IMPPAT Phytochemical information: 
Xanthohumol
Xanthohumol
Summary

SMILES: COc1cc(O)c(c(c1C(=O)/C=C/c1ccc(cc1)O)O)CC=C(C)C
InChI: InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
InChIKey: ORXQGKIUCDPEAJ-YRNVUSSQSA-N
DeepSMILES: COcccO)ccc6C=O)/C=C/cccccc6))O)))))))))O))CC=CC)C
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)c1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(CCC1CCCCC1)C1CCCCC1
Functional groups: cOC; cO; c/C=C/C(c)=O; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Linear 1,3-diarylpropanoids
ClassyFire Subclass: Chalcones and dihydrochalcones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Chalcones
Synonymous chemical names:
xanthohumol, Xanthohumol
External chemical identifiers:
CID:CID_639665; ChEMBL:CHEMBL253896; ChEBI:CHEBI:66331; ZINC:ZINC000005158937; FDASRS:T4467YT1NT; SureChEMBL:SCHEMBL143683; MolPort-001-740-284
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Xanthohumol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.4
Log P RDKit 4.22
Topological polar surface area (Å2) RDKit 86.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
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 17
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.19
Number of rotatable bonds RDKit 6
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 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2
Xanthohumol
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.41
Xanthohumol
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.86
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Xanthohumol
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000257497ANXA1800
ENSP00000261693SCARB1815
ENSP00000264005LCAT800
ENSP00000380252NFE2L2722
ENSP00000369050CYP1A1700
ENSP00000363965ALPL700
ENSP00000358327CASP7700
ENSP00000356438PTGS2700
ENSP00000355759PARP1700
ENSP00000351273CASP8700
ENSP00000346294S100A4824
ENSP00000332258DGAT1800
ENSP00000330237CASP9700
ENSP00000311032CASP3700
ENSP00000228841MYL2700
ENSP00000277541NOTCH1800
ENSP00000272937HES6800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.