semapimod   Click here for help

GtoPdb Ligand ID: 9211

Synonyms: CNI-1493
Compound class: Synthetic organic
Comment: Semapimod is an experimental anti-inflammatory compound. Structurally it is a tetravalent guanylhydrazone. The endoplasmic reticulum-localized chaperone gp96 (HSP90B1; P14625), which is involved in the biogenesis of Toll-like receptors (TLRs), is reported to be a molecular target of semapimod [1].
Note that we have drawn the molecule as specified by the IUPAC name submitted to the WHO as proposed INN (list 89). CHEMBL2107779 and PubChem CID 5745214 represent alternative tautomers.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 20
Hydrogen bond donors 10
Rotatable bonds 21
Topological polar surface area 365.24
Molecular weight 744.45
XLogP 5.49
No. Lipinski's rules broken 4
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Canonical SMILES O=C(Nc1cc(cc(c1)C(=NN=C(N)N)C)C(=NN=C(N)N)C)CCCCCCCCC(=O)Nc1cc(cc(c1)C(=NN=C(N)N)C)C(=NN=C(N)N)C
Isomeric SMILES O=C(Nc1cc(cc(c1)/C(=N\N=C(N)N)/C)/C(=N/N=C(N)N)/C)CCCCCCCCC(=O)Nc1cc(cc(c1)/C(=N\N=C(N)N)/C)/C(=N/N=C(N)N)/C
InChI InChI=1S/C34H52N18O2/c1-19(45-49-31(35)36)23-13-24(20(2)46-50-32(37)38)16-27(15-23)43-29(53)11-9-7-5-6-8-10-12-30(54)44-28-17-25(21(3)47-51-33(39)40)14-26(18-28)22(4)48-52-34(41)42/h13-18H,5-12H2,1-4H3,(H,43,53)(H,44,54)(H4,35,36,49)(H4,37,38,50)(H4,39,40,51)(H4,41,42,52)/b45-19-,46-20+,47-21-,48-22+
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
8349 semapimod
Synonyms Click here for help
Database Links Click here for help
CAS Registry No. 352513-83-8 (source: WHO INN record)
GtoPdb PubChem SID 315661287
PubChem CID 9854289
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UniChem Compound Search for chemical match using the InChIKey PWDYHMBTPGXCSN-BFKCERSTSA-N
UniChem Connectivity Search for chemical match using the InChIKey PWDYHMBTPGXCSN-BFKCERSTSA-N