U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C33H55NO8
Molecular Weight 593.7917
Optical Activity UNSPECIFIED
Defined Stereocenters 13 / 13
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of DISERMOLIDE

SMILES

C[C@@H](C\C(C)=C/[C@H](C)[C@@H](O)[C@@H](C)\C=C/[C@@H](O)C[C@@H]1OC(=O)[C@H](C)[C@@H](O)[C@H]1C)[C@@H](O)[C@H](C)[C@@H](OC(N)=O)[C@@H](C)\C=C/C=C

InChI

InChIKey=AADVCYNFEREWOS-OBRABYBLSA-N
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

HIDE SMILES / InChI
Disermolide (discodermolide) is the immunosuppressant and antineoplastic agent. The marine natural product discodermolide was first isolated in 1990 from the deep-water Caribbean sponge Discodermia dissoluta. It attacks cancer cells in a similar way to the successful cancer drug Taxol that has become the best-selling anticancer drug in history. Discodermolide is a microtubule-stabilizing agent with potential for the treatment of taxol-refractory malignancies. Discodermolide is a drug that functions as an immunosuppressant and induces G2/M phase cell-cycle arrest in lymphoid and non-lymphoid cells. The cytotoxicity of discodermolide cause cell-cycle arrest by mitosis and an important alteration at the level of microtubules. Discodermolide is a potent inducer of accelerated senescence. At present, Phase I trials with discodermolide has been discontinued as a consequence of unsafe efficacy and toxicity results.

Approval Year

PubMed

PubMed

TitleDatePubMed
Design and synthesis of (+)-discodermolide-paclitaxel hybrids leading to enhanced biological activity.
2011 Sep 22
Mariculture and natural production of the antitumoural (+)-discodermolide by the Caribbean marine sponge Discodermia dissoluta.
2013 Oct
Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions.
2014 Sep 1
Structural Basis of Microtubule Stabilization by Discodermolide.
2017 May 18
Patents
Name Type Language
DISERMOLIDE
INN  
INN  
Official Name English
DISCODERMOLIDE [MI]
Common Name English
DISCODERMOLIDE
MI  
Common Name English
disermolide [INN]
Common Name English
XAA-296
Code English
(+)-DISCODERMOLIDE
Common Name English
XAA296
Code English
2H-PYRAN-2-ONE, 6-((2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)-14-((AMINOCARBONYL)OXY)-2,6,12-TRIHYDROXY-5,7,9,11,13,15-HEXAMETHYL-3,8,16,18-NONADECATETRAEN-1-YL)TETRAHYDRO-4-HYDROXY-3,5-DIMETHYL-, (3R,4S,5R,6S)-
Common Name English
(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-OXOTETRAHYDRO-2H-PYRAN-2-YL)-5,7,9,11,13,15-HEXAMETHYLNONADECA-1,3,11,16-TETRAEN-6-YL CARBAMATE
Common Name English
Code System Code Type Description
ChEMBL
CHEMBL364447
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
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CAS
127943-53-7
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
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WIKIPEDIA
DISCODERMOLIDE
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
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MERCK INDEX
m4667
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
PRIMARY Merck Index
PUBCHEM
643668
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
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NCI_THESAURUS
C169917
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
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INN
8389
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
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MESH
C071229
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
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FDA UNII
DHG59994DN
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
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EPA CompTox
DTXSID40893493
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
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SMS_ID
300000034196
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
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