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MedKoo Cat#: 597912 | Name: Antrimycin

Description:

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

Antrimycin is an antibiotic.

Chemical Structure

Antrimycin
Antrimycin
CAS#80801-26-9

Theoretical Analysis

MedKoo Cat#: 597912

Name: Antrimycin

CAS#: 80801-26-9

Chemical Formula: C28H47N9O11

Exact Mass: 685.3395

Molecular Weight: 685.73

Elemental Analysis: C, 49.04; H, 6.91; N, 18.38; O, 25.66

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
Antrimycin; Cirratiomycin B; Antrimycin A;
IUPAC/Chemical Name
((E)-2-((S)-2-((S)-2-((2S,3S)-3-amino-2-((S)-2-(2-amino-3-hydroxy-2-(hydroxymethyl)propanamido)propanamido)butanoyl)-2,3,4,5-tetrahydropyridazine-3-carboxamido)propanamido)-3-methylpent-2-enoyl)-L-serine
InChi Key
JIGYSKMCUNIKPN-KYVSZOTASA-N
InChi Code
InChI=1S/C28H47N9O11/c1-6-13(2)19(24(44)34-17(10-38)26(46)47)35-21(41)15(4)32-23(43)18-8-7-9-31-37(18)25(45)20(14(3)29)36-22(42)16(5)33-27(48)28(30,11-39)12-40/h9,14-18,20,38-40H,6-8,10-12,29-30H2,1-5H3,(H,32,43)(H,33,48)(H,34,44)(H,35,41)(H,36,42)(H,46,47)/b19-13+/t14-,15-,16-,17-,18-,20-/m0/s1
SMILES Code
NC(CO)(CO)C(N[C@@H](C)C(N[C@@H]([C@H](C)N)C(N1[C@@H](CCC=N1)C(N[C@@H](C)C(N/C(C(N[C@@H](CO)C(O)=O)=O)=C(C)/CC)=O)=O)=O)=O)=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 685.73 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: Choi EM, Jung WW, Suh KS. Pinacidil protects osteoblastic cells against antimycin A-induced oxidative damage. Mol Med Rep. 2015 Jan;11(1):746-52. doi: 10.3892/mmr.2014.2721. Epub 2014 Oct 21. PubMed PMID: 25334089. 2: Li H, Zhu XL, Yang WC, Yang GF. Comparative kinetics of Qi site inhibitors of cytochrome bc1 complex: picomolar antimycin and micromolar cyazofamid. Chem Biol Drug Des. 2014 Jan;83(1):71-80. doi: 10.1111/cbdd.12199. Epub 2013 Sep 19. PubMed PMID: 23919901. 3: Iglesias DE, Bombicino SS, Valdez LB, Boveris A. Nitric oxide interacts with mitochondrial complex III producing antimycin-like effects. Free Radic Biol Med. 2015 Dec;89:602-13. doi: 10.1016/j.freeradbiomed.2015.08.024. Epub 2015 Oct 9. PubMed PMID: 26456055. 4: Zhang L, Mori T, Zheng Q, Awakawa T, Yan Y, Liu W, Abe I. Rational Control of Polyketide Extender Units by Structure-Based Engineering of a Crotonyl-CoA Carboxylase/Reductase in Antimycin Biosynthesis. Angew Chem Int Ed Engl. 2015 Nov 2;54(45):13462-5. doi: 10.1002/anie.201506899. Epub 2015 Sep 10. PubMed PMID: 26356484. 5: Rasimus-Sahari S, Mikkola R, Andersson MA, Jestoi M, Salkinoja-Salonen M. Streptomyces strains producing mitochondriotoxic antimycin A found in cereal grains. Int J Food Microbiol. 2016 Feb 2;218:78-85. doi: 10.1016/j.ijfoodmicro.2015.11.007. Epub 2015 Nov 24. PubMed PMID: 26619316. 6: Vanner SA, Li X, Zvanych R, Torchia J, Sang J, Andrews DW, Magarvey NA. Chemical and biosynthetic evolution of the antimycin-type depsipeptides. Mol Biosyst. 2013 Nov;9(11):2712-9. doi: 10.1039/c3mb70219g. PubMed PMID: 23989727. 7: Labs M, Rühle T, Leister D. The antimycin A-sensitive pathway of cyclic electron flow: from 1963 to 2015. Photosynth Res. 2016 Sep;129(3):231-8. doi: 10.1007/s11120-016-0217-2. Epub 2016 Jan 18. Review. PubMed PMID: 26781235. 8: Suh KS, Lee YS, Choi EM. The protective effects of Achyranthes bidentata root extract on the antimycin A induced damage of osteoblastic MC3T3-E1 cells. Cytotechnology. 2014 Dec;66(6):925-35. doi: 10.1007/s10616-013-9645-4. Epub 2013 Oct 10. PubMed PMID: 24113920; PubMed Central PMCID: PMC4235941. 9: Sugimoto K, Okegawa Y, Tohri A, Long TA, Covert SF, Hisabori T, Shikanai T. A single amino acid alteration in PGR5 confers resistance to antimycin A in cyclic electron transport around PSI. Plant Cell Physiol. 2013 Sep;54(9):1525-34. doi: 10.1093/pcp/pct098. Epub 2013 Jul 19. PubMed PMID: 23872270. 10: Liu J, Zhu X, Kim SJ, Zhang W. Antimycin-type depsipeptides: discovery, biosynthesis, chemical synthesis, and bioactivities. Nat Prod Rep. 2016 Oct 28;33(10):1146-65. doi: 10.1039/c6np00004e. Epub 2016 Jun 16. Review. PubMed PMID: 27307039. 11: Janetzko J, Batey RA. Organoboron-based allylation approach to the total synthesis of the medium-ring dilactone (+)-antimycin A(1b). J Org Chem. 2014 Aug 15;79(16):7415-24. doi: 10.1021/jo501134d. Epub 2014 Jul 25. PubMed PMID: 25019929. 12: Choi EM, Lee YS. Paeoniflorin isolated from Paeonia lactiflora attenuates osteoblast cytotoxicity induced by antimycin A. Food Funct. 2013 Sep;4(9):1332-8. doi: 10.1039/c3fo60147a. PubMed PMID: 23824342. 13: Sandy M, Zhu X, Rui Z, Zhang W. Characterization of AntB, a promiscuous acyltransferase involved in antimycin biosynthesis. Org Lett. 2013 Jul 5;15(13):3396-9. doi: 10.1021/ol4014365. Epub 2013 Jun 17. PubMed PMID: 23772837. 14: Antal TK, Kukarskikh GP, Bulychev AA, Tyystjärvi E, Krendeleva T. Antimycin A effect on the electron transport in chloroplasts of two Chlamydomonas reinhardtii strains. Planta. 2013 May;237(5):1241-50. doi: 10.1007/s00425-013-1843-y. Epub 2013 Jan 26. PubMed PMID: 23354456. 15: Seipke RF, Patrick E, Hutchings MI. Regulation of antimycin biosynthesis by the orphan ECF RNA polymerase sigma factor σ (AntA.). PeerJ. 2014 Feb 6;2:e253. doi: 10.7717/peerj.253. eCollection 2014. PubMed PMID: 24688837; PubMed Central PMCID: PMC3933326. 16: Yan Y, Chen J, Zhang L, Zheng Q, Han Y, Zhang H, Zhang D, Awakawa T, Abe I, Liu W. Multiplexing of combinatorial chemistry in antimycin biosynthesis: expansion of molecular diversity and utility. Angew Chem Int Ed Engl. 2013 Nov 18;52(47):12308-12. doi: 10.1002/anie.201305569. Epub 2013 Oct 2. PubMed PMID: 24123503. 17: Choi EM. Deoxyactein Isolated from Cimicifuga racemosa protects osteoblastic MC3T3-E1 cells against antimycin A-induced cytotoxicity. J Appl Toxicol. 2013 Jun;33(6):488-94. doi: 10.1002/jat.1784. Epub 2011 Dec 19. PubMed PMID: 22180388. 18: Wang J, Wen Y, Chen X, Lin Y, Zhou J, Xie Y, Wang H, Jiang H, Zheng W. Preparative separation of six antimycin A components from antimycin fermentation broth by high-speed counter-current chromatography. J Chromatogr A. 2010 Sep 3;1217(36):5687-92. doi: 10.1016/j.chroma.2010.07.003. Epub 2010 Jul 16. PubMed PMID: 20688334. 19: Riclea R, Aigle B, Leblond P, Schoenian I, Spiteller D, Dickschat JS. Volatile lactones from streptomycetes arise via the antimycin biosynthetic pathway. Chembiochem. 2012 Jul 23;13(11):1635-44. doi: 10.1002/cbic.201200260. Epub 2012 Jun 29. PubMed PMID: 22753047. 20: Choi EM. Magnolol protects osteoblastic MC3T3-E1 cells against antimycin A-induced cytotoxicity through activation of mitochondrial function. Inflammation. 2012 Jun;35(3):1204-12. doi: 10.1007/s10753-012-9430-0. PubMed PMID: 22281543.