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1404-64-4

1404-64-4 Structure

1404-64-4 Structure
IdentificationBack Directory
[Name]

SPARSOMYCIN
[CAS]

1404-64-4
[Synonyms]

U-19183
nsc59729
Aids012106
sparsomycin
Aids-012106
B 120121L19
Sparsomycin from Streptomyces sparsogenes
(E)-N-[(S)-1-(Hydroxymethyl)-2-[[(methylthio)methyl]sulfinyl]ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxopyrimidine-5-yl)propenamide
2-Propenamide, N-[(1S)-1-(hydroxymethyl)-2-[(R)-[(methylthio)methyl]sulfinyl]ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-, (2E)-
[Molecular Formula]

C13H19N3O5S2
[MDL Number]

MFCD01684112
[MOL File]

1404-64-4.mol
[Molecular Weight]

361.44
Chemical PropertiesBack Directory
[Melting point ]

208-209° (dec)
[alpha ]

D25 +69° (c = 0.5 in water)
[density ]

1.3893 (rough estimate)
[refractive index ]

1.6390 (estimate)
[storage temp. ]

2-8°C
[solubility ]

DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble
[form ]

A solid
[pka]

8.67 in water, 9.05 in 40% ethanol
[color ]

White to off-white
Safety DataBack Directory
[Hazard Codes ]

T+
[Risk Statements ]

28
[Safety Statements ]

28-36/37-45
[RIDADR ]

UN 2811 6.1/PG 2
[RTECS ]

WG5850000
[Toxicity]

LD50 in dogs, rats, mice (mg/kg): 0.5-1.0, 2.25, 4.32 i.v. (Ottenheijm, 1986); LD50 i.p. in mice: 2.4 mg/kg (Owen)
Hazard InformationBack Directory
[Description]

Sparsomycin is a bacterial metabolite and a nucleoside analog of uracil that has been found in S. sparsogenes and has diverse biological activities. It is active against KB carcinoma cells, Gram-positive and Gram-negative bacteria, and fungi. Sparsomycin is an inhibitor of peptidyl transferase that interferes with tRNA binding to the A-site of the peptidyl transfer center and increases the binding of peptidyl-tRNA to the P-site. It inhibits protein synthesis in bacteria, archaea, and eukaryotes. Sparsomycin reduces tumor growth in a P388 mouse leukemia model and in a Walker 256 carcinosarcoma rat model.
[Uses]

Research tool for studying protein biosynthesis.
[Uses]

Sparsomycin is an antibiotic that binds to active site and exit tunnel hydrophobic crevices of peptidyltransferase center of Haloarcula marismortui large ribosomal subunit.
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