(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 ID: 137569
• Molecular Formular: C47H51NO14
• Molecular Mass: 853.90614
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: taxol
• Synonyms: Paclitaxel

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 10.363949
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 3.5388339
• LogD (pH = 7.4): 3.5383687
• Log P: 3.53884
• Molar Refractivity: 218.2945 cm^3
• Polarizability: 86.54275 Å^3
• Polar Surface Area: 221.29 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 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
• Apperance: white powder
• Melting Point: 213 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -49°, c = 1 in methanol

Safety Information

• RTECS: DA8340700
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-37/38-41-42/43-62-68-68/20/21/22; 37/38-41-42/43-62-68
• Safety Statements: 22-26-36/37/39-45
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H318-H334-H335-H341-H361; H315-H317-H318-H334-H335-H341-H361-H371
• GHS Precautionary statements: P260-P280-P305 + P351 + P338-P342 + P311; P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: 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
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... BCL2(596)

Product Information

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

DETAILS

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.
Packaging
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.
Packaging
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).