IMPPAT Phytochemical information: 
Aglafoline
Aglafoline
Summary

SMILES: COc1ccc(cc1)[C@]12Oc3c([C@]2(O)[C@@H]([C@@H]([C@H]1c1ccccc1)C(=O)OC)O)c(OC)cc(c3)OC
InChI: InChI=1S/C28H28O8/c1-32-18-12-10-17(11-13-18)28-23(16-8-6-5-7-9-16)22(26(30)35-4)25(29)27(28,31)24-20(34-3)14-19(33-2)15-21(24)36-28/h5-15,22-23,25,29,31H,1-4H3/t22-,23-,25-,27+,28+/m1/s1
InChIKey: VFTGDXPPYSWBSO-GWNOIRNCSA-N
DeepSMILES: COcccccc6))[C@@]Occ[C@]5O)[C@@H][C@@H][C@H]8cccccc6)))))))C=O)OC))))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; COC(C)=O
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: Stilbenoids
Synonymous chemical names:
methyl rocaglate, aglafolin, Methyl rocaglate, methylrocaglate
External chemical identifiers:
CID:CID_393601; ChEMBL:CHEMBL394528; ChEBI:CHEBI:65374; ZINC:ZINC000005922875; SureChEMBL:SCHEMBL748617
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Aglafoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 492.52
Log P RDKit 3.14
Topological polar surface area (Å2) RDKit 103.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 7
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
Aglafoline
Drug-likeness
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 1
Ghose filter RDKit Failed
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 0.506205
Aglafoline
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.02
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
Aglafoline
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000354ENSG00000161960EIF4A11973BindingDB, ChEMBL, NPASS
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL, NPASS