An adenine nucleoside antibiotic with herbicidal activity
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Herbicidin A

Item No. 23485

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(7R)-1-(6-amino-9H-purin-9-yl)-6,10-anhydro-1,5-dideoxy-2-O-methyl-D-arabino-α-L-ido-7-undeculo-7,3-pyranose-1,4-furanuronic acid, 8-[(2E)-2-(hydroxymethyl)-2-butenoate], methyl ester
CAS Number
55353-31-6
Molecular Formula
C23H29N5O11
Formula Weight
551.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
λmax
260 nm
SMILES
O=C(/C(CO)=C/C)O[C@H]1[C@H](O)[C@@H](C(OC)=O)O[C@@]2([H])[C@@]1(O)O[C@@]([C@@H](OC)[C@H](N3C=NC4=C3N=CN=C4N)O5)([H])[C@@]5([H])C2
InChi Code
InChI=1S/C23H29N5O11/c1-4-9(6-29)21(31)38-17-13(30)15(22(32)35-3)37-11-5-10-14(39-23(11,17)33)16(34-2)20(36-10)28-8-27-12-18(24)25-7-26-19(12)28/h4,7-8,10-11,13-17,20,29-30,33H,5-6H2,1-3H3,(H2,24,25,26)/b9-4+/t10-,11-,13-,14+,15+,16-,17+,20-,23-/m1/s1
InChi Key
LOWKANMKNQBRPJ-MRAUHCMASA-N
Origin
Bacterium/Streptomyces sp. MST-94754
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Herbicidin A is an adenine nucleoside antibiotic originally isolated from S. saganonensis that exhibits herbicidal activity, particularly against dicotyledonous plants.1,2 It prevents rice seed germination (MIC = 6.25 µg/ml) and completely protects young rice plants from X. oryzae-induced leaf blight when applied at 100 ppm.1 In HEK293 cells, herbicidin A inhibits TNF-α-induced NF-κB activity and induces cytotoxicity (IC50s = 1.8 and 2.7 µM, respectively).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Arai, M., Haneishi, T., Kitahara, N., et al. Herbicidins A and B, two new antibiotics with herbicidal activity. I. Producing organism and biological activities. J. Antibiot. (Tokyo) 29(9), 863-869 (1976).

    2. Yoshikawa, H., Takiguchi, Y., and Terao, M. Terminal steps in the biosynthesis of herbicidins, nucleoside antibiotics. J. Antibiot. (Tokyo) 36(1), 30-35 (1983).

    3. Chai, X., Youn, U.J., Sun, D., et al. Herbicidin congeners, undecose nucleosides from an organic extract of Streptomyces sp. L-9-10. J. Nat. Prod. 77(2), 227-233 (2014).