WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 510292
CAS#: 591778-70-0 (HCl)
Description: CP-640186 is a potent inhibitor of mammalian ACCs and can reduce body weight and improve insulin sensitivity in test animals. CP-640186 has recently been shown to be a potent inhibitor of isoforms of mammalian ACCs with IC50 values of about 55 nM. This is currently the only reported potent inhibitor of mammalian ACCs. In cell cultures as well as in animal models, CP-640186 can reduce tissue malonyl-CoA levels, inhibit fatty acid biosynthesis, and stimulate fatty acid oxidation. Most importantly, CP-640186 can reduce body fat mass and body weight, and improve insulin sensitivity, validating ACCs as targets for antiobesity and antidiabetes drugs.
MedKoo Cat#: 510292
Name: CP640186 HCl
CAS#: 591778-70-0 (HCl)
Chemical Formula: C30H36ClN3O3
Molecular Weight: 522.09
Elemental Analysis: C, 69.02; H, 6.95; Cl, 6.79; N, 8.05; O, 9.19
Related CAS #: 591778-70-0 (HCl) 591778-68-6 (free base)
Synonym: CP640186; CP-640186; CP 640186; CP640,186; CP-640,186; CP 640,186.
IUPAC/Chemical Name: (R)-anthracen-9-yl(3-(morpholine-4-carbonyl)-[1,4'-bipiperidin]-1'-yl)methanone hydrochloride
InChi Key: DUBNXJIOBFRASV-GJFSDDNBSA-N
InChi Code: InChI=1S/C30H35N3O3.ClH/c34-29(32-16-18-36-19-17-32)24-8-5-13-33(21-24)25-11-14-31(15-12-25)30(35)28-26-9-3-1-6-22(26)20-23-7-2-4-10-27(23)28;/h1-4,6-7,9-10,20,24-25H,5,8,11-19,21H2;1H/t24-;/m1./s1
SMILES Code: O=C(C1=C2C=CC=CC2=CC3=CC=CC=C13)N4CCC(N5C[C@H](C(N6CCOCC6)=O)CCC5)CC4.[H]Cl
Appearance: Light yellow solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 522.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Yamashita T, Kamata M, Endo S, Yamamoto M, Kakegawa K, Watanabe H, Miwa K, Yamano T, Funata M, Sakamoto J, Tani A, Mol CD, Zou H, Dougan DR, Sang B, Snell G, Fukatsu K. Design, synthesis, and structure-activity relationships of spirolactones bearing 2-ureidobenzothiophene as acetyl-CoA carboxylases inhibitors. Bioorg Med Chem Lett. 2011 Nov 1;21(21):6314-8. doi: 10.1016/j.bmcl.2011.08.117. Epub 2011 Sep 6. PubMed PMID: 21944854.
2: Hess D, Chisholm JW, Igal RA. Inhibition of stearoylCoA desaturase activity blocks cell cycle progression and induces programmed cell death in lung cancer cells. PLoS One. 2010 Jun 30;5(6):e11394. doi: 10.1371/journal.pone.0011394. PubMed PMID: 20613975; PubMed Central PMCID: PMC2894866.
3: Xiang S, Callaghan MM, Watson KG, Tong L. A different mechanism for the inhibition of the carboxyltransferase domain of acetyl-coenzyme A carboxylase by tepraloxydim. Proc Natl Acad Sci U S A. 2009 Dec 8;106(49):20723-7. doi: 10.1073/pnas.0908431106. Epub 2009 Nov 19. PubMed PMID: 19926852; PubMed Central PMCID: PMC2791573.
4: Madauss KP, Burkhart WA, Consler TG, Cowan DJ, Gottschalk WK, Miller AB, Short SA, Tran TB, Williams SP. The human ACC2 CT-domain C-terminus is required for full functionality and has a novel twist. Acta Crystallogr D Biol Crystallogr. 2009 May;65(Pt 5):449-61. doi: 10.1107/S0907444909008014. Epub 2009 Apr 18. PubMed PMID: 19390150; PubMed Central PMCID: PMC2725780.
5: Hu HY, Huang YC, Yu HT, Zhang Y. (Anthracen-9-yl)(piperidin-1-yl)-methanone. Acta Crystallogr Sect E Struct Rep Online. 2008 Oct 15;64(Pt 11):o2120. doi: 10.1107/S1600536808033205. PubMed PMID: 21580982; PubMed Central PMCID: PMC2959661.
6: Patil PB, Minteer SD, Mielke AA, Lewis LR, Casmaer CA, Barrientos EJ, Ju JS, Smith JL, Fisher JS. Malonyl coenzyme A affects insulin-stimulated glucose transport in myotubes. Arch Physiol Biochem. 2007 Feb;113(1):13-24. PubMed PMID: 17522981.
7: Zhang H, Tweel B, Li J, Tong L. Crystal structure of the carboxyltransferase domain of acetyl-coenzyme A carboxylase in complex with CP-640186. Structure. 2004 Sep;12(9):1683-91. PubMed PMID: 15341732.
8: Harwood HJ Jr, Petras SF, Shelly LD, Zaccaro LM, Perry DA, Makowski MR, Hargrove DM, Martin KA, Tracey WR, Chapman JG, Magee WP, Dalvie DK, Soliman VF, Martin WH, Mularski CJ, Eisenbeis SA. Isozyme-nonselective N-substituted bipiperidylcarboxamide acetyl-CoA carboxylase inhibitors reduce tissue malonyl-CoA concentrations, inhibit fatty acid synthesis, and increase fatty acid oxidation in cultured cells and in experimental animals. J Biol Chem. 2003 Sep 26;278(39):37099-111. Epub 2003 Jul 3. PubMed PMID: 12842871.
591778-70-0 (CP-640186 HCl salt);
591778-68-6 (CP-640186 free base).