EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:29703 - validamycin A

Default Structure
ChEBI IDCHEBI:29703
ChEBI Namevalidamycin A
Stars
DefinitionA member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its β-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus.
Last Modified28 January 2016
DownloadsMolfile
FormulaC20H35NO13
Net Charge0
Average Mass497.494
Monoisotopic Mass497.21084
SMILESOCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
InChIInChI=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
InChIKeyJARYYMUOCXVXNK-CSLFJTBJSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Streptomyces hygroscopicus (ncbitaxon:1912) - PubMed (5549382)
Streptomyces hygroscopicus subsp. limoneus (ncbitaxon:264445) - PubMed (22961651)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
EC 2.4.1.231 [alpha,alpha-trehalose phosphorylase (configuration-retaining)] inhibitor  An EC 2.4.1.* (hexosyltransferase) inhibitor that interferes with the action of α,α-trehalose phosphorylase (configuration-retaining) (EC 2.4.1.231).
EC 3.2.1.28 (alpha,alpha-trehalase) inhibitor  An EC 2.4.1.* (hexosyltransferase) inhibitor that interferes with the action of α,α-trehalase (EC 2.4.1.28).
EC 2.4.1.64 (alpha,alpha-trehalose phosphorylase) inhibitor  An EC 2.4.1.* (hexosyltransferase) inhibitor that interferes with the action of α,α-trehalose phosphorylase (EC 2.4.1.64).
antifungal agrochemical  Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
fungicide  A substance used to destroy fungal pests.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Applications:
antifungal agrochemical  Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
fungicide  A substance used to destroy fungal pests.
ChEBI Ontology
Outgoing Relation(s)
validamycin A (CHEBI:29703) has role antifungal agrochemical (CHEBI:86328)
validamycin A (CHEBI:29703) has role EC 2.4.1.231 [α,α-trehalose phosphorylase (configuration-retaining)] inhibitor (CHEBI:83757)
validamycin A (CHEBI:29703) has role EC 2.4.1.64 (α,α-trehalose phosphorylase) inhibitor (CHEBI:83760)
validamycin A (CHEBI:29703) has role EC 3.2.1.28 (α,α-trehalase) inhibitor (CHEBI:83762)
validamycin A (CHEBI:29703) is a antibiotic fungicide (CHEBI:87114)
validamycin A (CHEBI:29703) is a polyol (CHEBI:26191)
validamycin A (CHEBI:29703) is a secondary amino compound (CHEBI:50995)
validamycin A (CHEBI:29703) is a validamycins (CHEBI:83745)
validamycin A (CHEBI:29703) is conjugate base of validamycin A(1+) (CHEBI:90869)
Incoming Relation(s)
validamycin A(1+) (CHEBI:90869) is conjugate acid of validamycin A (CHEBI:29703)
IUPAC Name 
(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexyl β-D-glucopyranoside
Synonyms  Source
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-inositolAlan Wood's Pesticides
(1S-(1α,4α,5β,6α))-1,5,6-trideoxy-4-O-β-D-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-D-chiro-inositolChemIDplus
1L-(1,3,4/2,6)-2,3-dihydroxy-6-hydroxymethyl-4-((1S,4R,5S,6S)-4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-enylamino)cyclohexyl β-D-glucopyranosideChemIDplus
jinganmycin AAlan Wood's Pesticides
D-1,5,6-trideoxy-3-O-β-D-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-D-chiroinositolChemIDplus
T-7545-AChemIDplus
Brand Names  Source
ValidacinChemIDplus
ValimonChemIDplus
Manual XrefsDatabases
677BPDB
C00018797KNApSAcK
C12112KEGG COMPOUND
HMDB0036592HMDB
validamycinAlan Wood's Pesticides
ValidamycinWikipedia
VALIDAMYCIN-AMetaCyc
Registry NumbersSources
Reaxys:5319831Reaxys
CAS:37248-47-8KEGG COMPOUND
CAS:37248-47-8ChemIDplus
Citations