IMPPAT Phytochemical information: 
Verlotorin

Verlotorin
Summary

SMILES: OO[C@@H]1CC/C(=C/[C@@H]2[C@@H](CCC1=C)C(=C)C(=O)O2)/C
InChI: InChI=1S/C15H20O4/c1-9-4-7-13(19-17)10(2)5-6-12-11(3)15(16)18-14(12)8-9/h8,12-14,17H,2-7H2,1H3/b9-8+/t12-,13+,14+/m0/s1
InChIKey: IXRHWRRLTANMPL-CVZWCJCVSA-N
DeepSMILES: OO[C@@H]CC/C=C/[C@@H][C@@H]CCC%10=C))))C=C)C=O)O5))))))/C
Scaffold Graph/Node/Bond level: C=C1CCCC=CC2OC(=O)C(=C)C2CC1
Scaffold Graph/Node level: CC1CCCCCC2OC(O)C(C)C2CC1
Scaffold Graph level: CC1CCCCCC2CC(C)C(C)C2CC1
Functional groups: COO; C/C(C)=C/C; C=C(C)C; C=C1CCOC1=O
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:
Verlotorin, verlotorin, Peroxycostunolide, peroxycostunolide
External chemical identifiers:
CID:CID_13895607; ChEBI:CHEBI:55361; ZINC:ZINC000064633485
Chemical structure download


Verlotorin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 264.32
Log P RDKit 3.02
Topological polar surface area (Å2) RDKit 55.76
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 3
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 1
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Verlotorin
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.259923


Verlotorin
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 -7.15
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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