Monactin | CAS#7182-54-9 | Marcrotetrolide antibiotic

MedKoo Cat#: 592358 | Name: Monactin

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Description:

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

Monactin is a Marcrotetrolide antibiotic produced by cycloheximide producing species of Streptomyces; it is homolog of nonactin from the same species.

Chemical Structure

Monactin

CAS#7182-54-9

Theoretical Analysis

MedKoo Cat#: 592358

Name: Monactin

CAS#: 7182-54-9

Chemical Formula: C41H66O12

Exact Mass: 750.4554

Molecular Weight: 750.97

Elemental Analysis: C, 65.58; H, 8.86; O, 25.57

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 400.00
5mg	USD 1,250.00

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Related CAS #

No Data

Synonym

Monactin

IUPAC/Chemical Name

Nonactin, 5-demethyl-5-ethyl-

InChi Key

YPUPRVWRYDPGCW-HKYUDYCSSA-N

InChi Code

InChI=1S/C41H66O12/c1-9-29-21-33-13-17-36(52-33)27(7)40(44)48-23(3)19-31-11-15-34(50-31)25(5)38(42)46-22(2)18-30-10-14-35(49-30)26(6)39(43)47-24(4)20-32-12-16-37(51-32)28(8)41(45)53-29/h22-37H,9-21H2,1-8H3/t22-,23-,24-,25-,26-,27+,28-,29-,30-,31-,32-,33-,34+,35-,36-,37-/m0/s1

SMILES Code

O=C([C@H]([C@@H]1CC[C@H](O1)C[C@H](C)OC([C@H]([C@@H]2CC[C@H](O2)C[C@H](C)OC([C@H]([C@@H]3O[C@H](C[C@H](C)O4)CC3)C)=O)C)=O)C)O[C@@H](CC)C[C@@H](O5)CC[C@H]5[C@@H](C)C4=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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Monactin is a mactrotetralide antibiotic and a non-selective ionophore for monovalent cations, including potassium, sodium, and lithium.

In vitro activity:

TBD

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 750.97 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:

TBD

In vitro protocol:

TBD

In vivo protocol:

TBD

1: Islam MT, Laatsch H, von Tiedemann A. Inhibitory Effects of Macrotetrolides from Streptomyces spp. On Zoosporogenesis and Motility of Peronosporomycete Zoospores Are Likely Linked with Enhanced ATPase Activity in Mitochondria. Front Microbiol. 2016 Nov 18;7:1824. eCollection 2016. PubMed PMID: 27917156; PubMed Central PMCID: PMC5114239. 2: Shishlyannikova TA, Kuzmin AV, Fedorova GA, Shishlyannikov SM, Lipko IA, Sukhanova EV, Belkova NL. Ionofore antibiotic polynactin produced by Streptomyces sp. 156A isolated from Lake Baikal. Nat Prod Res. 2017 Mar;31(6):639-644. doi: 10.1080/14786419.2016.1217203. Epub 2016 Aug 3. PubMed PMID: 27486824. 3: Harinantenaina Rakotondraibe L, Rasolomampianina R, Park HY, Li J, Slebodnik C, Brodie PJ, Blasiak LC, Hill R, TenDyke K, Shen Y, Cassera MB, Rejo F, Kingston DG. Antiproliferative and antiplasmodial compounds from selected Streptomyces species. Bioorg Med Chem Lett. 2015 Dec 1;25(23):5646-9. doi: 10.1016/j.bmcl.2015.07.103. Epub 2015 Aug 6. PubMed PMID: 26508548; PubMed Central PMCID: PMC4636933. 4: Crevelin EJ, Crotti AE, Zucchi TD, Melo IS, Moraes LA. Dereplication of Streptomyces sp. AMC 23 polyether ionophore antibiotics by accurate-mass electrospray tandem mass spectrometry. J Mass Spectrom. 2014 Nov;49(11):1117-26. doi: 10.1002/jms.3432. PubMed PMID: 25395127. 5: Silva LJ, Crevelin EJ, Souza WR, Moraes LA, Melo IS, Zucchi TD. Streptomyces araujoniae Produces a Multiantibiotic Complex with Ionophoric Properties to Control Botrytis cinerea. Phytopathology. 2014 Dec;104(12):1298-305. doi: 10.1094/PHYTO-11-13-0327-R. PubMed PMID: 24983843. 6: Täubel M, Sulyok M, Vishwanath V, Bloom E, Turunen M, Järvi K, Kauhanen E, Krska R, Hyvärinen A, Larsson L, Nevalainen A. Co-occurrence of toxic bacterial and fungal secondary metabolites in moisture-damaged indoor environments. Indoor Air. 2011 Oct;21(5):368-75. doi: 10.1111/j.1600-0668.2011.00721.x. Epub 2011 May 18. PubMed PMID: 21585551. 7: Jani P, Emmert J, Wohlgemuth R. Process analysis of macrotetrolide biosynthesis during fermentation by means of direct infusion LC-MS. Biotechnol J. 2008 Feb;3(2):202-8. PubMed PMID: 18064609. 8: Qin W, Zwicki T, Pretsch E. Improved detection limits and unbiased selectivity coefficients obtained by using ion-exchange resins in the inner reference solution of ion-selective polymeric membrane electrodes. Anal Chem. 2000 Jul 15;72(14):3236-40. PubMed PMID: 10939393. 9: Smith WC, Xiang L, Shen B. Genetic localization and molecular characterization of the nonS gene required for macrotetrolide biosynthesis in Streptomyces griseus DSM40695. Antimicrob Agents Chemother. 2000 Jul;44(7):1809-17. PubMed PMID: 10858335; PubMed Central PMCID: PMC89966. 10: Sverdlova AN, Solov'eva IV, Nefelova MV. [UV-spectroscopic study of complex formation between nonactin and picrates of monovalent cations]. Antibiot Khimioter. 1995 Apr;40(4):17-24. Russian. PubMed PMID: 7654094. 11: Orlova TI. [Macrotetrolide antibiotics from a recombinant strain of Streptococcus chrysomallus]. Antibiot Khimioter. 1993 Jul;38(7):3-6. Russian. PubMed PMID: 8161273. 12: Jizba J, Sedmera P, Zima J, Beran M, Blumauerová M, Kandybin NV, Samoukina GV. Macrotetrolide antibiotics produced by Streptomyces globisporus. Folia Microbiol (Praha). 1991;36(5):437-43. PubMed PMID: 1821868. 13: Bührer T, Peter H, Simon W. NH4+ ion-selective microelectrode based on the antibiotics nonactin/monactin. Pflugers Arch. 1988 Sep;412(4):359-62. PubMed PMID: 3174392. 14: Beran M, Jizba J, Blumauerová M, Nĕmecek J, Novák J, Zima J, Kandybin NV, Samoukina GV. Preparative high-performance liquid chromatography of macrotetrolides. J Chromatogr. 1988 Jun 17;442:431-5. PubMed PMID: 3417831. 15: Nefelova MV, Sverdlova AN, Egorov NS. [Directed synthesis of macrotetrolides]. Prikl Biokhim Mikrobiol. 1987 Nov-Dec;23(6):800-5. Russian. PubMed PMID: 3444814. 16: Ling GN, Ochsenfeld MM. Membrane lipid layers vs. polarized water dominated by fixed ions: a comparative study of the effects of three macrocyclic ionophores on the K+ permeability of frog skeletal muscle, frog ovarian eggs, and human erythrocytes. Physiol Chem Phys Med NMR. 1986;18(2):109-24. PubMed PMID: 3492720. 17: Nefelova MV, Sverdlova AN, Egorov NS. [Macrotetrolide antibiotics from mycelia of Streptomyces chrysomallus]. Antibiot Med Biotekhnol. 1985 Mar;30(3):163-6. Russian. PubMed PMID: 4015058. 18: Laprade R, Grenier F, Pagé-Dansereau M, Dansereau J. Carrier-mediated ion transport in lipid bilayer membranes. Can J Biochem Cell Biol. 1984 Aug;62(8):738-51. PubMed PMID: 6498590. 19: Lapointe JY, Laprade R. Kinetics of carrier-mediated ion transport in two new types of solvent-free lipid bilayers. Biophys J. 1982 Aug;39(2):141-50. PubMed PMID: 6896832; PubMed Central PMCID: PMC1328925. 20: Liedtke CM, Hopfer U. Mechanism of Cl- translocation across small intestinal brush-border membrane. I. Absence of Na+-Cl- cotransport. Am J Physiol. 1982 Mar;242(3):G263-71. PubMed PMID: 7065188.