IMPPAT Phytochemical information: 
4-Hydroxy-3,5,5-trimethylcyclohex-2-enone

4-Hydroxy-3,5,5-trimethylcyclohex-2-enone
Summary

SMILES: O=C1C=C(C)C(C(C1)(C)C)O
InChI: InChI=1S/C9H14O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4,8,11H,5H2,1-3H3
InChIKey: RLDREDRZMOWDOA-UHFFFAOYSA-N
DeepSMILES: O=CC=CC)CCC6)C)C))O
Scaffold Graph/Node/Bond level: O=C1C=CCCC1
Scaffold Graph/Node level: OC1CCCCC1
Scaffold Graph level: CC1CCCCC1
Functional groups: CC(=O)C=C(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbonyl compounds
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Apocarotenoids
NP Classifier Class: Apocarotenoids(ε-)
Synonymous chemical names:
4-hydroxy-3,5,5-trimethylcyclohexan-1-on-2-ene
External chemical identifiers:
CID:CID_566734; ChEMBL:CHEMBL463102; SureChEMBL:SCHEMBL6557553
Chemical structure download


4-Hydroxy-3,5,5-trimethylcyclohex-2-enone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 154.21
Log P RDKit 1.29
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 9
Number of heavy atoms RDKit 11
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


4-Hydroxy-3,5,5-trimethylcyclohex-2-enone
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 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.57


4-Hydroxy-3,5,5-trimethylcyclohex-2-enone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.86
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