Discodermolide
[CAS 127943-53-7]

Identification

• Name: Discodermolide
• Synonyms: [(1S,2S,3R,4S,6Z,8S,9S,10S,11Z,13S)-3,9,13-Trihydroxy-14-[(2S,3R,4S,5R)-4-Hydroxy-3,5-Dimethyl-6-Oxo-Tetrahydropyran-2-Yl]-2,4,6,8,10-Pentamethyl-1-[(1S,2Z)-1-Methylpenta-2,4-Dienyl]Tetradeca-6,11-Dienyl] Carbamate; Carbamic Acid [(1S,2S,3R,4S,6Z,8S,9S,10S,11Z,13S)-3,9,13-Trihydroxy-14-[(2S,3R,4S,5R)-4-Hydroxy-3,5-Dimethyl-6-Oxo-2-Tetrahydropyranyl]-2,4,6,8,10-Pentamethyl-1-[(1S,2Z)-1-Methylpenta-2,4-Dienyl]Tetradeca-6,11-Dienyl] Ester; Carbamic Acid [(1S,2S,3R,4S,6Z,8S,9S,10S,11Z,13S)-3,9,13-Trihydroxy-14-[(2S,3R,4S,5R)-4-Hydroxy-6-Keto-3,5-Dimethyl-Tetrahydropyran-2-Yl]-2,4,6,8,10-Pentamethyl-1-[(1S,2Z)-1-Methylpenta-2,4-Dienyl]Tetradeca-6,11-Dienyl] Ester
• Molecular Formula: C₃₃H₅₅NO₈
• Molecular Weight: 593.80
• CAS Registry Number: 127943-53-7
• SMILES: [C@@H]1(C(O[C@H]([C@H](C)[C@@H]1O)C[C@@H](\C=C/[C@@H]([C@@H]([C@H](\C=C(/C[C@@H]([C@H]([C@@H]([C@@H](OC(=O)N)[C@H](\C=C/C=C)C)C)O)C)C)C)O)C)O)=O)C
• InChI: 1S/C33H55NO8/c1-10-11-12-20(4)31(42-33(34)40)24(8)29(37)22(6)16-18(2)15-21(5)28(36)19(3)13-14-26(35)17-27-23(7)30(38)25(9)32(39)41-27/h10-15,19-31,35-38H,1,16-17H2,2-9H3,(H2,34,40)/b12-11-,14-13-,18-15-/t19-,20-,21-,22-,23-,24-,25+,26+,27-,28-,29+,30-,31-/m0/s1
• InChIKey: AADVCYNFEREWOS-OBRABYBLSA-N

Properties

• Density: 1.1±0.1g/cm³ (Cal.)
• Boiling point: 776.3±60.0°C at 760 mmHg (Cal.)
• Flash point: 423.3±32.9°C (Cal.)

References

• (1): Buey et al.. Cyclostreptin Binds Covalently to Microtubule Pores and Lumenal Taxoid Binding Sites, Nature Chemical Biology, 2007