基本情報
- CAS
1404-64-4- 標準SMILES
CSC[S@](=O)C[C@H](CO)NC(=O)/C=C/c1c(C)[nH]c(=O)[nH]c1=O- InChIKey
XKLZIVIOZDNKEQ-CLQLPEFOSA-N- 分子式
- C13H19N3O5S2
- 平均分子量
- 361.4 g/mol
- 単同位体質量
- 361.07661306
概要
An antitumor antibiotic produced by Streptomyces sparsogenes. It inhibits protein synthesis in 70S and 80S ribosomal systems.
名称と識別子
- 優先名称
- Sparsomycin
- IUPAC
- (E)-N-[(2S)-1-hydroxy-3-[(R)-methylsulfanylmethylsulfinyl]propan-2-yl]-3-(6-methyl-2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enamide
- 現地名
- スパルソマイシン
- 英語名
- SPARSOMYCIN
- 分子式
- C13H19N3O5S2
- 分子量
- 361.44
名称と別名
SPARSOMYCINEsparsomicinaSparsomycineSparsomycinum1404-64-4U-191836C940P63E7(+)-Sparsomycin(E)-N-[(2S)-1-hydroxy-3-[(R)-methylsulfanylmethylsulfinyl]propan-2-yl]-3-(6-methyl-2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enamide2-Propenamide, N-(1-(hydroxymethyl)-2-(((methylthio)methyl)sulfinyl)ethyl)-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-, (S-(E))-NSC-59729DTXSID40874469
名称をさらに表示
スパルソマイシン(E)-N-[(S)-1-(ヒドロキシメチル)-2-[[(メチルチオ)メチル]スルフィニル]エチル]-3-(1,2,3,4-テトラヒドロ-6-メチル-2,4-ジオキソピリミジン-5-イル)プロペンアミド(2E)-N-[(2S)-1-ヒドロキシ-3-(メチルスルファニル)メタンスルフィニルプロパン-2-イル]-3-(6-メチル-2,4-ジオキソ-1,2,3,4-テトラヒドロピリミジン-5-イル)プロパ-2-エンアミドnsc59729Aids012106Aids-012106Sparsomycin 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)propenamide2-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)-
物性
構造計算による物性
- XLogP
- -1.7
- 極性表面積
- 169 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 7
- 回転可能結合数
- 8
- 重原子数
- 23
- 形式電荷
- 0
- 複雑度
- 574
実験および物理化学的性質
LogP-1.71
物理化学的性質
- 融点
- 208 · 208-209° (dec)
- 比旋光度
- 25 · D25 +69° (c = 0.5 in water)
- 比重(密度)
- 1.3893 · 1.3893 (rough estimate)
- 屈折率
- 1.639 · 1.6390 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble
- 外見
- A solid
- 酸解離定数(Pka)
- 8.67 in · 8.67 in water, 9.05 in 40% ethanol
- 色
- White to off-white
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- rtecs
- WG5850000
- ridadr
- UN 2811 6.1/PG 2
- 毒性
- 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)
- risk_code
- 28
- hazard_code
- T+
- safety_code
- 28-36/37-45
化学と産業
薬理情報
MeSH Pharmacological Classification
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
応用分野
説明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.
使用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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