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CHEBI:66027 - (5R)-5-hydroxy-7-(4''-hydroxy-3''-methoxyphenyl)-1-phenyl-3-heptanone

ChEBI IDCHEBI:66027
ChEBI Name(5R)-5-hydroxy-7-(4''-hydroxy-3''-methoxyphenyl)-1-phenyl-3-heptanone
Stars
ASCII Name(5R)-5-hydroxy-7-(4''-hydroxy-3''-methoxyphenyl)-1-phenyl-3-heptanone
DefinitionA β-hydroxy ketone that is (5R)-5-hydroxyheptan-3-one substituted by a phenyl group at position 1 and a 4-hydroxy-3-methoxyphenyl moiety at position 7. Isolated from Alpinia officinarum, it exhibits antiviral activity against influenza virus.
Last Modified7 April 2017
DownloadsMolfile
FormulaC20H24O4
Net Charge0
Average Mass328.408
Monoisotopic Mass328.16746
SMILESCOc1cc(CC[C@@H](O)CC(=O)CCc2ccccc2)ccc1O
InChIInChI=1S/C20H24O4/c1-24-20-13-16(9-12-19(20)23)8-11-18(22)14-17(21)10-7-15-5-3-2-4-6-15/h2-6,9,12-13,18,22-23H,7-8,10-11,14H2,1H3/t18-/m1/s1
InChIKeyJHJPDDBIHSFERA-GOSISDBHSA-N
Species of MetaboliteComponentSourceComments
Alpinia officinarum (ncbitaxon:199623)
root (BTO:0001188) PubMed (731398)
rhizome (BTO:0001181) PubMed (731398)
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor  An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.
Application:
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor  An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.
ChEBI Ontology
Outgoing Relation(s)
(5R)-5-hydroxy-7-(4''-hydroxy-3''-methoxyphenyl)-1-phenyl-3-heptanone (CHEBI:66027) has role EC 3.2.1.18 (exo-α-sialidase) inhibitor (CHEBI:52425)
(5R)-5-hydroxy-7-(4''-hydroxy-3''-methoxyphenyl)-1-phenyl-3-heptanone (CHEBI:66027) has role plant metabolite (CHEBI:76924)
(5R)-5-hydroxy-7-(4''-hydroxy-3''-methoxyphenyl)-1-phenyl-3-heptanone (CHEBI:66027) is a guaiacols (CHEBI:134251)
(5R)-5-hydroxy-7-(4''-hydroxy-3''-methoxyphenyl)-1-phenyl-3-heptanone (CHEBI:66027) is a β-hydroxy ketone (CHEBI:55380)
IUPAC Name 
(5R)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-phenylheptan-3-one
Registry NumbersSources
Reaxys:5761856Reaxys
CAS:68622-73-1ChemIDplus
Citations