Validamycin A, Catalog: B1540

Alternate Names 1,5,6-trideoxy-4-O-β-D-glucopyranosyl-5-(hydroxymethyl)-1-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-D-chiro-inositol; Validamycin; Validacin; Valimon

Appearance White to off-white solid

CAS # 37248-47-8

Molecular Formula C₂₀H₃₅NO₁₃

Molecular Weight 497.49

Purity > 75%

Solubility DMSO (2 mg/ml)

SMILES C1C(C(C(C(C1NC2C=C(C(C(C2O)O)O)CO)O)O)OC3C(C(C(C(O3)CO)O)O)O)CO

InChi InChI=1S/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/t7-,8+,9+,10-,11-,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1

InChi Key JARYYMUOCXVXNK-CSLFJTBJSA-N

PubChem CID 443629

MDL Number MFCD09028089

Storage Conditions -20°C

Shipping Conditions Gel Pack

Usage For Research Use Only! Not For Use in Humans.

Handling Do not take it internally. Wear a glove and mask when handling the product. Protect from air and moisture.

Validamycin A is an antifungal agent that belongs to a class of antibiotics known as validamycins. It is produced by certain species of Streptomyces bacteria and exhibits antimicrobial properties, particularly against certain plant pathogens. It is used to protect rice plants against sheath blight caused by the pathogenic fungus, R. solani, due to its ability to inhibit trehalose, a trehalose-hydrolyzing enzyme (Ki = 1.9 nM; IC50 = 0.7 μM). It is also effective against the growth and sporulation of R. cerealis, F. culmorum, and other fungi.

Validamycin A acts by inhibiting the synthesis of trehalose, a sugar that plays a crucial role in protecting cells against stress conditions in many microorganisms, including fungi. By disrupting trehalose synthesis, the compound impairs the ability of fungi to withstand adverse environmental conditions.