5-{[(2S)-1-{[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-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-9-yl]oxy}-1-oxopropan-2-yl]carbamoyl}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

• ChemBase ID: 169296
• Molecular Formular: C71H66N2O21
• Molecular Mass: 1283.28454
• Monoisotopic Mass: 1282.41580714
• SMILES: C12=C([C@H](C[C@](C1(C)C)([C@H]([C@H]1[C@](C(=O)[C@@H]2OC(=O)C)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)OC(=O)[C@@H](NC(=O)c1ccc(c(c1)C(=O)O)c1c2c(oc3c1ccc(c3)O)cc(=O)cc2)C)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C
• Canonical SMILES: CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](OC(=O)[C@@H](NC(=O)c3ccc(c(c3)C(=O)O)c3c4ccc(=O)cc4oc4c3ccc(c4)O)C)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/C71H66N2O21/c1-35-51(91-67(86)57(78)56(39-17-11-8-12-18-39)73-62(80)40-19-13-9-14-20-40)33-71(87)61(93-66(85)41-21-15-10-16-22-41)59-69(7,60(79)58(89-37(3)74)55(35)68(71,5)6)52(32-53-70(59,34-88-53)94-38(4)75)92-65(84)36(2)72-63(81)42-23-26-45(48(29-42)64(82)83)54-46-27-24-43(76)30-49(46)90-50-31-44(77)25-28-47(50)54/h8-31,36,51-53,56-59,61,76,78,87H,32-34H2,1-7H3,(H,72,81)(H,73,80)(H,82,83)/t36-,51-,52-,53+,56-,57+,58+,59-,61-,69+,70-,71+/m0/s1
• InChIKey: JMWJJMCMRRQCSY-MVMRRDPFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[(2S)-1-{[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-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-9-yl]oxy}-1-oxopropan-2-yl]carbamoyl}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid
• IUPAC Traditional name: 5-{[(2S)-1-{[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-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-9-yl]oxy}-1-oxopropan-2-yl]carbamoyl}-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• Synonyms: (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-Bis(acetyloxy)-9-[(2R,3S)-3-(benzoylamino)-2-hydroxy-1-oxo-3-phenylpropoxy]-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-4-yl Ester N-[(3',6'-dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl)carbonyl]-L-alanine; 7-O-[N-(4’-Fluoresceincarbonyl)-L-alanyl] Taxol; Flutax 1

Database IDs

• CAS Number: 191930-58-2
• PubChem SID: 162263428
• PubChem CID: 16147640

CALCULATED PROPERTIES

• Acid pKa: 3.552519
• H Acceptors: 16
• H Donor: 6
• LogD (pH = 5.5): 4.233271
• LogD (pH = 7.4): 1.9609642
• Log P: 5.9313517
• Molar Refractivity: 342.7685 cm^3
• Polarizability: 128.7578 Å^3
• Polar Surface Area: 340.29 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol
• Apperance: Orange Solid

DETAILS

Toronto Research Chemicals - F599400

Flutax 1 is a fluorescent taxol derivative that binds to the taxol microtubule binding site with high affinity (Ka ~ 107M-1). Flutax 1 is useful for direct imaging of the microtubule cytoskeleton. Excitation maximum ~ 495 nm; emission maximum ~ 520 nm.

REFERENCES

• Evangelio, J.A., et al.: Cell Motil., Cytoskeleton, 39, 73 (1995)
• Souto, A.A., et al.: Angew. Chem. Int. Ed. Engl., 34, 2710 (1995)
• Abal., M., et al.: Cell Motil. Cytoskeleton, 49, 1 (1995)
• Diaz, J.F., et al.: J. Biol. Chem., 275, 26265, 2001,