Nosiheptide | CAS#56377-79-8 | antibacterial agent

MedKoo Cat#: 461457 | Name: Nosiheptide

Description:

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

Nosiheptide is a parent compound of thiopeptide family that exhibit potent activities against various bacterial pathogens. Note: Current batch has purity > 90%, which will be sold as is.

Chemical Structure

Nosiheptide

CAS#56377-79-8

Theoretical Analysis

MedKoo Cat#: 461457

Name: Nosiheptide

CAS#: 56377-79-8

Chemical Formula: C51H51N13O12S6

Exact Mass: 1229.2104

Molecular Weight: 1230.34

Elemental Analysis: C, 49.79; H, 4.18; N, 14.80; O, 15.60; S, 15.63

Price and Availability

Size	Price	Availability
10mg	USD 150.00	2 Weeks
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks

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Related CAS #

No Data

Synonym

Nosiheptide; Multhiomycin; Multiomycin; Nosiheptidum; RP 9671; RP-9671; RP9671;

IUPAC/Chemical Name

A name could not be generated for this structure.

InChi Key

OQAOHXRUMXWDLQ-ATVZKCIHSA-N

InChi Code

1S/C51H43N13O12S6/c1-5-23-46-60-28(14-79-46)41(70)56-25-10-33(67)50(74)76-11-21-7-6-8-24-34(21)18(2)35(54-24)51(75)82-17-31(57-42(71)29-15-80-47(25)61-29)48-58-26(12-78-48)37-22(45-59-30(13-77-45)43(72)64-36(20(4)65)44(73)55-23)9-32(66)38(63-37)49-62-27(16-81-49)40(69)53-19(3)39(52)68/h5-9,12-16,20,25,31,33,36,54,65-67H,3,10-11,17H2,1-2,4H3,(H2,52,68)(H,53,69)(H,55,73)(H,56,70)(H,57,71)(H,64,72)/b23-5-/t20-,25+,31+,33+,36+/m1/s1

SMILES Code

C/C=C1NC([C@H]([C@H](O)C)NC(C2csC(c3c(C4csC([C@@H]5CSC(c([nH]6)c(C)c7c6cccc7COC([C@H](C[C@@H](C8[N]C(C(N5)=O)cs8)NC(C9csC\1[N]9)=O)O)=O)=O)[N]4)nc(c%10scc(C(NC(C(N)=O)=C)=O)n%10)c(O)c3)[N]2)=O)=O

Appearance

Solid powder

Purity

>95% (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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

1. Yu X, Zhu R, Geng Z, Kong Y, Wang F, Dong L, Zhao L, Xue Y, Ma X, Huang H. Nosiheptide Harbors Potent In Vitro and Intracellular Inhbitory Activities against Mycobacterium tuberculosis. Microbiol Spectr. 2022 Dec 21;10(6):e0144422. doi: 10.1128/spectrum.01444-22. Epub 2022 Oct 12. PMID: 36222690; PMCID: PMC9769715. 2. Haste NM, Thienphrapa W, Tran DN, Loesgen S, Sun P, Nam SJ, Jensen PR, Fenical W, Sakoulas G, Nizet V, Hensler ME. Activity of the thiopeptide antibiotic nosiheptide against contemporary strains of methicillin-resistant Staphylococcus aureus. J Antibiot (Tokyo). 2012 Dec;65(12):593-8. doi: 10.1038/ja.2012.77. Epub 2012 Oct 10. PMID: 23047246; PMCID: PMC3528839.

In vitro activity:

In vivo activity:

TBD

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	125.0	101.60

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,230.34 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

Formulation protocol:

In vitro protocol:

In vivo protocol:

TBD

1: Mo Q, Zhang H, Liu Q, Tang X, Zhao L, Zan X, Song Y. Enhancing nosiheptide production in Streptomyces actuosus by heterologous expression of haemoprotein from Sinorhizobium meliloti. Lett Appl Microbiol. 2016 Jun;62(6):480-7. doi: 10.1111/lam.12575. PubMed PMID: 27096926. 2: Jiang L, Xue YJ, Liu WY, Ma M, Wu XR, Wang SZ, Chen YJ. The importance of start codon of nosM in nosiheptide production. Chin J Nat Med. 2015 Nov;13(11):854-860. doi: 10.1016/S1875-5364(15)30089-3. PubMed PMID: 26614460. 3: Yin S, Jiang H, Chen D, Murchie AI. Substrate recognition and modification by the nosiheptide resistance methyltransferase. PLoS One. 2015 Apr 24;10(4):e0122972. doi: 10.1371/journal.pone.0122972. eCollection 2015. PubMed PMID: 25910005; PubMed Central PMCID: PMC4409310. 4: Liu S, Guo H, Zhang T, Han L, Yao P, Zhang Y, Rong N, Yu Y, Lan W, Wang C, Ding J, Wang R, Liu W, Cao C. Structure-based Mechanistic Insights into Terminal Amide Synthase in Nosiheptide-Represented Thiopeptides Biosynthesis. Sci Rep. 2015 Aug 5;5:12744. doi: 10.1038/srep12744. PubMed PMID: 26244829; PubMed Central PMCID: PMC4525488. 5: Yamata T, Shimamura C, Asao M, Aita N, Chihara T. [Validation Study on a Method of Determination of Nosiheptide in Formula Feeds by HPLC-FL]. Shokuhin Eiseigaku Zasshi. 2015;56(4):173-7. doi: 10.3358/shokueishi.56.173. Japanese. PubMed PMID: 26346862. 6: Ji X, Li Y, Ding W, Zhang Q. Substrate-Tuned Catalysis of the Radical S-Adenosyl-L-Methionine Enzyme NosL Involved in Nosiheptide Biosynthesis. Angew Chem Int Ed Engl. 2015 Jul 27;54(31):9021-4. doi: 10.1002/anie.201503976. Epub 2015 Jul 3. PubMed PMID: 26138750. 7: Wang Y, Liu S, Yao P, Yu Y, Zhang Y, Lan W, Wang C, Ding J, Liu W, Cao C. Crystallographic analysis of NosA, which catalyzes terminal amide formation in the biosynthesis of nosiheptide. Acta Crystallogr F Struct Biol Commun. 2015 Aug;71(Pt 8):1033-7. doi: 10.1107/S2053230X15011085. Epub 2015 Jul 28. PubMed PMID: 26249695; PubMed Central PMCID: PMC4528937. 8: Wang Q, Zhang D, Li Y, Zhang F, Wang C, Liang X. Genome shuffling and ribosome engineering of Streptomyces actuosus for high-yield nosiheptide production. Appl Biochem Biotechnol. 2014 Jul;173(6):1553-63. doi: 10.1007/s12010-014-0948-5. Epub 2014 May 15. PubMed PMID: 24828581. 9: Ma M, Xue Y, Liu W, Zhang H, Kong L, Wang S, Chen Y. Directly utilizing an endogenous gene to dissect regulatory elements in the biosynthetic gene cluster of nosiheptide. Chem Commun (Camb). 2014 Sep 18;50(72):10430-3. doi: 10.1039/c4cc04974h. PubMed PMID: 25059114. 10: Zhou W, Liu X, Zhang P, Zhou P, Shi X. Effect analysis of mineral salt concentrations on nosiheptide production by Streptomyces actuosus Z-10 using response surface methodology. Molecules. 2014 Sep 26;19(10):15507-20. doi: 10.3390/molecules191015507. PubMed PMID: 25264834. 11: Haste NM, Thienphrapa W, Tran DN, Loesgen S, Sun P, Nam SJ, Jensen PR, Fenical W, Sakoulas G, Nizet V, Hensler ME. Activity of the thiopeptide antibiotic nosiheptide against contemporary strains of methicillin-resistant Staphylococcus aureus. J Antibiot (Tokyo). 2012 Dec;65(12):593-8. doi: 10.1038/ja.2012.77. Epub 2012 Oct 10. PubMed PMID: 23047246; PubMed Central PMCID: PMC3528839. 12: Liu W, Xue Y, Ma M, Wang S, Liu N, Chen Y. Multiple oxidative routes towards the maturation of nosiheptide. Chembiochem. 2013 Sep 2;14(13):1544-7. doi: 10.1002/cbic.201300427. Epub 2013 Aug 12. PubMed PMID: 23939763. 13: Liu W, Ma M, Xue Y, Liu N, Wang S, Chen Y. The C-terminal extended serine residue is absolutely required in nosiheptide maturation. Chembiochem. 2013 Mar 18;14(5):573-6. doi: 10.1002/cbic.201200681. Epub 2013 Feb 25. PubMed PMID: 23440918. 14: Wojtas KP, Riedrich M, Lu JY, Winter P, Winkler T, Walter S, Arndt HD. Total Synthesis of Nosiheptide. Angew Chem Int Ed Engl. 2016 Aug 8;55(33):9772-6. doi: 10.1002/anie.201603140. Epub 2016 Jun 27. PubMed PMID: 27345011. 15: Wang S, Zhou S, Liu W. Opportunities and challenges from current investigations into the biosynthetic logic of nosiheptide-represented thiopeptide antibiotics. Curr Opin Chem Biol. 2013 Aug;17(4):626-34. doi: 10.1016/j.cbpa.2013.06.021. Epub 2013 Jul 6. Review. PubMed PMID: 23838388. 16: Yang H, Wang Z, Shen Y, Wang P, Jia X, Zhao L, Zhou P, Gong R, Li Z, Yang Y, Chen D, Murchie AI, Xu Y. Crystal structure of the nosiheptide-resistance methyltransferase of Streptomyces actuosus. Biochemistry. 2010 Aug 3;49(30):6440-50. doi: 10.1021/bi1005915. PubMed PMID: 20550164. 17: Feng M, Cai Q, Shi X, Huang H, Zhou P, Guo X. Recombinant high-density lipoprotein complex as a targeting system of nosiheptide to liver cells. J Drug Target. 2008 Jul;16(6):502-8. doi: 10.1080/10611860802200938 . PubMed PMID: 18604663. 18: Li Y, Dosch DC, Woodman RH, Floss HG, Strohl WR. Transcriptional organization and regulation of the nosiheptide resistance gene in Streptomyces actuosus. J Ind Microbiol. 1991 Jul;8(1):1-12. Review. PubMed PMID: 1367329. 19: Yu Y, Guo H, Zhang Q, Duan L, Ding Y, Liao R, Lei C, Shen B, Liu W. NosA catalyzing carboxyl-terminal amide formation in nosiheptide maturation via an enamine dealkylation on the serine-extended precursor peptide. J Am Chem Soc. 2010 Nov 24;132(46):16324-6. doi: 10.1021/ja106571g. Epub 2010 Nov 3. PubMed PMID: 21047073; PubMed Central PMCID: PMC2990472. 20: Yang H, Wang P, Dong Z, Li X, Gong R, Yang Y, Li Z, Xu Y, Xu Y. Crystallization and preliminary crystallographic analysis of nosiheptide-resistance methyltransferase from Streptomyces actuosus in complex with SAM. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2010 May 1;66(Pt 5):579-82. doi: 10.1107/S1744309110011395. Epub 2010 Apr 30. PubMed PMID: 20445264; PubMed Central PMCID: PMC2864697.

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