Details of the Drug

General Information of Drug (ID: DM83WVF)

Drug Name
Apicidin
Synonyms
CHEMBL430060; OSI-2040; (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; Acipidin; AC1OCFAM; Apicidin _120249; SCHEMBL147997; ChEMBL_275631; GTPL7495; DTXSID40274182; MolPort-005-944-562; BDBM50238632; ZINC17654900; AKOS030622920; MCULE-8969470747; NCGC00165733-01
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 623.8
Logarithm of the Partition Coefficient (xlogp) 4.4
Rotatable Bond Count (rotbonds) 12
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C34H49N5O6
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
Canonical SMILES
CC[C@H](C)[C@H]1C(=O)N2CCCC[C@@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC3=CN(C4=CC=CC=C43)OC)CCCCCC(=O)CC
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
InChIKey
JWOGUUIOCYMBPV-GMFLJSBRSA-N
Cross-matching ID
PubChem CID
6918328
ChEBI ID
CHEMBL430060
TTD ID
D0W1PV
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Histone deacetylase (HDAC) TTBH0VX NOUNIPROTAC Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
7SK snRNA methylphosphate capping enzyme (MEPCE) OTRBQEYP MEPCE_HUMAN Gene/Protein Processing [3]
A-kinase anchor protein 8 (AKAP8) OTK3EQAI AKAP8_HUMAN Gene/Protein Processing [3]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Drug Response [4]
Ceramide glucosyltransferase OTRT5P5I CEGT_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase 5 activator 1 (CDK5R1) OTJELWK0 CD5R1_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [5]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [6]
Cytochrome c (CYCS) OTBFALJD CYC_HUMAN Protein Interaction/Cellular Processes [5]
Cytoplasmic polyadenylation element-binding protein 4 (CPEB4) OTW1SCZW CPEB4_HUMAN Gene/Protein Processing [3]
DmX-like protein 1 (DMXL1) OTWVL31L DMXL1_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7495).
2 Histone deacetylase inhibitors in cancer therapy: latest developments, trends and medicinal chemistry perspective. Anticancer Agents Med Chem. 2007 Sep;7(5):576-92.
3 Development and validation of the TGx-HDACi transcriptomic biomarker to detect histone deacetylase inhibitors in human TK6 cells. Arch Toxicol. 2021 May;95(5):1631-1645. doi: 10.1007/s00204-021-03014-2. Epub 2021 Mar 26.
4 Involvement of P-glycoprotein and MRP1 in resistance to cyclic tetrapeptide subfamily of histone deacetylase inhibitors in the drug-resistant osteosarcoma and Ewing's sarcoma cells. Int J Cancer. 2006 Jan 1;118(1):90-7. doi: 10.1002/ijc.21297.
5 Mechanism of apicidin-induced cell cycle arrest and apoptosis in Ishikawa human endometrial cancer cells. Chem Biol Interact. 2009 May 15;179(2-3):169-77. doi: 10.1016/j.cbi.2008.11.011. Epub 2008 Nov 25.
6 Modulation of cell cycles and apoptosis by apicidin in estrogen receptor (ER)-positive and-negative human breast cancer cells. Chem Biol Interact. 2008 Apr 15;172(3):235-44. doi: 10.1016/j.cbi.2008.01.007. Epub 2008 Feb 1.