IMPPAT Phytochemical information: 
Torilolide

Torilolide
Summary

SMILES: C/C=C(/C(=O)OC/C/1=C/CC/C(=C/[C@@H]2C(=C(C)C(=O)O2)CC1)/C)\C
InChI: InChI=1S/C20H26O4/c1-5-14(3)19(21)23-12-16-8-6-7-13(2)11-18-17(10-9-16)15(4)20(22)24-18/h5,8,11,18H,6-7,9-10,12H2,1-4H3/b13-11+,14-5+,16-8+/t18-/m1/s1
InChIKey: KGWAJNHQUWKJGM-CQIUZYDTSA-N
DeepSMILES: C/C=C/C=O)OC/C=C/CC/C=C/[C@@H]C=CC)C=O)O5)))CC\%10)))))/C)))))))))\C
Scaffold Graph/Node/Bond level: O=C1C=C2CCC=CCCC=CC2O1
Scaffold Graph/Node level: OC1CC2CCCCCCCCC2O1
Scaffold Graph level: CC1CC2CCCCCCCCC2C1
Functional groups: C/C=C(\C)C(=O)OC; C/C=C(/C)C; C/C(C)=C/C; CC1=C(C)C(=O)OC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Germacrane sesquiterpenoids
Synonymous chemical names:
Torilolide, torilolide
External chemical identifiers:
CID:CID_13715181
Chemical structure download


Torilolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 330.42
Log P RDKit 4.18
Topological polar surface area (Å2) RDKit 52.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
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 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2


Torilolide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
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 0.442314


Torilolide
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 -6.16
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No