IMPPAT Phytochemical information: 
Rocaglaol

Rocaglaol
Summary

SMILES: COc1ccc(cc1)[C@]12Oc3c([C@]2(O)[C@@H](C[C@H]1c1ccccc1)O)c(OC)cc(c3)OC
InChI: InChI=1S/C26H26O6/c1-29-18-11-9-17(10-12-18)26-20(16-7-5-4-6-8-16)15-23(27)25(26,28)24-21(31-3)13-19(30-2)14-22(24)32-26/h4-14,20,23,27-28H,15H2,1-3H3/t20-,23+,25+,26-/m0/s1
InChIKey: RRVZOJQBRVGMMK-HCBGRYSISA-N
DeepSMILES: COcccccc6))[C@@]Occ[C@]5O)[C@@H]C[C@H]8cccccc6))))))))O)))cOC))ccc6)OC
Scaffold Graph/Node/Bond level: c1ccc(C2CCC3c4ccccc4OC23c2ccccc2)cc1
Scaffold Graph/Node level: C1CCC(C2CCC3C4CCCCC4OC23C2CCCCC2)CC1
Scaffold Graph level: C1CCC(C2CCC3C4CCCCC4CC23C2CCCCC2)CC1
Functional groups: cOC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzofurans
ClassyFire Subclass: Flavaglines
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavan-3-ols
Synonymous chemical names:
Rocaglaol, rocaglaol
External chemical identifiers:
CID:CID_393602; ChEMBL:CHEMBL468454; ZINC:ZINC000003951623; SureChEMBL:SCHEMBL750024; MolPort-035-706-118
Chemical structure download


Rocaglaol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 434.49
Log P RDKit 3.74
Topological polar surface area (Å2) RDKit 77.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.31
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Rocaglaol
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 0.64


Rocaglaol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.71
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes