hymeglusin

Names

[ Name ]:
hymeglusin

[Synonym ]:
(2E,4E,7R)-11-[(2R,3R)-3-(Hydroxymethyl)-4-oxo-2-oxetanyl]-3,5,7-trimethyl-2,4-undecadienoic acid
2,4-Undecadienoic acid, 11-[(2R,3R)-3-(hydroxymethyl)-4-oxo-2-oxetanyl]-3,5,7-trimethyl-, (2E,4E,7R)-
hymeglusin

Biological Activity

[Description]:

Hymeglusin, as a fungal β-lactone antibiotic, is a HMG-CoA synthase inhibitor (IC50 = 0.12 μM). Hymeglusin covalently modifies the active Cys129 residue of the enzyme[2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Research Areas >> Metabolic Disease

[Target]

IC50: 1.2 μM (HMG-CoA)[2][3]

[In Vitro]

Hymeglusin inhibits dengue type 2 (DEN-2) New Guinea C (NGC) live virus replication in K562 cells. The therapeutic index (CC50/IC50) of Hymeglusin is 11. The EC50 of Hymeglusin in K562 cells is 4.5 μM[1].

[In Vivo]

At a dose of 25 mg/kg, hymeglusin inhibits cholesterol biosynthesis in rats by 45 %[2].

[References]

[1]. Rothwell C, et al. Cholesterol biosynthesis modulation regulates dengue viral replication. Virology. 2009 Jun 20;389(1-2):18-19.

[2]. Greenspan MD, et al. Inhibition of hydroxymethylglutaryl-coenzyme A synthase by L-659,699. Proc Natl Acad Sci U S A. 1987 Nov;84(21):7488-92.

[3]. Tomoda H, et al. Binding site for fungal beta-lactone hymeglusin on cytosolic 3-hydroxy-3-methylglutaryl coenzyme A synthase. Biochim Biophys Acta. 2004 Feb 27;1636(1):22-8.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
516.6±15.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₈H₂₈O₅

[ Molecular Weight ]:
324.412

[ Flash Point ]:
181.3±13.9 °C

[ Exact Mass ]:
324.193665

[ PSA ]:
83.83000

[ LogP ]:
2.59

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.510

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YQ1170000

CHEMICAL NAME :: 2,4-Undecadienoic acid, 11-(3-(hydroxymethyl)-4-oxo-2-oxetanyl)-3,5,7-trimeth yl-, (2R-(2-alpha(2E,4E,7R*),3-beta))-

CAS REGISTRY NUMBER :: 29066-42-0

LAST UPDATED :: 199406

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C18-H28-O5

MOLECULAR WEIGHT :: 324.46

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 41,247,1988

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 41,247,1988

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
YQ1170000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Characterization of peroxisomal 3-hydroxy-3-methylglutaryl coenzyme A reductase in UT2 cells: sterol biosynthesis, phosphorylation, degradation, and statin inhibition.

Biochemistry 39(1) , 237-47, (2000)

We have previously identified a CHO cell line (UT2 cells) that expresses only one 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase protein which is localized exclusively in peroxisomes [Engfe...

Binding site for fungal beta-lactone hymeglusin on cytosolic 3-hydroxy-3-methylglutaryl coenzyme A synthase.

Biochim. Biophys. Acta 1636(1) , 22-8, (2004)

We studied the molecular mechanism through which the fungal beta-lactone, hymeglusin, potently and specifically inhibits 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) synthase. [(14)C]Hymeglusin covalently...

Biosynthesis of antibiotic 1233A (F-244) and preparation of [14C]1233A.

J. Antibiot. 45(4) , 563-7, (1992)

The biosynthesis of antibiotic 1233A (F-244) was studied by feeding 13C-labeled precursors to the producing organism, Scopulariopsis sp. F-244. 13C NMR spectroscopy established that 1233A is derived f...

Related Compounds

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