Page last updated: 2024-12-07

5-methoxy-methylindoleacetic acid

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

Description

5-methoxy-methylindoleacetic acid: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID76151
CHEMBL ID1058
CHEBI ID172459
SCHEMBL ID454792
MeSH IDM0095505

Synonyms (51)

Synonym
AC-15884
CHEMBL1058
deschlorobenzoyl indomethacin
2-(5-methoxy-2-methyl-1h-indol-3-yl)acetic acid
n-deschlorobenzoyl indomethacin
CHEBI:172459
unii-ky9ad0aqm0
5-methoxy-methylindoleacetic acid
nsc 97026
deschlorobenzoylindomethacin
(des-4-chlorobenzoyl)indomethacin
ky9ad0aqm0 ,
einecs 220-734-7
5-methoxy-2-methylindol-3-ylacetic acid
OPREA1_768754
5-methoxy-2-methyl indole acetic acid
nsc-97026
5 miaa
2882-15-7
nsc97026
5-methoxy-2-methyl-3-indoleacetic acid, 98%
5-methoxy-2-methylindole-3-acetic acid
M-3534
(5-methoxy-2-methyl-1h-indol-3-yl)acetic acid
STK118562
AKOS001476087
5-methoxy-2-methyl-3-indoleacetic acid
1h-indole-3-acetic acid, 5-methoxy-2-methyl-
A22462
BBL008167
bdbm50427655
AM20040098
(5-methoxy-2-methyl-1h-indol-3-yl)-acetic acid
FT-0620554
SCHEMBL454792
AB01331434-02
5-methoxy-2-methyl-indolyl acetic acid
5-methoxy-2-methyl-3-indole acetic acid
mfcd00005618
(5-methoxy-2-methyl-1h-indol-3-yl)acetic acid #
TS-03131
DTXSID00183009
CS-W008567
5-meo,2-me-iaa
NCGC00338891-01
deacyl indomethacin
deacyl indomethacin [usp impurity]
5-methoxy-2-methyl-1h-indole-3-acetic acid
2-methyl-5-methoxy-3-indolylacetic acid
SY104037
5-methoxy-2-methyl-3-indolylacetic acid

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" A pharmacokinetic profile of indomethacin is shown, and some preliminary pharmacokinetic parameters of indomethacin obtained from one human volunteer are given."( Determination of indomethacin, its metabolites and their glucuronides in human plasma and urine by means of direct gradient high-performance liquid chromatographic analysis. Preliminary pharmacokinetics and effect of probenecid.
van den Biggelaar-Martea, M; Verwey-van Wissen, CP; Vree, TB, 1993
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
indole-3-acetic acidsAn indol-3-yl carboxylic acid in which the carboxylic acid specified is acetic acid.
[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]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aldo-keto reductase family 1 member C3Homo sapiens (human)IC50 (µMol)100.00000.05002.207010.0000AID729258
Aldo-keto reductase family 1 member C2 Homo sapiens (human)IC50 (µMol)100.00000.37004.09519.2800AID729259
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (32)

Processvia Protein(s)Taxonomy
retinoid metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
G protein-coupled receptor signaling pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
response to nutrientAldo-keto reductase family 1 member C3Homo sapiens (human)
steroid metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of cell population proliferationAldo-keto reductase family 1 member C3Homo sapiens (human)
male gonad developmentAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to starvationAldo-keto reductase family 1 member C3Homo sapiens (human)
farnesol catabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
cyclooxygenase pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
keratinocyte differentiationAldo-keto reductase family 1 member C3Homo sapiens (human)
progesterone metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
retinal metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
macromolecule metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
regulation of retinoic acid receptor signaling pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
renal absorptionAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to calcium ionAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to prostaglandin stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to corticosteroid stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to jasmonic acid stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to prostaglandin D stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
negative regulation of retinoic acid biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
regulation of testosterone biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of endothelial cell apoptotic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of reactive oxygen species metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member C2 Homo sapiens (human)
G protein-coupled receptor signaling pathwayAldo-keto reductase family 1 member C2 Homo sapiens (human)
digestionAldo-keto reductase family 1 member C2 Homo sapiens (human)
steroid metabolic processAldo-keto reductase family 1 member C2 Homo sapiens (human)
positive regulation of cell population proliferationAldo-keto reductase family 1 member C2 Homo sapiens (human)
epithelial cell differentiationAldo-keto reductase family 1 member C2 Homo sapiens (human)
progesterone metabolic processAldo-keto reductase family 1 member C2 Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member C2 Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member C2 Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionAldo-keto reductase family 1 member C2 Homo sapiens (human)
cellular response to jasmonic acid stimulusAldo-keto reductase family 1 member C2 Homo sapiens (human)
cellular response to prostaglandin D stimulusAldo-keto reductase family 1 member C2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (26)

Processvia Protein(s)Taxonomy
retinal dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
aldo-keto reductase (NADPH) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
estradiol 17-beta-dehydrogenase [NAD(P)] activityAldo-keto reductase family 1 member C3Homo sapiens (human)
all-trans-retinol dehydrogenase (NAD+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
oxidoreductase activity, acting on NAD(P)H, quinone or similar compound as acceptorAldo-keto reductase family 1 member C3Homo sapiens (human)
phenanthrene 9,10-monooxygenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
dihydrotestosterone 17-beta-dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin D2 11-ketoreductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
geranylgeranyl reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
ketoreductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin-F synthase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
15-hydroxyprostaglandin-D dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
androsterone dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
5alpha-androstane-3beta,17beta-diol dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone dehydrogenase (NAD+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
androstan-3-alpha,17-beta-diol dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone 17-beta-dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
ketosteroid monooxygenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
Delta4-3-oxosteroid 5beta-reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
bile acid bindingAldo-keto reductase family 1 member C3Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
estradiol 17-beta-dehydrogenase [NAD(P)] activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
oxidoreductase activity, acting on NAD(P)H, quinone or similar compound as acceptorAldo-keto reductase family 1 member C2 Homo sapiens (human)
phenanthrene 9,10-monooxygenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
carboxylic acid bindingAldo-keto reductase family 1 member C2 Homo sapiens (human)
bile acid bindingAldo-keto reductase family 1 member C2 Homo sapiens (human)
androstan-3-alpha,17-beta-diol dehydrogenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
ketosteroid monooxygenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
indanol dehydrogenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
androsterone dehydrogenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleusAldo-keto reductase family 1 member C3Homo sapiens (human)
cytoplasmAldo-keto reductase family 1 member C3Homo sapiens (human)
cytosolAldo-keto reductase family 1 member C3Homo sapiens (human)
extracellular exosomeAldo-keto reductase family 1 member C3Homo sapiens (human)
cytosolAldo-keto reductase family 1 member C3Homo sapiens (human)
cytosolAldo-keto reductase family 1 member C2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID217022Cytotoxicity against Chinese hamster lung fibroblasts (V79 cells) was determined by a clonogenic assay (colonies containing >50 cells were counted and surviving fractions (SF) calculated after 2 hr incubation)2002Bioorganic & medicinal chemistry letters, Sep-16, Volume: 12, Issue:18
Halogenated indole-3-acetic acids as oxidatively activated prodrugs with potential for targeted cancer therapy.
AID729258Inhibition of human recombinant AKR1C3-mediated NADP+-dependent oxidation of S-(+)-1,2,3,4-tetrahydro-1-naphthol2013Journal of medicinal chemistry, Mar-28, Volume: 56, Issue:6
Development of potent and selective indomethacin analogues for the inhibition of AKR1C3 (Type 5 17β-hydroxysteroid dehydrogenase/prostaglandin F synthase) in castrate-resistant prostate cancer.
AID296506Binding affinity to human serum albumin2007Bioorganic & medicinal chemistry, Jul-01, Volume: 15, Issue:13
Binding of ring-substituted indole-3-acetic acids to human serum albumin.
AID296505Octanol-water partition coefficient, log Kow of the compound2007Bioorganic & medicinal chemistry, Jul-01, Volume: 15, Issue:13
Binding of ring-substituted indole-3-acetic acids to human serum albumin.
AID729259Inhibition of human recombinant AKR1C2-mediated NADP+-dependent oxidation of S-(+)-1,2,3,4-tetrahydro-1-naphthol2013Journal of medicinal chemistry, Mar-28, Volume: 56, Issue:6
Development of potent and selective indomethacin analogues for the inhibition of AKR1C3 (Type 5 17β-hydroxysteroid dehydrogenase/prostaglandin F synthase) in castrate-resistant prostate cancer.
AID90866Rate constant for oxidation by HRP (horseradish peroxidase) was determined2002Bioorganic & medicinal chemistry letters, Sep-16, Volume: 12, Issue:18
Halogenated indole-3-acetic acids as oxidatively activated prodrugs with potential for targeted cancer therapy.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (33.33)18.7374
1990's3 (25.00)18.2507
2000's4 (33.33)29.6817
2010's1 (8.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.61

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 Index11.61 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.61)

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]