ADU-S100   Click here for help

GtoPdb Ligand ID: 10192

Synonyms: dithio-(Rp,Rp)-[cyclic[A(2',5')pA(3',5')p]] | MIW815 | ML RR-S2 CDA [1] | S100
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: ADU-S100 (a.k.a. ML RR-S2 CDA) is a synthetic cyclic dinucleotide STING agonist that is being developed as an immuno-oncology lead by Aduro BioTech and Novartis [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 18
Hydrogen bond donors 5
Rotatable bonds 2
Topological polar surface area 362.89
Molecular weight 690.06
XLogP -2.13
No. Lipinski's rules broken 1
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Canonical SMILES OC1C2COP(=O)(S)OC3C(COP(=S)(OC1C(O2)n1cnc2c1ncnc2N)O)OC(C3O)n1cnc2c1ncnc2N
Isomeric SMILES OC1[C@H]2COP(=O)(S)O[C@@H]3[C@@H](COP(=S)(O[C@H]1[C@@H](O2)n1cnc2c1ncnc2N)O)O[C@H]([C@@H]3O)n1cnc2c1ncnc2N
InChI InChI=1S/C20H24N10O10P2S2/c21-15-9-17(25-3-23-15)29(5-27-9)19-12(32)13-8(38-19)2-36-42(34,44)40-14-11(31)7(1-35-41(33,43)39-13)37-20(14)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-32H,1-2H2,(H,33,43)(H,34,44)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11?,12-,13-,14-,19-,20-,41?,42?/m1/s1
1. Corrales L, Glickman LH, McWhirter SM, Kanne DB, Sivick KE, Katibah GE, Woo SR, Lemmens E, Banda T, Leong JJ et al.. (2015)
Direct Activation of STING in the Tumor Microenvironment Leads to Potent and Systemic Tumor Regression and Immunity.
Cell Rep, 11 (7): 1018-30. [PMID:25959818]
2. Sivick KE, Desbien AL, Glickman LH, Reiner GL, Corrales L, Surh NH, Hudson TE, Vu UT, Francica BJ, Banda T et al.. (2018)
Magnitude of Therapeutic STING Activation Determines CD8+ T Cell-Mediated Anti-tumor Immunity.
Cell Rep, 25 (11): 3074-3085.e5. [PMID:30540940]