Structure Database (LMSD)

Common Name
Robinetin
Systematic Name
3,7,3',4',5'-Pentahydroxyflavone
Synonyms
LM ID
LMPK12111577
Formula
C15H10O7
Exact Mass
Calculate m/z
302.042655
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View NP-MRD ID(NMR) spectrum

Classification

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

Biological Context

Robinetin is a flavonol that has been found in R. pseudacacia and has diverse biological activities.1,2,3,4,5 It inhibits NADH oxidase with an IC50 value of 19 nmol/mg of protein in isolated beef heart mitochondria.2 Robinetin scavenges DPPH radicals in a cell-free assay and inhibits glutathione S-transferase (GST; IC50 = 1.39 µM for the equine liver enzyme).3,4 It also inhibits multidrug resistance-associated protein 1 (MRP1) and MRP2 in MDCK-II cells (IC50s = 13.6 and 15 µM, respectively, for the human proteins).5

This information has been provided by Cayman Chemical

References

1. Charlesworth, E.H., and Robinson, R. Anthoxanthins. Part XIII. Synthesis of a colouring matter of Robinia pseudacacia. J. Chem. Soc. 268-270 (1933).
2. Hodnick, W.F., Duval, D.L., and Pardini, R.S. Inhibition of mitochondrial respiration and cyanide-stimulated generation of reactive oxygen species by selected flavonoids. Biochem. Pharmacol. 47(3), 573-580 (1994).
3. Hyun, J., Woo, Y., Hwang, D.-S., et al. Relationships between structures of hydroxyflavones and their antioxidative effects. Bioorg. Med. Chem. Lett. 20(18), 5510-5513 (2010).
4. Boušová, I., Hájek, J., Dršata, J., et al. Naturally occurring flavonoids as inhibitors of purified cytosolic glutathione S-transferase. Xenobiotica 42(9), 872-879 (2012).
5. van Zanden, J.J., Wortelboer, H.M., Bijlsma, S., et al. Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2. Biochem. Pharmacol. 69(4), 699-708 (2005).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
SOEDEYVDCDYMMH-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H
SMILES (Click to copy)
C1(O)=CC2OC(C3C=C(O)C(O)=C(O)C=3)=C(O)C(=O)C=2C=C1

Other Databases

KEGG ID
C10177
CHEBI ID
8876
METABOLOMICS ID
FL5F1GNS0001
PubChem CID
5281692
Cayman ID
35272
PDB ID
LKR

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 3
Aromatic Rings 3
Rotatable Bonds 1
Van der Waals Molecular Volume 238.69
Topological Polar Surface Area 131.36
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 7
logP 2.89
Molar Refractivity 76.35

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Created at
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Updated at
30th Oct 2023