IMPPAT Phytochemical information: 
Methyl 2-(2-methoxy-4-hydroxyphenyl)-6-methoxy-3-benzofurancarboxylate

Methyl 2-(2-methoxy-4-hydroxyphenyl)-6-methoxy-3-benzofurancarboxylate
Summary

SMILES: COC(=O)c1c(oc2c1ccc(c2)OC)c1ccc(cc1OC)O
InChI: InChI=1S/C18H16O6/c1-21-11-5-7-12-15(9-11)24-17(16(12)18(20)23-3)13-6-4-10(19)8-14(13)22-2/h4-9,19H,1-3H3
InChIKey: FFAIKFRIUGUDRP-UHFFFAOYSA-N
DeepSMILES: COC=O)ccocc5cccc6)OC))))))))cccccc6OC))))O
Scaffold Graph/Node/Bond level: c1ccc(-c2cc3ccccc3o2)cc1
Scaffold Graph/Node level: C1CCC(C2CC3CCCCC3O2)CC1
Scaffold Graph level: C1CCC(C2CC3CCCCC3C2)CC1
Functional groups: cC(=O)OC; coc; cOC; cO
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
NP Classifier Class: 2-arylbenzofurans
Synonymous chemical names:
2-(4-hydroxy-2-methoxy-phenyl)-6-methoxy-benzofuran-3-carboxylic-acid
External chemical identifiers:
CID:CID_11738939; ChEBI:CHEBI:174407; ZINC:ZINC000013340678
Chemical structure download


Methyl 2-(2-methoxy-4-hydroxyphenyl)-6-methoxy-3-benzofurancarboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 328.32
Log P RDKit 3.61
Topological polar surface area (Å2) RDKit 78.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3


Methyl 2-(2-methoxy-4-hydroxyphenyl)-6-methoxy-3-benzofurancarboxylate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.74


Methyl 2-(2-methoxy-4-hydroxyphenyl)-6-methoxy-3-benzofurancarboxylate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.87
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No