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Xanthohumol

PubChem CID: 639665

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Compound Synonyms Xanthohumol, 6754-58-1, 569-83-5, Xantho-flav, 1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one, UNII-T4467YT1NT, (E/Z)-Xanthohumol, T4467YT1NT, CHEBI:66331, 2',4,4'-trihydroxy-6'-methoxy-3'-prenylchalcone, 1-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one, (2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one, Xanthohumol(Random Configuration), DTXSID00893171, (2E)-1-(2,4-DIHYDROXY-6-METHOXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE, (E)-1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, (E)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, 2-Propen-1-one, 1-(2,4-hydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-, (E)-, XanthoFlav, MFCD00210576, 2-propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-, Xanthohumol?, 2',4,4'-trihydroxy-6'-methoxy-3-prenylchalcone, 3'-(3,3-Dimethyl allyl)-2',4',4-trihydroxy-6'-methoxychalcone, 3'-[3,3-dimethyl allyl]-2',4',4-trihydroxy-6'-methoxychalcone, (2E)-1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, 2-propen-1-one, 1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-, (2E)-, Xanthohumol from hop (Humulus lupulus), Xanthohumol (Standard), XANTHOHUMOL [INCI], SCHEMBL143683, CHEMBL253896, MEGxp0_000104, Xanthohumol(RandomConfiguration), ACon1_001634, CHEBI:94745, HY-N1067A, HY-N1067R, DTXCID601323110, HMS3886H19, BCP18498, BDBM50384998, LMPK12120294, s7889, AKOS016010098, AKOS040762512, CCG-268086, DB15359, FX09701, (E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone, SMP2_000278, NCGC00180304-01, AC-31276, BS-17392, DA-68730, TS-10147, 1ST166072, CS-0159153, X0068, Q408088, BRD-K77390737-001-01-6, Q27166535, Xanthohumol, primary pharmaceutical reference standard, Xanthohumol from hop (Humulus lupulus), >=96% (HPLC), 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one, 2-Propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-, 614-078-4
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 87.0
Hydrogen Bond Donor Count 3.0
Pfizer 3 75 Rule False
Scaffold Graph Level CC(CCC1CCCCC1)C1CCCCC1
Np Classifier Class Chalcones
Deep Smiles COcccO)ccc6C=O)/C=C/cccccc6))O)))))))))O))CC=CC)C
Heavy Atom Count 26.0
Classyfire Class Linear 1,3-diarylpropanoids
Description Isolated from Humulus lupulus (hops). Xanthohumol is found in beer and alcoholic beverages.
Scaffold Graph Node Level OC(CCC1CCCCC1)C1CCCCC1
Classyfire Subclass Chalcones and dihydrochalcones
Isotope Atom Count 0.0
Molecular Complexity 514.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Uniprot Id n.a., O15530, P17252, Q04759, Q86VQ6, Q9Y6Y9, P09917, O14684, Q64669, Q8WTS6, P02766
Iupac Name (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Prediction Hob 1.0
Class Linear 1,3-diarylpropanoids
Veber Rule True
Classyfire Superclass Phenylpropanoids and polyketides
Target Id NPT1699, NPT570
Xlogp 5.1
Superclass Phenylpropanoids and polyketides
Subclass Chalcones and dihydrochalcones
Gsk 4 400 Rule False
Molecular Formula C21H22O5
Scaffold Graph Node Bond Level O=C(C=Cc1ccccc1)c1ccccc1
Prediction Swissadme 0.0
Inchi Key ORXQGKIUCDPEAJ-YRNVUSSQSA-N
Silicos It Class Moderately soluble
Fcsp3 0.1904761904761904
Logs -3.91
Rotatable Bond Count 6.0
State Solid
Logd 3.371
Synonyms 2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone, Xanthohumol, (2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one, Desmethylxanthohumol, 1-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one, xanthohumol
Substituent Name 3-prenylated chalcone, Cinnamylphenol, 2'-hydroxychalcone, Hydroxycinnamic acid or derivatives, Cinnamic acid or derivatives, Acylphloroglucinol derivative, Methoxyphenol, Phloroglucinol derivative, Benzenetriol, Acetophenone, Methoxybenzene, Aryl ketone, Styrene, Resorcinol, Phenol ether, Benzoyl, Anisole, Phenol, Alkyl aryl ether, Benzenoid, Monocyclic benzene moiety, Vinylogous acid, Alpha,beta-unsaturated ketone, Enone, Acryloyl-group, Ketone, Ether, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aromatic homomonocyclic compound
Esol Class Moderately soluble
Functional Groups CC=C(C)C, c/C=C/C(c)=O, cO, cOC
Compound Name Xanthohumol
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 354.147
Formal Charge 0.0
Monoisotopic Mass 354.147
Hydrogen Bond Acceptor Count 5.0
Molecular Weight 354.4
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 0.0
Total Bond Stereocenter Count 1.0
Molecular Framework Aromatic homomonocyclic compounds
Lipinski Rule Of 5 True
Esol -5.176930861538462
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+
Smiles CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)/C=C/C2=CC=C(C=C2)O)O)C
Nring 2.0
Np Classifier Biosynthetic Pathway Shikimates and Phenylpropanoids
Defined Bond Stereocenter Count 1.0
Egan Rule True
Taxonomy Direct Parent 3-prenylated chalcones
Np Classifier Superclass Flavonoids