IMPPAT Phytochemical information: 
(6S)-6-methyl-5-(3-oxobutyl)-2-propan-2-ylidenecyclohept-4-en-1-one

(6S)-6-methyl-5-(3-oxobutyl)-2-propan-2-ylidenecyclohept-4-en-1-one
Summary

SMILES: CC(=O)CCC1=CCC(=C(C)C)C(=O)C[C@@H]1C
InChI: InChI=1S/C15H22O2/c1-10(2)14-8-7-13(6-5-12(4)16)11(3)9-15(14)17/h7,11H,5-6,8-9H2,1-4H3/t11-/m0/s1
InChIKey: JWUVBGKPYDWLJC-NSHDSACASA-N
DeepSMILES: CC=O)CCC=CCC=CC)C))C=O)C[C@@H]7C
Scaffold Graph/Node/Bond level: C=C1CC=CCCC1=O
Scaffold Graph/Node level: CC1CCCCCC1O
Scaffold Graph level: CC1CCCCCC1C
Functional groups: CC(C)=O; CC=C(C)C; CC(=O)C(=C(C)C)C
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: Germacrane sesquiterpenoids
Synonymous chemical names:
curcumadione
External chemical identifiers:
CID:CID_21769417; ZINC:ZINC000014884878; SureChEMBL:SCHEMBL22804984
Chemical structure download


(6S)-6-methyl-5-(3-oxobutyl)-2-propan-2-ylidenecyclohept-4-en-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 234.34
Log P RDKit 3.62
Topological polar surface area (Å2) RDKit 34.14
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
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 1
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 3
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


(6S)-6-methyl-5-(3-oxobutyl)-2-propan-2-ylidenecyclohept-4-en-1-one
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 0
Ghose rule RDKit Passed
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 0.55


(6S)-6-methyl-5-(3-oxobutyl)-2-propan-2-ylidenecyclohept-4-en-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 -6.07
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 No
P-glycoprotein substrate SwissADME No