A bacterial metabolite
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Urdamycin A

Item No. 29510

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,4aR,12bS)-9-[2,6-dideoxy-3-O-[(2S,5S,6S)-5-[(2,6-dideoxy-β-D-arabino-hexopyranosyl)oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-β-D-arabino-hexopyranosyl]-3,4,4a,12b-tetrahydro-3,4a,8-trihydroxy-3-methyl-12b-[[(2S,5S,6S)-tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl]oxy]-benz[a]anthracene-1,7,12(2H)-trione
CAS Number
98474-21-6
Synonyms
  • Antibiotic A 32Y2
  • Kerriamycin B
  • NSC 372208
  • NSC 606397
Molecular Formula
C43H56O17
Formula Weight
844.9
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O[C@@H]1C[C@H](O[C@H]2CC[C@H](O[C@H]3[C@H](O)[C@@H](C)O[C@](C4=C(O)C(C(C(C=C[C@@](C[C@](O)(C)C5)(O)[C@]6(O[C@H]7CC[C@H](O)[C@H](C)O7)C5=O)=C6C8=O)=O)=C8C=C4)([H])C3)O[C@H]2C)O[C@H](C)[C@H]1O
InChi Code
InChI=1S/C43H56O17/c1-18-25(44)8-10-32(55-18)60-43-30(46)16-41(5,52)17-42(43,53)13-12-24-35(43)40(51)23-7-6-22(38(49)34(23)39(24)50)28-15-29(37(48)21(4)54-28)59-31-11-9-27(19(2)56-31)58-33-14-26(45)36(47)20(3)57-33/h6-7,12-13,18-21,25-29,31-33,36-37,44-45,47-49,52-53H,8-11,14-17H2,1-5H3/t18-,19-,20+,21+,25-,26+,27-,28+,29+,31-,32-,33-,36+,37+,41-,42-,43-/m0/s1
InChi Key
FJSYXNOFZQFOAN-FXPMUEKOSA-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

    $169

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    Product Description

    Urdamycin A is a bacterial metabolite originally isolated from S. fradiae that has antibacterial and anticancer activities.1,2 It is active against a variety of Gram-positive and Gram-negative bacteria, including B. subtilis and strains of Arthrobacter and Streptomyces, but not the fungus S. cerevisiae, in a disc assay when used at a concentration of 1 mg/ml.2 Urdamycin A is cytotoxic to L1210 and HT-29, but not A549, cancer cells (IC50s = 7.5, 5, and >10 µg/ml, respectively).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Henkel, T., Ciesiolka, T., Rohr, J., et al. Urdamycins, new angucycline antibiotics from Streptomyces fradiae. V. Derivatives of urdamycin A. J. Antibiot. (Tokyo) 42(2), 299-311 (1989).

    2. Drautz, H., Zähner, H., Rohr, J., et al. Metabolic products of microorganisms. 234. Urdamycins, new angucycline antibiotics from Streptomyces fradiae. I. Isolation, characterization and biological properties. J. Antibiot. (Tokyo) 39(12), 1657-1669 (1986).