apicidin   Click here for help

GtoPdb Ligand ID: 7495

Synonyms: OSI-2040
Antimalarial Ligand
Compound class: Natural product
Comment: Acipidin is a natural product fungal metabolite [2]. It inhibits cancer cell proliferation [3], via histone deacetylase (HDAC) inhibition.

The compound has broad-spectrum activity against apicomplexan parasites including Plasmodium species [2]. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 138.84
Molecular weight 623.37
XLogP 4.24
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES CCC(=O)CCCCCC1NC(=O)C2CCCCN2C(=O)C(NC(=O)C(NC1=O)Cc1cn(c2c1cccc2)OC)C(CC)C
Isomeric SMILES CCC(=O)CCCCC[C@@H]1NC(=O)[C@H]2CCCCN2C(=O)[C@@H](NC(=O)[C@@H](NC1=O)Cc1cn(c2c1cccc2)OC)[C@H](CC)C
InChI InChI=1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22-,26-,27-,29+,30-/m0/s1
Classification Click here for help
Compound class Natural product
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
Synonyms Click here for help
Database Links Click here for help
CAS Registry No. 183506-66-3 (source: Scifinder)
ChEMBL Ligand CHEMBL430060
GtoPdb PubChem SID 187051797
PubChem CID 6918328
Search Google for chemical match using the InChIKey JWOGUUIOCYMBPV-GMFLJSBRSA-N
Search Google for chemicals with the same backbone JWOGUUIOCYMBPV
UniChem Compound Search for chemical match using the InChIKey JWOGUUIOCYMBPV-GMFLJSBRSA-N
UniChem Connectivity Search for chemical match using the InChIKey JWOGUUIOCYMBPV-GMFLJSBRSA-N
Wikipedia Apicidin