Balanol

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 562880

CAS#: 63590-19-2

Description: Balanol is an ATP-competitive inhibitor of Protein Kinase C (PKC) and Protein Kinase A (PKA).


Price and Availability

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Balanol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 562880
Name: Balanol
CAS#: 63590-19-2
Chemical Formula: C28H26N2O10
Exact Mass: 550.1587
Molecular Weight: 550.52
Elemental Analysis: C, 61.09; H, 4.76; N, 5.09; O, 29.06


Synonym: Balanol; Ophiocordin; BA1; Azepinostatin; (-)-Balanol; (3R-trans)-Balanol;

IUPAC/Chemical Name: 2-[2,6-Dihydroxy-4-[(3R,4R)-3-[(4-hydroxybenzoyl)amino]azepan-4-yl]oxycarbonylbenzoyl]-3-hydroxybenzoic acid

InChi Key: XYUFCXJZFZPEJD-XMSQKQJNSA-N

InChi Code: InChI=1S/C28H26N2O10/c31-16-8-6-14(7-9-16)26(36)30-18-13-29-10-2-5-22(18)40-28(39)15-11-20(33)24(21(34)12-15)25(35)23-17(27(37)38)3-1-4-19(23)32/h1,3-4,6-9,11-12,18,22,29,31-34H,2,5,10,13H2,(H,30,36)(H,37,38)/t18-,22-/m1/s1

SMILES Code: O=C(O)C1=CC=CC(O)=C1C(C2=C(O)C=C(C(O[C@H]3[C@H](NC(C4=CC=C(O)C=C4)=O)CNCCC3)=O)C=C2O)=O


Technical Data

Appearance:
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

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).

Harmonized System Code:
2934.99.90.01


References

1: Qin L, Sankaran B, Aminzai S, Casteel D, Kim C. Structural basis for selective inhibition of human PKG Iα by the balanol-like compound N46. J Biol Chem. 2018 May 16. pii: jbc.RA118.002427. doi: 10.1074/jbc.RA118.002427. [Epub ahead of print] PubMed PMID: 29769318.

2: Hardianto A, Liu F, Ranganathan S. Molecular Dynamics Pinpoint the Global Fluorine Effect in Balanoid Binding to PKCε and PKA. J Chem Inf Model. 2018 Feb 26;58(2):511-519. doi: 10.1021/acs.jcim.7b00504. Epub 2018 Jan 27. PubMed PMID: 29341608.

3: Hardianto A, Yusuf M, Liu F, Ranganathan S. Exploration of charge states of balanol analogues acting as ATP-competitive inhibitors in kinases. BMC Bioinformatics. 2017 Dec 28;18(Suppl 16):572. doi: 10.1186/s12859-017-1955-7. PubMed PMID: 29297286; PubMed Central PMCID: PMC5751415.

4: Patel AR, Hardianto A, Ranganathan S, Liu F. Divergent response of homologous ATP sites to stereospecific ligand fluorination for selectivity enhancement. Org Biomol Chem. 2017 Feb 21;15(7):1570-1574. doi: 10.1039/c7ob00129k. Epub 2017 Jan 25. PubMed PMID: 28119986.

5: Kim J, Li G, Walters MA, Taylor SS, Veglia G. Uncoupling Catalytic and Binding Functions in the Cyclic AMP-Dependent Protein Kinase A. Structure. 2016 Mar 1;24(3):353-63. doi: 10.1016/j.str.2015.11.016. Epub 2016 Jan 28. PubMed PMID: 26833386; PubMed Central PMCID: PMC4775281.

6: Homan KT, Wu E, Cannavo A, Koch WJ, Tesmer JJ. Identification and characterization of amlexanox as a G protein-coupled receptor kinase 5 inhibitor. Molecules. 2014 Oct 22;19(10):16937-49. doi: 10.3390/molecules191016937. PubMed PMID: 25340299; PubMed Central PMCID: PMC4621012.

7: Saha T, Maitra R, Chattopadhyay SK. A unified approach to the important protein kinase inhibitor balanol and a proposed analogue. Beilstein J Org Chem. 2013 Dec 19;9:2910-5. doi: 10.3762/bjoc.9.327. eCollection 2013 Dec 19. PubMed PMID: 24454570; PubMed Central PMCID: PMC3896276.

8: Kumar KS. A chiron approach towards the synthesis of 3-hydroxy lysine and its derivatives. Bioorg Med Chem. 2013 Jun 15;21(12):3609-13. doi: 10.1016/j.bmc.2013.02.013. Epub 2013 Feb 21. PubMed PMID: 23490153.

9: Zhang D, Li S, Lu R, Li K, Luo F, Peng F, Hu F. [Influence of incubation time on metabolites in mycelia of Paecilomyces militaris]. Wei Sheng Wu Xue Bao. 2012 Dec 4;52(12):1477-88. Chinese. PubMed PMID: 23457797.

10: Ahmad S, Sutherland A. Stereoselective synthesis of hydroxylated 3-aminoazepanes using a multi-bond forming, three-step tandem process. Org Biomol Chem. 2012 Oct 3;10(41):8251-9. doi: 10.1039/c2ob26544c. PubMed PMID: 22961458.

11: Thal DM, Yeow RY, Schoenau C, Huber J, Tesmer JJ. Molecular mechanism of selectivity among G protein-coupled receptor kinase 2 inhibitors. Mol Pharmacol. 2011 Aug;80(2):294-303. doi: 10.1124/mol.111.071522. Epub 2011 May 19. PubMed PMID: 21596927; PubMed Central PMCID: PMC3141885.

12: Tesmer JJ, Tesmer VM, Lodowski DT, Steinhagen H, Huber J. Structure of human G protein-coupled receptor kinase 2 in complex with the kinase inhibitor balanol. J Med Chem. 2010 Feb 25;53(4):1867-70. doi: 10.1021/jm9017515. PubMed PMID: 20128603; PubMed Central PMCID: PMC3073382.

13: Pande V, Ramos MJ, Gago F. The Protein kinase inhibitor balanol: structure-activity relationships and structure-based computational studies. Anticancer Agents Med Chem. 2008 Aug;8(6):638-45. Review. PubMed PMID: 18690827.

14: Srivastava AK, Panda G. Total synthesis of (-)-balanol, all stereoisomers, their N-tosyl analogues, and fully protected ophiocordin: an easy route to hexahydroazepine cores from garner aldehydes. Chemistry. 2008;14(15):4675-88. doi: 10.1002/chem.200701991. PubMed PMID: 18399526.

15: Sullivan B, Gilmet J, Leisch H, Hudlicky T. Chiral version of the Burgess reagent and its reactions with oxiranes: application to the formal enantiodivergent synthesis of balanol. J Nat Prod. 2008 Mar;71(3):346-50. doi: 10.1021/np0705357. Epub 2008 Jan 19. PubMed PMID: 18205317.

16: Huang Z, Wong CF, Wheeler RA. Flexible protein-flexible ligand docking with disrupted velocity simulated annealing. Proteins. 2008 Apr;71(1):440-54. PubMed PMID: 17957770.

17: Zhao Y, Sanner MF. FLIPDock: docking flexible ligands into flexible receptors. Proteins. 2007 Aug 15;68(3):726-37. PubMed PMID: 17523154.

18: Wang M, Wong CF. Rank-ordering protein-ligand binding affinity by a quantum mechanics/molecular mechanics/Poisson-Boltzmann-surface area model. J Chem Phys. 2007 Jan 14;126(2):026101. PubMed PMID: 17228977.

19: Nettles JH, Jenkins JL, Bender A, Deng Z, Davies JW, Glick M. Bridging chemical and biological space: "target fishing" using 2D and 3D molecular descriptors. J Med Chem. 2006 Nov 16;49(23):6802-10. PubMed PMID: 17154510.

20: Unthank MG, Hussain N, Aggarwal VK. The use of vinyl sulfonium salts in the stereocontrolled asymmetric synthesis of epoxide- and aziridine-fused heterocycles: application to the synthesis of (-)-balanol. Angew Chem Int Ed Engl. 2006 Oct 27;45(42):7066-9. PubMed PMID: 17009383.