Equisetin
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Equisetin
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CAS No:
57749-43-6
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Formula:
C22H31NO4
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Chemical Name:
Equisetin
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Synonyms:
2,4-Pyrrolidinedione,5-(hydroxymethyl)-3-[hydroxy[(1S,2R,4aS,6R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-1,6-dimethyl-2-(1E)-1-propen-1-yl-1-naphthalenyl]methylene]-1-methyl-,(3E,5S)-;2,4-Pyrrolidinedione,5-(hydroxymethyl)-3-[hydroxy[1,2,4a,5,6,7,8,8a-octahydro-1,6-dimethyl-2-(1-propenyl)-1-naphthalenyl]methylene]-1-methyl-,[1S-[1α[E(R*)],2α(E),4aβ,6α,8aα]]-;2,4-Pyrrolidinedione,5-(hydroxymethyl)-3-[hydroxy[(1S,2R,4aS,6R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-1,6-dimethyl-2-(1E)-1-propenyl-1-naphthalenyl]methylene]-1-methyl-,(3E,5S)-;(3E,5S)-5-(Hydroxymethyl)-3-[hydroxy[(1S,2R,4aS,6R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-1,6-dimethyl-2-(1E)-1-propen-1-yl-1-naphthalenyl]methylene]-1-methyl-2,4-pyrrolidinedione;Equisetin;(-)-Equisetin
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CAS No:
Description
Equisetin is an N-methylserine-derived acyl tetramic acid isolated from a terrestrial fungus Fusarium equiseti NRRL 5537[1]. Equisetin is a tetramate-containing natural product with antibiotic and cytotoxic activity[2]. Equisetin inhibits the growth of Gram-positive bacteria and HIV-1 integrase activity but shows no activity against Gram-negative bacteria[3]. Equisetin is a Quorum-sensing inhibitor (QSI) that attenuates QS-regulated virulence phenotypes in P. aeruginosa without affecting
Equisetin is a member of the class of tetramic acids that is trichosetin in which the hydrogen attached to the lactam nitrogen has been replaced by a methyl group. It is produced by the filamentous fungus Fusarium heterosporum. It has a role as an antibacterial agent, a quorum sensing inhibitor, a HIV-1 integrase inhibitor and a fungal metabolite. It is an enol, a member of octahydronaphthalenes, a primary alcohol and a member of tetramic acids. It derives from a trichosetin. It is a conjugate acid of an equisetin(1-).
Equisetin Use and Manufacturing
The tetramic acid, equisetin, is produced by a number of species of Fusarium. Interest in equisetin emerged with reports of its inhibitory activity against HIV-1 integrase in vitro that was mechanistically distinct from previously described inhibitors. Equisetin inhibits 3' end-processing and strand transfer, as well as disintegration catalysed by either the full-length enzyme or the truncated integrase core.
Computed Properties
Molecular Weight:373.5
XLogP3:4.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:373.22530847
Monoisotopic Mass:373.22530847
Topological Polar Surface Area:77.8
Heavy Atom Count:27
Complexity:722
Defined Atom Stereocenter Count:6
Defined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes