Page last updated: 2024-12-06

5-methoxyindoleacetic acid

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

Description

5-methoxyindoleacetic acid (5-MIAA) is a naturally occurring plant hormone that belongs to the auxin family. It plays a crucial role in regulating plant growth and development, particularly in processes such as cell elongation, root development, and fruit ripening. 5-MIAA is synthesized through the indole-3-pyruvic acid pathway, a complex metabolic route involving multiple enzymatic steps. Its effects are typically attributed to its interaction with auxin receptors, leading to the activation of downstream signaling pathways. Researchers study 5-MIAA to gain a deeper understanding of plant growth mechanisms and to explore its potential applications in agriculture, such as improving crop yield and enhancing plant stress tolerance. Additionally, 5-MIAA has been investigated for its potential medicinal properties, including its anti-inflammatory and antioxidant activities. However, its use in humans remains under investigation.'

5-methoxyindoleacetic acid: serotonin metabolite [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5-methoxyindole-3-acetic acid : A member of the class of indole-3-acetic acids in which the hydrogen at position 5 of indole-3-acetic acid has been replaced by a methoxy group. [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]

Cross-References

ID SourceID
PubMed CID18986
CHEMBL ID85433
CHEBI ID28281
SCHEMBL ID674415
MeSH IDM0042033

Synonyms (71)

Synonym
MLS000515791
5-methoxy-3-indoleacetic acid
smr000112265
CHEMBL85433
EN300-39512
OPREA1_126132
2-(5-methoxy-1h-indol-3-yl)acetic acid
5-methoxyindole-3-acetic acid
einecs 222-438-3
5-methoxyindol-3-ylacetic acid
methoxyindoleacetic acid
indole-3-acetic acid, 5-methoxy-
5-methoxyindoleacetate
3471-31-6
5-methoxyindoleacetic acid
C05660
5-methoxy-3-indoleacetic acid, 98%
M-3474
indole-3-acetic acid, 5- methoxy-
50907E1A-6AC8-4D4D-8DE7-DD464A7A08C2
myi ,
(5-methoxy-1h-indol-3-yl)acetic acid
BMSE000694
1h-indole-3-acetic acid, 5-methoxy-
(5-methoxy-1h-indol-3-yl)-acetic acid
cocndhopihdthk-uhfffaoysa-
inchi=1/c11h11no3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12h,4h2,1h3,(h,13,14)
M1303
A6095
NCGC00247046-01
5-methoxyindole-3-aceticacid
AKOS005207167
HMS2267B20
msn7ck6eth ,
unii-msn7ck6eth
STL220637
FS-3050
AM20060864
FT-0620571
(5-methoxy-3-indolyl)acetic acid
(5-methoxy-3-indolyl)-acetic acid
(5-methoxyindol-3-yl)acetic acid
(5-methoxy-indol-3-yl)-acetic acid
SCHEMBL674415
5-methoxy-3-indolylacetic acid
5-methoxy-1h-indole-3-acetic acid
5-methyloxyindole-3-acetic acid
AC-22684
CS-W007566
DTXSID70188268
mfcd00005638
5-methoxy-3-indoleacetic acid, purum, >=99.0% (t)
5-methoxyindol-3-ylacetate
5-methoxyindole-3-acetate
methoxyindoleacetate
2-(5-methoxy-3-indolyl)acetic acid
SY030412
5-methoxy-indole acetate
142396-09-6
2-(5-methoxyindole-3-yl)acetic acid
2-(5-methoxy-1h-indol-3-yl)ethanoic acid
CHEBI:28281
Q6172526
BCP27387
1h-indole-3-acetic acid,5-methoxy-
5-methoxy-iaa
BBL100075
1h-indole-3-aceticacid,5-methoxy-,radicalion(1+)(9ci)
HY-W007566
PD126571
Z385472506
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (6)

RoleDescription
Brassica napus metaboliteAny plant metabolite that is produced by rapeseed (Brassica napus).
human urinary metaboliteAny metabolite (endogenous or exogenous) found in human urine samples.
antibacterial agentA substance (or active part thereof) that kills or slows the growth of bacteria.
marine xenobiotic metaboliteAny metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
carcinogenic agentA role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
rat metaboliteAny mammalian metabolite produced during a metabolic reaction in rat (Rattus norvegicus).
[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 (2)

ClassDescription
indole-3-acetic acidsAn indol-3-yl carboxylic acid in which the carboxylic acid specified is acetic acid.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[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]

Pathways (5)

PathwayProteinsCompounds
Tryptophan Metabolism1855
Tryptophan degradation ( Tryptophan degradation )6454
superpathway of tryptophan utilization4292
superpathway of melatonin degradation526
melatonin degradation II014

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency25.11890.177814.390939.8107AID2147
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency2.51190.28189.721235.4813AID2326
gemininHomo sapiens (human)Potency13.95200.004611.374133.4983AID624296; AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID90867Rate 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.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (55)

TimeframeStudies, This Drug (%)All Drugs %
pre-199031 (56.36)18.7374
1990's9 (16.36)18.2507
2000's10 (18.18)29.6817
2010's3 (5.45)24.3611
2020's2 (3.64)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.21

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 Index10.21 (24.57)
Research Supply Index4.09 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.21)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.72%)5.53%
Reviews2 (3.45%)6.00%
Case Studies2 (3.45%)4.05%
Observational0 (0.00%)0.25%
Other53 (91.38%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]