(3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid

• ChemBase编号: 134017
• 分子式: C21H39NO6
• 平均质量: 401.53746
• 单一同位素质量: 401.27773797
• SMILES: CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H](C(CO)(C(=O)O)N)O)O
• Canonical SMILES: CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H](C(C(=O)O)(CO)N)O)O
• InChI: InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
• InChIKey: ZZIKIHCNFWXKDY-GNTQXERDSA-N

名称和登记号

名称

• IUPAC标准名: (3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid; (2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
• IUPAC传统名: (3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid; myriocin
• 别名: [2S-(2R*,3S*,4S*,6E)]-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic Acid; (+)-Myriocin; NSC 177379; (2S,3R,4R)-(E)-2-Amino-3,4-dihydroxy-2-hydroxymethyl-14-oxoeicos-6-enoic Acid; Myriocin; (2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid; ISP-I; Thermozymocidin; Myriocin from Mycelia sterilia

登记号

• CAS号: 35891-70-4
• MDL号: MFCD01632772
• PubChem SID: 24896622; 162228294
• PubChem CID: 6438394

理论计算性质

• Acid pKa: 2.0621011
• 质子受体: 7
• 质子供体: 5
• LogD (pH = 5.5): 0.4919639
• LogD (pH = 7.4): 0.44911402
• Log P: 0.4920756
• 摩尔折射率: 109.3753 cm^3
• 极化性: 43.162376 Å^3
• 极化表面积: 141.08 Å^2
• 可自由旋转的化学键: 18
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: methanol: soluble2 mg/mL
• 外观: off-white powder

安全信息

• RTECS编号: JX3890000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 22
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)

详细说明

Sigma Aldrich - M1177

Biochem/physiol Actions
Fungal metabolite with potent immunosuppressant activity. Inhibits serine palmitoyltransferase at picomolar concentrations blocking synthesis of ceramide, a precursor of sphingomyelin and glycosphingolipids. Disrupts substratum adhesion of melanoma cells. It has been suggested that its immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis induction.

Toronto Research Chemicals - M884400

Myriocin is a atypical amino acid and an antibiotic with potent immunosuppressant activity. Studies suggest that the immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis induction. Myriocin very potent inhibitor of serine pal

参考文献

• Miyake, Y., et al.: Biochem. Biophys. Res. Commun., 211, 396 (1995)
• Hidari, K.I.P.J. et al.: J. Biol. Chem., 271, 14636 (1995)
• Nakamura, S. et al.: J. Biol. Chem., 271, 1255 (1995)
• De Zélicourt, A. et al.: Planta 230, 1047 (1995)