(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1,9,12-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-[(2E)-2-methylbut-2-enamido]-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 165441
• Molecular Formular: C43H51NO13
• Molecular Mass: 789.86394
• Monoisotopic Mass: 789.3360407
• SMILES: C12=C([C@H](C[C@](C1(C)C)([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)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)/C(=C/C)/C)O)C
• Canonical SMILES: C/C=C(/C(=O)N[C@H]([C@H](C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@@]4(CO[C@@H]4C[C@@H]([C@]3(C(=O)[C@@H](C(=C1C)C2(C)C)O)C)O)OC(=O)C)O)c1ccccc1)\C
• InChI: InChI=1S/C43H51NO13/c1-8-22(2)37(50)44-31(25-15-11-9-12-16-25)33(48)39(52)55-27-20-43(53)36(56-38(51)26-17-13-10-14-18-26)34-41(7,35(49)32(47)30(23(27)3)40(43,5)6)28(46)19-29-42(34,21-54-29)57-24(4)45/h8-18,27-29,31-34,36,46-48,53H,19-21H2,1-7H3,(H,44,50)/b22-8+/t27-,28-,29+,31-,32+,33+,34-,36-,41+,42-,43+/m0/s1
• InChIKey: ADDGUHVEJPNWQZ-GJKIWTKTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1,9,12-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-[(2E)-2-methylbut-2-enamido]-3-phenylpropanoyl]oxy}-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,15S)-4-(acetyloxy)-1,9,12-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-[(2E)-2-methylbut-2-enamido]-3-phenylpropanoyl]oxy}-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: (αR,βS)-α-Hydroxy-β-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]amino]benzenepropanoic Acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester; 10-Deacetyltaxol B; 10β-Deacetylcephalomanine; 10-Deacetyl Cephalomannine

Database IDs

• CAS Number: 76429-85-1
• PubChem SID: 162259574
• PubChem CID: 6440548

CALCULATED PROPERTIES

• Acid pKa: 10.958235
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 2.781939
• LogD (pH = 7.4): 2.7818978
• Log P: 2.7820187
• Molar Refractivity: 203.1508 cm^3
• Polarizability: 80.45161 Å^3
• Polar Surface Area: 215.22 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Off-White Solid
• Melting Point: 190-193°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D198650

10-Deacetyl Cephalomannine is a derivative of Cephalomannine (C258500).

REFERENCES

• Liu, J., et al.: J. Pharm. Biomed. Anal., 15, 1729 (1997)
• Montero, A., et al.: Lancet Oncol., 6, 229 (1997)
• Ojima, I., et al.: J. Nat. Prod. 72, 554 (1997)