agatolimod   

GtoPdb Ligand ID: 9843

Synonyms: CpG 7909 | CpG7909 | PF 3512676 | PF-3512676 | ProMune | VaxImmune
Compound class: Synthetic organic
Comment: Agatolimod is synthetic CpG oligodeoxynucleotide that acts as a TLR9 agonist [3]. We show the parent molecule, whereas the USAN specifies agatolimod sodium (PubChem CID 56841789), and the synonyms we list may also refer to the sodium congener. Its nucleotide sequence is d(P-thio)(T-C-G-T-C-G-T-T-T-T-G-T-C-G-T-T-T-T-G-T-C-G-T-T).
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 165
Hydrogen bond donors 55
Rotatable bonds 143
Topological polar surface area 3684.42
Molecular weight 7701.8
XLogP 18.21
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
Canonical SMILES OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1O)n1cc(C)c(=O)[nH]c1=O)O)n1cc(C)c(=O)[nH]c1=O)O)n1cnc2c1nc(N)[nH]c2=O)O)n1ccc(nc1=O)N)O)n1cc(C)c(=O)[nH]c1=O)O)n1cnc2c1nc(N)[nH]c2=O)O)n1cc(C)c(nc1=O)N)O)n1cc(C)c(nc1=O)N)O)n1cc(C)c(nc1=O)N)O)n1cc(C)c(nc1=O)N)O)n1cnc2c1nc(N)[nH]c2=O)O)n1ccc(nc1=O)N)O)n1cc(C)c(=O)[nH]c1=O)O)n1cnc2c1nc(N)[nH]c2=O)O)n1cc(C)c(=O)[nH]c1=O)O)n1cc(C)c(=O)[nH]c1=O)O)n1cc(C)c(nc1=O)N)O)n1cc(C)c(nc1=O)N)O)n1cnc(c1C)C(=O)NC(=C)N)O)n1ccc(nc1=O)N)O)n1cc(C)c(=O)[nH]c1=O)O)n1cnc2c1nc(N)[nH]c2=O)O)n1ccc(nc1=O)N)O)n1cc(C)c(=O)[nH]c1=O
Isomeric SMILES OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1OP(=S)(OCC1OC(CC1O)n1cc(C)c(=O)[nH]c1=O)O)n1cc(C)c(=O)[nH]c1=O)O)n1cnc2c1nc(N)[nH]c2=O)O)n1ccc(nc1=O)N)O)n1cc(C)c(=O)[nH]c1=O)O)n1cnc2c1nc(N)[nH]c2=O)O)n1cc(C)c(nc1=O)N)O)n1cc(C)c(nc1=O)N)O)n1cc(C)c(nc1=O)N)O)n1cc(C)c(nc1=O)N)O)n1cnc2c1nc(N)[nH]c2=O)O)n1ccc(nc1=O)N)O)n1cc(C)c(=O)[nH]c1=O)O)n1cnc2c1nc(N)[nH]c2=O)O)n1cc(C)c(=O)[nH]c1=O)O)n1cc(C)c(=O)[nH]c1=O)O)n1cc(C)c(nc1=O)N)O)n1cc(C)c(nc1=O)N)O)n1cnc(c1C)C(=O)NC(=C)N)O)n1ccc(nc1=O)N)O)n1cc(C)c(=O)[nH]c1=O)O)n1cnc2c1nc(N)[nH]c2=O)O)n1ccc(nc1=O)N)O)n1cc(C)c(=O)[nH]c1=O
InChI Key GUVMFDICMFQHSZ-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
International Nonproprietary Names
INN number INN
8910 agatolimod
Synonyms
CpG 7909 | CpG7909 | PF 3512676 | PF-3512676 | ProMune | VaxImmune
Database Links
CAS Registry No. 207623-20-9 (source: WHO INN record)
GtoPdb PubChem SID 363894137
PubChem CID 56841790
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