A macrolide polyketide with antimycobacterial and anticancer activities
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Amycolatopsin A

Item No. 31672

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3E,5E,7E,11E,13E,15E)-20-((R)-1-((2S,3R,4R,5S,6R)-5-(((2S,4S,5S,6R)-5-(((2S,4R,5R,6R)-4,5-dihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,4-dihydroxy-3-methoxy-6-(3-methoxypropyl)-5-methyltetrahydro-2H-pyran-2-yl)ethyl)-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-pentamethyloxacycloicosa-3,5,7,11,13,15-hexaen-2-one
CAS Number
2209112-96-7
Molecular Formula
C60H98O23
Formula Weight
1187.4
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
CC1C(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@@H]4O[C@H](C)[C@@H](O[C@@]5([H])C[C@@](C)(O)[C@H](O)[C@@H](C)O5)[C@@H](O)C4)(C)[C@@H](CCCOC)O3)OC(/C(C)=C/C(OC)=C\C(CO)=C/1)=O
InChi Code
InChI=1S/C60H98O23/c1-30-20-31(2)22-41(62)44(73-14)27-43(79-56(68)34(5)24-40(72-13)25-39(29-61)23-33(4)50(32(3)21-30)81-57-49(65)48(64)52(74-15)37(8)78-57)35(6)60(70)55(75-16)54(67)59(11,45(82-60)18-17-19-71-12)83-46-26-42(63)51(36(7)76-46)80-47-28-58(10,69)53(66)38(9)77-47/h20-25,33,35-38,41-55,57,61-67,69-70H,17-19,26-29H2,1-16H3/b30-20+,31-22+,32-21+,34-24+,39-23+,40-25+/t33?,35-,36-,37-,38-,41?,42+,43?,44?,45-,46+,47+,48-,49-,50?,51-,52-,53-,54-,55-,57-,58-,59-,60+/m1/s1
InChi Key
VGMCXRHEZZYRBZ-SYDHVEJSSA-N
Origin
Bacterium/Amycolatopsis sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Amycolatopsin A is a macrolide polyketide originally isolated from Amycolatopsis that has antimycobacterial and anticancer activities.1 It is active against M. bovis and M. tuberculosis (IC50s = 0.4 and 4.4 µM, respectively) but not B. subtilis, S. aureus, E. coli, or P. aeruginosa (IC50s = >30 µM for all). Amycolatopsin A is cytotoxic to SW620 colorectal and NCI H460 lung cancer cells (IC50s = 0.08 and 1.2 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).