kaempferol 3,7-di-O-alpha-L-rhamnoside (CHEBI:68883)

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CHEBI:68883 - kaempferol 3,7-di-O-α-L-rhamnoside

ChEBI ID	CHEBI:68883
ChEBI Name	kaempferol 3,7-di-O-α-L-rhamnoside
Stars
ASCII Name	kaempferol 3,7-di-O-alpha-L-rhamnoside
Definition	A glycosyloxyflavone that is kaempferol attached to α-L-rhamnopyranosyl residues at positions 3 and 7 respectively via glycosidic linkages. It has been isolated from the aerial parts of Vicia faba and Lotus edulis.
Secondary ChEBI ID	CHEBI:133236
Last Modified	15 March 2018
Submitter	Keeva
Downloads	Molfile

Formula	C27H30O14
Net Charge	0
Average Mass	578.523
Monoisotopic Mass	578.16356
SMILES	C[C@@H]1O[C@@H](Oc2cc(O)c3c(=O)c(O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)c(-c4ccc(O)cc4)oc3c2)[C@H](O)[C@H](O)[C@H]1O
InChI	InChI=1S/C27H30O14/c1-9-17(30)20(33)22(35)26(37-9)39-13-7-14(29)16-15(8-13)40-24(11-3-5-12(28)6-4-11)25(19(16)32)41-27-23(36)21(34)18(31)10(2)38-27/h3-10,17-18,20-23,26-31,33-36H,1-2H3/t9-,10-,17-,18-,20+,21+,22+,23+,26-,27-/m0/s1
InChIKey	PUPKKEQDLNREIM-QNSQPKOQSA-N

Wikipedia

Species of Metabolite	Component	Source	Comments
Lotus edulis (ncbitaxon:181270)
	leaf (BTO:0000713)	PubMed (22014228)	Methanolic extract of leaves and branches
	branch (BTO:0000148)	PubMed (22014228)	Methanolic extract of leaves and branches
Vicia faba (ncbitaxon:3906)
	leaf (BTO:0000713)	PubMed (22014228)	Methanolic extract of leaves and branches
	branch (BTO:0000148)	PubMed (22014228)	Methanolic extract of leaves and branches
Arabidopsis thaliana (ncbitaxon:3702)
	-	PubMed (27432888)
	-	MetaboLights (MTBLS129)
Hedyotis verticillata (ncbitaxon:462690)	leaf (BTO:0000713)	PubMed (7938277)
Sedum dendroideum (ncbitaxon:1239900)	leaf (BTO:0000713)	PubMed (24817132)
Bauhinia forficata (ncbitaxon:413686)	leaf (BTO:0000713)	PubMed (15501431)
Siraitia grosvenorii (ncbitaxon:190515)	fruit (BTO:0000486)	PubMed (16268506)
Hibiscus cannabinus (ncbitaxon:229543)	leaf (BTO:0000713)	PubMed (21512441)
Corynandra viscosa (ncbitaxon:190804)	leaf (BTO:0000713)	PubMed (28135851)
Justicia spicigera (ncbitaxon:141992)	-	PubMed (23211658)
Dryopteris crassirhizoma (ncbitaxon:97234)	-	PubMed (24013342)

Roles Classification

Biological Roles:

immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system.

apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.

plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

Applications:

hypoglycemic agent A drug which lowers the blood glucose level.

bone density conservation agent An agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis.

immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system.

anti-inflammatory agent Any compound that has anti-inflammatory effects.

antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.

ChEBI Ontology

Outgoing Relation(s)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) has functional parent kaempferol (CHEBI:28499)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) has role anti-inflammatory agent (CHEBI:67079)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) has role antidepressant (CHEBI:35469)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) has role antineoplastic agent (CHEBI:35610)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) has role apoptosis inducer (CHEBI:68495)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) has role bone density conservation agent (CHEBI:50646)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) has role hypoglycemic agent (CHEBI:35526)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) has role immunomodulator (CHEBI:50846)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) has role plant metabolite (CHEBI:76924)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) is a dihydroxyflavone (CHEBI:38686)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) is a glycosyloxyflavone (CHEBI:50018)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) is a monosaccharide derivative (CHEBI:63367)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) is a polyphenol (CHEBI:26195)
	kaempferol 3,7-di-O-α-L-rhamnoside (CHEBI:68883) is a α-L-rhamnoside (CHEBI:27848)

IUPAC Names
3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-deoxy-α-L-mannopyranoside
7-[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-deoxy-α-L-mannopyranoside

Synonyms	Source
3,7-bis((6-deoxy-α-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChemIDplus
lespedin	ChemIDplus
kaempferol 3,7-dirhamnoside	ChemIDplus
kaempferol 3,7-bisrhamnoside	ChemIDplus
kaempferitrin	ChemIDplus
lespenephryl	ChemIDplus

Manual Xrefs	Databases
LMPK12111865	LIPID MAPS
Kaempferitrin	Wikipedia
C16981	KEGG COMPOUND
kaempferol-3-rhamnoside-7-rhamnoside	MetaCyc
HMDB0037438	HMDB

Registry Numbers	Sources
Reaxys:73958	Reaxys
CAS:482-38-2	KEGG COMPOUND
CAS:482-38-2	ChemIDplus

Citations