Sinefungin

Names

[ Name ]:
Sinefungin

[Synonym ]:
(2S,5S)-2,5-Diamino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]hexanoic acid (non-preferred name)
Sinefungin
D-Glycero-α-L-talo-Decofuranuronic acid, 6,9-diamino-1- (6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-D-glycero-a-L-talo-decofuranuronic Acid
Antibiotic 32232RP
(5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]-L-norleucine
(5S)-5-Amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]-L-norleucine
UNII:W2U467CIIL

Biological Activity

[Description]:

Sinefungin is a potent inhibitor of virion mRNA(guanine-7-)-methyltransferase, mRNA(nucleoside-2'-)-methyltransferase, and viral multiplication[1]. Sinefungin, a SET7/9 inhibitor, ameliorates renal fibrosis by inhibiting H3K4 methylation [2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Epigenetics >> Histone Methyltransferase

Research Areas >> Inflammation/Immunology

[References]

[1]. Pugh CS, et al. Sinefungin, a potent inhibitor of virion mRNA(guanine-7-)-methyltransferase, mRNA(nucleoside-2'-)-methyltransferase, and viral multiplication. J Biol Chem. 1978 Jun 25;253(12):4075-7.

[2]. Sasaki K, et al. Inhibition of SET Domain-Containing Lysine Methyltransferase 7/9 Ameliorates Renal Fibrosis. J Am Soc Nephrol. 2016 Jan;27(1):203-15.

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
783.2±70.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₅H₂₃N₇O₅

[ Molecular Weight ]:
381.39

[ Flash Point ]:
427.5±35.7 °C

[ Exact Mass ]:
381.176056

[ PSA ]:
208.65000

[ LogP ]:
-1.33

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.832

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HE3140000

CHEMICAL NAME :: D-glycero-alpha-L-talo-Decofuranuronic acid, 6,9-diamino-1-(6-amino-9H-purin-9-yl)- 1,5,6,7,8,9-hexadeoxy-

CAS REGISTRY NUMBER :: 58944-73-3

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C15-H23-N7-O5

MOLECULAR WEIGHT :: 381.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

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

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 5,298,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 185 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: 26,463,1973

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
HE3140000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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