A non-selective monovalent cation ionophore
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Monactin

Item No. 25742

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,2R,5R,7R,10S,11S,14S,16S,19R,20R,23R,25R,28S,29S,32S,34S)-5-ethyl-2,11,14,20,23,29,32-heptamethyl-4,13,22,31,37,38,39,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
CAS Number
7182-54-9
Molecular Formula
C41H66O12
Formula Weight
751.0
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C(O[C@H](C)C[C@]1([H])O[C@@]([C@@H]2C)([H])CC1)[C@H](C)[C@@]3([H])CC[C@](C[C@H](C)OC([C@H]([C@@]4([H])O[C@](C[C@H](OC([C@H](C)[C@]5([H])O[C@](CC5)([H])C[C@H](C)OC2=O)=O)CC)([H])CC4)C)=O)([H])O3
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-/m1/s1
InChi Key
YPUPRVWRYDPGCW-IDBRQATOSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Monactin is a mactrotetralide antibiotic originally isolated from Streptomyces and a non-selective ionophore for monovalent cations, including potassium, sodium, and lithium.1,2 It has low antimicrobial activity but is more active than its homolog nonactin (Item No. 19468).3,4 Monactin induces swelling of rat liver mitochondria in medium containing either potassium or sodium, stimulates respiration, and uncouples oxidative phosphorylation.5 It also inhibits Wnt signaling via inhibition of TCF-β-catenin transcriptional activity.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Beck, J., Gerlach, H., Prelog, V., et al. Metabolic products of actinomycetes. XXXV. Constitution of the macrotetrolides, monactin, dinactin, and trinactin. Helv. Chim. Acta 45, 620-630 (1962).

    2. Harold, F.M., and Baarda, J.R. Effects of nigericin and monactin on cation permeability of Streptococcus faecalis and metabolic capacities of potassium-depleted cells. J. Bacteriol. 95(3), 816-823 (1968).

    3. Shaw, P.D. Nonactin and Related Antibiotics. Antibiotics (USSR) 1, 649-650 (1967).

    4. Meyers, E., Pansy, F.E., Perlman, D.H., et al. The in vitro activity of nonactin and its homologs, monactin, dinactin, and trinactin. J. Antibiot. (Tokyo) 18, 128-129 (1965).

    5. Graven, S.N., Lardy, H.A., and Estrada-O, S. Antibiotics as tools for metabolic studies. 8. Effect of nonactin homologs on alkali metal cation transport and rate of respiration in mitochondria. Biochem. 6(2), 365-371 (1967).

    6. Tamai, Y., Toume, K., Arai, M.A., et al. Nonactin and related compounds found in a screening program for Wnt signal inhibitory activity. Heterocycles 84(2), 1245-1250 (2012).