A polyketide macrolide with antimycobacterial and anticancer activities
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Amycolatopsin C

Item No. 33255

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3E,5Z,7Z,11E,13E,15Z)-10-(((2S,3R,4R,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-17-hydroxy-7-(hydroxymethyl)-5,18-dimethoxy-3,9,11,13,15-pentamethyl-20-((S)-1-((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-3-methoxy-6-(3-methoxypropyl)-5-methyltetrahydro-2H-pyran-2-yl)ethyl)oxacycloicosa-3,5,7,11,13,15-hexaen-2-one
Molecular Formula
C47H76O17
Formula Weight
913.1
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
CC(/C=C(CO)/C=C(OC)/C=C1\C)C(O[C@@H]2[C@H](O)[C@@H](O)[C@H](OC)[C@@H](C)O2)/C(C)=C/C(C)=C/C(C)=C\C(O)C(OC)CC([C@H](C)[C@@]3(O)[C@H](OC)[C@@H](O)[C@@](O)(C)[C@@H](CCCOC)O3)OC1=O
InChi Code
InChI=1S/C47H76O17/c1-25-17-26(2)19-34(49)36(58-11)23-35(30(6)47(55)43(60-13)42(52)46(8,54)37(64-47)15-14-16-56-9)62-44(53)29(5)21-33(57-10)22-32(24-48)20-28(4)40(27(3)18-25)63-45-39(51)38(50)41(59-12)31(7)61-45/h17-22,28,30-31,34-43,45,48-52,54-55H,14-16,23-24H2,1-13H3/b25-17+,26-19-,27-18+,29-21+,32-20-,33-22-/t28?,30-,31+,34?,35?,36?,37+,38+,39+,40?,41+,42+,43+,45+,46+,47-/m0/s1
InChi Key
VTVRDHRYRTVEOZ-LISIYSTMSA-N
Origin
Bacterium/Amycolatopsis sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

    $208

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    500 µg

    $777

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    Cayman Chemical
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    Product Description

    Amycolatopsin C is a polyketide macrolide originally isolated from Amycolatopsis that has antimycobacterial and anticancer activities.1 It is active against M. bovis and M. tuberculosis (IC50s = 2.7 and 5.7 µM, respectively) but not B. subtilis, S. aureus, E. coli, or P. aeruginosa (IC50s = >30 µM for all). Amycolatopsin C is cytotoxic to SW620 colorectal and NCI H460 lung cancer cells (IC50s = 10 and 5.9 µM, respectively).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Khalil, Z.G., Salim, A.A., Vuong, D., et al. Amycolatopsins A-C: Antimycobacterial glycosylated polyketide macrolides from the Australian soil Amycolatopsis sp. MST-108494. J. Antibiot. (Tokyo) 70(12), 1097-1103 (2017).