(2R)-2-[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanamido]-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid

• ChemBase编号: 155386
• 分子式: C20H25N5O10
• 平均质量: 495.44
• 单一同位素质量: 495.16014203
• SMILES: C[C@H]([C@@H](c1ccc(cn1)O)O)[C@@H](C(=O)N[C@H]([C@@H]1[C@H]([C@H]([C@@H](O1)n1ccc(=O)[nH]c1=O)O)O)C(=O)O)N
• Canonical SMILES: OC(=O)[C@@H]([C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(=O)[nH]c1=O)NC(=O)[C@H]([C@@H]([C@@H](c1ccc(cn1)O)O)C)N
• InChI: InChI=1S/C20H25N5O10/c1-7(13(28)9-3-2-8(26)6-22-9)11(21)17(31)24-12(19(32)33)16-14(29)15(30)18(35-16)25-5-4-10(27)23-20(25)34/h2-7,11-16,18,26,28-30H,21H2,1H3,(H,24,31)(H,32,33)(H,23,27,34)/t7-,11-,12+,13-,14-,15+,16+,18+/m0/s1
• InChIKey: WWJFFVUVFNBJTN-JKEIIPFCSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-2-[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanamido]-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
• IUPAC传统名: (R)-[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanamido][(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
• 别名: Nikkomycin; Nikkomycin Z from Streptomyces tendae

登记号

• CAS号: 59456-70-1
• MDL号: MFCD00869648
• Beilstein号: 873216
• PubChem SID: 162249524; 24897849; 24886404
• PubChem CID: 9935526

理论计算性质

• Acid pKa: 2.6059542
• 质子受体: 12
• 质子供体: 8
• LogD (pH = 5.5): -5.647641
• LogD (pH = 7.4): -5.7942843
• Log P: -5.64964
• 摩尔折射率: 111.8356 cm^3
• 极化性: 44.594955 Å^3
• 极化表面积: 244.87 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

分子性质

安全信息

• RTECS编号: BA2928200
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C; 2-8°C

产品相关信息

• 纯度: ≥90% (HPLC); ≥96.0% (HPLC)
• Empirical Formula (Hill Notation): C20H25N5O10

详细说明

Sigma Aldrich - N8028

Application
Nikkomycin Z is used as a selective competitive inhibitor of chitin synthetase 3 in studies on fungal cell wall development. It is a potential treatment for human Encephalitozoon hellem, a microsporidian species1 and is used to study the changes of chitin and β--glucan under Nikkomycin Z exposure2.
Biochem/physiol Actions
Nikkomycin Z inhibits chitin synthase from converting UDP-GlcNAc into cell wall chitin due to its structural resemblance to UDP-N-acetylglucosamine3. Nikkomycin Z has potent antifungal, insecticidal and acaridicial activity.