(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase编号: 137569
• 分子式: C47H51NO14
• 平均质量: 853.90614
• 单一同位素质量: 853.33095532
• SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)O)OC(=O)c1ccccc1)(CO4)OC(=O)C)O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)C[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
• InChIKey: RCINICONZNJXQF-MZXODVADSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• IUPAC传统名: taxol
• 别名: Paclitaxel

登记号

• CAS号: 33069-62-4
• MDL号: MFCD00869953
• Beilstein号: 1420457
• PubChem SID: 24277878; 24899998; 162231831; 24900422
• PubChem CID: 36314

理论计算性质

• Acid pKa: 10.363949
• 质子受体: 10
• 质子供体: 4
• LogD (pH = 5.5): 3.5388339
• LogD (pH = 7.4): 3.5383687
• Log P: 3.53884
• 摩尔折射率: 218.2945 cm^3
• 极化性: 86.54275 Å^3
• 极化表面积: 221.29 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: soluble50 mg/mL; DMSO: soluble50 mg/mL (can be stored frozen for several months); ethanol: soluble; H2O: soluble (hydrolyzes); methanol: soluble (undergoes transesterification); methanol: soluble50 mg/mL, clear, colorless
• 外观: white powder
• 熔点: 213 °C (dec.)(lit.)
• 比旋光度: [α]20/D -49°, c = 1 in methanol

安全信息

• RTECS编号: DA8340700
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22-37/38-41-42/43-62-68-68/20/21/22; 37/38-41-42/43-62-68
• 安全公开号: 22-26-36/37/39-45
• GHS危险品标识: GHS05; GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H315-H317-H318-H334-H335-H341-H361; H315-H317-H318-H334-H335-H341-H361-H371
• GHS警示性声明: P260-P280-P305 + P351 + P338-P342 + P311; P261-P280-P305 + P351 + P338-P342 + P311
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• 保存温度: -20°C; 2-8°C

药理学性质

• 相关基因信息: human ... BCL2(596)

产品相关信息

• 纯度: ≥95% (HPLC); ≥97%; 95%
• 杂质: ≤1% methyl alcohol and ethyl alcohol; ≤4% water; natural taxane impurities, none detected(except ≤0.5% paclitaxel degradation products.)
• 生物来源: from semisynthetic (from Taxus sp.); from Taxus brevifolia; from Taxus yannanensis
• Empirical Formula (Hill Notation): C47H51NO14

详细说明

Sigma Aldrich - T7191

Caution
Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.
Biochem/physiol Actions
Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).

Sigma Aldrich - T1912

Caution
Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.
Biochem/physiol Actions
Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).

Sigma Aldrich - T7402

Caution
Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.
包装
1, 5, 25 mg in glass bottle
Biochem/physiol Actions
Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).

Sigma Aldrich - 417017

Caution
Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.
包装
1 mg in glass bottle
Biochem/physiol Actions
Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).

Sigma Aldrich - 86346

Caution
Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.
Biochem/physiol Actions
Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).