A fungal metabolite with diverse biological activities
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Napyradiomycin A1

Item No. 29215

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,4aR,10aS)-3,4a-dichloro-10a-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-3,4,4a,10a-tetrahydro-6,8-dihydroxy-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione
CAS Number
103106-24-7
Molecular Formula
C25H30Cl2O5
Formula Weight
481.4
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
OC1=CC(O)=C2C(C([C@@](OC(C)(C)[C@H](Cl)C3)(C/C=C(C)/CC/C=C(C)/C)[C@@]3(Cl)C2=O)=O)=C1
InChi Code
InChI=1S/C25H30Cl2O5/c1-14(2)7-6-8-15(3)9-10-25-21(30)17-11-16(28)12-18(29)20(17)22(31)24(25,27)13-19(26)23(4,5)32-25/h7,9,11-12,19,28-29H,6,8,10,13H2,1-5H3/b15-9+/t19-,24+,25+/m1/s1
InChi Key
BCPWMPCOEAOEDD-NQSCOFRMSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $208

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    Product Description

    Napyradiomycin A1 is a fungal metabolite originally isolated from C. rubra and has diverse biological activities.1,2 It is active against S. aureus, M. luteus, B. anthracis, C. bovis, and M. smegmatis (MICs = 1.56-12.5 µg/ml).1 Napyradiomycin A1 is an estrogen receptor antagonist (IC50 = 4.2 µM in rat uterine homogenates).2 It also inhibits mitochondrial NADH:ubiquinone oxidoreductase (complex I) and succinate:ubiquinone oxidoreductase (complex II) activities in bovine heart homogenates (IC50s = 20 and 9.7 µM, respectively).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shiomi, K., Iinuma, H., Hamada, M., et al. Novel antibiotics napyradiomycins. Production, isolation, physico-chemical properties and biological activity. J. Antibiot. (Tokyo) 39(4), 487-493 (1986).

    2. Hori, Y., Abe, Y., Shigematsu, N., et al. Napyradiomycins A and B1: Non-steroidal estrogen-receptor antagonists produced by a Streptomyces. J. Antibiot. (Tokyo) 46(12), 1890-1893 (1993).

    3. Yamamoto, K., Tashiro, E., Motohashi, K., et al. Napyradiomycin A1, an inhibitor of mitochondrial complexes I and II. J. Antibiot. (Tokyo) 65(4), 211-214 (2012).