(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid

• ChemBase编号: 179831
• 分子式: C5H11NO2S
• 平均质量: 149.21134
• 单一同位素质量: 149.0510496
• SMILES: [C@@H](C(=O)O)(C(S)(C)C)N
• Canonical SMILES: N[C@@H](C(S)(C)C)C(=O)O
• InChI: InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)
• InChIKey: VVNCNSJFMMFHPL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
• IUPAC传统名: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid; depen
• 别名: D-Penicillamine; Depen; Distamine; D-Mercaptovaline; D-Penamine; Kuprenil; Penicillamine (Cuprimine)

登记号

• CAS号: 52-67-5
• PubChem SID: 164235741
• PubChem CID: 92863

理论计算性质

• Acid pKa: 2.555553
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -2.1465738
• LogD (pH = 7.4): -2.1542492
• Log P: -2.1465182
• 摩尔折射率: 37.225 cm^3
• 极化性: 15.067698 Å^3
• 极化表面积: 63.32 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

药理学性质

• 作用靶点: Others
• 生物活性机理: a substance that is much more soluble than cystine and is excreted readily.; Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity.; Chelating agent recommended for the removal of excess copper in patients with Wilson's disease.; From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine.; Penicillamine also reduces excess cystine excretion in cystinuria.; Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed.; The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity.; This is done, at least in part, by disulfide interchange between penicillamine and cystine, resulting in formation of penicillamine-cysteine disulfide,; Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins.

产品相关信息

• 成盐信息: Free Base
• 应用领域: Antiinflammatory; Antirheumatic; Chelating agent used in therapy of metal poisoning, and for Wilson's disease, scleroderma and rheumatoid arthritis

参考文献

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