IMPPAT Phytochemical information: 
[(1S,2R,6R)-2-[2,6-dihydroxy-4-[6-hydroxy-7-(3-methylbut-2-enyl)-1-benzofuran-2-yl]phenyl]-6-(2,4-dihydroxyphenyl)-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-7-(3-methylbut-2-enyl)-1-benzofuran-2-yl]phenyl]-6-(2,4-dihydroxyphenyl)-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(cc1O)O)C)c1c(O)cc(cc1O)c1oc2c(c1)ccc(c2CC=C(C)C)O)C
InChI: InChI=1S/C44H44O9/c1-22(2)6-10-29-34(46)15-13-31(42(29)51)43(52)40-32(28-12-9-27(45)21-36(28)48)16-24(5)17-33(40)41-37(49)18-26(19-38(41)50)39-20-25-8-14-35(47)30(44(25)53-39)11-7-23(3)4/h6-9,12-15,17-21,32-33,40,45-51H,10-11,16H2,1-5H3/t32-,33+,40-/m0/s1
InChIKey: XMXZFZDVDCIFKB-PZZKLQKOSA-N
DeepSMILES: CC=CCccO)cccc6O))C=O)[C@@H][C@@H]C=CC[C@H]6cccccc6O)))O)))))))C)))ccO)cccc6O)))coccc5)cccc6CC=CC)C)))))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 t
External chemical identifiers:
CID:CID_102375662; ZINC:ZINC000086034679
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-7-(3-methylbut-2-enyl)-1-benzofuran-2-yl]phenyl]-6-(2,4-dihydroxyphenyl)-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 716.83
Log P RDKit 9.77
Topological polar surface area (Å2) RDKit 171.82
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 44
Number of heavy atoms RDKit 53
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 33
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 9
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-7-(3-methylbut-2-enyl)-1-benzofuran-2-yl]phenyl]-6-(2,4-dihydroxyphenyl)-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 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.06
[(1S,2R,6R)-2-[2,6-dihydroxy-4-[6-hydroxy-7-(3-methylbut-2-enyl)-1-benzofuran-2-yl]phenyl]-6-(2,4-dihydroxyphenyl)-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 Insoluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -3.69
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 Yes