Global Information Lookup Global Information

Discodermolide information


Discodermolide
(+)-Discodermolide
Names
Systematic IUPAC name
(3Z,5S,6S,7S,8R,9S,11Z,13S,14S,15S,16Z,18S)-8,14,18-Trihydroxy-19-[(2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxooxan-2-yl]-5,7,9,11,13,15-hexamethylnonadeca-1,3,11,16-tetraen-6-yl carbamate
Identifiers
CAS Number
  • 127943-53-7 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEMBL
  • ChEMBL364447 checkY
ChemSpider
  • 558787 checkY
KEGG
  • C16746 checkY
PubChem CID
  • 643668
UNII
  • DHG59994DN checkY
CompTox Dashboard (EPA)
  • DTXSID40893493 Edit this at Wikidata
InChI
  • 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 checkY
    Key: AADVCYNFEREWOS-OBRABYBLSA-N checkY
  • InChI=1/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
    Key: AADVCYNFEREWOS-OBRABYBLBY
SMILES
  • O=C1[C@H](C)[C@@H](O)[C@@H](C)[C@H](C[C@H](O)/C=C\[C@H](C)[C@H](O)[C@@H](C)\C=C(C[C@H](C)[C@@H](O)[C@H](C)[C@@H](OC(N)=O)[C@@H](C)\C=C/C=C)\C)O1
  • C[C@H]1[C@@H](OC(=O)[C@@H]([C@H]1O)C)C[C@@H](/C=C\[C@H](C)[C@@H]([C@@H](C)/C=C(/C)\C[C@H](C)[C@H]([C@H](C)[C@H]([C@@H](C)/C=C\C=C)OC(=O)N)O)O)O
Properties
Chemical formula
C33H55NO8
Molar mass 593.79 g/mol
Melting point 112 to 113 °C (234 to 235 °F; 385 to 386 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

(+)-Discodermolide is a polyketide natural product found to stabilize microtubules. (+)-discodermolide was isolated by Gunasekera and his co-workers at the Harbor Branch Oceanographic Institute from the deep-sea sponge Discodermia dissoluta in 1990.[1] (+)-Discodermolide was found to be a potent inhibitor of tumor cell growth in several MDR cancer cell lines. (+)-discodermolide also shows some unique characters, including a linear backbone structure, immunosuppressive properties both in vitro and in vivo,[2][3] potent induction of an accelerated senescence phenotype,[4] and synergistic antiproliferative activity in combination with paclitaxel.[5] Discodermolide was recognized as one of the most potent natural promoters of tubulin assembly. A large number of efforts toward the total synthesis of (+)-discodermolide were directed by its interesting biological activities and extreme scarcity of natural sources (0.002% w/w from frozen marine sponge). The compound supply necessary for complete clinical trials cannot be met by harvesting, isolation, and purification. As of 2005, attempts at synthesis or semi-synthesis by fermentation have proven unsuccessful. As a result, all discodermolide used in preclinical studies and clinical trials has come from large-scale total synthesis.[6]

  1. ^ Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. J. Org. Chem. 1990, 55, 4912-4915. (doi:10.1021/jo00303a029)
  2. ^ Longley, R. E.; Caddigan, D.; Harmody, D.; Gunasekera, M.; Gunasekera, S. P. Transplantation 1991, 52, 650-655.
  3. ^ Longley, R. E.; Caddigan, D.; Harmody, D.; Gunasekera, M.; Gunasekera, S. P. Transplantation 1991, 52, 656-661.
  4. ^ Klein, L.; Freeze, B. S.; Smith, A. B., III; Horwitz, S. B. Cell Cycle 2005, 4, 501–507.
  5. ^ Longley, R. E.; Gunasekera, S. P.; Faherty, D.; McLane, J.; Dumont, F. Ann. N.Y. Acad. Sci. 1993, 696, 94–107.
  6. ^ Mickel, S. J. et al. Org. Process Res. Dev. 2004, 8

and 11 Related for: Discodermolide information

Request time (Page generated in 0.5219 seconds.)

Discodermolide

Last Update:

(+)-Discodermolide is a polyketide natural product found to stabilize microtubules. (+)-discodermolide was isolated by Gunasekera and his co-workers at...

Word Count : 3460

Discodermia dissoluta

Last Update:

chemists due to its production of a potent chemical compound called (+)-discodermolide, which has potential therapeutic applications for cancer treatment....

Word Count : 483

Mitotic inhibitor

Last Update:

multidrug resistant cell lines. Discodermolide was initially found to have immunosuppressive and antifungal activities. Discodermolide is a polyhydroxylated alketetraene...

Word Count : 6908

Kosan Biosciences

Last Update:

Kosan Biosciences was acquired by Bristol-Myers Squibb for $190M. Discodermolide is a recently discovered polyketide natural product found to be a potent...

Word Count : 365

Roche ester

Last Update:

starting blocks for the synthesis of many targets including dictyostatin, discodermolide and spongidepsin. Shin, Youseung; Fournier, Jean-Hugues; Fukui, Yoshikazu;...

Word Count : 150

Polyketide

Last Update:

family (HSP90 inhibitors) The cholesterol lowering agent lovastatin Discodermolide Aflatoxin Usnic acid Anthracimycin Anthramycin Olivetolic acid (intermediate...

Word Count : 2213

Epothilone

Last Update:

second methyl group was integrated by a C-methyl-transferase domain. Discodermolide Rosenberg, Steven; DeVita, Vincent T.; Hellman, Samuel (2005). Cancer:...

Word Count : 2163

Natural product

Last Update:

under investigation as possible therapies include the antitumour agents discodermolide (from the sponge Discodermia dissoluta), eleutherobin (from the coral...

Word Count : 9571

Molecular glue

Last Update:

molecular glues took a significant turn in 1996 with the discovery that discodermolide stabilized the association of alpha and beta tubulin monomers, functioning...

Word Count : 2100

Susan Band Horwitz

Last Update:

mechanisms still remain to be similar. One in particular is called, discodermolide. Dr. Horwitz and her team were interested in not only the binding site...

Word Count : 1301

Discodermia

Last Update:

is of interest to bio and organic chemists because it produces (+)-discodermolide, a polyketide natural product with immunosuppressive and cancer killing...

Word Count : 334

PDF Search Engine © AllGlobal.net