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

• ChemBase ID: 165438
• Molecular Formular: C29H36O10
• Molecular Mass: 544.59014
• Monoisotopic Mass: 544.23084735
• SMILES: C1(=C2C([C@@](C[C@H]1O)([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[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-/m1/s1
• InChIKey: YWLXLRUDGLRYDR-LHDQCKIRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15R)-4-(acetyloxy)-1,9,12,15-tetrahydroxy-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: (1S,2S,3R,4S,7R,9S,10S,12R,15R)-4-(acetyloxy)-1,9,12,15-tetrahydroxy-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-(2aα,4β,4aβ,6β,9β,11α,12α,12aα,12bα)]-12b-(Acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one; 13-epi-10-DAB; (-)-10-Deacetyl-13-epibaccatin III; 13-Epi-10-deacetylbaccatin III; 13-epi-10-Deacetyl Baccatin III

Database IDs

• CAS Number: 172018-16-5
• PubChem SID: 162259571
• PubChem CID: 5317065

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

DETAILS

Toronto Research Chemicals - D198265

13-epi-10-Deacetyl Baccatin III is a new analog of 10-Deacetylbaccatin III (D198250).

REFERENCES

• Gabetta, B., et al.: J. Natural Products, 58, 1508 (1995)