IMPPAT Phytochemical information: 
(4R,4aR,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-2-hydroxy-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydro-4H-naphthalen-1-one
(4R,4aR,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-2-hydroxy-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydro-4H-naphthalen-1-one
Summary

SMILES: CC1=C(O)C(=O)[C@@H]2[C@]([C@H]1/C=C/c1cocc1)(C)CCCC2(C)C
InChI: InChI=1S/C20H26O3/c1-13-15(7-6-14-8-11-23-12-14)20(4)10-5-9-19(2,3)18(20)17(22)16(13)21/h6-8,11-12,15,18,21H,5,9-10H2,1-4H3/b7-6+/t15-,18-,20+/m0/s1
InChIKey: JPMIIVCZMUYZRA-MMZWZMGNSA-N
DeepSMILES: CC=CO)C=O)[C@@H][C@][C@H]6/C=C/ccocc5))))))))C)CCCC6C)C
Scaffold Graph/Node/Bond level: O=C1C=CC(C=Cc2ccoc2)C2CCCCC12
Scaffold Graph/Node level: OC1CCC(CCC2CCOC2)C2CCCCC12
Scaffold Graph level: CC1CCC(CCC2CCCC2)C2CCCCC12
Functional groups: CC(=C(O)C(=O)C)C; c/C=C/C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Labdane diterpenoids
Synonymous chemical names:
Hedychenone, 7-hydroxy, 7-hydroxyhedychenone
External chemical identifiers:
CID:CID_12189408; ChEMBL:CHEMBL466121; ZINC:ZINC000038539887
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(4R,4aR,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-2-hydroxy-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydro-4H-naphthalen-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 314.43
Log P RDKit 5.16
Topological polar surface area (Å2) RDKit 50.44
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 2
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 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
(4R,4aR,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-2-hydroxy-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydro-4H-naphthalen-1-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.820316
(4R,4aR,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-2-hydroxy-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydro-4H-naphthalen-1-one
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 -4.85
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No