(1S,2S,3R,4S,7R,9S,10S,12R,15S)-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 (2E)-2-methylbut-2-enoate

• ChemBase ID: 165476
• Molecular Formular: C27H38O10
• Molecular Mass: 522.58462
• Monoisotopic Mass: 522.24649742
• 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)/C(=C/C)/C)O)(C)C)C
• Canonical SMILES: C/C=C(/C(=O)O[C@H]1[C@@H]2[C@@]3(CO[C@@H]3C[C@@H]([C@@]2(C)C(=O)[C@@H](C2=C([C@H](C[C@]1(O)C2(C)C)O)C)O)O)OC(=O)C)\C
• InChI: InChI=1S/C27H38O10/c1-8-12(2)23(33)36-22-20-25(7,16(30)9-17-26(20,11-35-17)37-14(4)28)21(32)19(31)18-13(3)15(29)10-27(22,34)24(18,5)6/h8,15-17,19-20,22,29-31,34H,9-11H2,1-7H3/b12-8+/t15-,16-,17+,19+,20-,22-,25+,26-,27+/m0/s1
• InChIKey: GADAUHGBDGVMET-ORSMARSKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-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 (2E)-2-methylbut-2-enoate
• IUPAC Traditional name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-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 (2E)-2-methylbut-2-enoate
• Synonyms: (2E)-2-Methyl-2-butenoic Acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-12-yl Ester; 2-Debenzoyl-2-tigloyl 10-DAB; 2-Debenzoyl-2-tigloyl 10-Deacetyl Baccatin III

Database IDs

• CAS Number: 171926-87-7
• PubChem SID: 162259609
• PubChem CID: 71315226

CALCULATED PROPERTIES

• Acid pKa: 10.29434
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.31923395
• LogD (pH = 7.4): 0.31868777
• Log P: 0.31924093
• Molar Refractivity: 130.2049 cm^3
• Polarizability: 51.988945 Å^3
• Polar Surface Area: 159.82 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 198-200°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - D203500

2-Debenzoyl-2-tigloyl 10-Deacetyl Baccatin III is a new analog of 10-Deacetylbaccatin III (D198250).

REFERENCES

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