A natural eNOS inhibitor
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Iromycin A

Item No. 19621

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-[(2E,5E)-3,7-dimethyl-2,5-octadien-1-yl]-4-hydroxy-3-methyl-5-propyl-2(1H)-pyridinone
CAS Number
213137-53-2
Synonyms
  • NK 26588
Molecular Formula
C19H29NO2
Formula Weight
303.4
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Slightly Soluble
SMILES
CC1=C(O)C(CCC)=C(C/C=C(C)/C/C=C/C(C)C)NC1=O
InChi Code
InChI=1S/C19H29NO2/c1-6-8-16-17(20-19(22)15(5)18(16)21)12-11-14(4)10-7-9-13(2)3/h7,9,11,13H,6,8,10,12H2,1-5H3,(H2,20,21,22)/b9-7+,14-11+
InChi Key
HVAVEUHAOCVIPN-DTCTWCMCSA-N
Origin
Bacterium/Streptomyces bottropensis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $248

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    1 mg

    $393

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    Product Description

    Iromycin A is a bacterial pyridone metabolite that inhibits nitric oxide synthase (NOS) activity, with selectivity for NOS III (endothelial NOS) over NOS I (neuronal NOS).1,2 Iromycin metabolites and derivatives block NADH oxidation in beef heart submitochondrial particles (IC50 = 0.461 µM for iromycin A).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shojaei, H., Li-Böhmer, Z., and von Zezschwitz, P. Iromycins: A new family of pyridone metabolites from Streptomyces sp. II. Convergent total synthesis. The Journal of Organic Chemistry 72(14), 5091-5097 (2007).

    2. Surup, F., Wagner, O., von Frieling, J., et al. The iromycins, a new family of pyridone metabolites from Streptomyces sp. I. Structure, NOS inhibitory activity, and biosynthesis. The Journal of Organic Chemistry 72(14), 5085-5090 (2007).

    3. Surup, F., Shojaei, H., von Zezschwitz, P., et al. Iromycins from Streptomyces sp. and from synthesis: New inhibitors of the mitochondrial electron transport chain. Bioorg. Med. Chem. 16(4), 1738-1746 (2008).