Compounds > 2-nitrophenyl-beta-d-glucopyranoside
Page last updated: 2024-12-07

2-nitrophenyl-beta-d-glucopyranoside

2-nitrophenyl-beta-d-glucopyranoside is a synthetic glycosidic compound that is commonly used as a substrate for studying the activity of β-glucosidases, enzymes that hydrolyze β-glucosidic bonds. It is synthesized by reacting 2-nitrophenol with β-D-glucopyranose in the presence of a catalyst. The nitro group on the phenyl ring enhances the compound's reactivity, making it an effective substrate for β-glucosidases. Its importance stems from its role as a model compound for understanding the catalytic mechanism of these enzymes. By studying the kinetics and thermodynamics of its hydrolysis, researchers can gain insights into the enzyme's active site and the factors that influence its activity. This information is crucial for developing new drugs that target β-glucosidases, which play a role in various physiological processes, including carbohydrate metabolism, detoxification, and the regulation of immune responses. 2-nitrophenyl-beta-d-glucopyranoside is also used in analytical chemistry for the colorimetric determination of β-glucosidase activity. Its hydrolysis releases 2-nitrophenol, a yellow-colored compound, which can be quantified spectrophotometrically. '

Cross-References

ID SourceID
PubMed CID92941
CHEMBL ID4442376
SCHEMBL ID150630
MeSH IDM0070325

Synonyms (33)

Synonym
2816-24-2
2-nitrophenyl beta-d-glucopyranoside, powder
o-nitrophenyl-beta-d-galactopyranoside
2-nitrophenyl-beta-d-glucopyranoside
o-nitrophenyl beta-glucoside
(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxane-3,4,5-triol
AKOS003631730
n-[5-[(9,10-dioxo-1-anthryl)amino]-9,10-dioxo-1-anthryl]benzamide
A819354
2-nitrophenyl beta-d-glucopyranoside
2-nitrophenyl beta-d-glucoside
o-nitrophenyl beta-d-glucopyranoside
ortho-nitrophenyl-beta-d-glucopyranoside
nsc 1947
beta-d-glucopyranoside, 2-nitrophenyl
einecs 220-568-5
glucopyranoside, o-nitrophenyl, beta-d-
2-nitrophenyl |a-d-glucopyranoside
SCHEMBL150630
2-nitrophenyl b-d-glucopyranoside
(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(2-nitrophenoxy)tetrahydro-2h-pyran-3,4,5-triol
mfcd00065048
2-nitrophenyl-i(2)-d-glucopyranoside
b-d-glucopyranoside, 2-nitrophenyl
AKOS034830278
ortho-nitrophenyl beta-d-glucopyranoside
2-nitrophenyl-b-d-glucopyranoside
CHEMBL4442376
DTXSID901300913
2-nitrophenyl beta -d-glucopyranoside
HY-W013254
CS-W013970
EN300-7375394
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
detection of chemical stimulus involved in sensory perception of bitter tasteTaste receptor type 2 member 16Homo sapiens (human)
G protein-coupled receptor signaling pathwayTaste receptor type 2 member 16Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
G protein-coupled receptor activityTaste receptor type 2 member 16Homo sapiens (human)
protein bindingTaste receptor type 2 member 16Homo sapiens (human)
bitter taste receptor activityTaste receptor type 2 member 16Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
endoplasmic reticulumTaste receptor type 2 member 16Homo sapiens (human)
trans-Golgi networkTaste receptor type 2 member 16Homo sapiens (human)
plasma membraneTaste receptor type 2 member 16Homo sapiens (human)
external side of plasma membraneTaste receptor type 2 member 16Homo sapiens (human)
membraneTaste receptor type 2 member 16Homo sapiens (human)
membraneTaste receptor type 2 member 16Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (12.50)18.7374
1990's2 (25.00)18.2507
2000's3 (37.50)29.6817
2010's2 (25.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.56 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.76 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
formic acid
formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.		1.9910monocarboxylic acidantibacterial agent;
astringent;
metabolite;
protic solvent;
solvent
glycine
[no description available]		1.9910alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		2.0310mitomycinalkylating agent;
antineoplastic agent
serine
Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.		210L-alpha-amino acid;
proteinogenic amino acid;
serine family amino acid;
serine zwitterion;
serine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
glutamine
Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.		1.9910amino acid zwitterion;
glutamine family amino acid;
glutamine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
Escherichia coli metabolite;
human metabolite;
metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
asparagine
Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.		210amino acid zwitterion;
asparagine;
aspartate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
2,2-bis(bromomethyl)-1,3-propanediol
2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source		1.9610primary alcohol
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		1.9910glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
sodium azide
Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).		1.9910inorganic sodium saltantibacterial agent;
explosive;
mitochondrial respiratory-chain inhibitor;
mutagen
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		3.5180D-glucopyranoseepitope;
mouse metabolite
4-nitrophenyl beta-d-glucoside
4-nitrophenyl beta-D-glucoside: RN given refers to (beta)-anomer; see also (alpha)-anomer: 3767-28-0; cpd with unspecified anomer: 5779-46-4. 4-nitrophenyl beta-D-glucoside : A beta-D-glucoside that is beta-D-glucopyranose in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group.		2.0210beta-D-glucoside;
C-nitro compound		chromogenic compound
2',4'-dinitrophenylglucopyranoside
2',4'-dinitrophenylglucopyranoside: substrate of exoglucanase		1.9910
ConditionIndicatedRelationship StrengthStudiesTrials
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