CHEBI:136828 - 4'-O-methylxanthohumol

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ChEBI Name 4'-O-methylxanthohumol
ChEBI ID CHEBI:136828
ChEBI ASCII Name 4'-O-methylxanthohumol
Definition A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2' and 4, methoxy group at positions 4' and 6' and a prenyl group at position 3'.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H24O5
Net Charge 0
Average Mass 368.424
Monoisotopic Mass 368.16237
InChI InChI=1S/C22H24O5/c1-14(2)5-11-17-19(26-3)13-20(27-4)21(22(17)25)18(24)12-8-15-6-9-16(23)10-7-15/h5-10,12-13,23,25H,11H2,1-4H3/b12-8+
InChIKey UVBDKJHYMQEAQV-XYOKQWHBSA-N
SMILES C1(=C(CC=C(C)C)C(=C(C(=O)/C=C/C2=CC=C(C=C2)O)C(=C1)OC)O)OC
Metabolite of Species Details
Humulus lupulus var. cordifolius (NCBI:txid278022) See: PubMed
Roles Classification
Biological Role(s): EC 1.14.18.1 (tyrosinase) inhibitor
Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 4'-O-methylxanthohumol (CHEBI:136828) has functional parent trans-chalcone (CHEBI:48965)
4'-O-methylxanthohumol (CHEBI:136828) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
4'-O-methylxanthohumol (CHEBI:136828) is a aromatic ether (CHEBI:35618)
4'-O-methylxanthohumol (CHEBI:136828) is a chalcones (CHEBI:23086)
4'-O-methylxanthohumol (CHEBI:136828) is a polyphenol (CHEBI:26195)
4'-O-methylxanthohumol (CHEBI:136828) is conjugate acid of 4'-O-methylxanthohumol(1−) (CHEBI:134309)
Incoming 4'-O-methylxanthohumol(1−) (CHEBI:134309) is conjugate base of 4'-O-methylxanthohumol (CHEBI:136828)
IUPAC Name
(2E)-1-[2-hydroxy-4,6-dimethoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms Sources
3'-(isoprenyl)-2',4-dihydroxy-4',6'-dimethoxychalcone ChEBI
4'-methylxanthohumol ChEBI
Manual Xrefs Databases
C00007100 KNApSAcK
CPD-7122 MetaCyc
LMPK12120318 LIPID MAPS
View more database links
Registry Numbers Types Sources
123316-63-2 CAS Registry Number KNApSAcK
6983932 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10783982 PubMed citation Europe PMC
26162028 PubMed citation Europe PMC
Last Modified
06 February 2018