IMPPAT Phytochemical information: 
(E,2R)-2-[(2R,5R)-5-ethenyl-5-methyloxolan-2-yl]-6-hydroxy-6-methylhept-4-en-3-one
(E,2R)-2-[(2R,5R)-5-ethenyl-5-methyloxolan-2-yl]-6-hydroxy-6-methylhept-4-en-3-one
Summary

SMILES: C=C[C@@]1(C)CC[C@@H](O1)[C@H](C(=O)/C=C/C(O)(C)C)C
InChI: InChI=1S/C15H24O3/c1-6-15(5)10-8-13(18-15)11(2)12(16)7-9-14(3,4)17/h6-7,9,11,13,17H,1,8,10H2,2-5H3/b9-7+/t11-,13+,15-/m0/s1
InChIKey: WQUKMIHCFQFPQG-HVMVKINISA-N
DeepSMILES: C=C[C@@]C)CC[C@@H]O5)[C@H]C=O)/C=C/CO)C)C)))))C
Scaffold Graph/Node/Bond level: C1CCOC1
Scaffold Graph/Node level: C1CCOC1
Scaffold Graph level: C1CCCC1
Functional groups: C=CC; COC; C/C=C/C(C)=O; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Oxolanes
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Farnesane sesquiterpenoids
Synonymous chemical names:
hydroxy-davanone, hydroxydavanone
External chemical identifiers:
CID:CID_20839480
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(E,2R)-2-[(2R,5R)-5-ethenyl-5-methyloxolan-2-yl]-6-hydroxy-6-methylhept-4-en-3-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 252.35
Log P RDKit 2.64
Topological polar surface area (Å2) RDKit 46.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 18
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 0.2
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 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1
(E,2R)-2-[(2R,5R)-5-ethenyl-5-methyloxolan-2-yl]-6-hydroxy-6-methylhept-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 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 0.6
(E,2R)-2-[(2R,5R)-5-ethenyl-5-methyloxolan-2-yl]-6-hydroxy-6-methylhept-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 -6.50
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