Compounds > Pechueloic acid
Page last updated: 2024-11-13

Pechueloic acid

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 CID24094149
CHEMBL ID1956398
CHEBI ID183941
SCHEMBL ID13250880

Synonyms (17)

Synonym
MEGXP0_001667
ACON1_001383
NCGC00180565-01
BRD-K13964656-001-01-2
2-[(5r,8s,8as)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-enoic acid
CHEBI:183941
pechueloic acid
CHEMBL1956398
SCHEMBL13250880
NCGC00180565-02
2-((5r,8s,8as)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl) acrylic acid
83161-56-2
HY-N3016
CS-0022973
MS-23517
E88596
AKOS040740904

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 (1)

ClassDescription
sesquiterpenoidAny terpenoid derived from a sesquiterpene. The term includes compounds in which the C15 skeleton of the parent sesquiterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[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 (33)

Assay IDTitleYearJournalArticle
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.
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.
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.
AID648646Antiinfluenza activity against influenza A virus H1N1 infected in MDCK cells assessed as inhibition of virus-induced cytopathic effect after 36 hrs2012Bioorganic & medicinal chemistry letters, Mar-15, Volume: 22, Issue:6
Synthesis and anti-influenza activity of aminoalkyl rupestonates.
AID1432502Antiviral activity against Influenza A virus H3N2 infected in MDCK cells assessed as inhibition of virus-induced cytopathic effect after 40 hrs2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Structure-activity relationship studies of 1-(1'-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses.
AID1578004Selectivity index, ratio of TC50 for cytotoxicity against dog MDCK cells to IC50 for antiviral activity against Influenza A virus H1N1 infected in dog MDCK cells2019Bioorganic & medicinal chemistry letters, 10-01, Volume: 29, Issue:19
Novel amides modified rupestonic acid derivatives as anti-influenza virus reagents.
AID648649Selectivity index, ratio of TC50 for MDCK cells to IC50 for influenza A virus H3N22012Bioorganic & medicinal chemistry letters, Mar-15, Volume: 22, Issue:6
Synthesis and anti-influenza activity of aminoalkyl rupestonates.
AID1432501Cytotoxicity against MDCK cells after 48 hrs by by Reed and Muench analysis2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Structure-activity relationship studies of 1-(1'-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses.
AID648648Cytotoxicity against MDCK cells2012Bioorganic & medicinal chemistry letters, Mar-15, Volume: 22, Issue:6
Synthesis and anti-influenza activity of aminoalkyl rupestonates.
AID1578005Antiviral activity against Influenza A virus H3N2 infected in dog MDCK cells assessed as inhibition in virus-induced cytopathic effect incubated for 40 hrs2019Bioorganic & medicinal chemistry letters, 10-01, Volume: 29, Issue:19
Novel amides modified rupestonic acid derivatives as anti-influenza virus reagents.
AID1077006Cytotoxicity against MDCK cells after 48 hrs2014European journal of medicinal chemistry, Apr-09, Volume: 761,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses.
AID1162204Cytotoxicity against mouse RAW264.7 cells at 0.01 to 100 uM after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
New guaiane sesquiterpenes from Artemisia rupestris and their inhibitory effects on nitric oxide production.
AID1077005Antiviral activity against Influenza A virus (A/FM/1/1947(H1N1)) infected in MDCK cells assessed as inhibition of virus-induced cytopathicity after 40 hrs2014European journal of medicinal chemistry, Apr-09, Volume: 761,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses.
AID1077000Selectivity index, ratio of TC50 for MDCK cells to IC50 for Influenza A virus A/hanfang/359/95(H3N2)2014European journal of medicinal chemistry, Apr-09, Volume: 761,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses.
AID1578007Antiviral activity against Influenza B virus infected in MDCK cells assessed as inhibition in virus-induced cytopathic effect incubated for 40 hrs2019Bioorganic & medicinal chemistry letters, 10-01, Volume: 29, Issue:19
Novel amides modified rupestonic acid derivatives as anti-influenza virus reagents.
AID1578008Selectivity index, ratio of TC50 for cytotoxicity against dog MDCK cells to IC50 for antiviral activity against Influenza B virus infected in dog MDCK cells2019Bioorganic & medicinal chemistry letters, 10-01, Volume: 29, Issue:19
Novel amides modified rupestonic acid derivatives as anti-influenza virus reagents.
AID1578003Antiviral activity against Influenza A virus H1N1 infected in dog MDCK cells assessed as inhibition in virus-induced cytopathic effect incubated for 40 hrs2019Bioorganic & medicinal chemistry letters, 10-01, Volume: 29, Issue:19
Novel amides modified rupestonic acid derivatives as anti-influenza virus reagents.
AID1432503Antiviral activity against Influenza A virus H1N1 infected in MDCK cells assessed as inhibition of virus-induced cytopathic effect after 40 hrs2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Structure-activity relationship studies of 1-(1'-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses.
AID1432504Antiviral activity against Influenza B virus infected in MDCK cells assessed as inhibition of virus-induced cytopathic effect after 40 hrs2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Structure-activity relationship studies of 1-(1'-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses.
AID1076998Selectivity index, ratio of TC50 for MDCK cells to IC50 for Influenza B virus jifang/13/972014European journal of medicinal chemistry, Apr-09, Volume: 761,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses.
AID1578006Selectivity index, ratio of TC50 for cytotoxicity against dog MDCK cells to IC50 for antiviral activity against Influenza A virus H3N2 infected in dog MDCK cells2019Bioorganic & medicinal chemistry letters, 10-01, Volume: 29, Issue:19
Novel amides modified rupestonic acid derivatives as anti-influenza virus reagents.
AID1076999Antiviral activity against Influenza B virus jifang/13/97 infected in MDCK cells assessed as inhibition of virus-induced cytopathicity after 40 hrs2014European journal of medicinal chemistry, Apr-09, Volume: 761,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses.
AID1578002Cytotoxicity against MDCK cells assessed as reduction in cell viability incubated for 48 hrs2019Bioorganic & medicinal chemistry letters, 10-01, Volume: 29, Issue:19
Novel amides modified rupestonic acid derivatives as anti-influenza virus reagents.
AID1077004Selectivity index, ratio of TC50 for MDCK cells to IC50 for Influenza A virus (A/FM/1/1947(H1N1))2014European journal of medicinal chemistry, Apr-09, Volume: 761,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses.
AID648647Antiinfluenza activity against influenza B virus infected in MDCK cells assessed as inhibition of virus-induced cytopathic effect after 36 hrs2012Bioorganic & medicinal chemistry letters, Mar-15, Volume: 22, Issue:6
Synthesis and anti-influenza activity of aminoalkyl rupestonates.
AID1162203Inhibition of NO production in LPS-stimulated mouse RAW264.7 cells pre-incubated for 2 hrs before LPS stimulation for 24 hrs by Griess assay method2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
New guaiane sesquiterpenes from Artemisia rupestris and their inhibitory effects on nitric oxide production.
AID1432506Selectivity index, ratio of TC50 for MDCK cells to IC50 for Influenza A virus H1N1 infected in MDCK cells2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Structure-activity relationship studies of 1-(1'-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses.
AID1432507Selectivity index, ratio of TC50 for MDCK cells to IC50 for Influenza B virus infected in MDCK cells2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Structure-activity relationship studies of 1-(1'-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses.
AID1077002Selectivity index, ratio of TC50 for MDCK cells to IC50 for Influenza A virus (A/Tianjinjinnan/15/2009/H1N1)2014European journal of medicinal chemistry, Apr-09, Volume: 761,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses.
AID648645Antiinfluenza activity against influenza A virus H3N2 infected in MDCK cells assessed as inhibition of virus-induced cytopathic effect after 36 hrs2012Bioorganic & medicinal chemistry letters, Mar-15, Volume: 22, Issue:6
Synthesis and anti-influenza activity of aminoalkyl rupestonates.
AID1432505Selectivity index, ratio of TC50 for MDCK cells to IC50 for Influenza A virus H3N2 infected in MDCK cells2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Structure-activity relationship studies of 1-(1'-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (75.00)24.3611
2020's2 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.31

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

MetricThis Compound (vs All)
Research Demand Index12.31 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.31)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pimagedine
pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.		2.110guanidines;
one-carbon compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 1.4.3.4 (monoamine oxidase) inhibitor
ribavirin
Rebetron: Rebetron is tradename		3.03401-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
oseltamivir
Oseltamivir: An acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.. oseltamivir : A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.		2.8330acetamides;
amino acid ester;
cyclohexenecarboxylate ester;
primary amino compound		antiviral drug;
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor;
environmental contaminant;
prodrug;
xenobiotic
tamiflu
[no description available]		2.0710phosphate salt
nevadensin
nevadensin: from Lysionotus pauceflora Maxim; RN & N1 from 9th CI. nevadensin : A trimethoxyflavone that is flavone substituted by methoxy groups at positions 6, 8 and 4' and hydroxy groups at positions 5 and 7 respectively.		2.110dihydroxyflavone;
trimethoxyflavone		plant metabolite
luteolin
[no description available]		2.1103'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
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.		2.110beta-D-glucoside;
glycosyloxyflavone;
monosaccharide derivative;
trihydroxyflavone		antioxidant;
plant metabolite
chrysoeriol
chrysoeriol: isolated from leaves of Eurya japonica & E. emarginata. 4',5,7-trihydroxy-3'-methoxyflavone : The 3'-O-methyl derivative of luteolin.		2.110monomethoxyflavone;
trihydroxyflavone		antineoplastic agent;
antioxidant;
metabolite
linarin
linarin: flavone glycoside isolated from leaves of Linaria japonica MIQ		2.110
tilianin
tilianin: from several medicinal plants including Agastache rugosa and Dracocephalum moldavia		2.110
ConditionIndicatedRelationship StrengthStudiesTrials
Grippe
[description not available]		02.5220
Influenza, Human
An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.		02.5220
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