IMPPAT Phytochemical information: 
3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one

3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
Summary

SMILES: COc1c(O)cc2c(c1O)c(=O)c(co2)c1ccc(c(c1)O)O
InChI: InChI=1S/C16H12O7/c1-22-16-11(19)5-12-13(15(16)21)14(20)8(6-23-12)7-2-3-9(17)10(18)4-7/h2-6,17-19,21H,1H3
InChIKey: VYCWOMOGAIPFPW-UHFFFAOYSA-N
DeepSMILES: COccO)cccc6O))c=O)cco6))cccccc6)O))O
Scaffold Graph/Node/Bond level: O=c1c(-c2ccccc2)coc2ccccc12
Scaffold Graph/Node level: OC1C(C2CCCCC2)COC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CCC1C1CCCCC1
Functional groups: cOC; cO; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflav-2-enes
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
irilin d
External chemical identifiers:
CID:CID_10495590; ChEMBL:CHEMBL469927; ZINC:ZINC000014645991; SureChEMBL:SCHEMBL571722
Chemical structure download


3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 316.27
Log P RDKit 2.29
Topological polar surface area (Å2) RDKit 120.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 7
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 1
Shape complexity RDKit 0.06
Number of rotatable bonds RDKit 2
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


3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.535213


3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.61
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No