(1R,2S,3R,4S,7R,9S,10S,12R,15R,16S)-4-(acetyloxy)-1,9,12,15,16-pentahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 170406
• Molecular Formular: C29H36O11
• Molecular Mass: 560.58954
• Monoisotopic Mass: 560.22576197
• SMILES: C1(=C2C([C@@]([C@H]([C@@H]1O)O)([C@H]([C@H]1[C@](C(=O)[C@@H]2O)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)O)C)OC(=O)c1ccccc1)O)(C)C)C
• 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@@H](O)[C@H](O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
• InChI: InChI=1S/C29H36O11/c1-13-18-20(33)22(34)27(5)16(31)11-17-28(12-38-17,40-14(2)30)21(27)24(39-25(36)15-9-7-6-8-10-15)29(37,26(18,3)4)23(35)19(13)32/h6-10,16-17,19-21,23-24,31-33,35,37H,11-12H2,1-5H3/t16-,17+,19+,20+,21-,23-,24-,27+,28-,29+/m0/s1
• InChIKey: FNZPZCTVRVPPAB-YZSQHPIKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3R,4S,7R,9S,10S,12R,15R,16S)-4-(acetyloxy)-1,9,12,15,16-pentahydroxy-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: (1R,2S,3R,4S,7R,9S,10S,12R,15R,16S)-4-(acetyloxy)-1,9,12,15,16-pentahydroxy-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
• Synonyms: (2aR,4S,4aS,6R,9R,10S,11R,12S,12aR,12bS)-12b-(Acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,10,11-pentahydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one; 4β-Hydroxy-10-DAB; 10-Deacetyl-14β-hydroxybaccatin III; 14β-Hydroxy-10-deacetylbaccatin III; 14β-Hydroxy-10-desacetylbaccatin III; 14β-Hydroxydeacetylbaccatin III; 14β-Hydroxy 10-Deacetyl Baccatin IIIDISCONTINUED

Database IDs

• CAS Number: 145533-34-2
• PubChem SID: 164226316
• PubChem CID: 5318183

CALCULATED PROPERTIES

• Acid pKa: 9.805175
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.08871263
• LogD (pH = 7.4): -0.09039504
• Log P: -0.088691145
• Molar Refractivity: 137.2942 cm^3
• Polarizability: 55.07453 Å^3
• Polar Surface Area: 180.05 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 218-220°C (dec.)

DETAILS

Toronto Research Chemicals - H932500

14β-Hydroxy 10-Deacetyl Baccatin III is a novel derivative of 10-Deacetylbaccatin III (D198250) with antitumor and antimitotic activity.

REFERENCES

• Barboni, L., et al.: Bioorg. Med. Chem. Lett., 16, 5389 (2006)