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

SMILES: CC(=CCc1c(O)cc(cc1O)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(cc1)O)C
InChI: InChI=1S/C40H38O8/c1-22(2)4-14-29-35(45)20-26(21-36(29)46)39(47)37-31(25-8-12-28(42)13-9-25)18-23(3)19-32(37)38-34(44)17-15-30(40(38)48)33(43)16-7-24-5-10-27(41)11-6-24/h4-13,15-17,19-21,31-32,37,41-42,44-46,48H,14,18H2,1-3H3/b16-7+/t31-,32+,37-/m1/s1
InChIKey: MYKDNKGHXHALEF-SJIVMEQQSA-N
DeepSMILES: CC=CCccO)cccc6O)))C=O)[C@H][C@H]C=CC[C@@H]6cccccc6))O)))))))C)))ccO)cccc6O))C=O)/C=C/cccccc6))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 v
External chemical identifiers:
CID:CID_45485203; ChEMBL:CHEMBL570609; ZINC:ZINC000049694946
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(E)-1-[3-[(1S,5S,6R)-6-[3,5-dihydroxy-4-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 646.74
Log P RDKit 8.04
Topological polar surface area (Å2) RDKit 155.52
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 40
Number of heavy atoms RDKit 48
Number of heteroatoms RDKit 8
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-[(1S,5S,6R)-6-[3,5-dihydroxy-4-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)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 0.06
(E)-1-[3-[(1S,5S,6R)-6-[3,5-dihydroxy-4-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)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 -4.59
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