1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(octadecylamino)-1,2-dihydropyrimidin-2-one

• ChemBase编号: 133370
• 分子式: C27H49N3O5
• 平均质量: 495.69506
• 单一同位素质量: 495.36722168
• SMILES: CCCCCCCCCCCCCCCCCCNc1ccn(c(=O)n1)[C@H]1[C@H]([C@@H]([C@H](O1)CO)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCCCCNc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@H]([C@@H]1O)O)CO
• InChI: InChI=1S/C27H49N3O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-28-23-18-20-30(27(34)29-23)26-25(33)24(32)22(21-31)35-26/h18,20,22,24-26,31-33H,2-17,19,21H2,1H3,(H,28,29,34)/t22-,24-,25+,26-/m1/s1
• InChIKey: HQHQCEKUGWOYPS-URBBEOKESA-N

名称和登记号

名称

• IUPAC标准名: 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(octadecylamino)-1,2-dihydropyrimidin-2-one
• IUPAC传统名: 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(octadecylamino)pyrimidin-2-one
• 别名: N(4)-octadecyl-ara-C; N4-Stearyl-Ara C; NOAC; N4-Octadecylcytosine β-D-arabinofuranoside

登记号

• CAS号: 158233-67-1
• MDL号: MFCD00467196
• PubChem SID: 24898023; 162227647
• PubChem CID: 133043

理论计算性质

• Acid pKa: 12.553241
• 质子受体: 7
• 质子供体: 4
• LogD (pH = 5.5): 5.027951
• LogD (pH = 7.4): 5.0279493
• Log P: 5.0279527
• 摩尔折射率: 137.607 cm^3
• 极化性: 54.394547 Å^3
• 极化表面积: 114.62 Å^2
• 可自由旋转的化学键: 20
• 里宾斯基五规则: false

分子性质

安全信息

• RTECS编号: UW7370900
• 德国WGK号: 3

详细说明

Sigma Aldrich - O5508

Other Notes
Lipophilic, cytotoxic derivative of cytosine arabinoside
Application
N4-Stearyl-Ara C (N(4)-octadecyl-ara-C, NOAC) is a lipophilic derivative of Ara-C used to improve the incorporation of Ara-C, an anti-cancer agent, into lipid bilayers of liposomes and/or target cells.