Neoxaline

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

MedKoo CAT#: 584838

CAS#: 71812-10-7

Description: Neoxaline is an alkaloid isolated from fermentation broth of Aspergillus japonicus.

Chemical Structure

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Neoxaline
CAS# 71812-10-7
Instruction

Theoretical Analysis

MedKoo Cat#: 584838
Name: Neoxaline
CAS#: 71812-10-7
Chemical Formula: C23H25N5O4
Exact Mass: 435.19
Molecular Weight: 435.484
Elemental Analysis: C, 63.44; H, 5.79; N, 16.08; O, 14.70

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Neoxaline; Nedoxaline

IUPAC/Chemical Name: 1H,5H-Imidazo(1',2':1,2)pyrido(2,3-b)indole-2,5(3H)-dione, 7a-(1,1-dimethyl-2-propenyl)-6,7,7a,12-tetrahydro-6-hydroxy-3-(1H-imidazol-4-ylmethylene)-12-methoxy-

InChi Key: HHLNXXASUKFCCX-YVLHZVERSA-N

InChi Code: InChI=1S/C23H25N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-10,12-13,18,29H,1,11H2,2-4H3,(H,24,25)(H,26,30)/b17-10-

SMILES Code: O=C1NC23N(OC)C4=C(C=CC=C4)C2(C(C)(C)C=C)CC(O)C(N3/C1=C\C5=CNC=N5)=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: >3 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 435.48 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Hirano A, Iwai Y, Masuma R, Tei K, Omura S. Neoxaline, a new alkaloid produced by Aspergillus japonicus. Production, isolation and properties. J Antibiot (Tokyo). 1979 Aug;32(8):781-5. PubMed PMID: 500498.



2: Ideguchi T, Yamada T, Shirahata T, Hirose T, Sugawara A, Kobayashi Y, Ōmura S, Sunazuka T. Asymmetric total synthesis of neoxaline. J Am Chem Soc. 2013 Aug 28;135(34):12568-71. doi: 10.1021/ja406657v. Epub 2013 Aug 19. PubMed PMID: 23957424.



3: Sunazuka T, Shirahata T, Tsuchiya S, Hirose T, Mori R, Harigaya Y, Kuwajima I, Omura S. A concise stereoselective route to the indoline spiroaminal framework of neoxaline and oxaline. Org Lett. 2005 Mar 3;7(5):941-3. PubMed PMID: 15727480.



4: Martín JF, Liras P. Evolutionary formation of gene clusters by reorganization: the meleagrin/roquefortine paradigm in different fungi. Appl Microbiol Biotechnol. 2016 Feb;100(4):1579-87. doi: 10.1007/s00253-015-7192-y. Epub 2015 Dec 15. Review. PubMed PMID: 26668029.



5: Ries MI, Ali H, Lankhorst PP, Hankemeier T, Bovenberg RA, Driessen AJ, Vreeken RJ. Novel key metabolites reveal further branching of the roquefortine/meleagrin
biosynthetic pathway. J Biol Chem. 2013 Dec 27;288(52):37289-95. doi: 10.1074/jbc.M113.512665. Epub 2013 Nov 13. PubMed PMID: 24225953; PubMed Central PMCID: PMC3873581.



6: Fungaro MHP, Ferranti LS, Massi FP, da Silva JJ, Sartori D, Taniwaki MH, Frisvad JC, Iamanaka BT. Aspergillus labruscus sp. nov., a new species of Aspergillus section Nigri discovered in Brazil. Sci Rep. 2017 Jul 24;7(1):6203. doi: 10.1038/s41598-017-06589-y. PubMed PMID: 28740180; PubMed Central PMCID: PMC5524721.



7: Overy DP, Nielsen KF, Smedsgaard J. Roquefortine/oxaline biosynthesis pathway metabolites in Penicillium ser. Corymbifera: in planta production and implications for competitive fitness. J Chem Ecol. 2005 Oct;31(10):2373-90. Epub 2005 Sep 28. PubMed PMID: 16195849.



8: Yamada T, Ideguchi-Matsushita T, Hirose T, Shirahata T, Hokari R, Ishiyama A, Iwatsuki M, Sugawara A, Kobayashi Y, Otoguro K, Ōmura S, Sunazuka T. Asymmetric Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework. Chemistry. 2015 Aug 10;21(33):11855-64. doi: 10.1002/chem.201501150. Epub 2015 Jul 6. PubMed PMID: 26147398.



9: Koizumi Y, Arai M, Tomoda H, Omura S. Oxaline, a fungal alkaloid, arrests the cell cycle in M phase by inhibition of tubulin polymerization. Biochim Biophys Acta. 2004 Jul 23;1693(1):47-55. PubMed PMID: 15276324.



10: Sunazuka T, Hirose T, Omura S. Efficient total synthesis of novel bioactive microbial metabolites. Acc Chem Res. 2008 Feb;41(2):302-14. doi: 10.1021/ar6000044. Epub 2008 Jan 25. PubMed PMID: 18217720.



11: Noonim P, Mahakarnchanakul W, Varga J, Frisvad JC, Samson RA. Two novel species of Aspergillus section Nigri from Thai coffee beans. Int J Syst Evol Microbiol. 2008 Jul;58(Pt 7):1727-34. doi: 10.1099/ijs.0.65694-0. PubMed PMID: 18599725.



12: Parenicová L, Skouboe P, Frisvad J, Samson RA, Rossen L, ten Hoor-Suykerbuyk M, Visser J. Combined molecular and biochemical approach identifies Aspergillus japonicus and Aspergillus aculeatus as two species. Appl Environ Microbiol. 2001 Feb;67(2):521-7. PubMed PMID: 11157212; PubMed Central PMCID: PMC92616.