A bacterial metabolite with antibacterial and anti-inflammatory activities
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Salinamide A

Item No. 44993

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(2R,3R)-3-hydroxy-2,4-dimethyl-1-oxopentyl]-L-threonyl-D-alloisoleucyl-(2S)-2-(4-hydroxyphenyl)glycyl-N-methyl-L-phenylalanyl-D-allothreonyl-O-[N-[(2E)-3-[(2S)-2-[(1R)-1-hydroxyethyl]-2-oxiranyl]-1-oxo-2-propen-1-yl]glycyl]-, (6→1 )-lactone, L-serine, cyclic (1′→3)-ether
CAS Number
152340-22-2
Molecular Formula
C51H69N7O15
Formula Weight
1020.1
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
O=C([C@H](CC1=CC=CC=C1)N(C([C@](NC([C@@](NC([C@@H](NC([C@@H]([C@H](O)C(C)C)C)=O)[C@@H](C)O2)=O)([H])[C@@H](C)CC)=O)([H])C3=CC=C(O[C@@H]([C@@]4(CO4)/C=C/C(NCC5=O)=O)C)C=C3)=O)C)N[C@@]([C@H](O)C)([H])C(N[C@](CO5)([H])C2=O)=O
InChi Code
InChI=1S/C51H69N7O15/c1-10-27(4)39-46(65)57-42-33-16-18-34(19-17-33)73-31(8)51(25-71-51)21-20-37(60)52-23-38(61)70-24-35(50(69)72-30(7)41(48(67)54-39)56-44(63)28(5)43(62)26(2)3)53-47(66)40(29(6)59)55-45(64)36(58(9)49(42)68)22-32-14-12-11-13-15-32/h11-21,26-31,35-36,39-43,59,62H,10,22-25H2,1-9H3,(H,52,60)(H,53,66)(H,54,67)(H,55,64)(H,56,63)(H,57,65)/b21-20+/t27-,28+,29+,30+,31+,35-,36-,39+,40+,41-,42-,43+,51-/m0/s1
InChi Key
UIHLRTKYJPYYEU-UMPSVNBLSA-N
Origin
Bacteria/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Salinamide A is a bicyclic depsipeptide bacterial metabolite originally isolated from C. xamachana that has antibacterial and anti-inflammatory activities.1,2 It is an inhibitor of E. coli RNA polymerase (IC50 = 0.5 µM).2 Salinamide A is active against the Gram-positive bacteria S. pneumoniae and S. pyogenes (MICs = 4 µg/ml for both).1 It also reduces ear edema by 84% in mice when administered at a dose of 50 µg/animal.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Trischman, J.A., Tapiloas, D.M., Jensen, P.R., et al. Salinamides A and B: Anti-inflammatory depsipeptides from a marine streptomycete. J. Am. Chem. Soc. 116(2), 757-758 (1994).

    2. Miao, S., Anstee, M.R., LaMarco, K., et al. Inhibition of bacterial RNA polymerases. Peptide metabolites from the cultures of Streptomyces sp. J. Nat. Prod. 60(8), 858-861 (1997).