LIT-001   Click here for help

GtoPdb Ligand ID: 10444

Synonyms: compound 57 [PMID: 30199637]
Compound class: Synthetic organic
Comment: LIT-001 is a non-peptide oxytocin (OT) receptor agonist [1]. The compound is brain penetrant and active in vivo by intraperitoneal injection. OT receptor agonists are predicted to promote prosocial effects in individuals with disorders such as autism spectrum disorders (ASD), who exhibit social interaction deficits. LIT-001 provides an in vivo pharmacological tool compound that is suitable for furthering the study of the effects of OT receptor agonism in autism.
A search of PubChem for 'LIT-001' produces a single CID (137701510), but this is for the R optical isomer of the chemical structure. The primary reference for LIT-001 by Frantz et al. defines the molecule as the S isomer (and as the trifluoroacetate salt) [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 117.83
Molecular weight 531.24
XLogP 4.15
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES S=C(C1CCCN1C(=O)NCc1ccc(cc1C)C(=O)N1Cc2cnn(c2Nc2c1cccc2)C)N(C)C
Isomeric SMILES S=C(C1CCCN1C(=O)NCc1ccc(cc1C)C(=O)N1Cc2cnn(c2Nc2c1cccc2)C)N(C)C
InChI InChI=1S/C28H33N7O2S/c1-18-14-19(11-12-20(18)15-29-28(37)34-13-7-10-24(34)27(38)32(2)3)26(36)35-17-21-16-30-33(4)25(21)31-22-8-5-6-9-23(22)35/h5-6,8-9,11-12,14,16,24,31H,7,10,13,15,17H2,1-4H3,(H,29,37)
InChI Key AOPORIRPXVMWSL-UHFFFAOYSA-N
Bioactivity Comments
Peripheral intraperitoneal administration of LIT-001 leads to a reduction in social interaction deficits in the Oprm1-/- mouse model of autism [1]. Activation of V2 receptors by LIT-001 is unlikely to impact social behaviour as V2 receptors are not expressed in the central nervous system, but it may contribute to fluid retention [2].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
OT receptor Primary target of this compound Hs Agonist Agonist 6.7 pKi - 1
pKi 6.7 (Ki 2.26x10-7 M) [1]
Description: Binding affinity determined by a TR-FRET binding assay on HEK cells expressing SNAP-tagged OT receptors using 20 nM fluorescent DY647 and increasing concentration of competitor.
V1A receptor Hs Agonist Agonist 5.9 pKi - 1
pKi 5.9 (Ki 1.253x10-6 M) [1]
Description: Binding affinity determined by a TR-FRET binding assay on HEK cells expressing SNAP-tagged V1a receptors using 20 nM fluorescent DY647 and increasing concentration of competitor.
V2 receptor Hs Agonist Agonist 5.8 pKi - 1
pKi 5.8 (Ki 1.666x10-6 M) [1]
Description: Binding affinity determined by a TR-FRET binding assay on HEK cells expressing SNAP-tagged V2 receptors using 20 nM fluorescent DY647 and increasing concentration of competitor.