5'-Methoxyhydnocarpin

5'-Methoxyhydnocarpin (5′-MHC) is a chemical compound that has been isolated from Berberis^[1] and Hydnocarpus wightianus.^[2]

5'-Methoxyhydnocarpin

Names
IUPAC name (5′′R,6′′R)-5,7-Dihydroxy-6′′-(4-hydroxy-3-methoxyphenyl)-5′′-(hydroxymethyl)-5′-methoxy-5′′,6′′-dihydro[1,4]dioxino[2′′,3′′:3′,4′]flavone
Systematic IUPAC name 5,7-Dihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-8-methoxy-2,3-dihydro-1,4-benzodioxin-6-yl]-4H-1-benzopyran-4-one
Other names 5′-MHC
Identifiers
CAS Number	54431-77-5^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:69451
ChEMBL	ChEMBL328060
ChemSpider	4445172
KEGG	C11162
PubChem CID	5281879
InChI InChI=1S/C26H22O10/c1-32-19-5-12(3-4-15(19)29)25-23(11-27)36-26-21(33-2)6-13(7-22(26)35-25)18-10-17(31)24-16(30)8-14(28)9-20(24)34-18/h3-10,23,25,27-30H,11H2,1-2H3/t23-,25-/m1/s1 Key: NIOAGUZTTGFPGK-ILBGXUMGSA-N InChI=1/C26H22O10/c1-32-19-5-12(3-4-15(19)29)25-23(11-27)36-26-21(33-2)6-13(7-22(26)35-25)18-10-17(31)24-16(30)8-14(28)9-20(24)34-18/h3-10,23,25,27-30H,11H2,1-2H3/t23-,25-/m1/s1 Key: NIOAGUZTTGFPGK-ILBGXUMGBF
SMILES COC1=CC(=CC2=C1O[C@@H]([C@H](O2)C3=CC(=C(C=C3)O)OC)CO)C4=CC(=O)C5=C(C=C(C=C5O4)O)O
Properties
Chemical formula	C26H22O10
Molar mass	494.452 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5′-MHC potentiates the antimicrobial effect of berberine in vitro.^[1]

References

1. Stermitz, F. R.; Lorenz, P; Tawara, J. N.; Zenewicz, L. A.; Lewis, K. (February 15, 2000). "Synergy in a medicinal plant: antimicrobial action of berberine potentiated by 5'-methoxyhydnocarpin, a multidrug pump inhibitor". Proceedings of the National Academy of Sciences. 97 (4). National Academy of Sciences: 1433–1437. Bibcode:2000PNAS...97.1433S. doi:10.1073/pnas.030540597. ISSN 1091-6490. PMC 26451. PMID 10677479.
2. Williams, Cheryll (2013). Medicinal Plants in Australia Volume 4: An Antipodean Apothecary. Rosenberg Publishing. p. 171. ISBN 978-1-925078-08-4.