A fungal metabolite with diverse biological activities
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Aranciamycin

Item No. 29575

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3S,4R)-4-[(6-deoxy-2-O-methyl-α-L-mannopyranosyl)oxy]-3,4-dihydro-2,5,7-trihydroxy-3-methoxy-2-methyl-1,6,11(2H)-naphthacenetrione
CAS Number
72389-06-1
Synonyms
  • NSC 369226
Molecular Formula
C27H28O12
Formula Weight
544.5
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C1C2=CC3=C([C@@H](O[C@H]4[C@H](OC)[C@H](O)[C@@H](O)[C@H](C)O4)[C@H](OC)[C@](C)(O)C3=O)C(O)=C2C(C5=C(O)C=CC=C51)=O
InChi Code
InChI=1S/C27H28O12/c1-9-17(29)21(33)23(36-3)26(38-9)39-22-16-12(24(34)27(2,35)25(22)37-4)8-11-15(20(16)32)19(31)14-10(18(11)30)6-5-7-13(14)28/h5-9,17,21-23,25-26,28-29,32-33,35H,1-4H3/t9-,17-,21+,22+,23+,25-,26-,27+/m0/s1
InChi Key
PGCZNTNNZCKKFG-LJUYJRHKSA-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

    $255

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    Product Description

    Aranciamycin is a fungal metabolite that has been found in Streptomyces and has diverse biological activities.1,2 It inhibits C. histolyticum collagenase but not elastase or trypsin in cell-free assays (IC50s = 0.37, >10, and >10 µM, respectively).1 Aranciamycin is active against M. bovis and B. subtilis (MICs = 30 and 15 µM, respectively).2 It is cytotoxic to HepG2 cells (IC50 = 18 µM).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bols, M., Biderup, L., Hansen, J., et al. Inhibition of collagenase by aranciamycin and aranciamycin derivatives. J. Med. Chem. 35(15), 1768-2771 (1992).

    2. Khalil, Z.G., Raju, R., Piggott, A.M., et al. Aranciamycins I and J, antimycobacterial anthracyclines from an Australian marine-derived Streptomyces sp. J. Nat. Prod. 78(4), 949-952 (2015).