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Validamycin

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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^Y
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^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 theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Validamycin is anantibiotic andfungicide produced byStreptomyces hygroscopicus. It is used as an inhibitor oftrehalase.^[1] It is used for the control ofsheath blight of rice and damping-off of cucumbers.

^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.

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