IMPPAT Phytochemical information: 
[(1S,2R,6R)-2-[2,6-dihydroxy-4-(6-hydroxy-1-benzofuran-2-yl)phenyl]-6-(4-hydroxyphenyl)-4-methylcyclohex-3-en-1-yl]-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]methanone
[(1S,2R,6R)-2-[2,6-dihydroxy-4-(6-hydroxy-1-benzofuran-2-yl)phenyl]-6-(4-hydroxyphenyl)-4-methylcyclohex-3-en-1-yl]-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]methanone
Summary

SMILES: CC(=CCc1c(O)ccc(c1O)C(=O)[C@@H]1[C@@H](C=C(C[C@H]1c1ccc(cc1)O)C)c1c(O)cc(cc1O)c1oc2c(c1)ccc(c2)O)C
InChI: InChI=1S/C39H36O8/c1-20(2)4-11-27-31(42)13-12-28(38(27)45)39(46)36-29(22-5-8-25(40)9-6-22)14-21(3)15-30(36)37-32(43)16-24(17-33(37)44)34-18-23-7-10-26(41)19-35(23)47-34/h4-10,12-13,15-19,29-30,36,40-45H,11,14H2,1-3H3/t29-,30+,36-/m0/s1
InChIKey: RQIKMRKKKIMUNB-BLBFUMABSA-N
DeepSMILES: CC=CCccO)cccc6O))C=O)[C@@H][C@@H]C=CC[C@H]6cccccc6))O)))))))C)))ccO)cccc6O)))coccc5)cccc6)O))))))))))))))))))))))C
Scaffold Graph/Node/Bond level: O=C(c1ccccc1)C1C(c2ccc(-c3cc4ccccc4o3)cc2)C=CCC1c1ccccc1
Scaffold Graph/Node level: OC(C1CCCCC1)C1C(C2CCCCC2)CCCC1C1CCC(C2CC3CCCCC3O2)CC1
Scaffold Graph level: CC(C1CCCCC1)C1C(C2CCCCC2)CCCC1C1CCC(C2CC3CCCCC3C2)CC1
Functional groups: CC=C(C)C; cO; coc; cC(C)=O; CC(C)=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: 2-arylbenzofuran flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids|Flavonoids
NP Classifier Class: 2-arylbenzofurans|Chalcones
Synonymous chemical names:
mulberrofuran e
External chemical identifiers:
CID:CID_100930829; ZINC:ZINC000086034599
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,2R,6R)-2-[2,6-dihydroxy-4-(6-hydroxy-1-benzofuran-2-yl)phenyl]-6-(4-hydroxyphenyl)-4-methylcyclohex-3-en-1-yl]-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]methanone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 632.71
Log P RDKit 8.56
Topological polar surface area (Å2) RDKit 151.59
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 39
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 31
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 5
Total number of rings RDKit 6
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 6
[(1S,2R,6R)-2-[2,6-dihydroxy-4-(6-hydroxy-1-benzofuran-2-yl)phenyl]-6-(4-hydroxyphenyl)-4-methylcyclohex-3-en-1-yl]-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]methanone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0771205
[(1S,2R,6R)-2-[2,6-dihydroxy-4-(6-hydroxy-1-benzofuran-2-yl)phenyl]-6-(4-hydroxyphenyl)-4-methylcyclohex-3-en-1-yl]-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]methanone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -4.29
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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