lisofylline

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Ligands
lisofylline

GtoPdb Ligand ID: 9225

Synonyms: (R)-lisophylline | CT-1501R

Comment: Lisophylline is an active metabolite of pentoxifylline. The compound has novel anti-inflammatory properties, likely through inhibition of IL-12 signalling and STAT-4 activation [2]. It is reported to prevent type 1 diabetes in preclinical models [3] and improve the function and viability of isolated or transplanted pancreatic islets [1]. Evidence suggests that combined treatment with lisofylline (for its anti-inflammatory action) and exendin-4 (to enhance beta-cell proliferation) can reverse autoimmune diabetes in the non-obese diabetic (NOD) mouse model [4].

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2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	4
Hydrogen bond donors	1
Rotatable bonds	5
Topological polar surface area	82.05
Molecular weight	280.15
XLogP	2.31
No. Lipinski's rules broken	0

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

Canonical SMILES	CC(CCCCn1c(=O)c2n(C)cnc2n(c1=O)C)O
Isomeric SMILES	C[C@H](CCCCn1c(=O)c2n(C)cnc2n(c1=O)C)O
InChI	InChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3/t9-/m1/s1
InChI Key	NSMXQKNUPPXBRG-SECBINFHSA-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/)