IMPPAT Phytochemical information: 
2-[(6S,6aR,10aR)-1-hydroxy-3-(6-hydroxy-1-benzofuran-2-yl)-7,7,9-trimethyl-6,6a,8,10a-tetrahydrobenzo[c]chromen-6-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol
2-[(6S,6aR,10aR)-1-hydroxy-3-(6-hydroxy-1-benzofuran-2-yl)-7,7,9-trimethyl-6,6a,8,10a-tetrahydrobenzo[c]chromen-6-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol
Summary

SMILES: Oc1ccc2c(c1)oc(c2)c1cc(O)c(c(c1)O)[C@H]1Oc2cc(cc(c2[C@H]2[C@@H]1C(C)(C)CC(=C2)C)O)c1cc2c(o1)cc(cc2)O
InChI: InChI=1S/C38H32O8/c1-18-8-25-34-26(41)11-22(30-13-20-5-7-24(40)16-32(20)45-30)14-33(34)46-37(36(25)38(2,3)17-18)35-27(42)9-21(10-28(35)43)29-12-19-4-6-23(39)15-31(19)44-29/h4-16,25,36-37,39-43H,17H2,1-3H3/t25-,36-,37+/m0/s1
InChIKey: GKHRLTCUMXVTAV-YRVPZNQBSA-N
DeepSMILES: Occcccc6)occ5)cccO)ccc6)O))[C@H]Occcccc6[C@H][C@@H]%10CC)C)CC=C6)C)))))))O)))cccco5)cccc6))O
Scaffold Graph/Node/Bond level: C1=CC2c3ccc(-c4cc5ccccc5o4)cc3OC(c3ccc(-c4cc5ccccc5o4)cc3)C2CC1
Scaffold Graph/Node level: C1CCC2OC(C3CCC(C4OC5CC(C6CC7CCCCC7O6)CCC5C5CCCCC54)CC3)CC2C1
Scaffold Graph level: C1CCC2CC(C3CCC(C4CC5CC(C6CC7CCCCC7C6)CCC5C5CCCCC45)CC3)CC2C1
Functional groups: cO; CC(C)=CC; coc; cOC
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: Stilbenoids|Isoflavonoids
NP Classifier Class: 2-arylbenzofurans|Oligomeric stibenes
Synonymous chemical names:
dimoracin
External chemical identifiers:
CID:CID_102150173; ZINC:ZINC000238747777
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-[(6S,6aR,10aR)-1-hydroxy-3-(6-hydroxy-1-benzofuran-2-yl)-7,7,9-trimethyl-6,6a,8,10a-tetrahydrobenzo[c]chromen-6-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 616.67
Log P RDKit 9.25
Topological polar surface area (Å2) RDKit 136.66
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 38
Number of heavy atoms RDKit 46
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 30
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 6
Total number of rings RDKit 8
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 8
2-[(6S,6aR,10aR)-1-hydroxy-3-(6-hydroxy-1-benzofuran-2-yl)-7,7,9-trimethyl-6,6a,8,10a-tetrahydrobenzo[c]chromen-6-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Good
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 0.12
2-[(6S,6aR,10aR)-1-hydroxy-3-(6-hydroxy-1-benzofuran-2-yl)-7,7,9-trimethyl-6,6a,8,10a-tetrahydrobenzo[c]chromen-6-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.51
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