{[(2S,3R)-2-amino-3-hydroxyoctadecyl]oxy}phosphonic acid

• ChemBase编号: 155619
• 分子式: C18H40NO5P
• 平均质量: 381.487661
• 单一同位素质量: 381.26441002
• SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](COP(=O)(O)O)N)O
• Canonical SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](COP(=O)(O)O)N)O
• InChI: InChI=1S/C18H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/t17-,18+/m0/s1
• InChIKey: YHEDRJPUIRMZMP-ZWKOTPCHSA-N

名称和登记号

名称

• IUPAC标准名: {[(2S,3R)-2-amino-3-hydroxyoctadecyl]oxy}phosphonic acid
• IUPAC传统名: dihydrosphingosine 1-phosphate
• 别名: [R-(R*,S*)]-2-Amino-1,3-octadecanediol 1-(Dihydrogen Phosphate); (2S,3R)-Sphinganine 1-Phosphate; C18-Dihydrosphingosine 1-Phosphate; Dihydrosphingosine-1-phosphate; Sphinganine 1-Phosphate; (2S,3R)-2-Amino-1,3-octadecanediol 1-(Dihydrogen Phosphate); D-erythro-Dihydro-D-sphingosine-1-phosphate; D-erythro-Dihydrosphingosine 1-phosphate

登记号

• CAS号: 19794-97-9
• MDL号: MFCD00871363
• PubChem SID: 24893757; 162249757
• PubChem CID: 644260

理论计算性质

• Acid pKa: 1.5211388
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): 3.6023884
• LogD (pH = 7.4): 2.7415223
• Log P: 3.6368678
• 摩尔折射率: 101.8023 cm^3
• 极化性: 40.90807 Å^3
• 极化表面积: 113.01 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: Hot Acetic Acid; methanol: THF: water (6:3:1): >0.5 mg/mL
• 外观: White to Beige Solid; yellow waxy solid
• 熔点: 175-177°C

安全信息

• 保存条件: -20°C Freezer
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... S1PR1(1901), S1PR2(9294), S1PR3(1903), S1PR4(8698), S1PR5(53637)

产品相关信息

• 纯度: ≥98% (TLC)
• Empirical Formula (Hill Notation): C18H40NO5P

详细说明

Sigma Aldrich - D3439

Biochem/physiol Actions
Negative control for sphingosine-1-phosphate.

Toronto Research Chemicals - D449500

May be used as a negative control for C2 Ceramide.

参考文献

• Bielawska, A., et al.: J. Biol. Chem., 268, 26226 (1993)