ixabepilone   

GtoPdb Ligand ID: 6824

Synonyms: azaepothilone B | BMS 247550-1 | BMS-247550 | BMS-247550-01 | Ixempra®
ixabepilone is an approved drug (FDA (2007))
Compound class: Synthetic organic
Comment: A pan tubulin inhibitor. This compound is an analogue of a natural substance produced by Sorangium cellulosum and acts to stabilise microtubules.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 140.29
Molecular weight 506.28
XLogP 1.61
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C1NC(CC2OC2(C)CCCC(C(C(C(=O)C(C(C1)O)(C)C)C)O)C)C(=Cc1csc(n1)C)C
Isomeric SMILES O=C1N[C@@H](C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](C1)O)(C)C)C)O)C)/C(=C/c1csc(n1)C)/C
InChI InChI=1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
InChI Key FABUFPQFXZVHFB-PVYNADRNSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2007))
IUPAC Name
(1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-1,5,7,9,9-pentamethyl-14-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-13-azabicyclo[14.1.0]heptadecane-8,12-dione
International Nonproprietary Names
INN number INN
8390 ixabepilone
Synonyms
azaepothilone B | BMS 247550-1 | BMS-247550 | BMS-247550-01 | Ixempra®
Database Links
CAS Registry No. 219989-84-1
ChEMBL Ligand CHEMBL1201752
DrugBank Ligand DB04845
DrugCentral Ligand 1517
GtoPdb PubChem SID 178103430
PubChem CID 6445540
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Wikipedia Ixabepilone