apicidin   

GtoPdb Ligand ID: 7495

Synonyms: OSI-2040
Comment: Acipidin is a natural product fungal metabolite [2]. It inhibits cancer cell proliferation [3], via histone deacetylase (HDAC) inhibition.
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key JWOGUUIOCYMBPV-GMFLJSBRSA-N
Classification
Compound class Natural product or derivative
IUPAC Name
(3S,6S,9S,12R)-3-[(2S)-butan-2-yl]-6-[(1-methoxyindol-3-yl)methyl]-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone
Synonyms
OSI-2040
Database Links
CAS Registry No. 183506-66-3 (source: Scifinder)
ChEMBL Ligand CHEMBL430060
GtoPdb PubChem SID 187051797
PubChem CID 6918328
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Search UniChem for chemicals with the same backbone JWOGUUIOCYMBPV
Wikipedia Apicidin