defoslimod   Click here for help

GtoPdb Ligand ID: 9024

Synonyms: OM 174 | OM-174
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Defoslimod is an analogue of lipopolysaccharide endotoxin-derived lipid A obtained from E. coli [1]. It was developed as an immunotherapeutic agent for the treatment of cancer. Defoslimod acts as an agonist of Toll-like receptors 2 and 4 (TLR2 and TLR4) [2].
We show the structure with chemical formula provided in the INN record for the compound (C52H100N2O20P2). PubChem CID 56841121, which claims to represent defoslimod has an extra carbon atom and two associated hydrogens (C53H102N2O20P2). But note also that the structure reported in [1] only has 51 carbon atoms.
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 22
Hydrogen bond donors 11
Rotatable bonds 48
Topological polar surface area 366.48
Molecular weight 1134.63
XLogP 10.1
No. Lipinski's rules broken 4

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCCCCCCCC(CC(=O)NC1C(OC(C(C1O)O)COC1OC(CO)C(C(C1NC(=O)CC(OC(=O)CCCCCCCCCCC)CCCCCCCCCCC)O)OP(=O)(O)O)OP(=O)(O)O)O
Isomeric SMILES CCCCCCCCCCC[C@H](CC(=O)N[C@H]1[C@H](O[C@@H]([C@H]([C@@H]1O)O)CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1NC(=O)C[C@@H](OC(=O)CCCCCCCCCCC)CCCCCCCCCCC)O)OP(=O)(O)O)OP(=O)(O)O)O
InChI InChI=1S/C52H100N2O20P2/c1-4-7-10-13-16-19-22-25-28-31-38(56)34-42(57)53-45-48(61)47(60)41(72-52(45)74-76(66,67)68)37-69-51-46(49(62)50(40(36-55)71-51)73-75(63,64)65)54-43(58)35-39(32-29-26-23-20-17-14-11-8-5-2)70-44(59)33-30-27-24-21-18-15-12-9-6-3/h38-41,45-52,55-56,60-62H,4-37H2,1-3H3,(H,53,57)(H,54,58)(H2,63,64,65)(H2,66,67,68)/t38-,39+,40-,41-,45-,46-,47-,48-,49-,50-,51-,52-/m1/s1
InChI Key GOWLTLODGKPXMN-MEKRSRHXSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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