IMPPAT Phytochemical information: 
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-12,12-dimethyl-8a,9,10,11,12a,13-hexahydro-8H-chromeno[7,8-c][2]benzoxepin-4-one
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-12,12-dimethyl-8a,9,10,11,12a,13-hexahydro-8H-chromeno[7,8-c][2]benzoxepin-4-one
Summary

SMILES: COc1cc(ccc1O)c1cc(=O)c2c(o1)c1CC3C(COc1cc2O)CCCC3(C)C
InChI: InChI=1S/C26H28O6/c1-26(2)8-4-5-15-13-31-22-12-20(29)24-19(28)11-21(32-25(24)16(22)10-17(15)26)14-6-7-18(27)23(9-14)30-3/h6-7,9,11-12,15,17,27,29H,4-5,8,10,13H2,1-3H3
InChIKey: BEKKBGJECYLADF-UHFFFAOYSA-N
DeepSMILES: COcccccc6O))))ccc=O)cco6)cCCCCOc7cc%11O))))))CCCC6C)C
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2c3c(ccc12)OCC1CCCCC1C3
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2C1CCC1OCC3CCCCC3CC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2C1CCC1CCC3CCCCC3CC12
Functional groups: cOC; cO; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
Ugonin B, ugonin b
External chemical identifiers:
CID:CID_5315114; SureChEMBL:SCHEMBL19665246
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-12,12-dimethyl-8a,9,10,11,12a,13-hexahydro-8H-chromeno[7,8-c][2]benzoxepin-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 436.5
Log P RDKit 5.26
Topological polar surface area (Å2) RDKit 89.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-12,12-dimethyl-8a,9,10,11,12a,13-hexahydro-8H-chromeno[7,8-c][2]benzoxepin-4-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.57
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-12,12-dimethyl-8a,9,10,11,12a,13-hexahydro-8H-chromeno[7,8-c][2]benzoxepin-4-one
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 High
Log Kp (Skin permeation, cm/s) SwissADME -4.76
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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