IMPPAT Phytochemical information: 
1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one

1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one
Summary

SMILES: C/C=C/C(=O)C1=C(C)CC(CC1(C)C)O
InChI: InChI=1S/C13H20O2/c1-5-6-11(15)12-9(2)7-10(14)8-13(12,3)4/h5-6,10,14H,7-8H2,1-4H3/b6-5+
InChIKey: UPRXEFYRIACHQZ-AATRIKPKSA-N
DeepSMILES: C/C=C/C=O)C=CC)CCCC6C)C)))O
Scaffold Graph/Node/Bond level: C1=CCCCC1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: C/C=C/C(=O)C(=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 (β-)
Synonymous chemical names:
3-hydroxy-beta-damascone, damascone, beta 3-hydroxy
External chemical identifiers:
CID:CID_6420999; ChEBI:CHEBI:168043; SureChEMBL:SCHEMBL11788398
Chemical structure download


1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 208.3
Log P RDKit 2.63
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 13
Number of heavy atoms RDKit 15
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 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 2
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


1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-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 0.708228


1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-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 -6.06
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