Structure Database (LMSD)
Common Name
Negletein
Systematic Name
Synonyms
3D model of Negletein
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Negletein is a flavonoid that has been found in S. oblonga and has diverse biological activities.1,2,3 It inhibits biofilm formation by S. aureus, B. subtilis, P. aeruginosa, and E. coli when used at a concentration of 32 µg/ml.1 Negletein induces cytotoxicity in SW460 and DLD-1 colorectal cancer cells (IC50s = 29.41 and 30.93 µM, respectively) but not HT-29 colon cancer or HepG2 hepatocellular carcinoma cells (IC50s = >40 µM for both).4 It decreases LPS-induced nitric oxide (NO) production and secreted TNF-α and IL-1β levels in J774A.1 macrophages when used at a concentration of 0.01 µM.2 Negletein (10 µM), alone and in combination with nerve growth factor (NGF), increases neurite outgrowths, levels of growth-associated protein 43 (GAP43) and decreases serum deprivation-induced death in PC12 adrenal medulla cells.3
This information has been provided by Cayman Chemical
References
1. Rajendran, N., Subramaniam, S., Christena, L.R., et al. Antimicrobial flavonoids isolated from Indian medicinal plant Scutellaria oblonga inhibit biofilms formed by common food pathogens. Nat. Prod. Res. 30(17), 2002-2006 (2016).
2. Wang, S.-H., Chen, C.-H., Lo, C.-Y., et al. Synthesis and biological evaluation of novel 7-O-lipophilic substituted baicalein derivatives as potential anticancer agents. Med. Chem. Comm. 6, 1864-1873 (2015).
3. Phan, C.-W., Sabaratnam, V., Bovicelli, P., et al. Negletein as a neuroprotectant enhances the action of nerve growth factor and induces neurite outgrowth in PC12 cells. Biofactors 42(6), 591-599 (2016).
4. Singh, B., Sidiq, T., Joshi, P., et al. Anti-inflammatory and immunomodulatory flavones from Actinocarya tibetica Benth. Nat. Prod. Res. 27(23), 2227-2230 (2013).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
ZTHLHHDJRXJGRX-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O5/c1-20-13-8-12-14(16(19)15(13)18)10(17)7-11(21-12)9-5-3-2-4-6-9/h2-8,18-19H,1H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=CC=CC=3)=CC(=O)C=2C(O)=C1O
Other Databases
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
NP-MRD ID(NMR)
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
3
Aromatic Rings
3
Rotatable Bonds
2
Van der Waals Molecular Volume
238.41
Topological Polar Surface Area
79.90
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
5
logP
3.78
Molar Refractivity
77.91
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Updated at
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