IMPPAT Phytochemical information: 
3-Benzofurancarboxamide, 2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxyphenyl)ethyl)-5-((1E)-3-((2-(4-hydroxyphenyl)ethyl)amino)-3-oxo-1-propenyl)-7-methoxy-, (2R,3R)-rel-
3-Benzofurancarboxamide, 2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxyphenyl)ethyl)-5-((1E)-3-((2-(4-hydroxyphenyl)ethyl)amino)-3-oxo-1-propenyl)-7-methoxy-, (2R,3R)-rel-
Summary

SMILES: COc1cc(/C=C/C(=O)NCCc2ccc(cc2)O)cc2c1O[C@@H]([C@H]2C(=O)NCCc1ccc(cc1)O)c1ccc(c(c1)OC)O
InChI: InChI=1S/C36H36N2O8/c1-44-30-21-25(8-13-29(30)41)34-33(36(43)38-18-16-23-5-11-27(40)12-6-23)28-19-24(20-31(45-2)35(28)46-34)7-14-32(42)37-17-15-22-3-9-26(39)10-4-22/h3-14,19-21,33-34,39-41H,15-18H2,1-2H3,(H,37,42)(H,38,43)/b14-7+/t33-,34+/m0/s1
InChIKey: DROXVBRNXCRUHP-XALRPAEYSA-N
DeepSMILES: COccc/C=C/C=O)NCCcccccc6))O)))))))))))ccc6O[C@@H][C@H]5C=O)NCCcccccc6))O))))))))))cccccc6)OC)))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccc2c(c1)C(C(=O)NCCc1ccccc1)C(c1ccccc1)O2)NCCc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCC2OC(C3CCCCC3)C(C(O)NCCC3CCCCC3)C2C1)NCCC1CCCCC1
Scaffold Graph level: CC(CCCC1CCCCC1)CCC1CCC2CC(C3CCCCC3)C(C(C)CCCC3CCCCC3)C2C1
Functional groups: cOC; cO; c/C=C/C(=O)NC; CNC(C)=O
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: Lignans
NP Classifier Class: Neolignans
Synonymous chemical names:
grossamide, Grossamide
External chemical identifiers:
CID:CID_101262727; ZINC:ZINC000085826837; FDASRS:63RFK5Z1GK
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3-Benzofurancarboxamide, 2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxyphenyl)ethyl)-5-((1E)-3-((2-(4-hydroxyphenyl)ethyl)amino)-3-oxo-1-propenyl)-7-methoxy-, (2R,3R)-rel-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 624.69
Log P RDKit 4.77
Topological polar surface area (Å2) RDKit 146.58
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 28
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.22
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
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
3-Benzofurancarboxamide, 2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxyphenyl)ethyl)-5-((1E)-3-((2-(4-hydroxyphenyl)ethyl)amino)-3-oxo-1-propenyl)-7-methoxy-, (2R,3R)-rel-
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
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 0.141802
3-Benzofurancarboxamide, 2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxyphenyl)ethyl)-5-((1E)-3-((2-(4-hydroxyphenyl)ethyl)amino)-3-oxo-1-propenyl)-7-methoxy-, (2R,3R)-rel-
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 -6.60
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes