omacetaxine mepesuccinate   Click here for help

GtoPdb Ligand ID: 7454

Synonyms: CGX-635 | HHT | homoharringtonine | Myelostat® | Synribo®
Approved drug PDB Ligand
omacetaxine mepesuccinate is an approved drug (FDA (2012))
Compound class: Natural product
Comment: Omacetaxine mepesuccinate is a semi-synthetic derivative of the alkaloid cephalotaxine from Cephalotaxus harringtonia. Note that this compound is represented on Drugbank with slightly different stereochemistry by the entry DB04865.

omacetaxine mepesuccinate is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 8
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 123.99
Molecular weight 545.26
XLogP 1.72
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC(=O)CC(C(=O)OC1C(=CC23C1c1cc4OCOc4cc1CCN3CCC2)OC)(CCCC(O)(C)C)O
Isomeric SMILES COC(=O)C[C@@](C(=O)O[C@@H]1C(=C[C@]23[C@@H]1c1cc4OCOc4cc1CCN3CCC2)OC)(CCCC(O)(C)C)O
InChI InChI=1S/C29H39NO9/c1-27(2,33)8-5-10-29(34,16-23(31)36-4)26(32)39-25-22(35-3)15-28-9-6-11-30(28)12-7-18-13-20-21(38-17-37-20)14-19(18)24(25)28/h13-15,24-25,33-34H,5-12,16-17H2,1-4H3/t24-,25-,28+,29-/m1/s1
InChI Key HYFHYPWGAURHIV-JFIAXGOJSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes (FDA (2012))
Approved drug? Yes. FDA (2012)
International Nonproprietary Names Click here for help
INN number INN
8885 omacetaxine mepesuccinate
Synonyms Click here for help
CGX-635 | HHT | homoharringtonine | Myelostat® | Synribo®
Database Links Click here for help
CAS Registry No. 26833-87-4
ChEBI CHEBI:71019
ChEMBL Ligand CHEMBL46286
DrugCentral Ligand 4677
GtoPdb PubChem SID 187051757
PubChem CID 285033
RCSB PDB Ligand HMT
Search Google for chemical match using the InChIKey HYFHYPWGAURHIV-JFIAXGOJSA-N
Search Google for chemicals with the same backbone HYFHYPWGAURHIV
Search PubMed clinical trials omacetaxine mepesuccinate
Search PubMed titles omacetaxine mepesuccinate
Search PubMed titles/abstracts omacetaxine mepesuccinate
UniChem Compound Search for chemical match using the InChIKey HYFHYPWGAURHIV-JFIAXGOJSA-N
UniChem Connectivity Search for chemical match using the InChIKey HYFHYPWGAURHIV-JFIAXGOJSA-N
Wikipedia Omacetaxine mepesuccinate

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MedChemExpress
Homoharringtonine (links to external site)
Cat. No. HY-14944