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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:29703
ChEMBL
  • ChEMBL520780
ChemSpider
  • 16736085
ECHA InfoCard 100.120.044 Edit this at Wikidata
EC Number
  • 609-372-4
KEGG
  • C12112
PubChem CID
  • 443629
UNII
  • 313E9620QS checkY
CompTox Dashboard (EPA)
  • DTXSID4058073 Edit this at Wikidata
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
  • 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
Chemical compound

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.

See also

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.