Compounds > valiolamine
Page last updated: 2024-12-08

valiolamine

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

Description

valiolamine: isolated from Streptomyces hygroscopicus; RN from CA Index; RN not in Chemline 2/85 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID174312
CHEMBL ID222396
CHEMBL ID9216
MeSH IDM0127419

Synonyms (30)

Synonym
83465-22-9
AC-1555
valiolamine hydrate
d-epi-inositol, 4-amino-3,4-dideoxy-2-c-(hydroxymethyl)-, hydrate
4-amino-3,4-dideoxy-2-c-(hydroxymethyl)-d-epi-inositol hydrate
valiolamine
CHEMBL222396 ,
bdbm50241137
chembl9216
valinolamine
5-amino-1-hydroxymethyl-cyclohexane-1,2,3,4-tetraol
bdbm50024129
A840578
(1s,2s,3r,4s,5s)-5-amino-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol;valiolamine
(1s,2s,3r,4s,5s)-5-amino-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
AKOS006287538
(1s,2s,3r,4s,5s)-5-amino-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol
4-amino-3,4-dideoxy-2-c-(hydroxymethyl)-d-epi-inositol
VDLOJRUTNRJDJO-ZYNSJIGGSA-N
mfcd07773061
AS-14081
C76668
5-amino-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
DTXSID601003447
4-amino-3.4-dideoxy-2-c-(hydroxymethyl)-d-epi-inositol
w9s ,
QHW83U8Q5B
eb-0155
d-epi-inositol, 4-amino-3,4-dideoxy-2-c-(hydroxymethyl)-
eb0155

Research Excerpts

Overview

Valiolamine is a particularly effective inhibitor of oligosaccharide glucosidases I and II and of lysosomal alpha-glucosidase.

ExcerptReferenceRelevance
"Valiolamine is a particularly effective inhibitor of oligosaccharide glucosidases I and II and of lysosomal alpha-glucosidase."( Inhibitory effect of pseudo-aminosugars on oligosaccharide glucosidases I and II and on lysosomal alpha-glucosidase from rat liver.
Kamata, K; Kameda, Y; Matsui, K; Takeuchi, M; Yoshida, M, 1990)		1

Effects

Valiolamine has more potent alpha-glucosidase inhibitory activity against porcine intestinal sucrase, maltase and isomaltase than valienamine, validamine and hydroxyvalidamine which were reported as building blocks of validamycins.

ExcerptReferenceRelevance
"Valiolamine has more potent alpha-glucosidase inhibitory activity against porcine intestinal sucrase, maltase and isomaltase than valienamine, validamine and hydroxyvalidamine which were reported as building blocks of validamycins and microbial oligosaccharide alpha-glucosidase inhibitors."( Valiolamine, a new alpha-glucosidase inhibiting aminocyclitol produced by Streptomyces hygroscopicus.
Asano, N; Fukase, H; Horii, S; Kameda, Y; Matsui, K; Takeuchi, M; Yamaguchi, T; Yoshikawa, M, 1984)		2.43
"Valiolamine has more potent carbohydrase inhibitory activity than validamine or valienamine, and the apparent Ki values of valiolamine for sucrase, maltase, glucoamylase, isomaltase and trehalase activities were 3.2 x 10(-7), 2.9 x 10(-6), 1.2 x 10(-6), 9.1 x 10(-7) and 4.9 x 10(-5) M, respectively, which are 10(-5) to 10(-3) times smaller than the apparent Km values."( Inhibitory effect of validamine, valienamine and valiolamine on activities of carbohydrases in rat small intestinal brush border membranes.
Asano, N; Kameda, Y; Matsui, K; Takai, N; Takeuchi, M, 1990)		1.25
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Maltase-glucoamylase, intestinalHomo sapiens (human)IC50 (µMol)2.20000.04003.46529.0000AID104666
Lysosomal alpha-glucosidaseHomo sapiens (human)IC50 (µMol)57.00000.06002.28897.8000AID342799
Sucrase-isomaltase, intestinalHomo sapiens (human)IC50 (µMol)0.04900.04902.72947.8000AID208984
Sucrase-isomaltase, intestinalRattus norvegicus (Norway rat)IC50 (µMol)1.39500.04001.848310.0000AID342795; AID342797
Glycogen debranching enzymeOryctolagus cuniculus (rabbit)IC50 (µMol)31.00000.11000.69752.1000AID342805
Lysosomal alpha-glucosidaseRattus norvegicus (Norway rat)IC50 (µMol)18.00000.08002.50619.8500AID342793
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
maltose catabolic processMaltase-glucoamylase, intestinalHomo sapiens (human)
starch catabolic processMaltase-glucoamylase, intestinalHomo sapiens (human)
dextrin catabolic processMaltase-glucoamylase, intestinalHomo sapiens (human)
maltose metabolic processLysosomal alpha-glucosidaseHomo sapiens (human)
regulation of the force of heart contractionLysosomal alpha-glucosidaseHomo sapiens (human)
diaphragm contractionLysosomal alpha-glucosidaseHomo sapiens (human)
heart morphogenesisLysosomal alpha-glucosidaseHomo sapiens (human)
glycogen catabolic processLysosomal alpha-glucosidaseHomo sapiens (human)
sucrose metabolic processLysosomal alpha-glucosidaseHomo sapiens (human)
glucose metabolic processLysosomal alpha-glucosidaseHomo sapiens (human)
lysosome organizationLysosomal alpha-glucosidaseHomo sapiens (human)
locomotory behaviorLysosomal alpha-glucosidaseHomo sapiens (human)
tissue developmentLysosomal alpha-glucosidaseHomo sapiens (human)
aorta developmentLysosomal alpha-glucosidaseHomo sapiens (human)
vacuolar sequesteringLysosomal alpha-glucosidaseHomo sapiens (human)
muscle cell cellular homeostasisLysosomal alpha-glucosidaseHomo sapiens (human)
neuromuscular process controlling postureLysosomal alpha-glucosidaseHomo sapiens (human)
neuromuscular process controlling balanceLysosomal alpha-glucosidaseHomo sapiens (human)
cardiac muscle contractionLysosomal alpha-glucosidaseHomo sapiens (human)
glycophagyLysosomal alpha-glucosidaseHomo sapiens (human)
sucrose catabolic processSucrase-isomaltase, intestinalHomo sapiens (human)
polysaccharide digestionSucrase-isomaltase, intestinalHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
catalytic activityMaltase-glucoamylase, intestinalHomo sapiens (human)
glucan 1,4-alpha-glucosidase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
alpha-1,4-glucosidase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
protein bindingMaltase-glucoamylase, intestinalHomo sapiens (human)
amylase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
carbohydrate bindingMaltase-glucoamylase, intestinalHomo sapiens (human)
maltose alpha-glucosidase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
alpha-1,4-glucosidase activityLysosomal alpha-glucosidaseHomo sapiens (human)
carbohydrate bindingLysosomal alpha-glucosidaseHomo sapiens (human)
maltose alpha-glucosidase activityLysosomal alpha-glucosidaseHomo sapiens (human)
alpha-glucosidase activityLysosomal alpha-glucosidaseHomo sapiens (human)
oligo-1,6-glucosidase activitySucrase-isomaltase, intestinalHomo sapiens (human)
sucrose alpha-glucosidase activitySucrase-isomaltase, intestinalHomo sapiens (human)
protein bindingSucrase-isomaltase, intestinalHomo sapiens (human)
carbohydrate bindingSucrase-isomaltase, intestinalHomo sapiens (human)
alpha-1,4-glucosidase activitySucrase-isomaltase, intestinalHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
plasma membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
apical plasma membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
extracellular exosomeMaltase-glucoamylase, intestinalHomo sapiens (human)
tertiary granule membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
ficolin-1-rich granule membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
lysosomeLysosomal alpha-glucosidaseHomo sapiens (human)
lysosomal membraneLysosomal alpha-glucosidaseHomo sapiens (human)
plasma membraneLysosomal alpha-glucosidaseHomo sapiens (human)
membraneLysosomal alpha-glucosidaseHomo sapiens (human)
azurophil granule membraneLysosomal alpha-glucosidaseHomo sapiens (human)
lysosomal lumenLysosomal alpha-glucosidaseHomo sapiens (human)
intracellular membrane-bounded organelleLysosomal alpha-glucosidaseHomo sapiens (human)
extracellular exosomeLysosomal alpha-glucosidaseHomo sapiens (human)
tertiary granule membraneLysosomal alpha-glucosidaseHomo sapiens (human)
ficolin-1-rich granule membraneLysosomal alpha-glucosidaseHomo sapiens (human)
autolysosome lumenLysosomal alpha-glucosidaseHomo sapiens (human)
Golgi apparatusSucrase-isomaltase, intestinalHomo sapiens (human)
plasma membraneSucrase-isomaltase, intestinalHomo sapiens (human)
brush borderSucrase-isomaltase, intestinalHomo sapiens (human)
apical plasma membraneSucrase-isomaltase, intestinalHomo sapiens (human)
extracellular exosomeSucrase-isomaltase, intestinalHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID208984Alpha-D-glucosidase inhibitory activity and enzyme inhibition in vitro against porcine sucrase1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Synthesis and alpha-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents.
AID104666Inhibitory activity against porcine maltase1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Synthesis and alpha-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents.
AID342793Inhibition of rat intestinal brush border membrane maltase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID1895992Inhibition of full length human recombinant Endoplasmic reticulum alpha-glucosidase 1 expressed in Escherichia coli using trisaccharide as substrate incubated for 60 mins2021Journal of medicinal chemistry, 12-23, Volume: 64, Issue:24
N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum α-Glucosidases I and II with Antiviral Activity.
AID342795Inhibition of rat intestinal brush border membrane isomaltase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID342804Inhibition of rabbit glycogen phosphorylase B at 400 uM2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID1895996Antiviral activity against SARS-CoV-2 England/2/2022 assessed as reduction in viral infection2021Journal of medicinal chemistry, 12-23, Volume: 64, Issue:24
N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum α-Glucosidases I and II with Antiviral Activity.
AID342805Inhibition of rabbit muscle amylo-1,6-glucosidase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID342797Inhibition of rat intestinal brush border membrane sucrase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID342802Inhibition of human lysosomal beta-glucosidase at 1000 uM2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID1895994Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability incubated for 3 to 5 days by Cell titer-glo luminescent assay2021Journal of medicinal chemistry, 12-23, Volume: 64, Issue:24
N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum α-Glucosidases I and II with Antiviral Activity.
AID342809Inhibition of pig intestinal maltase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID342810Inhibition of pig intestinal sucrase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID342799Inhibition of human lysosomal alpha-glucosidase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID1895993Inhibition of full length N-terminal his6-tagged mouse recombinant Endoplasmic reticulum alpha-glucosidase 2 expressed in DH10 Escherichia coli using Fluorogenic 1,4-methyl-lumbelliferon as substrate preincubated for 60 mins followed by substrate addition2021Journal of medicinal chemistry, 12-23, Volume: 64, Issue:24
N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum α-Glucosidases I and II with Antiviral Activity.
AID1895995Antiviral activity against DENV New Guinea C strain infected in African green monkey Vero cells assessed as reduction in viral infection measured after 5 days by plaque assay2021Journal of medicinal chemistry, 12-23, Volume: 64, Issue:24
N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum α-Glucosidases I and II with Antiviral Activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (20.00)18.7374
1990's2 (13.33)18.2507
2000's5 (33.33)29.6817
2010's3 (20.00)24.3611
2020's2 (13.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.35

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 Index21.35 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.88 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (18.75%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (81.25%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
inositol
Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.		10.56130cyclitol;
hexol
3-hydroxybutanal
[no description available]		2.0410
cyclohexanol
Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.		3.830cyclohexanols;
secondary alcohol		solvent
2-nitrobenzenesulfenyl chloride
2-nitrobenzenesulfenyl chloride: structure		2.0510
1-deoxynojirimycin
1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.		2.52202-(hydroxymethyl)piperidine-3,4,5-triol;
piperidine alkaloid		anti-HIV agent;
anti-obesity agent;
bacterial metabolite;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
hepatoprotective agent;
hypoglycemic agent;
plant metabolite
miglustat
miglustat: a glucosylceramide synthase inhibitor. miglustat : A hydroxypiperidine that is deoxynojirimycin in which the amino hydrogen is replaced by a butyl group.		2.3110piperidines;
tertiary amino compound		anti-HIV agent;
EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor
fagomine
fagomine: structure in first source		2.0410piperidines
cyanates
Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).		2.0510
homonojirimycin
homonojirimycin: inhibits alpha-glucosidase; RN given for (2R-(2alpha,3alpha,4beta,5alpha,6beta))-isomer; structure in first source		2.0410
valienamine
valienamine: intermediate formed by microbial degradation of validamycins; structure given in first source		7.6630
miglitol
[no description available]		2.0410piperidines
vibo-quercitol
vibo-quercitol: structure in first source		8.1310
ao 128
AO 128: alpha-glucosidase inhibitor; structure given in first source		4.460organic molecular entity
acarbose
[no description available]		2.0410amino cyclitol;
glycoside
validamine
validamine: RN given from CA Index Guide; RN not in Chemline 11/84; structure given in first source. validamine : An amino cyclitol consisting of 1D-chiro-inositol lacking the 6-hydroxy group and having those at positions 1 and 5 replaced by amino and hydroxymethyl groups respectively.		7.6630amino cyclitol
isofagomine
[no description available]		2.0410piperidines
1,4-dideoxy-1,4-imino-d-arabinitol
[no description available]		2.0410
ConditionIndicatedRelationship StrengthStudiesTrials
Acid beta-Glucosidase Deficiency
[description not available]		02.0410
Gaucher Disease
An autosomal recessive disorder caused by a deficiency of acid beta-glucosidase (GLUCOSYLCERAMIDASE) leading to intralysosomal accumulation of glycosylceramide mainly in cells of the MONONUCLEAR PHAGOCYTE SYSTEM. The characteristic Gaucher cells, glycosphingolipid-filled HISTIOCYTES, displace normal cells in BONE MARROW and visceral organs causing skeletal deterioration, hepatosplenomegaly, and organ dysfunction. There are several subtypes based on the presence and severity of neurological involvement.		02.0410
2019 Novel Coronavirus Disease
[description not available]		02.610
Innate Inflammatory Response
[description not available]		02.0810
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0810