Validamycin

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
	Systematic IUPAC name (2R,3R,4S,5S,6R)-2-{[(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]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
	Other names Validamycin A; Valimon; Validacin
Identifiers
CAS Number	37248-47-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29703;
ChEMBL	ChEMBL520780;
ChemSpider	16736085;
ECHA InfoCard	100.120.044
EC Number	609-372-4;
KEGG	C12112;
PubChem CID	443629;
UNII	313E9620QS ;
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

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.

References

^ 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.