IMPPAT Phytochemical information: 
6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-2,2-dimethyl-8-phenyl-8,9-dihydropyrano[2,3-f]chromen-10-one
6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-2,2-dimethyl-8-phenyl-8,9-dihydropyrano[2,3-f]chromen-10-one
Summary

SMILES: O=C1CC(Oc2c1c1OC(C)(C)C=Cc1c(c2Cc1c(O)c(C)c(c(c1O)C(=O)C)O)O)c1ccccc1
InChI: InChI=1S/C30H28O8/c1-14-24(33)18(27(36)22(15(2)31)25(14)34)12-19-26(35)17-10-11-30(3,4)38-29(17)23-20(32)13-21(37-28(19)23)16-8-6-5-7-9-16/h5-11,21,33-36H,12-13H2,1-4H3
InChIKey: ZMESDDISZUDKEI-UHFFFAOYSA-N
DeepSMILES: O=CCCOcc6cOCC)C)C=Cc6cc%10CccO)cC)ccc6O))C=O)C)))O)))))))O)))))))))))cccccc6
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)Oc2c(Cc3ccccc3)cc3c(c21)OCC=C3
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2C(CC3CCCCC3)CC3CCCOC3C12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2C(CC3CCCCC3)CC3CCCCC3C12
Functional groups: cC(=O)C; cOC; cC=CC; cO; cC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Pyranoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavanones
Synonymous chemical names:
isorottlerin
External chemical identifiers:
CID:CID_5318656; ChEMBL:CHEMBL4450525
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-2,2-dimethyl-8-phenyl-8,9-dihydropyrano[2,3-f]chromen-10-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 516.55
Log P RDKit 5.5
Topological polar surface area (Å2) RDKit 133.52
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.03
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 22
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.27
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
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 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-2,2-dimethyl-8-phenyl-8,9-dihydropyrano[2,3-f]chromen-10-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
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 0.334117
6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-2,2-dimethyl-8-phenyl-8,9-dihydropyrano[2,3-f]chromen-10-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.95
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No