Page last updated: 2024-11-08

agnuside

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

Description

agnuside: isolated from Vitex peduncularis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

agnuside : A benzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with the primary hydroxy group of aucubin. It is an iridoid glycoside found in several Vitex plants including Vitex agnus-castus. [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]

FloraRankFlora DefinitionFamilyFamily Definition
VitexgenusA genus of trees in the Lamiaceae family containing assorted flavonoids with possible analgesic and antineoplastic properties. The fruit of these trees is used in herbal preparations.[MeSH]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]

Cross-References

ID SourceID
PubMed CID442416
CHEMBL ID483223
CHEBI ID2515
SCHEMBL ID382107
MeSH IDM0421990

Synonyms (36)

Synonym
ACON1_000039
MEGXP0_000767
agnuside
11027-63-7
C09765
NCGC00168851-01
BRD-K25132901-001-01-5
[(1s,4ar,5s,7as)-5-hydroxy-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
CHEMBL483223
jb24q0ot9g ,
(-)-buddlejoside a
buddlejoside a
unii-jb24q0ot9g
agnoside
AKOS015896848
.beta.-d-glucopyranoside, (1s,4ar,5s,7as)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(((4-hydroxybenzoyl)oxy)methyl)cyclopenta(c)pyran-1-yl
.beta.-d-glucopyranoside, 1,4a,5,7a-tetrahydro-5-hydroxy-7-(((4-hydroxybenzoyl)oxy)methyl)cyclopenta(c)pyran-1-yl, (1.alpha.,4a.alpha.,5.alpha.,7a.alpha.)-
agnuside [usp-rs]
SCHEMBL382107
CHEBI:2515 ,
[(1s,4ar,5s,7as)-1-(beta-d-glucopyranosyloxy)-5-hydroxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
DTXSID10149191 ,
[(1s,4ar,5s,7as)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
agnusid
mfcd00210471
NCGC00168851-03
((1s,4ar,5s,7as)-5-hydroxy-1-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl)methyl 4-hydroxybenzoate
Q16826128
CS-0022789
HY-N2518
AS-79164
beta-d-glucopyranoside, (1s,4ar,5s,7as)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(((4-hydroxybenzoyl)oxy)methyl)cyclopenta(c)pyran-1-yl
agnuside (usp-rs)
dtxcid9071682
((1s,4ar,5s,7as)-1-(beta-d-glucopyranosyloxy)-5-hydroxy-1,4a,5,7a-tetrahydrocyclopenta(c)pyran-7-yl)methyl 4-hydroxybenzoate
beta-d-glucopyranoside, 1,4a,5,7a-tetrahydro-5-hydroxy-7-(((4-hydroxybenzoyl)oxy)methyl)cyclopenta(c)pyran-1-yl, (1alpha,4aalpha,5alpha,7aalpha)-

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The mean absolute bioavailability (%F) of AGN was∼0."( Plasma pharmacokinetics, bioavailability and tissue distribution of agnuside following peroral and intravenous administration in mice using liquid chromatography tandem mass spectrometry.
Bhateria, M; Bhatta, RS; Puttrevu, SK; Ramakrishna, R; Singh, R, 2016
)
0.67
"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 (4)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
pro-angiogenic agentAny compound that promotes the growth of new blood vessels from pre-existing vessels.
cyclooxygenase 2 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
[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 (7)

ClassDescription
terpene glycosideA terpenoid in which one or more hydroxy functions are glycosylated.
iridoid monoterpenoidOne of a class of monoterpenoids biosynthesized from isoprene and often intermediates in the biosynthesis of alkaloids. Iridoids usually consist of a cyclopentane ring fused to a six-membered oxygen heterocycle; cleavage of a bond in the cyclopentane ring gives rise to the subclass known as secoiridoids.
benzoate esterEsters of benzoic acid or substituted benzoic acids.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
beta-D-glucosideAny D-glucoside in which the anomeric centre has beta-configuration.
cyclopentapyran
monosaccharide derivativeA carbohydrate derivative that is formally obtained from a monosaccharide.
[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 (24)

Assay IDTitleYearJournalArticle
AID1585168Effect on cell morphology in HUVEC at 1 to 2500 ng/ml after 24 to 96 hrs by DAPI staining-based spectrofluorometric analysis2018European journal of medicinal chemistry, Dec-05, Volume: 160Identification and characterization of agnuside, a natural proangiogenic small molecule.
AID467895Antiviral activity against HCV expressing E1E2 glycoprotein with Vpr-deficient HIV vector assessed as inhibition of viral entry in human Huh7 cells at 20 ug/ml after 72 hrs by luciferase reporter gene assay in presence of beta-glucosidase enzyme for 0.5 h2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
AID1251041Inhibition of COX2 (unknown origin) assessed as PGH2 production at 100 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID1251036Inhibition of COX1 (unknown origin) assessed as PGH2 production at 10 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID1585172Pro-angiogenic activity in HUVEC assessed as increase in tubular network formation at 0.1 ng/ml preincubated for 30 mins followed by ZM 323881 HCl addition and measured after 22 hrs by phase-contrast image analysis2018European journal of medicinal chemistry, Dec-05, Volume: 160Identification and characterization of agnuside, a natural proangiogenic small molecule.
AID1585165Pro-angiogenic activity in HUVEC assessed as increase in cell proliferation at 2500 ng/ml after 96 hrs by DAPI staining-based spectrofluorometric analysis relative to control2018European journal of medicinal chemistry, Dec-05, Volume: 160Identification and characterization of agnuside, a natural proangiogenic small molecule.
AID467896Antiviral activity against HCV expressing E1E2 glycoprotein with Vpr-deficient HIV vector assessed as inhibition of viral entry in human Huh7 cells at 20 ug/ml after 72 hrs by luciferase reporter gene assay in presence of beta-glucosidase enzyme for 4 hrs2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
AID333729Inhibition of 5-lipoxygenase activity at 1000 uM by ferric-xylenol orange peroxide assay relative to control2004Journal of natural products, Dec, Volume: 67, Issue:12
New acylated iridoid glucosides from Vitex altissima.
AID1585173Antimigratory activity in HUVEC assessed as wound closure at 100 ng/ml after 24 hrs by phase-contrast microscopic analysis2018European journal of medicinal chemistry, Dec-05, Volume: 160Identification and characterization of agnuside, a natural proangiogenic small molecule.
AID1585167Pro-angiogenic activity in HUVEC assessed as increase in cell proliferation after 96 hrs by DAPI staining-based spectrofluorometric analysis2018European journal of medicinal chemistry, Dec-05, Volume: 160Identification and characterization of agnuside, a natural proangiogenic small molecule.
AID1585171Pro-angiogenic activity in HUVEC assessed as increase in tubular network formation at 0.1 ng/ml after 22 hrs by phase-contrast image analysis2018European journal of medicinal chemistry, Dec-05, Volume: 160Identification and characterization of agnuside, a natural proangiogenic small molecule.
AID1251038Inhibition of COX1 (unknown origin) assessed as PGH2 production at 100 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID1585169Pro-angiogenic activity in HUVEC assessed as increase in meshes formation after 22 hrs by phase-contrast image analysis2018European journal of medicinal chemistry, Dec-05, Volume: 160Identification and characterization of agnuside, a natural proangiogenic small molecule.
AID1585166Pro-angiogenic activity in HUVEC assessed as increase in cell proliferation at 2500 ng/ml after 24 to 72 hrs by DAPI staining-based spectrofluorometric analysis relative to control2018European journal of medicinal chemistry, Dec-05, Volume: 160Identification and characterization of agnuside, a natural proangiogenic small molecule.
AID1585170Pro-angiogenic activity in HUVEC assessed as increase in meshes formation at 0.1 to 10 ng/ml after 22 hrs by phase-contrast image analysis2018European journal of medicinal chemistry, Dec-05, Volume: 160Identification and characterization of agnuside, a natural proangiogenic small molecule.
AID1251039Inhibition of COX2 (unknown origin) assessed as PGH2 production at 10 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID1251040Inhibition of COX2 (unknown origin) assessed as PGH2 production at 35 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID467894Antiviral activity against HCV expressing E1E2 glycoprotein with Vpr-deficient HIV vector assessed as inhibition of viral entry in human Huh7 cells at 20 ug/ml measured after 72 hrs by luciferase reporter gene assay2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
AID1251037Inhibition of COX1 (unknown origin) assessed as PGH2 production at 35 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
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.
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.
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.
[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-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (25.00)29.6817
2010's9 (56.25)24.3611
2020's3 (18.75)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.75

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 Index31.75 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.90 (4.65)
Search Engine Demand Index53.91 (26.88)
Search Engine Supply Index2.97 (0.95)

This Compound (31.75)

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]