Kaempferide

Kaempferide
Names

IUPAC name 3,5,7-Trihydroxy-4′-methoxyflavone
Systematic IUPAC name 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Other names Kaempferid 4′-Methylkaempferol Kaempferol 4′-methyl ether 4′-O-Methylkaempferol
Identifiers
CAS Number	491-54-3^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:6099^N
ChEMBL	ChEMBL40919^N
ChemSpider	4444985^N
ECHA InfoCard	100.007.036
KEGG	C10098^N
PubChem CID	5281666
UNII	508XL61MPD^Y
CompTox Dashboard (EPA)	DTXSID9034155
InChI InChI=1S/C16H12O6/c1-21-10-4-2-8(3-5-10)16-15(20)14(19)13-11(18)6-9(17)7-12(13)22-16/h2-7,17-18,20H,1H3^N Key: SQFSKOYWJBQGKQ-UHFFFAOYSA-N^N InChI=1/C16H12O6/c1-21-10-4-2-8(3-5-10)16-15(20)14(19)13-11(18)6-9(17)7-12(13)22-16/h2-7,17-18,20H,1H3 Key: SQFSKOYWJBQGKQ-UHFFFAOYAC
SMILES COC1=CC=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O COC1=CC=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O
Properties
Chemical formula	C₁₆H₁₂O₆
Molar mass	300.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Kaempferide is an O-methylated flavonol, a type of chemical compound. It can be found in Kaempferia galanga (aromatic ginger). It has been noted to inhibit pancreatic cancer growth by blockading an EGFR-related pathway.^[1]

Metabolism

The enzyme kaempferol 4'-O-methyltransferase uses S-adenosyl-L-methionine and kaempferol to produce S-adenosyl-L-homocysteine and kaempferide.

Glycosides

Icariin is the tert-amyl alcohol derivative of kaempferide 3,7-O-diglycoside.

References

^ Lee, Jungwhoi; Kim, Jae Hoon (2016). "Kaempferol Inhibits Pancreatic Cancer Cell Growth and Migration through the Blockade of EGFR-Related Pathway In Vitro". PLOS ONE. 11 (5): e0155264. Bibcode:2016PLoSO..1155264L. doi:10.1371/journal.pone.0155264. PMC 4866780. PMID 27175782.

External links

Kaempferide at the HMDB

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)