IMPPAT Phytochemical information: 
Thespesone

Thespesone
Summary

SMILES: O=C1C(=C(O)c2c(C1=O)c(C)cc1c2C(C)CO1)C
InChI: InChI=1S/C15H14O4/c1-6-4-9-10(7(2)5-19-9)12-11(6)15(18)14(17)8(3)13(12)16/h4,7,16H,5H2,1-3H3
InChIKey: NBWHNPKICLVSGW-UHFFFAOYSA-N
DeepSMILES: O=CC=CO)ccC6=O))cC)ccc6CC)CO5))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=Cc2c(ccc3c2CCO3)C1=O
Scaffold Graph/Node level: OC1CCC2C3CCOC3CCC2C1O
Scaffold Graph level: CC1CCC2C3CCCC3CCC2C1C
Functional groups: CC1=C(O)ccC(=O)C1=O; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Naphthoquinones
Synonymous chemical names:
Thespesone, thespesone
External chemical identifiers:
CID:CID_5321934
Chemical structure download


Thespesone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 258.27
Log P RDKit 2.55
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 4
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 10
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3


Thespesone
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 0.73


Thespesone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -6.51
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No