A bacterial metabolite
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Padanamide A

Item No. 25085

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(S)-N-((2S,3S,4S)-5-(((S)-1-carbamoyl-2-oxopyrrolidin-3-yl)amino)-3-hydroxy-4-methyl-5-oxo-1-phenylpentan-2-yl)-2-((2R,3R)-3-hydroxy-2-(2-methoxyacetamido)-4-methylpentanoyl)hexahydropyridazine-3-carboxamide
CAS Number
1314881-80-5
Molecular Formula
C31H47N7O9
Formula Weight
661.8
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C([C@@H](C)[C@H](O)[C@H](CC1=CC=CC=C1)NC([C@H]2N(C([C@H](NC(COC)=O)[C@H](O)C(C)C)=O)NCCC2)=O)N[C@@H]3C(N(C(N)=O)CC3)=O
InChi Code
InChI=1S/C31H47N7O9/c1-17(2)25(40)24(36-23(39)16-47-4)30(45)38-22(11-8-13-33-38)28(43)35-21(15-19-9-6-5-7-10-19)26(41)18(3)27(42)34-20-12-14-37(29(20)44)31(32)46/h5-7,9-10,17-18,20-22,24-26,33,40-41H,8,11-16H2,1-4H3,(H2,32,46)(H,34,42)(H,35,43)(H,36,39)/t18-,20-,21-,22-,24+,25+,26-/m0/s1
InChi Key
IAYPOIKGUHHBAU-DYTCPEOESA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Padanamide A is a bacterial metabolite originally isolated from a marine Streptomyces species.1 It is active against five strains of P. falciparum (EC50s = 160-340 nM), is not cytotoxic to HEK293 or HepG2 human cell lines, but is cytotoxic to Jurkat T lymphocytes with an IC50 value of approximately 60 µg/ml.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nam, S.J., Kauffman, C.A., Jensen, P.R., et al. Isolation and characterization of actinoramides A-C, highly modified peptides from a marine Streptomyces sp. Tetrahedron 67(35), 6707-6712 (2011).

    2. Cheng, K.-C., Cao, S., Raveh, A., et al. Actinoramide A identified as a potent antimalarial from titration-based screening of marine natural product extracts. J. Nat. Prod. 78(10), 2411-2422 (2015).

    3. Williams, D.E., Dalisay, D.S., Patrick, B.O., et al. Padanamides A and B, highly modified linear tetrapeptides produced in culture by a Streptomyces sp. isolated from a marine sediment. Org. Lett. 13(15), 3936-3939 (2011).