Sinefungin
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Sinefungin
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CAS No:
58944-73-3
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Formula:
C15H23N7O5
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Chemical Name:
Sinefungin
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Synonyms:
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-α-L-talo-decofuranuronic acid;Sinefungin;32232RP;RP 32232;Antibiotic A 9145;A 9145;Antibiotic 32232RP;Compound 57926;Adenosyl-Ornithine;39315-74-7;66771-93-5;66807-50-9
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CAS No:
Description
Sinefungin is an adenosine that is the the delta-(5'-adenosyl) derivative of ornithine. It has a role as an antifungal agent and an antimicrobial agent. It is a member of adenosines and a non-proteinogenic alpha-amino acid. It derives from a L-ornithine.|Sinefungin is a solid. This compound belongs to the purine nucleosides and analogues. These are compounds comprising a purine base attached to a sugar. The proteins that adenosyl-ornithine target include RdmB, modification methylase TaqI, rRNA (adenine-N6-)-methyltransferase, and modification methylase RsrI.|Sinefungin is a natural nucleoside related to S-adenosylmethionine that has been isolated from Streptomyces species with antifungal, antiviral and antiparasitic activity. Sinefungin inhibits DNA methyltransferase which leads to an inhibition of DNA synthesis.
Characteristics
209 Ų
1.91±0.1 g/cm3
783.2±70.0 °C(Predicted)
LD50 s.c. in mice: 185 mg/kg (Hamill, Hoehn, J. Antibiot.)
pKa (66% DMF): 2.9, 3.9, 8.9, 10.2(at 25℃)
Safety Information
3
22
36
HE3140000
Xn
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 103 companies from 2 notifications to the ECHA C&L Inventory.
Drug Information
Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)|Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)|Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)
A 9145
Sinefungin Use and Manufacturing
Sinefungin, a polar nucleoside antifungal active with broad biological activity, was isolated from a number of species of Streptomyces in the early 1970s. Sinefungin acts by inhibiting a wide range of methyltransferases, including the methylation of bases in DNA and RNA which alters cytosine deamination and gene expression. Sinefungin is widely used as a bioprobe to block methyltransferase-dependent pathways.
Computed Properties
Molecular Weight:381.39
XLogP3:-4.3
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:7
Exact Mass:381.17606686
Monoisotopic Mass:381.17606686
Topological Polar Surface Area:209
Heavy Atom Count:27
Complexity:529
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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