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MedKoo Cat#: 562880 | Name: Balanol

Description:

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

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

Chemical Structure

Balanol
Balanol
CAS#63590-19-2

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

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
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
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 550.52 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.

Recalculate based on batch purity %
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: 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.