lisofylline   

GtoPdb Ligand ID: 9225

Synonyms: (R)-lisophylline | CT-1501R
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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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
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
Classification
Compound class Synthetic organic
Prodrug pentoxifylline
IUPAC Name
1-[(5R)-5-hydroxyhexyl]-3,7-dimethylpurine-2,6-dione
International Nonproprietary Names
INN number INN
7322 lisofylline
Synonyms
(R)-lisophylline | CT-1501R
Database Links
CAS Registry No. 100324-81-0
ChEMBL Ligand CHEMBL1411
GtoPdb PubChem SID 315661300
PubChem CID 501254
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