CHEBI:29703 - validamycin A

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ChEBI Name validamycin A
ChEBI ID CHEBI:29703
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H35NO13
Net Charge 0
Average Mass 497.49080
Monoisotopic Mass 497.211
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
InChIKey JARYYMUOCXVXNK-CSLFJTBJSA-N
SMILES OC[C@H]1C[C@H](N[C@H]2C=C(CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Streptomyces hygroscopicus (NCBI:txid1912) See: PubMed
Streptomyces hygroscopicus subsp. limoneus (NCBI:txid264445) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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 alpha,alpha-trehalose phosphorylase (configuration-retaining) (EC 2.4.1.231).
EC 2.4.1.64 (alpha,alpha-trehalose phosphorylase) inhibitor
An EC 2.4.1.* (hexosyltransferase) inhibitor that interferes with the action of alpha,alpha-trehalose phosphorylase (EC 2.4.1.64).
EC 3.2.1.28 (alpha,alpha-trehalase) inhibitor
An EC 2.4.1.* (hexosyltransferase) inhibitor that interferes with the action of alpha,alpha-trehalase (EC 2.4.1.28).
antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
fungicide
A substance used to destroy fungal pests.
(via antibiotic fungicide )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via validamycins )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via validamycins )
Application(s): antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
fungicide
A substance used to destroy fungal pests.
(via antibiotic fungicide )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(+)-validamycin A ChEBI
(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-inositol ChemIDplus
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-inositol Alan Wood's Pesticides
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-glucopyranoside ChemIDplus
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-chiroinositol ChemIDplus
jinganmycin A Alan Wood's Pesticides
T-7545-A ChemIDplus
Validamycin KEGG COMPOUND
Brand Names Sources
Validacin ChemIDplus
Valimon ChemIDplus
Manual Xrefs Databases
677 BPDB
C00018797 KNApSAcK
C12112 KEGG COMPOUND
HMDB0036592 HMDB
validamycin Alan Wood's Pesticides
Validamycin Wikipedia
VALIDAMYCIN-A MetaCyc
View more database links
Registry Numbers Types Sources
37248-47-8 CAS Registry Number KEGG COMPOUND
37248-47-8 CAS Registry Number ChemIDplus
5319831 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18943474 PubMed citation Europe PMC
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Last Modified
28 January 2016