Compounds > Shanzhiside methyl ester
Page last updated: 2024-11-12

Shanzhiside methyl ester

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

Cross-References

ID SourceID
PubMed CID13892722
CHEMBL ID1081414
CHEBI ID193584

Synonyms (27)

Synonym
ACON1_000460
MEGXP0_000430
ACON0_000910
shanzhiside methyl ester
64421-28-9
NCGC00169057-01
BRD-K61757038-001-01-0
CHEMBL1081414
methyl (1s,4as,5r,7s,7as)-5,7-dihydroxy-7-methyl-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1h-cyclopenta[c]pyran-4-carboxylate
CHEBI:193584
S9307
AC-34703
shanzhiside methylester
mfcd00017416
NCGC00169057-02
shanzhisidemethylester
AKOS030573532
shanzhisidmethylester
HY-N0630
F17713
Z3247556297
hanzhiside methyl ester
methyl (1s,4as,5r,7s,7as)-5,7-dihydroxy-7-methyl-1-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
(1s,4as,5r,7s,7as)-methyl 5,7-dihydroxy-7-methyl-1-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
CCG-268713
CS-0009621
MS-26955

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]

Drug Classes (2)

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.
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.
[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 (18)

Assay IDTitleYearJournalArticle
AID467899Antiviral 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 assay2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
AID1204899Cytotoxicity against Stat3-activated human MDA-MB-231 cells assessed as growth inhibition at 20 ug/ml after 72 hrs by CyQuant assay2015Journal of natural products, Feb-27, Volume: 78, Issue:2
Iridoid glycosides from Barleria lupulina.
AID467897Antiviral activity against HCV infected in human Huh7 cells assessed as inhibition of viral replication after 72 hrs by NS5A staining2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
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.
AID671428Inhibition of LPS-induced NF-KB transcriptional activity expressed in HEK-293 cells at 10 ug/ml after 4 hrs by luciferase reporter gene assay relative to LPS-treated group2012Bioorganic & medicinal chemistry letters, Jul-01, Volume: 22, Issue:13
Iridoid glucosides and a C₁₃-norisoprenoid from Lamiophlomis rotata and their effects on NF-κB activation.
AID1204902Antioxidant activity assessed as DPPH free radical scavenging activity measured as decoloration of a MeOH solution after 10 mins by spectrophotometry2015Journal of natural products, Feb-27, Volume: 78, Issue:2
Iridoid glycosides from Barleria lupulina.
AID467898Inhibition of human recombinant GST-tagged CD81 protein assessed as HCV E1E2 binding after 1 hr by Western blot analysis2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
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.
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.
AID1204901Cytotoxicity against Stat3-activated mouse NIH/3T3 cells assessed as growth inhibition at 20 ug/ml after 72 hrs by CyQuant assay2015Journal of natural products, Feb-27, Volume: 78, Issue:2
Iridoid glycosides from Barleria lupulina.
AID671427Inhibition of LPS-induced NF-KB transcriptional activity expressed in HEK-293 cells at 1 ug/ml after 4 hrs by luciferase reporter gene assay relative to LPS-treated group2012Bioorganic & medicinal chemistry letters, Jul-01, Volume: 22, Issue:13
Iridoid glucosides and a C₁₃-norisoprenoid from Lamiophlomis rotata and their effects on NF-κB activation.
AID671429Inhibition of LPS-induced NF-KB transcriptional activity expressed in HEK-293 cells at 100 ug/ml after 4 hrs by luciferase reporter gene assay relative to LPS-treated group2012Bioorganic & medicinal chemistry letters, Jul-01, Volume: 22, Issue:13
Iridoid glucosides and a C₁₃-norisoprenoid from Lamiophlomis rotata and their effects on NF-κB activation.
AID1204900Cytotoxicity against Stat3-activated human U251MG cells assessed as growth inhibition at 20 ug/ml after 72 hrs by CyQuant assay2015Journal of natural products, Feb-27, Volume: 78, Issue:2
Iridoid glycosides from Barleria lupulina.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's3 (50.00)24.3611
2020's2 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.31

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 Index31.31 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index5.21 (4.65)
Search Engine Demand Index27.14 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.31)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
gallic acid
gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.		2.1110trihydroxybenzoic acidantineoplastic agent;
antioxidant;
apoptosis inducer;
astringent;
cyclooxygenase 2 inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
geroprotector;
human xenobiotic metabolite;
plant metabolite
cornin iridoid
cornin iridoid: structure		2.0510terpene glycoside
loganin
[no description available]		2.4620beta-D-glucoside;
cyclopentapyran;
enoate ester;
iridoid monoterpenoid;
methyl ester;
monosaccharide derivative;
secondary alcohol		anti-inflammatory agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
EC 3.4.23.46 (memapsin 2) inhibitor;
neuroprotective agent;
plant metabolite
loganic acid
loganic acid: structure. loganic acid : A cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by beta-D-glucosyloxy, hydroxy and methyl groups respectively		2.0510alpha,beta-unsaturated monocarboxylic acid;
cyclopentapyran;
glucoside		plant metabolite
aucubin
[no description available]		2.0510organic molecular entitymetabolite
geniposide
[no description available]		2.0510terpene glycoside
8-o-acetyl shanzhiside methyl ester
8-O-acetyl shanzhiside methyl ester: an iridoid glucoside; from Phlomis mongolica Turcz; RN given refers to (1S-(1alpha,4aalpha,5alpha,7alpha,7aalpha))-isomer; structure given in first source		2.4920
agnuside
agnuside: isolated from Vitex peduncularis; structure in first source. 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.		2.0510benzoate ester;
beta-D-glucoside;
cyclopentapyran;
iridoid monoterpenoid;
monosaccharide derivative;
phenols;
terpene glycoside		anti-inflammatory agent;
cyclooxygenase 2 inhibitor;
plant metabolite;
pro-angiogenic agent
genipin
[no description available]		2.0510iridoid monoterpenoidanti-inflammatory agent;
antioxidant;
apoptosis inhibitor;
cross-linking reagent;
hepatotoxic agent;
uncoupling protein inhibitor
sesamoside
sesamoside: an iridoid glucoside; from Phlomis mongolica Turz; RN given refers to (1aR-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-isomer; structure given in first source		2.0710
quercetin
[no description available]		2.11107-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
harpagoside
harpagoside: glycoside of a cyclopenta[c]pyran from root of S. African plant Harpagophytum procumbens DC; structure in Negwer, 5th ed, #5281, 7th ed #9921; Harpagophytum extract WS 1531 is plant extract containing harpagoside; Antidiabetic Agent		2.0510terpene glycoside
lamalbid
lamalbid: from Pedicula dicora		2.4620
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		2.1110ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
ConditionIndicatedRelationship StrengthStudiesTrials
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