H3/b10-7-/t11-,12+,14-/m1/s1
InChIKey: AXGJIHAKGFPXOX-VBRKHYKASA-N
DeepSMILES: C=CCC/C=C\C=O)[C@@H][C@@H][C@@H]9CC4C)C)))))O)))/C
Scaffold Graph/Node/Bond level: C=C1CCC=CC(=O)CC2CCC12
Scaffold Graph/Node level: CC1CCCCC(O)CC2CCC12
Scaffold Graph level: CC1CCCCC(C)C2CCC2C1
Functional groups: C=C(C)C; C/C=C(/C)C(=O)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Caryophyllane sesquiterpenoids|Humulane sesquiterpenoids
Synonymous chemical names:
buddledin b
External chemical identifiers:
CID:CID_6443194; ZINC:ZINC000105386670
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2R,4Z,9S)-2-hydroxy-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-3-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 234.34
Log P RDKit 2.88
Topological polar surface area (Å2) RDKit 37.3
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
(1R,2R,4Z,9S)-2-hydroxy-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-3-one
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.654336
(1R,2R,4Z,9S)-2-hydroxy-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-3-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 -5.67
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 No