Structure Database (LMSD)

Common Name
Rhamnocitrin
Systematic Name
3,4',5-Trihydroxy-7-methoxyflavone
Synonyms
  • 7-Methylkaempferol
LM ID
LMPK12112589
Formula
C16H12O6
Exact Mass
Calculate m/z
300.06339
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavones and Flavonols [PK1211]

Biological Context

Rhamnocitrin is a flavonoid that has been found in C. erythrophyllum and has diverse biological activities.1,2 It is active against S. sonei, S. aureus, and M. luteus when used at concentrations ranging from 25 to 100 µg/ml.1 Rhamnocitrin scavenges DPPH radicals in a cell-free assay (IC50 = ~25 µM).2 It also inhibits LPS- and IFN-γ-induced production of nitric oxide (NO), TNF-α, and IL-6 in isolated mouse peritoneal macrophages.

This information has been provided by Cayman Chemical

References

1. Fang, S.-H., Rao, Y.K., and Tzeng, Y.-M. Anti-oxidant and inflammatory mediator’s growth inhibitory effects of compounds isolated from Phyllanthus urinaria. J. Ethnopharmacol. 116(2), 333-340 (2008).
2. Martini, N.D., Katerere, D.R.P., and Eloff, J.N. Biological activity of five antibacterial flavonoids from Combretum erythrophyllum (Combretaceae). J. Ethnopharmacol. 93(2-3), 207-212 (2004).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)
MQSZRBPYXNEFHF-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O6/c1-21-10-6-11(18)13-12(7-10)22-16(15(20)14(13)19)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=CC(O)=CC=3)=C(O)C(=O)C=2C(O)=C1

Other Databases

KEGG ID
C17059
CHEBI ID
80897
METABOLOMICS ID
FL5FCANS0001
PubChem CID
5320946
Cayman ID
36272

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 3
Aromatic Rings 3
Rotatable Bonds 2
Van der Waals Molecular Volume 247.20
Topological Polar Surface Area 100.13
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 3.49
Molar Refractivity 79.57

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Created at
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Updated at
9th Jun 2022