Details of the Drug

General Information of Drug (ID: DM5JKNF)

Drug Name
Silvestrol
Synonyms Naturally derived compounds (cancer); Naturally derived compounds (cancer), Bristol-Myers Squibb/National Cancer Institute
Indication
Disease Entry ICD 11 Status REF
Middle East Respiratory Syndrome (MERS) 1D64 Investigative [1]
Solid tumour/cancer 2A00-2F9Z Investigative [2]
Therapeutic Class
Antiviral Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 654.7
Logarithm of the Partition Coefficient (xlogp) 1.6
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 13
Chemical Identifiers
Formula
C34H38O13
IUPAC Name
methyl (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
Canonical SMILES
CO[C@H]1[C@@H](O[C@H](CO1)[C@@H](CO)O)OC2=CC3=C(C(=C2)OC)[C@@]4([C@@H]([C@@H]([C@H]([C@@]4(O3)C5=CC=C(C=C5)OC)C6=CC=CC=C6)C(=O)OC)O)O
InChI
InChI=1S/C34H38O13/c1-40-20-12-10-19(11-13-20)34-27(18-8-6-5-7-9-18)26(30(38)42-3)29(37)33(34,39)28-23(41-2)14-21(15-24(28)47-34)45-32-31(43-4)44-17-25(46-32)22(36)16-35/h5-15,22,25-27,29,31-32,35-37,39H,16-17H2,1-4H3/t22-,25-,26-,27-,29-,31-,32-,33+,34+/m1/s1
InChIKey
GVKXFVCXBFGBCD-QKDMMWSPSA-N
Cross-matching ID
PubChem CID
11787114
ChEBI ID
CHEBI:66484
CAS Number
697235-38-4
TTD ID
D0AJ1V

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
HUMAN eukaryotic initiation factor-4A (eIF4A) TTIGYVZ IF4A1_HUMAN ; IF4A2_HUMAN ; IF4A3_HUMAN Inhibitor [1]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Broad-spectrum antiviral activity of the eIF4A inhibitor silvestrol against corona- and picornaviruses. Antiviral Res. 2018 Feb;150:123-129.
2 The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
3 Resistance to the translation initiation inhibitor silvestrol is mediated by ABCB1/P-glycoprotein overexpression in acute lymphoblastic leukemia cells. AAPS J. 2011 Sep;13(3):357-64.