ixabepilone   Click here for help

GtoPdb Ligand ID: 6824

Synonyms: azaepothilone B | BMS 247550-1 | BMS-247550 | BMS-247550-01 | Ixempra®
Approved drug PDB Ligand
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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2007))
IUPAC Name Click here for help
(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 Click here for help
INN number INN
8390 ixabepilone
Synonyms Click here for help
azaepothilone B | BMS 247550-1 | BMS-247550 | BMS-247550-01 | Ixempra®
Database Links Click here for help
CAS Registry No. 219989-84-1
ChEMBL Ligand CHEMBL1201752
DrugBank Ligand DB04845
DrugCentral Ligand 1517
GtoPdb PubChem SID 178103430
PubChem CID 6445540
RCSB PDB Ligand GZX
Search Google for chemical match using the InChIKey FABUFPQFXZVHFB-PVYNADRNSA-N
Search Google for chemicals with the same backbone FABUFPQFXZVHFB
Search PubMed clinical trials ixabepilone
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UniChem Compound Search for chemical match using the InChIKey FABUFPQFXZVHFB-PVYNADRNSA-N
UniChem Connectivity Search for chemical match using the InChIKey FABUFPQFXZVHFB-PVYNADRNSA-N
Wikipedia Ixabepilone