lirodegimod

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Ligands
lirodegimod

GtoPdb Ligand ID: 13231

Comment: The chemical structure for lirodegimod was re-drawn from proposed INN list 130 (Feb. 2024), in which the compound is described as a signal transducer and activator of transcription 3 (STAT3) degradation inducer with potential antineoplastic action. In the absence of published information about lirodegimod (March 2024), structural motifs suggest that this is a PROTAC class degrader with a VHL-binding moiety to target the bound STAT3 to the von Hippel-Lindau (VHL) Cullin 2-Ring ubiquitin ligase for proteasomal degradation, and a STAT3-binding domain that is structurally related to that of the declared STAT3 PROTAC SD-36. We will update this entry as soon as more information becomes freely available.
STAT3 degradation is a novel anti-cancer strategy, as an alternative to pharmacological inhibtion.

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	24
Hydrogen bond donors	9
Rotatable bonds	29
Topological polar surface area	383.98
Molecular weight	1257.78
XLogP	-0.6
No. Lipinski's rules broken	4

SMILES / InChI / InChIKey

Canonical SMILES	C[C@@H](C1=CC=C(C=C1)C2=C(C)N=CS2)NC(=O)[C@]3([H])C[C@H](CN3C(=O)[C@]([H])(C(C)(C)C)NC(=O)CCCC4=CC=CC(=C4Cl)OC[C@H](CCC(=O)N)NC(=O)[C@]5([H])CC[C@]6([H])CCN(CC([H])(C(=O)N65)NC(=O)C7=CC8=C(C=CC(=C8)C(=O)P(=O)(O)O)N7)C(=O)C)O
Isomeric SMILES	[H][C@@](NC(=O)CCCC1=CC=CC(OC[C@H](CCC(N)=O)NC(=O)[C@]2([H])CC[C@]3([H])CCN(CC([H])(NC(=O)C4=CC5=C(N4)C=CC(=C5)C(=O)P(O)(O)=O)C(=O)N23)C(C)=O)=C1Cl)(C(=O)N6C[C@H](O)C[C@@]6([H])C(=O)N[C@@H](C)C7=CC=C(C=C7)C8=C(C)N=CS8)C(C)(C)C
InChI	InChI=1S/C60H74ClN10O14PS/c1-32(35-13-15-37(16-14-35)52-33(2)63-31-87-52)64-56(78)47-27-42(73)28-70(47)58(80)53(60(4,5)6)68-50(75)12-8-10-36-9-7-11-48(51(36)61)85-30-40(18-22-49(62)74)65-55(77)46-21-19-41-23-24-69(34(3)72)29-45(57(79)71(41)46)67-54(76)44-26-39-25-38(17-20-43(39)66-44)59(81)86(82,83)84/h7,9,11,13-17,20,25-26,31-32,40-42,45-47,53,66,73H,8,10,12,18-19,21-24,27-30H2,1-6H3,(H2,62,74)(H,64,78)(H,65,77)(H,67,76)(H,68,75)(H2,82,83,84)/t32-,40-,41+,42+,45?,46-,47-,53+/m0/s1
InChI Key	OANZCHOMQTZJOO-KMHQXASGSA-N