Validamycin

Validamycin is an antibiotic and fungicide produced by Streptomyces hygroscopicus. It is used as an inhibitor of trehalase.[1] It is used for the control of sheath blight of rice and damping-off of cucumbers.

Validamycin

Names
IUPAC name (1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-{[(1S,4S,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexyl β-D-glucopyranoside
Other names Validamycin A; Valimon; Validacin
Identifiers
CAS Number	37248-47-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29703
ChEMBL	ChEMBL520780
ChemSpider	16736085
ECHA InfoCard	100.120.044
UNII	313E9620QS^Y
CompTox Dashboard (EPA)	DTXSID4058073
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 Key: JARYYMUOCXVXNK-IMTORBKUSA-N InChI=1/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 Key: JARYYMUOCXVXNK-IMTORBKUBD
SMILES OC/C3=C/[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]3O
Properties
Chemical formula	C20H35NO13
Molar mass	497.494 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References

1. Li, H.; Su, H.; Kim, S. B.; Chang, Y. K.; Hong, S. K.; Seo, Y. G.; Kim, C. J. (2011). "Enhanced production of trehalose in Escherichia coli by homologous expression of otsBA in the presence of the trehalase inhibitor, validamycin A, at high osmolarity". Journal of Bioscience and Bioengineering. 113 (2): 224–32. doi:10.1016/j.jbiosc.2011.09.018. PMID 22036231.