lisofylline   Click here for help

GtoPdb Ligand ID: 9225

Synonyms: (R)-lisophylline | CT-1501R
Immunopharmacology Ligand
Compound class: Synthetic organic
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].
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 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
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 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
References
1. Cui P, Macdonald TL, Chen M, Nadler JL. (2006)
Synthesis and biological evaluation of lisofylline (LSF) analogs as a potential treatment for Type 1 diabetes.
Bioorg Med Chem Lett, 16 (13): 3401-5. [PMID:16650991]
2. Rice GC, Rosen J, Weeks R, Michnick J, Bursten S, Bianco JA, Singer JW. (1994)
CT-1501R selectively inhibits induced inflammatory monokines in human whole blood ex vivo.
Shock, 1 (4): 254-66. [PMID:7735959]
3. Tersey SA, Carter JD, Rosenberg L, Taylor-Fishwick DA, Mirmira RG, Nadler JL. (2012)
Amelioration of type 1 diabetes following treatment of non-obese diabetic mice with INGAP and lisofylline.
J Diabetes Mellitus, 2 (2): 251-257. [PMID:26473085]
4. Yang Z, Chen M, Carter JD, Nunemaker CS, Garmey JC, Kimble SD, Nadler JL. (2006)
Combined treatment with lisofylline and exendin-4 reverses autoimmune diabetes.
Biochem Biophys Res Commun, 344 (3): 1017-22. [PMID:16643856]