(1S,2S,3S,4R,7R,9R,10R,12R,15S)-4-(acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0?,??.0?,?]heptadec-13-en-2-yl benzoate

• ChemBase ID: 105758
• Molecular Formular: C29H36O10
• Molecular Mass: 544.59014
• Monoisotopic Mass: 544.23084735
• SMILES: CC1=C2[C@H](C(=O)[C@@]3(C)[C@@H](C[C@@H]4[C@](CO4)([C@@H]3[C@@H]([C@](C[C@@H]1O)(C2(C)C)O)OC(=O)c1ccccc1)OC(=O)C)O)O
• Canonical SMILES: CC(=O)O[C@]12CO[C@@H]1C[C@H]([C@]1([C@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
• InChI: InChI=1S/C29H36O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,21-22,24,31-33,36H,11-13H2,1-5H3/t17-,18+,19+,21+,22+,24-,27-,28+,29+/m0/s1
• InChIKey: YWLXLRUDGLRYDR-YLPZXOTFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3S,4R,7R,9R,10R,12R,15S)-4-(acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0?,??.0?,?]heptadec-13-en-2-yl benzoate
• IUPAC Traditional name: (1S,2S,3S,4R,7R,9R,10R,12R,15S)-4-(acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0?,??.0?,?]heptadec-13-en-2-yl benzoate
• Synonyms: 10-DAB III; 10-DEACETYLBACCATIN III

Database IDs

• CAS Number: 32981-86-5
• PubChem SID: 162093826
• PubChem CID: 11886832

CALCULATED PROPERTIES

• Acid pKa: 10.294341
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.6015966
• LogD (pH = 7.4): 0.6010504
• Log P: 0.6016035
• Molar Refractivity: 136.1971 cm^3
• Polarizability: 54.406586 Å^3
• Polar Surface Area: 159.82 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 2-8°C

Product Information

• Purity: ≥95%

DETAILS

MP Biomedicals - 02193978

From Taxus baccata Purity: =95%
An intermediate in the synthesis of paclitaxel (taxol) and derivatives.

REFERENCES

• Denis, J-N., et al., J. Amer. Chem. Soc., 110: 5917 (1988).