lirodegimod   Click here for help

GtoPdb Ligand ID: 13231

Compound class: Synthetic organic
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
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
signal transducer and activator of transcription 3 Hs None Binding - - -
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Description: PROTAC degrader