147444-03-9

147444-03-9 structure

Name: Pyripyropene A
Chemical Name: pyripyropene A
CAS Number: 147444-03-9
Molecular Formula: C₃₁H₃₇NO₁₀
Molecular Weight: 583.626
Catalog: Research Areas Cardiovascular Disease
Create Date: 2018-04-03 08:00:00
Modify Date: 2024-01-09 21:54:44
Pyripyropene A is a potent and selective sterol O-acyltransferase 2 (SOAT2)/acyl-coenzyme A:cholesterol acyltransferase 2 (ACAT2) inhibitor, with an IC50 of 0.07 µM. Pyripyropene A attenuates hypercholesterolemia and atherosclerosis in vivo[1][2][3][4].

Name	pyripyropene A
Synonyms	Homopurine 1,3,5,7-Tetraazanaphthalene (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-(Acetoxymethyl)-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromene-3,6-diyl diacetate (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-(Acetoxymethyl)-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromene-3,6-diyl diacetate 2H,11H-Naphtho[2,1-b]pyrano[3,4-e]pyran-11-one, 3,6-bis(acetyloxy)-4-[(acetyloxy)methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-9-(3-pyridinyl)-, (3S,4R,4aR,6S,6aS,12R,12aS,12bS)- pyripropen A Pyrimidopyrimidin

Description	Pyripyropene A is a potent and selective sterol O-acyltransferase 2 (SOAT2)/acyl-coenzyme A:cholesterol acyltransferase 2 (ACAT2) inhibitor, with an IC50 of 0.07 µM. Pyripyropene A attenuates hypercholesterolemia and atherosclerosis in vivo[1][2][3][4].
Related Catalog	Research Areas >> Cardiovascular Disease Research Areas >> Infection Research Areas >> Inflammation/Immunology
Target	IC50: 0.07 µM (ACAT2)[1]
In Vitro	Pyripyropene A (0-100 µM; 72 hours) exhibits anti-proliferative activity against HUVECs, and with an IC50 value of 1.8 µM[1]. Pyripyropene A (10 µM ; 24 hours) inhibits VEGF (20 ng/ml)-induced migration and tubular formation of HUVECs in dose-dependent fashion[1]. Pyripyropene A do not show growth inhibitory effects against KB3-1, K562 and Neuro2A cells[1]. Cell Proliferation Assay[1] Cell Line: HUVECs Concentration: 0-100 µM Incubation Time: 72 hours Result: Exhibited anti-proliferative activity against HUVECs with an IC50 value of 1.8 µM.
In Vivo	Pyripyropene A (10-50 mg/kg per day; p.o; 12 weeks) reduces the levels of plasma cholesterol, very-low-density lipoprotein (VLDL), and low-density lipoprotein (LDL) and hepatic cholesterol content in apolipoprotein E-knockout mice. And Pyripyropene A-treated mice display reduction of atherogenic lesion areas in the aortae and heart[3]. Pyripyropene A inhibits the hepatic e acyl–coenzyme A:cholesterol acyltransferase 2 (ACAT2) activity in vivo[3]. Pyripyropene A displays a half-life (t1/2) of 0.693/λ, where λ represented the terminal slope of the log-linear portion of concentration time profile[4]. Animal Model: Male C57BL/6 mice[2] Dosage: 0 mg/kg, 1 mg/kg, 10 mg/kg, 50 mg/kg, 100 mg/kg Administration: Oral administration; daily; for 12 weeks Result: Reduced atherogenic lesion areas in the aortae and heart. Animal Model: 9-week old male ICR mice (pharmacokinetic analysis)[4] Dosage: 5 mg/kg ,10 mg/kg Administration: Oral administration Result: t1/2 = 0.693/λ
References	[1]. Hayashi A, et al. Pyripyropenes, fungal sesquiterpenes conjugated with alpha-pyrone and pyridine moieties, exhibits anti-angiogenic activity against human umbilical vein endothelial cells. Biol Pharm Bull. 2009 Jul;32(7):1261-5. [2]. Ohtawa M, et al. Design and Synthesis of A-Ring Simplified Pyripyropene A Analogues as Potent and Selective Synthetic SOAT2 Inhibitors. ChemMedChem. 2018 Mar 6;13(5):411-421. [3]. Ohshiro T, et al. Pyripyropene A, an acyl-coenzyme A:cholesterol acyltransferase 2-selective inhibitor, attenuates hypercholesterolemia and atherosclerosis in murine models of hyperlipidemia. Arterioscler Thromb Vasc Biol. 2011 May;31(5):1108-15. [4]. Lee KR , et al. Determination of Penicillium griseofulvum-oriented pyripyropene A, a selective inhibitor of acyl-coenzyme A:cholesterol acyltransferase 2, in mouse plasma using liquid chromatography-tandem mass spectrometry and its application to pharmacokinetic studies. Biomed Chromatogr. 2019 Feb;33(2):e4388.

Density	1.3±0.1 g/cm3
Boiling Point	690.8±55.0 °C at 760 mmHg
Melting Point	153-154°C (lit.)
Molecular Formula	C₃₁H₃₇NO₁₀
Molecular Weight	583.626
Flash Point	371.6±31.5 °C
Exact Mass	583.241760
PSA	151.46000
LogP	2.68
Vapour Pressure	0.0±2.3 mmHg at 25°C
Index of Refraction	1.587

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QL6289000

CHEMICAL NAME :: 2H,11H-Naphtho(2,1-b)pyrano(3,4-e)pyran-11-one, 1,3,4,4a,5,6a,12,12a,12b-decahydro-4- ((acetyloxy)methyl)-3,6-bis(acetyloxy)-12-hydroxy-9-( 3-pyridinyl)-4,6a,12b -trimethyl-

CAS REGISTRY NUMBER :: 147444-03-9

LAST UPDATED :: 199509

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C31-H37-N-O10

MOLECULAR WEIGHT :: 583.69

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >200 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: 47,148,1994

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