Page last updated: 2024-11-08

validamycin a

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

validamycin A : 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 beta-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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID443629
CHEMBL ID1923413
CHEBI ID29703
SCHEMBL ID3121491
MeSH IDM0097144

Synonyms (49)

Synonym
d-chiro-inositol, 1,5,6-trideoxy-3-o-beta-d-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-, (1s-(1-alpha,4-alpha,5-beta,6-alpha))-
t-7545-a
d-1,5,6-trideoxy-3-o-beta-d-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-d-chiroinositol
(1s-(1a,4a,5b,6a))-1,5,6-trideoxy-3-o-b-d-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-d-chiro-inositol
hsdb 6745
1l-(1,3,4/2,6)-2,3-dihydroxy-6-hydromethyl-4-((1s,4r,5s,6s)-4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-enylamino)cyclohexyl beta-d-glucopyranoside
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 beta-d-glucopyranoside
(1s-(1alpha,4alpha,5beta,6alpha))-1,5,6-trideoxy-4-o-beta-d-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-d-chiro-inositol
validamycin
validacin
validamycin a
valimon
37248-47-8
(2r,3r,4s,5s,6r)-2-[(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]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
AKOS016012982
313e9620qs ,
unii-313e9620qs
chebi:29703 ,
CHEMBL1923413
SCHEMBL3121491
d-1,5,6-trideoxy-3-o-.beta.-d-glucopyranosyl-5- (hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2- cyclohexen-1-yl)amino)-d-chiroinositol
d-chiro-inositol, 1,5,6-trideoxy-3-o-.beta.-d-glucopyranosyl- 5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2- cyclohexen-1-yl)amino)-, (1s-(1-.alpha.,4-.alpha.,5-.beta.,6- .alpha.))-
validamycins validamycin a [mi]
validamycin a [hsdb]
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 .beta.-d-glucopyranoside
1l-(1,3,4/2,6)-2,3-dihydroxy-6-hydromethyl-4-((1s,4r,5s,6s)- 4,5,6-trihydroxy-3-hydroxymethylcyclohex-2- enylamino)cyclohexyl .beta.-d-glucopyranoside
(1s-(1.alpha.,4.alpha.,5.beta.,6.alpha.))-1,5,6-trideoxy-4-o-.beta.-d- glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3- (hydroxymethyl)-2-cyclohexen-1-yl)amino)-d-chiro-inositol
d-chiro-inositol, 1,5,6-trideoxy-4-o-.beta.-d-glucopyranosyl-5-(hydroxymethyl)-1-(((1s,4r,5s,6s)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-
(1s-(1a,4a,5b,6a))-1,5,6-trideoxy-3-o-b-d-glucopyranosyl-5- (hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2- cyclohexen-1-yl)amino)-d-chiro-inositol
d-chiro-inositol, 1,5,6-trideoxy-4-o-.beta.-d-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-, (1s-(1.alpha.,4.alpha.,5.beta.,6.alpha.))-
DTXSID4058073
1,5,6-trideoxy-4-o-beta-d-glucopyranosyl-5-(hydroxymethyl)-1-[[(1s,4r,5s,6s)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-d-chiro-inositol
(+)-validamycin a
jinganmycin a
W-204201
AC-32607
(2r,3r,4s,5s,6r)-2-[(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]cyclohexoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
ag-f-30599
d-chiro-inositol,1,5,6-trideoxy-3-o-beta-d-glucopyranosyl-
validamycin a, pestanal(r), analytical standard
HY-B0856
CS-0012869
(2r,3r,4s,5s,6r)-2-((1r,2r,3s,4s,6r)-2,3-dihydroxy-6-(hydroxymethyl)-4-((1s,4r,5s,6s)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enylamino)cyclohexyloxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol
mfcd09028089
AS-15281
cepex 10sl; validacin
(2r,3r,4s,5s,6r)-2-(((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)oxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol
58194-43-7
d-chiro-inositol, 1,5,6-trideoxy-4-o-.beta.-d-glucopyranosyl-5-(hydroxymethyl)-1-[[(1s,4r,5s,6s)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-

Research Excerpts

Overview

Valentamycin A (VAL-A) is a C7N aminocyclitol antibiotic produced by Streptomyces hygroscopicus var. 5008. It is an effective antifungal agent widely used in Asian countries as crop protectant.

ExcerptReferenceRelevance
"Validamycin A (VAL-A) is a widely used antifungal antibiotic for the treatment of sheath blight disease of rice and other plants. "( Enhanced production of validamycin A in Streptomyces hygroscopicus 5008 by engineering validamycin biosynthetic gene cluster.
Kim, BG; Zhong, JJ; Zhou, TC, 2014
)
2.16
"Validamycin A (VAL-A) is an important agricultural antibiotic produced by Streptomyces hygroscopicus 5008, which uses starch as carbon source occupying about 20% of total production cost. "( Production of validamycin A from hemicellulose hydrolysate by Streptomyces hygroscopicus 5008.
Zhong, JJ; Zhou, TC, 2015
)
2.22
"Validamycin A (VAL-A) is a C7N aminocyclitol antibiotic produced by Streptomyces hygroscopicus var. "( Positive and negative regulation of GlnR in validamycin A biosynthesis by binding to different loci in promoter region.
Bai, L; Kang, Q; Qu, S; Wang, L; Wu, H, 2015
)
2.12
"Validamycin A (VAL-A) is an important and widely used agricultural antibiotic. "( Impact of nitrogen concentration on validamycin A production and related gene transcription in fermentation of Streptomyces hygroscopicus 5008.
Bai, L; Deng, Z; Wei, ZH; Zhong, JJ, 2012
)
2.1
"Validamycin A (Val-A) is an effective antifungal agent widely used in Asian countries as crop protectant. "( Structural and functional analysis of validoxylamine A 7'-phosphate synthase ValL involved in validamycin A biosynthesis.
Bai, L; Huang, L; Ji, X; Li, L; Zhang, H; Zheng, L; Zhou, X, 2012
)
2.04

Actions

validamycin A was used to inhibit in vivo trehalase activity in tobacco enabling the study of subsequent changes in new C partitioning into cellulosic biomass and lignin precursors.

ExcerptReferenceRelevance
"Validamycin A induced an increase of trehalose concentration in root nodules of M."( Validamycin A improves the response of Medicago truncatula plants to salt stress by inducing trehalose accumulation in the root nodules.
Lluch, C; López, M; Tejera, NA, 2009
)
2.52
"Validamycin A was used to inhibit in vivo trehalase activity in tobacco enabling the study of subsequent changes in new C partitioning into cellulosic biomass and lignin precursors. "( Inhibition of trehalose breakdown increases new carbon partitioning into cellulosic biomass in Nicotiana tabacum.
Best, M; Ferrieri, RA; Koenig, K; McDonald, K; Rogers, A; Schueller, M, 2011
)
1.81

Treatment

ExcerptReferenceRelevance
"Treatment with validamycin A, a trehalose analog with antifungal activity, leads to a rapid reduction in trehalose levels, despite its known role as a trehalase inhibitor."( Impact of temperature stress and validamycin A on compatible solutes and fumonisin production in F. verticillioides: role of trehalose-6-phosphate synthase.
Boudreau, BA; Brown, DW; Busman, M; Kendra, DF; Larson, TM; McQuade, KL; Roberts, ES, 2013
)
1.01
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
EC 2.4.1.231 [alpha,alpha-trehalose phosphorylase (configuration-retaining)] inhibitorAn 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) inhibitorAn 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) inhibitorAn EC 2.4.1.* (hexosyltransferase) inhibitor that interferes with the action of alpha,alpha-trehalase (EC 2.4.1.28).
antifungal agrochemicalAny substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
validamycinsAny of the inositol-derived beta-D-glucoside antibiotics produced by Streptomyces hygroscopicus.
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
polyolA compound that contains two or more hydroxy groups.
antibiotic fungicideAny antibiotic antifungal agent that has been used as a fungicide.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1080699Antifungal activity against Corticium sasaki infected compound pre-treated rice plant seedlings through soil application of fungus assessed as rice sheath blight disease control efficacy at 50 ug/mL under greenhouse conditions2009Journal of agricultural and food chemistry, Jul-08, Volume: 57, Issue:13
Antifungal activity of CHE-23C, a dimeric sesquiterpene from Chloranthus henryi.
AID1080702Antifungal activity against Corticium sasaki infected compound pre-treated rice plant seedlings through soil application of fungus assessed as rice sheath blight disease control efficacy at 5 ug/mL under greenhouse conditions2009Journal of agricultural and food chemistry, Jul-08, Volume: 57, Issue:13
Antifungal activity of CHE-23C, a dimeric sesquiterpene from Chloranthus henryi.
AID750180Antifungal activity against Gibberella saubinettii assessed as inhibition of mycelia elongation rate at 50 ppm after 48 hrs relative to control2013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimicrobical evaluation of a novel class of 1,3,4-thiadiazole: derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety.
AID750178Antifungal activity against Cercospora beticola assessed as inhibition of mycelia elongation rate at 50 ppm after 48 hrs relative to control2013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimicrobical evaluation of a novel class of 1,3,4-thiadiazole: derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety.
AID1082453In vivo antifungal activity against Rhizoctonia solani infected rice seedlings assessed as control of rice sheath blight disease development at 5 ug/ml treated 1 day before spore inoculation measured 3-7 days after inoculation2011Journal of agricultural and food chemistry, Oct-26, Volume: 59, Issue:20
Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.
AID750181Antifungal activity against Fusarium oxysporum assessed as inhibition of mycelia elongation rate at 50 ppm after 48 hrs relative to control2013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimicrobical evaluation of a novel class of 1,3,4-thiadiazole: derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety.
AID1882201Antifungal activity against Rhizoctonia solani2022European journal of medicinal chemistry, Feb-05, Volume: 229Natural and synthetic β-carboline as a privileged antifungal scaffolds.
AID750179Antifungal activity against Physalospora pyricola assessed as inhibition of mycelia elongation rate at 50 ppm after 48 hrs relative to control2013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimicrobical evaluation of a novel class of 1,3,4-thiadiazole: derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety.
AID632678Antifungal activity against Rhizoctonia solani assessed as growth inhibition at 500 ug/mL by potted plant test2011Bioorganic & medicinal chemistry letters, Dec-01, Volume: 21, Issue:23
Molecular design, synthesis and bioactivity of glycosyl hydrazine and hydrazone derivatives: notable effects of the sugar moiety.
AID1083138Fungicidal activity against Rhizoctonia solani infected drug-pretreated cucumber two seeded leaves assessed as decrease in disease index at 3% AS formulation (acetone Rvb = 2.22 +/-0.79%)2012Journal of agricultural and food chemistry, Nov-28, Volume: 60, Issue:47
Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4-oxadiazole derivatives.
AID1082454In vivo antifungal activity against Rhizoctonia solani infected rice seedlings assessed as control of rice sheath blight disease development at 50 ug/ml treated 1 day before spore inoculation measured 3-7 days after inoculation2011Journal of agricultural and food chemistry, Oct-26, Volume: 59, Issue:20
Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.
AID750177Antifungal activity against Rhizoctonia solani assessed as inhibition of mycelia elongation rate at 50 ppm after 48 hrs relative to control2013European journal of medicinal chemistry, Jun, Volume: 64Synthesis and antimicrobical evaluation of a novel class of 1,3,4-thiadiazole: derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (78)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (5.13)18.7374
1990's4 (5.13)18.2507
2000's20 (25.64)29.6817
2010's39 (50.00)24.3611
2020's11 (14.10)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.37

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.37 (24.57)
Research Supply Index4.37 (2.92)
Research Growth Index5.22 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index3.00 (0.95)

This Compound (21.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (3.85%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other75 (96.15%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]