Compounds > Pechueloic acid
Page last updated: 2024-08-03 10:05:37

Pechueloic acid

Description

Pechueloic acid : no description available [CHeBI]

Cross-References

ID SourceID
PubMed CID24094149
CHEMBL ID1956398
SCHEMBL ID13250880
CHEBI ID183941

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

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).

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
ISSN: 1091-6490		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
ISSN: 2472-5560		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
ISSN: 1091-6490		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
ISSN: 1521-0111		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
ISSN: 1521-0111		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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: 76ISSN: 1768-32541,2,3-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
ISSN: 1464-3405		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: 76ISSN: 1768-32541,2,3-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: 76ISSN: 1768-32541,2,3-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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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: 76ISSN: 1768-32541,2,3-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
ISSN: 1464-3405		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: 76ISSN: 1768-32541,2,3-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
ISSN: 1464-3405		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: 76ISSN: 1768-32541,2,3-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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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
ISSN: 1464-3405		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: 76ISSN: 1768-32541,2,3-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
ISSN: 1464-3405		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
ISSN: 1464-3405		Structure-activity relationship studies of 1-(1'-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses.

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

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%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
chamazulene
0
sesquiterpenoid00low000000
mansonone c
0
1,2-naphthoquinones;
sesquiterpenoid		00low000000
artemether
0
artemisinin derivative;
cyclic acetal;
organic peroxide;
semisynthetic derivative;
sesquiterpenoid		antimalarial00low000000
elemol
0
olefinic compound;
sesquiterpenoid;
tertiary alcohol		fragrance;
plant metabolite		00low000000
spathulenol
0
carbotricyclic compound;
olefinic compound;
sesquiterpenoid;
tertiary alcohol		anaesthetic;
plant metabolite;
vasodilator agent;
volatile oil component		00low000000
xanthorrhizol
0
sesquiterpenoid00low000000
phomenone
0
sesquiterpenoid00low000000
judaicin (eudesmane naphthofuran)
0
sesquiterpenoid00low000000
hernandulcin
0
sesquiterpenoid00low000000
ar-turmerone
0
enone;
sesquiterpenoid		EC 3.1.1.7 (acetylcholinesterase) inhibitor;
plant metabolite		00low000000
frullanolide
0
sesquiterpenoid00low000000
albicanol
0
carbobicyclic compound;
homoallylic alcohol;
primary alcohol;
sesquiterpenoid		antifeedant;
antifungal agent;
antineoplastic agent;
fungal metabolite;
mammalian metabolite;
marine metabolite;
plant metabolite		00low000000
valeranone
0
sesquiterpenoid00low000000
aromadendrene
0
sesquiterpenoid00low000000
procurcumenol
0
sesquiterpenoid00low000000
fumagillol
0
secondary alcohol;
sesquiterpenoid;
spiro-epoxide		antimicrobial agent00low000000
illudin m
0
sesquiterpenoid00low000000
illudin s
0
sesquiterpenoid00low000000
o-(chloroacetylcarbamoyl)fumagillol
0
carbamate ester;
organochlorine compound;
semisynthetic derivative;
sesquiterpenoid;
spiro-epoxide		angiogenesis inhibitor;
antineoplastic agent;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
methionine aminopeptidase 2 inhibitor;
retinoic acid receptor alpha antagonist		00low000000
bakkenolide a
0
sesquiterpenoid00low000000
bisabolol
0
sesquiterpenoid00low000000
solavetivone
0
cyclic ketone;
sesquiterpenoid;
spiro compound		phytoalexin;
plant metabolite		00low000000
macrocarpal b
0
sesquiterpenoid00low000000
bucladesine
0
sesquiterpenoid00low000000
elatol
0
sesquiterpenoid00low000000
7-hydroxycadalin
0
sesquiterpenoid00low000000
2-[(4,4-dimethyl-2,6-dioxocyclohexyl)-(3-pyridinyl)methyl]-5,5-dimethylcyclohexane-1,3-dione
0
sesquiterpenoid00low000000
2-hydroxy-2,2-bis(4-methylphenyl)-N'-(2-pyridinyl)acetohydrazide
0
sesquiterpenoid00low000000
nootkatone
0
carbobicyclic compound;
enone;
sesquiterpenoid		fragrance;
insect repellent;
plant metabolite		00low000000
bisabolol
0
sesquiterpenoid00low000000
drimenol
0
homoallylic alcohol;
octahydronaphthalenes;
primary alcohol;
sesquiterpenoid		00low000000
atractylon
0
sesquiterpenoid00low000000
zoapatanol
0
sesquiterpenoid00low000000
budlein a
0
sesquiterpenoid00low000000
petasin
0
alicyclic ketone;
enoate ester;
enone;
sesquiterpenoid		anti-allergic agent;
EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} activator;
plant metabolite;
vasodilator agent		00low000000
astrogorgiadiol
0
sesquiterpenoid00low000000
anhydrovitamin a
0
sesquiterpenoid00low000000
rotundone
0
sesquiterpenoid00low000000
4-nerolidylcatechol
0
sesquiterpenoid00low000000
alpha-isomethylionone
0
sesquiterpenoid00low000000
grifolin
0
sesquiterpenoid00low000000
s-trans,trans-farnesylthiosalicylic acid
0
sesquiterpenoid00low000000
zerumbone
0
cyclic ketone;
sesquiterpenoid		anti-inflammatory agent;
glioma-associated oncogene inhibitor;
plant metabolite		00low000000
aurachin d
0
sesquiterpenoid00low000000
deoxyelephantopin
0
sesquiterpenoid00low000000
ascofuranone
0
dihydroxybenzaldehyde;
meroterpenoid;
monochlorobenzenes;
olefinic compound;
resorcinols;
sesquiterpenoid;
tetrahydrofuranone		angiogenesis inhibitor;
antilipemic drug;
antineoplastic agent;
antiprotozoal drug;
fungal metabolite		00low000000
fusarin c
0
sesquiterpenoid00low000000
n-acetyl-s-farnesylcysteine
0
sesquiterpenoid00low000000
tautomycetin
0
sesquiterpenoid00low000000
valerenic acid
0
carbobicyclic compound;
monocarboxylic acid;
sesquiterpenoid		GABA modulator;
plant metabolite;
sedative;
volatile oil component		00low000000
artesunate
0
artemisinin derivative;
cyclic acetal;
dicarboxylic acid monoester;
hemisuccinate;
semisynthetic derivative;
sesquiterpenoid		antimalarial;
antineoplastic agent;
ferroptosis inducer		00low000000
dihydroartemisinin
0
sesquiterpenoidantimalarial00low000000
xenovulene a
0
cyclic ether;
enone;
organic heterotetracyclic compound;
sesquiterpenoid		GABA antagonist;
metabolite		00low000000
LSM-1328
0
sesquiterpenoid00low000000
jaeschkeanadiol
0
sesquiterpenoid00low000000
hypnophilin
0
sesquiterpenoid00low000000
artemisic acid
0
carbobicyclic compound;
monocarboxylic acid;
octahydronaphthalenes;
sesquiterpenoid		metabolite00low000000
dihydroartemisinic acid
0
carbobicyclic compound;
monocarboxylic acid;
octahydronaphthalenes;
sesquiterpenoid		plant metabolite00low000000
ascochlorin
0
cyclohexanones;
dihydroxybenzaldehyde;
meroterpenoid;
monochlorobenzenes;
olefinic compound;
resorcinols;
sesquiterpenoid		angiogenesis inhibitor;
antifungal agent;
antineoplastic agent;
antiprotozoal drug;
fungal metabolite		00low000000
cubebol
0
carbotricyclic compound;
sesquiterpenoid;
tertiary alcohol		00low000000
5-methyl-2-(3-oxo-1,2,2-trimethylcyclopentyl)benzoquinone
0
sesquiterpenoid00low000000
laurinterol
0
organobromine compound;
phenols;
sesquiterpenoid		antibacterial agent;
apoptosis inducer;
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor;
metabolite		00low000000
pyripyropene a
0
organic heterotetracyclic compound;
sesquiterpenoid		acyl-CoA:cholesterol acyltransferase 2 inhibitor;
metabolite		00low000000
viridiflorol
0
carbotricyclic compound;
sesquiterpenoid;
tertiary alcohol		anti-inflammatory agent;
antifeedant;
antimycobacterial drug;
plant metabolite;
volatile oil component		00low000000
cyperotundone
0
sesquiterpenoid00low000000
oplodiol
0
carbobicyclic compound;
octahydronaphthalenes;
secondary alcohol;
sesquiterpenoid;
tertiary alcohol		plant metabolite00low000000
curcumol
0
sesquiterpenoid00low000000
isotrichodermin
0
sesquiterpenoid00low000000
saliniketal a
0
sesquiterpenoid00low000000
saliniketal b
0
sesquiterpenoid00low000000
atheronal-a
0
sesquiterpenoid00low000000
albaflavenone
0
carbocyclic antibiotic;
carbotricyclic compound;
cyclic terpene ketone;
enone;
sesquiterpenoid		bacterial metabolite00low000000
(+)-(7S)-sydonic acid
0
aromatic alcohol;
monohydroxybenzoic acid;
sesquiterpenoid		Aspergillus metabolite00low000000
armillaridin
0
benzoate ester;
sesquiterpenoid		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
pimagedine
1
guanidines;
one-carbon compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 1.4.3.4 (monoamine oxidase) inhibitor		2014201410.0low000010
ribavirin
4
1-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		201220198.5high000040
oseltamivir
3
acetamides;
amino acid ester;
cyclohexenecarboxylate ester;
primary amino compound		antiviral drug;
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor;
environmental contaminant;
prodrug;
xenobiotic		201420197.3medium000030
tamiflu
1
phosphate salt2012201212.0medium000010
nevadensin
1
dihydroxyflavone;
trimethoxyflavone		plant metabolite2014201410.0low000010
luteolin
1
3'-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		2014201410.0low000010
luteolin-7-glucoside
1
beta-D-glucoside;
glycosyloxyflavone;
monosaccharide derivative;
trihydroxyflavone		antioxidant;
plant metabolite		2014201410.0low000010
chrysoeriol
1
monomethoxyflavone;
trihydroxyflavone		antineoplastic agent;
antioxidant;
metabolite		2014201410.0low000010
linarin
1
2014201410.0low000010
tilianin
1
2014201410.0low000010
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Congenital Zika Syndrome0
1
202020204.0medium000010
Disease Models, Animal0
1
202020204.0medium000010
Grippe0
2
201220198.5high000020
Influenza, Human0
2
201220198.5high000020
Zika Virus Infection0
1
202020204.0medium000010

Bioavailability (1)

ArticleYear
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology, , Volume: 96, Issue:5		2019