Compounds > benzyl d-glucopyranoside
Page last updated: 2024-12-08

benzyl d-glucopyranoside

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

Description

benzyl beta-D-glucopyranoside : A beta-D-glucoside that is beta-D-glucopyranose in which the hydroxy group at position 1R is substituted by a benzyloxy group. [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 CID188977
CHEMBL ID2336738
CHEBI ID141411
SCHEMBL ID5026363
MeSH IDM0395212

Synonyms (45)

Synonym
(2r,3r,4s,5s,6r)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
benzyl .beta.-d-glucopyranoside
TIMTEC1_005150
ACON1_002322
NCGC00169955-01
benzyl-beta-d-glucoside
C2542227-8A44-4AA0-ACE1-5CB5555F52EE
HMS1548K02
BRD-K55170554-001-02-6
benzyl |a-d-glucopyranoside
benzyl beta-d-glucopyranoside
CHEBI:141411
1-o-benzyl-beta-d-glucopyranose
4304-12-5
(2r,3r,4s,5s,6r)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol
phenylmethyl beta-d-glucopyranoside
benzyl-o-beta-d-glucopyranoside
(2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-phenylmethoxyoxane-3,4,5-triol
unii-7ill1ijm8r
7ill1ijm8r ,
AKOS016012289
CHEMBL2336738
GKHCBYYBLTXYEV-UJPOAAIJSA-N
SCHEMBL5026363
benzyl glucoside
(-)-benzyl .beta.-d-glucoside
.beta.-d-glucopyranoside, phenylmethyl
benzyl alcohol glucoside
benzyl-o-.beta.-d-glucopyranoside
benzyl alcohol-7-o-beta-d-glucopyranoside
benzyl alcohol-7-o-beta-d-glucoside
benzyl glucopyranoside, >=95% (lc/ms-elsd)
NCGC00169955-02
ncgc00169955-02_c13h18o6_benzyl beta-d-glucopyranoside
124492-59-7
CS-0210263
Q27268359
benzyl beta-d-glucoside
D86091
benzyl hexopyranoside
DTXSID30962864
WS-01270
benzyl ?-d-glucopyranoside
benzyl beta -d-glucopyranoside
(2r,3r,4s,5s,6r)-2-(benzyloxy)-6-(hydroxymethyl)oxane-3,4,5-triol

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (2)

ClassDescription
beta-D-glucosideAny D-glucoside in which the anomeric centre has beta-configuration.
benzenesAny benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives.
[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 (21)

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.
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.
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.
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.
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.
AID1187905Inhibition of alpha-glucosidase (unknown origin) using 3 mM p-NPG solution at 50 uM relative to control2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID1187910Metal chelating activity of the compound assessed as Cu2+ chelating activity at 10 uM by fluorescence assay relative to control2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID1176142Cytotoxicity against mouse RAW264.7 cells at 50 uM by MTT assay2015Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2
Anti-inflammatory components of Chrysanthemum indicum flowers.
AID1176144Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated nitric oxide production at 0.4 to 10 uM after 24 hrs by Griess assay2015Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2
Anti-inflammatory components of Chrysanthemum indicum flowers.
AID1616813Cytoprotective activity against CdCl2-induced cell death in human HEK293T cells assessed as increase in cell viability preincubated for 2 hrs followed by CdCl2 treatment and measured after 48 hrs by MTT assay2019Journal of natural products, 10-25, Volume: 82, Issue:10
Constituents from the Leaves of
AID1187907Antioxidant activity assessed as trolox equivalent of AAPH radical scavenging activity at 10 uM after 2 mins by ORAC-RCoo assay2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID1616814Cytoprotective activity against CdCl2-induced cell death in human HEK293T cells at 25 to 100 uM preincubated for 2 hrs followed by CdCl2 treatment and measured after 12 hrs by MTT assay2019Journal of natural products, 10-25, Volume: 82, Issue:10
Constituents from the Leaves of
AID1698073Neuroprotective activity against glutamate-induced cell death in mouse HT-22 cells assessed as increase in cell viability after 24 hrs by EZ-Cytox assay
AID1187908Antioxidant activity assessed as copper(I)ion reduction power at 1 uM after 1 hr by cupric ion reducing antioxidant capacity assay2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID1187906Antioxidant activity assessed as trolox equivalent of AAPH radical scavenging activity at 1 uM after 2 mins by ORAC-RCoo assay2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
AID1176148Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated TNFalpha production at 0.4 to 2 uM by ELISA2015Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2
Anti-inflammatory components of Chrysanthemum indicum flowers.
AID1176146Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated TNFalpha production at 10 uM by ELISA2015Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2
Anti-inflammatory components of Chrysanthemum indicum flowers.
AID736009Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by microplate reader2013Journal of natural products, Feb-22, Volume: 76, Issue:2
Flavone tetraglycosides and benzyl alcohol glycosides from the Mongolian medicinal plant Dracocephalum ruyschiana.
AID1187909Antioxidant activity assessed as copper(I)ion reduction power at 10 uM after 1 hr by cupric ion reducing antioxidant capacity assay2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's7 (70.00)24.3611
2020's3 (30.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.13

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 Index13.13 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index5.53 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.13)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
4-hydroxybenzaldehyde
[no description available]		2.0810hydroxybenzaldehydeEC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor;
mouse metabolite;
plant metabolite
4,4'-bisphenol f
4,4'-bisphenol F: RN given refers to parent cpd. bisphenol F : A bisphenol that is methane in which two of the hydrogens have been replaced by 4-hydroxyphenyl groups.		2.0810bisphenol;
diarylmethane		environmental food contaminant;
xenoestrogen
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
[no description available]		2.0810chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
2-hydroxychavicol
2-hydroxychavicol: antimutagen from betel leaf; structure given in first source		2.110
acarbose
[no description available]		2.110amino cyclitol;
glycoside
ferulic acid
ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.		2.0810ferulic acidsanti-inflammatory agent;
antioxidant;
apoptosis inhibitor;
cardioprotective agent;
MALDI matrix material;
plant metabolite
trans-4-coumaric acid
hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.		2.08104-coumaric acidfood component;
mouse metabolite;
plant metabolite
chlorogenic acid
caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.		3.4220cinnamate ester;
tannin		food component;
plant metabolite
eugenyl-beta-d-glucopyranoside
[no description available]		2.0810
quercetin 3-o-glucuronide
quercetin 3-O-glucuronide: structure in first source. miquelianin : A quercetin O-glycoside that consists of quercetin attached to a beta-D-glucuronopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from Salvia and Phaseolus vulgaris, it exhibits antioxidant and antidepressant activities.		2.0810beta-D-glucosiduronic acid;
quercetin O-glycoside		antidepressant;
antioxidant;
metabolite
quercetin
[no description available]		3.03107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
luteolin-7-glucoside
luteolin-7-glucoside: has both antiasthmatic and antineoplastic activities; has 3C protease inhibitory activity; isolated from Ligustrum lucidum. luteolin 7-O-beta-D-glucoside : A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.		3.0310beta-D-glucoside;
glycosyloxyflavone;
monosaccharide derivative;
trihydroxyflavone		antioxidant;
plant metabolite
apigetrin
apigetrin: structure given in first source. apigenin 7-O-beta-D-glucoside : A glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.		3.0310beta-D-glucoside;
dihydroxyflavone;
glycosyloxyflavone;
monosaccharide derivative		antibacterial agent;
metabolite;
non-steroidal anti-inflammatory drug
quercetin 3-o-glucopyranoside
quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells		2.5320beta-D-glucoside;
monosaccharide derivative;
quercetin O-glucoside;
tetrahydroxyflavone		antineoplastic agent;
antioxidant;
antipruritic drug;
bone density conservation agent;
geroprotector;
histamine antagonist;
osteogenesis regulator;
plant metabolite
rutin
Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.		2.5320disaccharide derivative;
quercetin O-glucoside;
rutinoside;
tetrahydroxyflavone		antioxidant;
metabolite
tricin
tricin: from Spartina cynosuroides and other plants; structure		3.03103'-methoxyflavones;
dimethoxyflavone;
trihydroxyflavone		EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
metabolite
cynarine
cynarine: active principle of the artichoke; functions primarily as a cholagogue and choleretic and also as antilipemic agent		3.0310alkyl caffeate ester;
quinic acid		plant metabolite
3,4-di-o-caffeoylquinic acid
3,4-di-O-caffeoylquinic acid: isolated from Siphonostegia chinensis		2.0810quinic acid
astragalin
kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.		2.0810beta-D-glucoside;
kaempferol O-glucoside;
monosaccharide derivative;
trihydroxyflavone		plant metabolite;
trypanocidal drug
quercimeritrin
quercimeritrin: from Rumex luminiastrum. quercetin 7-O-beta-D-glucoside : A quercetin O-glucoside in which a glucosyl residue is attached at position 7 of quercetin via a beta-glycosidic linkage.		3.0310beta-D-glucoside;
flavonols;
monosaccharide derivative;
quercetin O-glucoside;
tetrahydroxyflavone		antioxidant;
metabolite
syringin
syringin: a phenylpropanoid glycoside; see also eleutherosides & lyoniside for eleutheroside A: 474-58-8. syringin : A monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage.		3.0310beta-D-glucoside;
dimethoxybenzene;
monosaccharide derivative;
primary alcohol		hepatoprotective agent;
plant metabolite
isorhamnetin 3-o-glucoside
isorhamnetin 3-O-glucoside: from the flowers of Persea gratissima; structure in first source. isorhamnetin 3-O-beta-D-glucopyranoside : A glycosyloxyflavone that is isorhamnetin substituted at position 3 by a beta-D-glucosyl residue.		3.0310beta-D-glucoside;
glycosyloxyflavone;
monomethoxyflavone;
monosaccharide derivative;
trihydroxyflavone		metabolite
methyl-p-coumarate
methyl-p-coumarate: structure in first source. 4-coumaric acid methyl ester : A cinnamate ester that is the methyl ester of 4-coumaric acid.		2.08104-coumaric acid methyl ester
narcissin flavonol
narcissin flavonol: flavanol glycoside from Strumpfia maritima; do not confuse with other narcissin in Chemline, an alkaloid (lycorine (NM))		2.2110disaccharide derivative;
glycosyloxyflavone;
monomethoxyflavone;
trihydroxyflavone
indigo carmine
3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.		2.0810
methyl chlorogenate
methyl chlorogenate: from Eriobotrya japonica; structure in first source		3.0310quinic acid
methyl 3,5-di-o-caffeoyl quinate
3,5-dicaffeoylquinic acid methyl ester: results suggest that the effect of 3,5-dicaffeoylquinic esters on CHS is associated with a decrease in the production of interleukins, but not with the inhibition of iNOS expression. Moreover, esterification of the carboxyl group at C-1 enhanced protection against tyrosine nitration in the skin. methyl 3,5-di-O-caffeoyl quinate : A methyl ester resulting from the formal condensation of the carboxy group of 3,5-di-O-caffeoyl quinic acid with methanol. Isolated from Suaeda glauca and Dichrocephala bicolor, it exhibits hepatoprotective activity.		3.0310
Phenylethyl beta-D-glucopyranoside
[no description available]		3.0310glycoside
tachioside
tachioside: from the linseed meal; structure in first source		2.110
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
Innate Inflammatory Response
[description not available]		03.0310
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.		03.0310
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