Classification Term: 303
Indole-3-acetic acid derivatives (ontology term: CHEMONTID:0001252)
Compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole." []
found 16 associated metabolites at category metabolite taxonomy ontology rank level.
Ancestor: Indolyl carboxylic acids and derivatives
Child Taxonomies: There is no child term of current ontology term.
5-Hydroxyindoleacetic acid
5-Hydroxyindoleacetic acid, also known as 5-hydroxyindole-3-acetate or 5-HIAA, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. In humans, 5-hydroxyindoleacetic acid is a breakdown product of serotonin that is excreted in the urine and it also participates in a number of enzymatic reactions. 5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde; which is catalyzed by the mitochondrial enzyme aldehyde dehydrogenase. In addition, 5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine through its interaction with the enzyme acetylserotonin O-methyltransferase. 5-Hydroxyindoleacetic acid is also involved in the metabolism of tryptophan. 5-Hydroxyindoleacetic acid has been found to be associated with several human diseases such as brunner syndrome, friedreichs ataxia, schizophrenia, and olivopontocerebral atrophy; 5-hydroxyindoleacetic acid has also been linked to the inborn metabolic disorder sepiapterin reductase deficiency. Elevated levels of 5-hydroxyindoleacetic acid in urine (>20 uM) are indicative of appendicitis and gastroenteritis (PMID: 11462886). Serotonin and 5-Hydroxyindoleacetic acid are produced in excess amounts by carcinoid tumors, and levels of these substances may be measured in the urine to test for carcinoid tumors (NCI). 5-Hydroxyindoleacetic acid has also been found to be a product of human gut microbiota. 5-Hydroxyindoleacetic acid (5-HIAA) is the main metabolite of serotonin in the human body. In chemical analysis of urine samples, 5-HIAA is used to determine the bodys levels of serotonin. 5-Hydroxyindole-3-acetic acid is found in many foods, some of which are pitanga, dandelion, coconut, and white cabbage. 5-Hydroxyindole-3-acetic acid is the main metabolite of serotonin or metanephrines, which can be used as a biomarker of neuroendocrine tumors.
5-Methoxyindoleacetate
5-Methoxyindoleacetate, also known as 5-methoxy-IAA or 5-MIAA, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Methoxyindoleacetic acid is formed through oxidative deamination. It is identified in the urine, and the concentration is determined to be 1.3 µg/mL using GC-MS (PMID: 12908946). An increase in urinary 5-MIAA excretion was shown in patients with cancer of the stomach, rectum, and lung (PMID: 2446428). D006133 - Growth Substances > D010937 - Plant Growth Regulators > D007210 - Indoleacetic Acids 5-methoxyindoleacetic acid(5-MIAA) is formed through oxidative deamination. COVID info from PDB, Protein Data Bank KEIO_ID M078; [MS2] KO009067 KEIO_ID M078 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 5-Methoxyindole-3-acetic acid is a metabolite of Melatonin[1].
Indoleacetic acid
Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Higher levels of IAA are associated with bacteria from Clostridium species including C. stricklandii, C. lituseburense, C. subterminale, and C. putrefaciens (PMID: 12173102). IAA can be found in Agrobacterium, Azospirillum, Bacillus, Bradyrhizobium, Clostridium, Enterobacter, Pantoea, Pseudomonas, Rhizobium (PMID: 12173102, PMID: 17555270, PMID: 12147474, PMID: 19400643, PMID: 9450337, PMID: 21397014) (https://link.springer.com/chapter/10.1007/978-1-4612-3084-7_7) (https://escholarship.org/uc/item/1bf1b5m3). Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. IAA frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with phenylketonuria (PMID: 13610897). IAA has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Using material extracted from human urine, it was discovered by Kogl in 1933 that indoleacetic acid is also an important plant hormone (PMID: 13610897). Specifically, IAA is a member of the group of phytohormones called auxins. IAA is generally considered to be the most important native auxin. Plant cells synthesize IAA from tryptophan (Wikipedia). IAA and some derivatives can be oxidized by horseradish peroxidase (HRP) into cytotoxic species. IAA is only toxic after oxidative decarboxylation; the effect of IAA/HRP is thought to be due in part to the formation of methylene-oxindole, which may conjugate with DNA bases and protein thiols. IAA/HRP could be used as the basis for targeted cancer, a potential new role for plant auxins in cancer therapy (PMID: 11163327). 1h-indol-3-ylacetic acid, also known as (indol-3-yl)acetate or heteroauxin, belongs to indole-3-acetic acid derivatives class of compounds. Those are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 1h-indol-3-ylacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 1h-indol-3-ylacetic acid is a mild, odorless, and sour tasting compound and can be found in a number of food items such as sweet bay, chinese bayberry, winter squash, and linden, which makes 1h-indol-3-ylacetic acid a potential biomarker for the consumption of these food products. 1h-indol-3-ylacetic acid can be found primarily in most biofluids, including blood, feces, saliva, and urine, as well as throughout most human tissues. 1h-indol-3-ylacetic acid exists in all living species, ranging from bacteria to humans. In humans, 1h-indol-3-ylacetic acid is involved in the tryptophan metabolism. Moreover, 1h-indol-3-ylacetic acid is found to be associated with appendicitis and irritable bowel syndrome. 1h-indol-3-ylacetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. CONFIDENCE standard compound; INTERNAL_ID 190; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3375; ORIGINAL_PRECURSOR_SCAN_NO 3371 CONFIDENCE standard compound; INTERNAL_ID 190; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3366; ORIGINAL_PRECURSOR_SCAN_NO 3363 CONFIDENCE standard compound; INTERNAL_ID 190; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3365; ORIGINAL_PRECURSOR_SCAN_NO 3361 CONFIDENCE standard compound; INTERNAL_ID 190; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3395; ORIGINAL_PRECURSOR_SCAN_NO 3391 DATA_PROCESSING MERGING RMBmix ver. 0.2.7; CONFIDENCE standard compound; INTERNAL_ID 190; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3366; ORIGINAL_PRECURSOR_SCAN_NO 3363 CONFIDENCE standard compound; INTERNAL_ID 190; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3369; ORIGINAL_PRECURSOR_SCAN_NO 3366 CONFIDENCE standard compound; INTERNAL_ID 190; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3385; ORIGINAL_PRECURSOR_SCAN_NO 3380 D006133 - Growth Substances > D010937 - Plant Growth Regulators > D007210 - Indoleacetic Acids Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 275; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 2796 CONFIDENCE standard compound; INTERNAL_ID 166 COVID info from COVID-19 Disease Map Corona-virus KEIO_ID I038 Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 3-Indoleacetic acid (Indole-3-acetic acid) is the most common natural plant growth hormone of the auxin class. It can be added to cell culture medium to induce plant cell elongation and division. 3-Indoleacetic acid (Indole-3-acetic acid) is the most common natural plant growth hormone of the auxin class. It can be added to cell culture medium to induce plant cell elongation and division.
Methyl indole-3-acetate
Indole-3-methyl acetate, also known as methyl indole-3-acetate (methyl-IAA), is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID: 30120222). Pediatric enthesitis-related arthritis (ERA) patients (i.e. spondyloarthropathy associated with inflammatory bowel disease) have intestinal inflammation and decreased gut microbial diversity. Such alterations in the gut microbiota resulted in the reduction of tryptophan metabolism and several tryptophan metabolites in pediatric ERA fecal samples, including indole-3-methyl acetate (PMID: 27786174). Indole-3-methyl acetate is found in apple, and has been isolated from immature seeds of beach pea (Lathyrus maritimus), Vicia amurensis, wild soybean (Glycine soja), lobiya (Vigna catiang var. sinensis) and hyacinth bean (Dolichos lablab). Isolated from immature seeds of beach pea (Lathyrus maritimus), Vicia amurensis, wild soybean (Glycine soja), lobiya (Vigna catiang variety sinensis) and hyacinth bean (Dolichos lablab). Indole-3-methyl acetate is found in many foods, some of which are gram bean, yellow wax bean, common bean, and sweet orange. Methyl 2-(1H-indol-3-yl)acetate is an endogenous metabolite.
Indole-3-acetyl-myo-inositol
1H-Indol-3-ylacetyl-myo-inositol is found in cereals and cereal products. 1H-Indol-3-ylacetyl-myo-inositol is present in Oryza sativa (rice) and Zea mays (corn Present in Oryza sativa (rice) and Zea mays (corn). 1H-Indol-3-ylacetyl-myo-inositol is found in cereals and cereal products, rice, and corn.
4-O-(Indole-3-acetyl)-D-glucopyranose
4-o-(indole-3-acetyl)-d-glucopyranose, also known as indole-3-acetyl-beta-1-D-glucose or B-D-glucopyranose, 1-(1h-indole-3-acetic acid), belongs to indole-3-acetic acid derivatives class of compounds. Those are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 4-o-(indole-3-acetyl)-d-glucopyranose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4-o-(indole-3-acetyl)-d-glucopyranose can be found in corn, which makes 4-o-(indole-3-acetyl)-d-glucopyranose a potential biomarker for the consumption of this food product. D006133 - Growth Substances > D010937 - Plant Growth Regulators > D007210 - Indoleacetic Acids
Methyl 4-chloro-1H-indole-3-acetate
Auxin from the seeds of Pisum sativum (pea). Methyl 4-chloro-1H-indole-3-acetate is found in many foods, some of which are pulses, grass pea, lentils, and broad bean. Methyl 4-chloro-1H-indole-3-acetate is found in broad bean. Auxin from the seeds of Pisum sativum (pea). D006133 - Growth Substances > D010937 - Plant Growth Regulators > D007210 - Indoleacetic Acids
4-Chloro-1H-indole-3-acetic acid
Auxin from the seeds of Pisum sativum (pea) and isolated from Pinus sylvestris (Scotch pine). 4-Chloro-1H-indole-3-acetic acid is found in many foods, some of which are broad bean, pulses, common pea, and grass pea. 4-Chloro-1H-indole-3-acetic acid is found in broad bean. Auxin from the seeds of Pisum sativum (pea) and isolated from Pinus sylvestris (Scotch pine). D006133 - Growth Substances > D010937 - Plant Growth Regulators > D007210 - Indoleacetic Acids
N-Deschlorobenzoyl indomethacin
N-Deschlorobenzoyl indomethacin is only found in individuals that have used or taken Indomethacin. N-Deschlorobenzoyl indomethacin is a metabolite of Indomethacin. N-deschlorobenzoyl indomethacin belongs to the family of Indole-3-acetic Acid Derivatives. These are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. D006133 - Growth Substances > D010937 - Plant Growth Regulators > D007210 - Indoleacetic Acids
2-[5-Methoxy-2-methyl-1-[(4-methylsulfanylphenyl)methyl]indol-3-yl]propanoic acid
C21H23NO3S (369.1398568000001)
D006133 - Growth Substances > D010937 - Plant Growth Regulators > D007210 - Indoleacetic Acids
3-Des(dimethylaminoethyl)-3-acetic acid zolmitriptan
Auxin
Auxins are a class of plant growth substances and morphogens (often called phytohormone or plant hormone). Auxins have an essential role in coordination of many growth and behavioral processes in the plants life cycle. IAA (indole-3-acetic acid) is the most abundant and the basic native auxin in plants. Auxin is found in soft-necked garlic.
indole-3-acetyl-beta-4-D-glucose
Indole-3-acetyl-beta-4-d-glucose belongs to indole-3-acetic acid derivatives class of compounds. Those are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. Indole-3-acetyl-beta-4-d-glucose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Indole-3-acetyl-beta-4-d-glucose can be found in a number of food items such as tamarind, black-eyed pea, sweet potato, and sourdough, which makes indole-3-acetyl-beta-4-d-glucose a potential biomarker for the consumption of these food products.
indole-3-acetyl-beta-6-D-glucose
Indole-3-acetyl-beta-6-d-glucose belongs to indole-3-acetic acid derivatives class of compounds. Those are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. Indole-3-acetyl-beta-6-d-glucose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Indole-3-acetyl-beta-6-d-glucose can be found in a number of food items such as apple, coconut, black mulberry, and american butterfish, which makes indole-3-acetyl-beta-6-d-glucose a potential biomarker for the consumption of these food products.