Compounds > phenyl beta-d-glucopyranoside
Page last updated: 2024-12-06

phenyl beta-d-glucopyranoside

Description

phenylglucoside: RN given refers to (beta-(D))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65080
CHEMBL ID4105357
CHEBI ID8083
SCHEMBL ID1004929
MeSH IDM0484467

Synonyms (49)

Synonym
bdbm36025
(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-phenoxy-tetrahydropyran-3,4,5-triol
.beta.-d-glucopyranoside, phenyl
beta-d-glucopyranoside, phenyl
phenyl beta-d-glucoside
einecs 215-978-6
phenol glucoside
glucopyranoside, phenyl-, beta-d-
brn 0087517
1464-44-4
aryl beta-d-glucoside
C03097
phenylglucoside
phenyl beta-d-glucopyranoside
phenyl beta-d-glucopyranoside, 97%
phenyl-beta-d-glucopyranoside
phenyl-beta-d-glucoside
(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
BMSE000770
HMS1614E16
P0178
mfcd00204281
AKOS001669140
4w3pgi3766 ,
unii-4w3pgi3766
5-17-07-00046 (beilstein handbook reference)
phenyl .beta.-d-glucoside
glucopyranoside, phenyl-, .beta.-d-
phenyl .beta.-d-glucopyranoside
SCHEMBL1004929
CHEBI:8083
c12h16o6
phenyl-.beta.-d-glucopyranoside
phenyl-.beta.-d-glucoside
(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-phenoxytetrahydro-2h-pyran-3,4,5-triol
CCG-249827
AS-59078
NCGC00385978-01
(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-phenoxy-tetrahydro-2h-pyran-3,4,5-triol
Q27107738
CHEMBL4105357
D82047
DTXSID40883677
A884507
phenyl beta -d-glucopyranoside
CS-W012565
gtpl12455
HY-W011849
phenyl-(c)micro-d-glucopyranoside

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51

Dosage Studied

ExcerptRelevanceReference
"The metabolic fates of 14C-phenol and its model plant conjugates 14C-phenyl glucoside and 14C-phenyl 6-O-malonyl-glucoside have been compared following equimolar oral dosing to rats (1."( A comparison of the metabolic fate of phenol, phenyl glucoside and phenyl 6-O-malonyl-glucoside in the rat.
Edwards, VT; Hutson, DH; Jones, BC, 1986)		0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
glycosideA glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
[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]

Pathways (1)

PathwayProteinsCompounds
glycogen degradation I850

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Taste receptor type 2 member 16Homo sapiens (human)EC50 (µMol)482.09200.00490.15500.2500AID1618141; AID1619328; AID1619330; AID1619458; AID1619466
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

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]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1439304Inhibition of Ascaris suum T6PP using T6P as substrate assessed as fraction of enzyme unbound with compound by measuring ratio of initial velocities of T6P substrate hydrolysis in presence and absence of compound at 1 mM after 5 mins by BioMol green dye b2017European journal of medicinal chemistry, Mar-10, Volume: 128Rational design of reversible inhibitors for trehalose 6-phosphate phosphatases.
AID1439303Inhibition of Brugia malayi T6PP using T6P as substrate assessed as fraction of enzyme unbound with compound by measuring ratio of initial velocities of T6P substrate hydrolysis in presence and absence of compound at 1 mM after 5 mins by BioMol green dye 2017European journal of medicinal chemistry, Mar-10, Volume: 128Rational design of reversible inhibitors for trehalose 6-phosphate phosphatases.
AID1439305Inhibition of Mycobacterium tuberculosis T6PP using T6P as substrate assessed as fraction of enzyme unbound with compound by measuring ratio of initial velocities of T6P substrate hydrolysis in presence and absence of compound at 1 mM after 5 mins by BioM2017European journal of medicinal chemistry, Mar-10, Volume: 128Rational design of reversible inhibitors for trehalose 6-phosphate phosphatases.
AID1439306Inhibition of Shigella boydii T6PP using T6P as substrate assessed as fraction of enzyme unbound with compound by measuring ratio of initial velocities of T6P substrate hydrolysis in presence and absence of compound at 1 mM after 5 mins by BioMol green dy2017European journal of medicinal chemistry, Mar-10, Volume: 128Rational design of reversible inhibitors for trehalose 6-phosphate phosphatases.
AID1439307Inhibition of Salmonella typhimurium T6PP using T6P as substrate assessed as fraction of enzyme unbound with compound by measuring ratio of initial velocities of T6P substrate hydrolysis in presence and absence of compound at 1 mM after 5 mins by BioMol g2017European journal of medicinal chemistry, Mar-10, Volume: 128Rational design of reversible inhibitors for trehalose 6-phosphate phosphatases.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (12.50)18.7374
1990's2 (12.50)18.2507
2000's4 (25.00)29.6817
2010's6 (37.50)24.3611
2020's2 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.61

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 Index19.61 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.81 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.61)

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%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phenol
[no description available]		210phenolsantiseptic drug;
disinfectant;
human xenobiotic metabolite;
mouse metabolite
sucrose
Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.		2.0310glycosyl glycosidealgal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
sweetening agent
n-pentanol
n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.		2.0210pentanol;
short-chain primary fatty alcohol		human metabolite;
plant metabolite
beta-glucono-1,5-lactone
beta-glucono-1,5-lactone: structure. D-glucono-1,5-lactone : An aldono-1,5-lactone obtained from D-gluconic acid.		1.9610aldono-1,5-lactone;
gluconolactone		animal metabolite;
mouse metabolite
trehalose
alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.		2.1510trehaloseEscherichia coli metabolite;
geroprotector;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
copper gluconate
Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.		1.9610organic molecular entity
cellobiose
beta-cellobiose : A cellobiose with beta configuration at the reducing-end glucose residue.		2.0210cellobioseepitope
carbonates
Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.		210carbon oxoanion
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.		3.71100D-glucopyranoseepitope;
mouse metabolite
trichlorosucrose
trichlorosucrose: sweetness intensity roughly 600 times that of sucrose and is nonnutritive and noncaloric; largely unabsorbed in the gastrointestinal tract. sucralose : A disaccharide derivative consisting of 4-chloro-4-deoxy-alpha-D-galactopyranose and 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranose units linked by a glycosidic bond.		2.0310disaccharide derivative;
organochlorine compound		environmental contaminant;
sweetening agent;
xenobiotic
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
arabinose
[no description available]		2.0810L-arabinoseEscherichia coli metabolite;
mouse metabolite
salicin
[no description available]		2.0310aromatic primary alcohol;
aryl beta-D-glucoside;
benzyl alcohols		antipyretic;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
prodrug
glycosides
[no description available]		2.6730
zeolites
[no description available]		2.0310
acebutolol
alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.		2.0310alpha-D-glucosyl-(1->4)-D-mannopyranose
ConditionIndicatedRelationship StrengthStudiesTrials
Encephalitis, Polio
[description not available]		02.0610
Poliomyelitis
An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)		02.0610
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.2510
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510
Acquired Immune Deficiency Syndrome
[description not available]		01.9910
Acquired Immunodeficiency Syndrome
An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.		01.9910
chemdatabank.com