| Identification | Back Directory | [Name]
Xanthohumol D | [CAS]
274675-25-1 | [Synonyms]
Xanthohumol D
2-Propen-1-one,1-[2,4-dihydroxy-3-(2-hydroxy-3-methyl-3-buten-1-yl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)-,(2E)- | [Molecular Formula]
C21H22O6 | [MOL File]
274675-25-1.mol | [Molecular Weight]
370.4 |
| Chemical Properties | Back Directory | [Boiling point ]
624.2±55.0 °C(Predicted) | [density ]
1.303±0.06 g/cm3(Predicted) | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
powder | [pka]
7.13±0.50(Predicted) | [color ]
Yellow | [InChI]
InChI=1S/C21H22O6/c1-12(2)17(24)10-15-18(25)11-19(27-3)20(21(15)26)16(23)9-6-13-4-7-14(22)8-5-13/h4-9,11,17,22,24-26H,1,10H2,2-3H3/b9-6+ | [InChIKey]
IIWLGOCXDBSFCM-RMKNXTFCSA-N | [SMILES]
C(C1=C(OC)C=C(O)C(CC(O)C(C)=C)=C1O)(=O)/C=C/C1=CC=C(O)C=C1 |
| Hazard Information | Back Directory | [Uses]
Xanthohumol D, isolated from hops, is an inhibitor of quinone reductase-2 (QR-2) with the IC50 value of 110 μM, and binds to the active site of QR-2. Xanthohumol D shows antiproliferative activity on human cancer cell lines in vitro[1][2]. | [Definition]
ChEBI:Xanthohumol D is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a 2-hydroxy-3-methylbut-3-en-1-yl group at position 3'. It has been isolated as a racemate from Humulus lupulus and has been shown to exhibit inhibitory activity against NO production. It has a role as a metabolite and an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is a member of chalcones, a polyphenol, an aromatic ether and a secondary alcohol. | [target]
IFN-γ | NO | [References]
[1] Choi Y, et al. Screening natural products for inhibitors of quinone reductase-2 using ultrafiltration LC-MS. Anal Chem. 2011 Feb 1;83(3):1048-52. DOI:10.1021/ac1028424
[2] Tronina T, et al. Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro. Bioorg Med Chem. 2013 Apr 1;21(7):2001-6. DOI:10.1016/j.bmc.2013.01.026 |
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