KAEMPFEROL-3-ALPHA-L-RHAMNOPYRANOSYL(1-6)-BETA-D-GLUCOPYRANOSIDE

Structure

2D structure of KAEMPFEROL-3-ALPHA-L-RHAMNOPYRANOSYL(1-6)-BETA-D-GLUCOPYRANOSIDE
2D structure
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3D model

Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 5318767

Names and identifiers

Name

KAEMPFEROL-3-ALPHA-L-RHAMNOPYRANOSYL(1-6)-BETA-D-GLUCOPYRANOSIDE

Also reported as

KAEMPFEROL-3-O-BETA-D-RUTINOSIDE; KAEMPFEROL-3-O-RHAMNOSYL-GLUCOSIDE; KAEMPFEROL-3-RHAMNOGLUCOSIDE; NICOTIFLORIN

IUPAC name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=C(C3=O)C(=CC(=C4)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)O

General information

Molecular formula

C27H30O15

Molecular weight

594.52 g/mol

Monoisotopic mass

594.1585 Da

Classification

Pathway:
Superclass:
Class:
Glycoside:
Yes

Chemical classification: NPClassifier (Kim et al., 2021)

Plants with the compound

Plant Plant part Amount Reference
Agrimonia eupatoria L. subsp. eupatoria aerial parts -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Arctium minus (Hill) Bernh. - -
Saleh, N.A.M., Bohm, B.A. (1971). Flavonoids of Arctium minus (Compositae). Experientia, 27, 1494 doi:10.1007/bf02154314
Artemisia alba Turra root -
Marco, J.A., Barbera, O., Sanchez-parareda, J. (1987). Flavonol and coumarin glycosides from Artemisia incanescens. J Nat Prod, 50(4), 774-775 doi:10.1021/np50052a045
Astragalus monspessulanus L. subsp. monspessulanus - -
Chemical composition and antioxidant activity of Astragalus monspessulanus L. growing in semiarid areas of Algeria Flavoalkaloids and Flavonoids from Astragalus monspessulanus
Bryonia dioica Jacq. pollen -
Imperato, F. (1980). Five plants of the family Cucurbitaceae with flavonoid patterns of pollens different from those of corresponding stigmas. Experientia, 36, 1136-1137 doi:10.1007/bf01976084
Equisetum telmateia Ehrh. aerial parts -
Veit, M., Beckert, C., Hohne, C., Bauer, K., Geiger, H. (1995). Interspecific and intraspecific variation of phenolics in the genus Equisetum subgenus Equisetum. Phytochemistry, 38(4), 881-891 doi:10.1016/0031-9422(94)00658-g
Eupatorium cannabinum L. subsp. cannabinum - -
Aquino, R., D'agostino, M., Domestico, M., Senatore, F., Schettino, O. (1988). Flavonoid glycosides from Eupatorium cannabinum subsp. cannabinum. Fitoterapia, 59(3), 236-238
Eupatorium cannabinum L. subsp. cannabinum aerial parts -
Elema, E.T., Schripsema, J., Malingre, T.M. (1989). Flavones and flavonol glycosides from Eupatorium cannabinum L. Pharm Weekbl(Sci Ed), 11(5), 161-164 doi:10.1007/bf01959464
Fallopia convolvulus (L.) Á.Löve leaf -
Kim, M.H., Park, J.H., Park, C.W. (2000). Flavonoid chemistry of Fallopia section fallopia (Polygonaceae). Biochem Syst Ecol, 28(5), 433-441 doi:10.1016/s0305-1978(99)00084-8
Hedera helix L. subsp. helix aerial parts -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Humulus lupulus L. fruit -
CRC Handbook of Medicinal Herbs and/or CRC Handbook of Proximate Analyses
Humulus lupulus L. fruit -
List, P.H. and Horhammer, L., Hager's Handbuch der Pharmazeutischen Praxis, Vols. 2-6, Springer-Verlag, Berlin, 1969-1979.
Larix decidua Mill. leaf -
Niemann, G.J., Baas, W.J. (1978). Phenolics from Larix needles. xiv. flavonoids and phenolic glucosides and ester of L. decidua. Z Naturforsch Ser C, 33, 780 doi:10.1515/znc-1978-9-1030
Lotus corniculatus L. leaf -
Reynaud, J., Jay, M., Raynaud, J. (1982). Flavonoid glycosides of Lotus corniculatus (Leguminosae). Phytochemistry, 21, 2604-2605 doi:10.1016/0031-9422(82)85271-0
Parietaria officinalis L. - -
Circosta, C., Limardi, F., Occhiuto, F. (1992). Antibronchospastic activity of flavonol glycosides of different extracts from Parietaria officinalis L. Riv Ital Eppos, 3(7), 42-48
Parietaria officinalis L. flower -
Budzianowski, J., Skrzypczak, L., Walkowiak, D. (1985). Flavonoids of Parietaria officinalis. J Nat Prod, 48(2), 336-337 doi:10.1021/np50038a033
Primula veris L. subsp. columnae (Ten.) Maire & Petitm. flower -
Karl, C., Muller, G., Pedersen, P.A. (1981). Flavonoids in the flowers of Primula officinalis. Planta Med, 41, 96-99
Pteridium aquilinum (L.) Kuhn subsp. aquilinum - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Pyrus communis L. subsp. pyraster (L.) Ehrh. - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Solidago virgaurea L. subsp. virgaurea flower -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Urtica dioica L. flower 4000 ppm
Jim Duke's personal files.
Vicia sativa L. aerial parts -
Gamal-eldeen, A.M., Kawashty, S.A., Ibrahim, L.F., Shabana, M.M., El-negoumy, S.I. (2004). Evaluation of antioxidant, anti-inflammatory, and antinociceptive properties of aerial parts of Vicia sativa and its flavonoids J Nat Remedies, 4(1), 81-96
Vicia segetalis Thuill. aerial parts -
Gamal-eldeen, A.M., Kawashty, S.A., Ibrahim, L.F., Shabana, M.M., El-negoumy, S.I. (2004). Evaluation of antioxidant, anti-inflammatory, and antinociceptive properties of aerial parts of Vicia sativa and its flavonoids J Nat Remedies, 4(1), 81-96
Vitis ×instabilis Ardenghi, Galasso, Banfi & Lastrucci leaf -
Moore, M.O., Giannasi, D.E. (1987). Foliar flavonoids of selected Vitis taxa in the southeastern united states. Biochem Syst Ecol, 15(1), 79-83 doi:10.1016/0305-1978(87)90085-8