IMPPAT Phytochemical information: 
(E)-1-[3-[(1R,5R,6S)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(2,4-dihydroxyphenyl)prop-2-en-1-one
(E)-1-[3-[(1R,5R,6S)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(2,4-dihydroxyphenyl)prop-2-en-1-one
Summary

SMILES: CC(=CCc1c(O)ccc(c1O)C(=O)[C@@H]1[C@@H](C=C(C[C@H]1c1ccc(cc1)O)C)c1c(O)ccc(c1O)C(=O)/C=C/c1ccc(cc1O)O)C
InChI: InChI=1S/C40H38O9/c1-21(2)4-12-27-33(44)16-14-29(38(27)47)40(49)36-30(23-5-9-25(41)10-6-23)18-22(3)19-31(36)37-34(45)17-13-28(39(37)48)32(43)15-8-24-7-11-26(42)20-35(24)46/h4-11,13-17,19-20,30-31,36,41-42,44-48H,12,18H2,1-3H3/b15-8+/t30-,31+,36-/m0/s1
InChIKey: WDCSNUYKXLXPBM-NQPIAKRTSA-N
DeepSMILES: CC=CCccO)cccc6O))C=O)[C@@H][C@@H]C=CC[C@H]6cccccc6))O)))))))C)))ccO)cccc6O))C=O)/C=C/cccccc6O)))O)))))))))))))))))))))))C
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)c1cccc(C2C=CCC(c3ccccc3)C2C(=O)c2ccccc2)c1
Scaffold Graph/Node level: OC(CCC1CCCCC1)C1CCCC(C2CCCC(C3CCCCC3)C2C(O)C2CCCCC2)C1
Scaffold Graph level: CC(CCC1CCCCC1)C1CCCC(C2CCCC(C3CCCCC3)C2C(C)C2CCCCC2)C1
Functional groups: CC=C(C)C; cO; c/C=C/C(c)=O; cC(C)=O; CC(C)=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Diarylheptanoids
ClassyFire Subclass: Linear diarylheptanoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Chalcones
Synonymous chemical names:
kuwanon q
External chemical identifiers:
CID:CID_21637737; ZINC:ZINC000085991678
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(E)-1-[3-[(1R,5R,6S)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(2,4-dihydroxyphenyl)prop-2-en-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 662.74
Log P RDKit 7.75
Topological polar surface area (Å2) RDKit 175.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 40
Number of heavy atoms RDKit 49
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 32
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
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
(E)-1-[3-[(1R,5R,6S)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(2,4-dihydroxyphenyl)prop-2-en-1-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Bad
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 0.05
(E)-1-[3-[(1R,5R,6S)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(2,4-dihydroxyphenyl)prop-2-en-1-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -4.55
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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