fosigotifator   Click here for help

GtoPdb Ligand ID: 12886

Synonyms: ABBV-CLS-7262 | compound 131 [US20220251123A1]
Compound class: Synthetic organic
Comment: The structure for fosigotifator was obtained from proposed INN list 129 (August 2023) where it is described as a eukaryotic translation initiation factor 2B (eIF2B) activator. Fosigotifator is one of the prodrug compounds claimed in patent US20220251123A1 [2]. It is likely that this is the Abbvie/Calico CNS-penetrant clinical lead ABBV-CLS-7262, that is designed to activate eIF2B and thereby modulate the integrated stress response (ISR) [4] as a mechanism to treat a range of conditions, including neurodegenerative and metabolic diseases [1,3,5].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 11
Hydrogen bond donors 4
Rotatable bonds 14
Topological polar surface area 162.46
Molecular weight 639.37
XLogP 1.11
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES C1=C(C=C(C(=C1)Cl)F)OCC(=O)NC23CCC(CC2)([C@H](C3)OCOP(=O)(O)O)NC(=O)COC4=CC=C(C(=C4)F)Cl
Isomeric SMILES C1CC2(CCC1(C[C@@H]2OCOP(=O)(O)O)NC(=O)COC3=CC(=C(C=C3)Cl)F)NC(=O)COC4=CC(=C(C=C4)Cl)F
InChI InChI=1S/C25H27Cl2F2N2O9P/c26-17-3-1-15(9-19(17)28)37-12-22(32)30-24-5-7-25(8-6-24,21(11-24)39-14-40-41(34,35)36)31-23(33)13-38-16-2-4-18(27)20(29)10-16/h1-4,9-10,21H,5-8,11-14H2,(H,30,32)(H,31,33)(H2,34,35,36)/t21-,24?,25?/m0/s1
InChI Key IURMHIZNAHLQRX-ANYOXOOPSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[(2S)-1,4-bis[[2-(4-chloro-3-fluorophenoxy)acetyl]amino]-2-bicyclo[2.2.2]octanyl]oxymethyl dihydrogen phosphate
Synonyms Click here for help
ABBV-CLS-7262 | compound 131 [US20220251123A1]
Database Links Click here for help
CAS Registry No. 2415715-84-1 (source: WHO INN record)
GtoPdb PubChem SID 485206007
PubChem CID 153563259
Search Google for chemical match using the InChIKey IURMHIZNAHLQRX-ANYOXOOPSA-N
Search Google for chemicals with the same backbone IURMHIZNAHLQRX
UniChem Compound Search for chemical match using the InChIKey IURMHIZNAHLQRX-ANYOXOOPSA-N
UniChem Connectivity Search for chemical match using the InChIKey IURMHIZNAHLQRX-ANYOXOOPSA-N