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57749-43-6

57749-43-6 structure
57749-43-6 structure
  • Name: Equisetin
  • Chemical Name: (3E,5S)-3-[[(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(E)-prop-1-enyl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-hydroxymethylidene]-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione
  • CAS Number: 57749-43-6
  • Molecular Formula: C22H31NO4
  • Molecular Weight: 373.48600
  • Catalog: Signaling Pathways Metabolic Enzyme/Protease HIV Integrase
  • Create Date: 2018-09-14 01:50:00
  • Modify Date: 2024-01-03 15:04:33
  • 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 the growth of bacterias, serves as a leading compound for the treatment of P. aeruginosa infections[4].

Name (3E,5S)-3-[[(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(E)-prop-1-enyl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-hydroxymethylidene]-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione
Synonyms Equisetin
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 the growth of bacterias, serves as a leading compound for the treatment of P. aeruginosa infections[4].
Related Catalog
References

[1]. Burmeister HR, et al. Antibiotic produced by Fusarium equiseti NRRL 5537. Antimicrob Agents Chemother. 1974 Jun;5(6):634-9.

[2]. Vesonder RF, et al. Equisetin, an antibiotic from Fusarium equiseti NRRL 5537, identified as a derivative of N-methyl-2, 4-pyrollidone. J Antibiot (Tokyo). 1979 Jul;32(7):759-61.

[3]. Lee J, et al. The hierarchy quorum sensing network in Pseudomonas aeruginosa. Protein Cell. 2015 Jan;6(1):26-41.

[4]. Zhang M, et al. Equisetin as potential quorum sensing inhibitor of Pseudomonas aeruginosa. Biotechnol Lett. 2018 May;40(5):865-870.

Density 1.187 g/cm3
Boiling Point 513.6ºC at 760 mmHg
Molecular Formula C22H31NO4
Molecular Weight 373.48600
Flash Point 264.4ºC
Exact Mass 373.22500
PSA 77.84000
LogP 2.95920
Index of Refraction 1.587

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KD7986000
CHEMICAL NAME :
Equisetin
CAS REGISTRY NUMBER :
57749-43-6
LAST UPDATED :
199403
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C22-H31-N-O4
MOLECULAR WEIGHT :
373.54

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
63 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 5,634,1974