acifran   Click here for help

GtoPdb Ligand ID: 1595

Synonyms: AY-25712 | D02753 | reductol
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 63.6
Molecular weight 218.06
XLogP 1.64
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)C1=CC(=O)C(O1)(C)c1ccccc1
Isomeric SMILES OC(=O)C1=CC(=O)C(O1)(C)c1ccccc1
InChI InChI=1S/C12H10O4/c1-12(8-5-3-2-4-6-8)10(13)7-9(16-12)11(14)15/h2-7H,1H3,(H,14,15)
InChI Key DFDGRKNOFOJBAJ-UHFFFAOYSA-N
References
1. Jung JK, Johnson BR, Duong T, Decaire M, Uy J, Gharbaoui T, Boatman PD, Sage CR, Chen R, Richman JG et al.. (2007)
Analogues of acifran: agonists of the high and low affinity niacin receptors, GPR109a and GPR109b.
J Med Chem, 50 (7): 1445-8. [PMID:17358052]
2. Mahboubi K, Witman-Jones T, Adamus JE, Letsinger JT, Whitehouse D, Moorman AR, Sawicki D, Bergenhem N, Ross SA. (2006)
Triglyceride modulation by acifran analogs: activity towards the niacin high and low affinity G protein-coupled receptors HM74A and HM74.
Biochem Biophys Res Commun, 340 (2): 482-90. [PMID:16389067]
3. Taggart AK, Kero J, Gan X, Cai TQ, Cheng K, Ippolito M, Ren N, Kaplan R, Wu K, Wu TJ et al.. (2005)
(D)-beta-Hydroxybutyrate inhibits adipocyte lipolysis via the nicotinic acid receptor PUMA-G.
J Biol Chem, 280 (29): 26649-52. [PMID:15929991]
4. Wise A, Foord SM, Fraser NJ, Barnes AA, Elshourbagy N, Eilert M, Ignar DM, Murdock PR, Steplewski K, Green A et al.. (2003)
Molecular identification of high and low affinity receptors for nicotinic acid.
J Biol Chem, 278 (11): 9869-74. [PMID:12522134]