IMPPAT Phytochemical information: 
Dehydrosesquicineole

Dehydrosesquicineole
Summary

SMILES: CC(=CCCC1(C)O[C@]2(C)CC[C@@H]1C=C2)C
InChI: InChI=1S/C15H24O/c1-12(2)6-5-9-15(4)13-7-10-14(3,16-15)11-8-13/h6-7,10,13H,5,8-9,11H2,1-4H3/t13-,14-,15?/m0/s1
InChIKey: VLUGOADEEDGFLB-ZYOSVBKOSA-N
DeepSMILES: CC=CCCCC)O[C@]C)CC[C@@H]6C=C6)))))))))))C
Scaffold Graph/Node/Bond level: C1=CC2CCC1CO2
Scaffold Graph/Node level: C1CC2CCC1CO2
Scaffold Graph level: C1CC2CCC1CC2
Functional groups: CC=C(C)C; COC; CC=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Pyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Bisabolane sesquiterpenoids
Synonymous chemical names:
dehydro-sesquicineole, dehydro-sesquicineol
External chemical identifiers:
CID:CID_6430797
Chemical structure download


Dehydrosesquicineole
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 220.36
Log P RDKit 4.25
Topological polar surface area (Å2) RDKit 9.23
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 1
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 4
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
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 3


Dehydrosesquicineole
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.65


Dehydrosesquicineole
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 -4.92
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