(1S,3S)-12-(benzoyloxy)-1-{[(2R,4R,5R,6R)-5-(benzoyloxy)-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-6-methyloxan-2-yl]oxy}-3-[2-(benzoyloxy)acetyl]-3-hydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl benzoate

• ChemBase编号: 169043
• 分子式: C70H55NO17
• 平均质量: 1182.1822
• 单一同位素质量: 1181.34699931
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1OC(=O)c1ccccc1)C[C@](C[C@@H]2O[C@H]1C[C@H]([C@H]([C@H](O1)C)OC(=O)c1ccccc1)NC(=O)OCC1c2c(c3c1cccc3)cccc2)(C(=O)COC(=O)c1ccccc1)O)OC(=O)c1ccccc1)OC
• Canonical SMILES: COc1cccc2c1C(=O)c1c(C2=O)c(OC(=O)c2ccccc2)c2c(c1OC(=O)c1ccccc1)[C@@H](O[C@@H]1O[C@H](C)[C@@H]([C@@H](C1)NC(=O)OCC1c3ccccc3c3c1cccc3)OC(=O)c1ccccc1)C[C@](C2)(O)C(=O)COC(=O)c1ccccc1
• InChI: InChI=1S/C70H55NO17/c1-39-62(86-66(76)41-22-9-4-10-23-41)51(71-69(79)83-37-50-46-30-17-15-28-44(46)45-29-16-18-31-47(45)50)34-55(84-39)85-53-36-70(80,54(72)38-82-65(75)40-20-7-3-8-21-40)35-49-57(53)64(88-68(78)43-26-13-6-14-27-43)59-58(63(49)87-67(77)42-24-11-5-12-25-42)60(73)48-32-19-33-52(81-2)56(48)61(59)74/h3-33,39,50-51,53,55,62,80H,34-38H2,1-2H3,(H,71,79)/t39-,51-,53+,55+,62+,70+/m1/s1
• InChIKey: CLQNPWZHCRPHCS-YRFWCRKLSA-N

名称和登记号

名称

• IUPAC标准名: (1S,3S)-12-(benzoyloxy)-1-{[(2R,4R,5R,6R)-5-(benzoyloxy)-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-6-methyloxan-2-yl]oxy}-3-[2-(benzoyloxy)acetyl]-3-hydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl benzoate
• IUPAC传统名: (1S,3S)-12-(benzoyloxy)-1-{[(2R,4R,5R,6R)-5-(benzoyloxy)-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-6-methyloxan-2-yl]oxy}-3-[2-(benzoyloxy)acetyl]-3-hydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-5-yl benzoate
• 别名: (8S,10S)-7,8,9,10-tetrahydro-8-hydroxy-6,11-dibenzoyloxy-8-(2-benzoyloxyacetyl)-1-methoxy-10-[[2,3,6-trideoxy-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-benzyloxy-α-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione; N-(9-Fluorenylmethoxycarbonyl)-4',6,8,11-tetra-O-benzoyl Doxorubicin

登记号

• PubChem SID: 162263175
• PubChem CID: 71316787

理论计算性质

• Acid pKa: 12.571355
• 质子受体: 12
• 质子供体: 2
• LogD (pH = 5.5): 12.748803
• LogD (pH = 7.4): 12.7488
• Log P: 12.748803
• 摩尔折射率: 317.9615 cm^3
• 极化性: 124.432945 Å^3
• 极化表面积: 242.66 Å^2
• 可自由旋转的化学键: 21
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Dichloromethane
• 外观: Yellow Solid

详细说明

Toronto Research Chemicals - F472435

N-(9-Fluorenylmethoxycarbonyl) Doxorubicin (F472430) derivative. Used in the preparation of a modified Doxorubicin (ANG1007) and Etoposide (ANG1009) useful due to their brain penetration ability.

参考文献

• Che, C. et al.: J. Med. Chem. 53, 2814 (2010)