Structure Database (LMSD)

Common Name
Butein
Systematic Name
Synonyms
LM ID
LMPK12120111
Formula
C15H12O5
Exact Mass
Calculate m/z
272.068475
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]
Chalcones and dihydrochalcones [PK1212]

Biological Context

Butein is a plant polyphenol that is classified as a chalcone, due to the propenone linkage between the phenol groups. Like other polyphenols, butein is a potent antioxidant and affects the numerous pathways modulated by oxidant tone, including inflammation, cancer, and immune response.1,2,3 It inhibits 5-lipoxygenase, the enoyl-acyl-carrier protein reductase of P. falciparum, angiotensin-converting enzyme, and Src kinase (IC50 or Ki values of 0.01, 2.97, 0.73, and 65 μM, respectively).4,5,6,7 Butein is also a sirtuin activator, increasing trichostatin A -insensitive deacetylase activity.8,9

This information has been provided by Cayman Chemical

References

1. McArdle, B.M., Campitelli, M.R., and Quinn, R.J. A common protein fold topology shared by flavonoid biosynthetic enzymes and therapeutic targets. J. Nat. Prod. 69(1), 14-17 (2006).
2. Sharma, S.K., Parasuraman, P., Kumar, G., et al. Green tea catechins potentiate triclosan binding to enoyl-ACP reductase from Plasmodium falciparum (PfENR). J. Med. Chem. 50(4), 765-775 (2007).
3. Yadav, V.R., Prasad, S., Sung, B., et al. The role of chalcones in suppression of NF-κB-mediated inflammation and cancer. Int. Immunopharmacol. 11(3), 295-309 (2011).
4. Sogawa, S., Nihro, Y., Ueda, H., et al. 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors. J. Med. Chem. 36(24), 3904-3909 (1993).
5. Lee, E.H., Song, D.G., Lee, J.Y., et al. Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts. Biol. Pharm. Bull. 31(8), 1626-1630 (2008).
6. Gupta, S.C., Kim, J.H., Prasad, S., et al. Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals. Cancer Metastasis Rev. 29(3), 405-434 (2010).
7. Bonesi, M., Loizzo, M.R., Statti, G.A., et al. The synthesis and angiotensin converting enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives. Bioorg. Med. Chem. Lett. 20(6), 1990-1993 (2010).
8. Szczepankiewicz, B.G., and Ng, P.Y. Sirtuin modulators: Targets for metabolic diseases and beyond. Curr. Top. Med. Chem. 8(17), 1533-1544 (2008).
9. Wood, J.G., Rogina, B., Lavu, S., et al. Sirtuin activators mimic caloric restriction and delay ageing in metazoans. Nature 430, 686-689 (2004).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
AYMYWHCQALZEGT-ORCRQEGFSA-N
InChi (Click to copy)
InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+
SMILES (Click to copy)
C1(O)=CC=C(C(=O)/C=C/C2C=CC(O)=C(O)C=2)C(O)=C1

Other Databases

Wikipedia
Butein
KEGG ID
C08578
CHEBI ID
3237
METABOLOMICS ID
FL1C1CNS0001
PubChem CID
5281222
Cayman ID
15371
PDB ID
BUN

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 2
Aromatic Rings 2
Rotatable Bonds 3
Van der Waals Molecular Volume 244.37
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 2.41
Molar Refractivity 72.91

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