RMC-5552   Click here for help

GtoPdb Ligand ID: 12338

Synonyms: compound 38 [PMID: 36533617] | RMC5552
Compound class: Synthetic organic
Comment: RMC-5552 is a selective bi-steric inhibitor of mTORC1 [1]. Mechanistically it interacts with both the orthosteric and allosteric binding sites of mTOR, and inhibits phosphorylation of S6K and 4EBP1 (to provide anti-tumour activity) whilst sparing mTORC2-mediated effects on AKT signalling and glucose metabolism. It was developed for potential to treat mTORC1-activated tumours, and is an active clinical lead (Jan 2023).
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 32
Hydrogen bond donors 6
Rotatable bonds 40
Topological polar surface area 432.51
Molecular weight 1776.97
XLogP 5.21
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
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Canonical SMILES CO[C@@H]1C[C@@H](CC[C@H]1OC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCC(=O)N1CCc2c(C1)ccc(c2)Cn1nc(c2c1ncnc2N)c1ccc2c(c1)nc(o2)N)C[C@H]([C@@H]1C[C@@H](O)[C@H](C)/C=C(\C)/[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C(/[C@H](C[C@H]2O[C@](C(=O)C(=O)N3[C@H](C(=O)O1)CCCC3)(O)[C@H](C)CC2)OC)\C)C
Isomeric SMILES [C@@H]12CCCCN1C(=O)C(=O)[C@]1([C@@H](CC[C@@H](C[C@H](OC)/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H]([C@@H](C[C@H](OC2=O)[C@@H](C[C@H]2C[C@H]([C@@H](CC2)OC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCC(=O)N2CCc3c(ccc(Cn4c5ncnc(N)c5c(n4)c4ccc5c(c4)nc(o5)N)c3)C2)OC)C)O)C)/C)O)OC)C)C)/C)O1)C)O
InChI InChI=1S/C93H136N10O24/c1-59-16-12-11-13-17-60(2)77(113-8)54-71-24-19-65(7)93(112,127-71)86(108)89(109)102-30-15-14-18-73(102)90(110)124-78(55-74(104)61(3)49-64(6)84(107)85(115-10)83(106)63(5)48-59)62(4)50-66-21-25-76(79(52-66)114-9)126-92(111)96-29-33-117-35-37-119-39-41-121-43-45-123-47-46-122-44-42-120-40-38-118-36-34-116-32-28-80(105)101-31-27-68-51-67(20-22-70(68)57-101)56-103-88-81(87(94)97-58-98-88)82(100-103)69-23-26-75-72(53-69)99-91(95)125-75/h11-13,16-17,20,22-23,26,49,51,53,58-59,61-63,65-66,71,73-74,76-79,84-85,104,107,112H,14-15,18-19,21,24-25,27-48,50,52,54-57H2,1-10H3,(H2,95,99)(H,96,111)(H2,94,97,98)/b13-11+,16-12+,60-17+,64-49+/t59-,61-,62-,63-,65-,66+,71+,73+,74-,76-,77+,78+,79-,84-,85+,93-/m1/s1
InChI Key IUTYTXDIGUNPAA-GKVGALOGSA-N
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Molecular structure representations generated using Open Babel