| Record Information |
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| Version | 2.0 |
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| Creation Date | 2014-08-29 05:47:06 UTC |
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| Update Date | 2014-12-24 20:26:40 UTC |
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| Accession Number | T3D4152 |
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| Identification |
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| Common Name | Indoleacetic acid |
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| Class | Small Molecule |
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| Description | Indoleacetic acid is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. 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 ( Using material extracted from human urine, it was discovered by Kogl in 1933 that Indoleacetic acid is also an important plant hormone 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. IAA and some derivatives can be oxidised by horseradish peroxidase (HRP) to 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 therapy involving antibody-, polymer-, or gene-directed approaches, a potential new role for plant auxins in cancer therapy. (1, 2). |
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| Compound Type | - Food Toxin
- Industrial/Workplace Toxin
- Lachrymator
- Metabolite
- Natural Compound
- Organic Compound
- Uremic Toxin
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| Chemical Structure | |
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| Synonyms | | Synonym | | (1H-Indol-3-yl)-acetate | | (1H-Indol-3-yl)-acetic acid | | 1H-Indol-3-ylacetate | | 1H-Indol-3-ylacetic acid | | 1H-Indole-3-acetate | | 1H-Indole-3-acetic acid | | 2-(1H-Indol-3-yl)acetate | | 2-(1H-Indol-3-yl)acetic acid | | 2-(3-Indolyl)acetate | | 2-(3-Indolyl)acetic acid | | 3-(Carboxymethyl)indole | | 3-IAA | | 3-Indole-Acetic acid | | 3-Indoleacetate | | 3-Indoleacetic acid | | 3-Indolylacetate | | 3-Indolylacetic acid | | alpha-Indol-3-yl-acetic acid | | b-Indoleacetate | | b-Indoleacetic acid | | b-Indolylacetate | | b-Indolylacetic acid | | beta-Indole-3-acetic acid | | beta-Indoleacetate | | beta-Indoleacetic acid | | beta-Indolylacetate | | beta-Indolylacetic acid | | Heteroauxin | | Indol-3-ylacetate | | Indol-3-ylacetic acid | | Indole-3-acetate | | Indole-3-acetic acid | | Indoleacetate | | Indolyl-3-acetate | | Indolyl-3-acetic acid | | Indolylacetate | | Indolylacetic acid | | Kyselina 3-indolyloctova | | Rhizopin | | Rhizopon A | | Skatole carboxylate | | Skatole carboxylic acid |
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| Chemical Formula | C10H9NO2 |
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| Average Molecular Mass | 175.184 g/mol |
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| Monoisotopic Mass | 175.063 g/mol |
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| CAS Registry Number | 87-51-4 |
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| IUPAC Name | 2-(1H-indol-3-yl)acetic acid |
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| Traditional Name | β-indole-3-acetic acid |
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| SMILES | OC(=O)CC1=CNC2=CC=CC=C12 |
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| InChI Identifier | InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13) |
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| InChI Key | InChIKey=SEOVTRFCIGRIMH-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Indoles and derivatives |
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| Sub Class | Indolyl carboxylic acids and derivatives |
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| Direct Parent | Indole-3-acetic acid derivatives |
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| Alternative Parents | |
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| Substituents | - Indole-3-acetic acid derivative
- 3-alkylindole
- Indole
- Substituted pyrrole
- Benzenoid
- Heteroaromatic compound
- Pyrrole
- Azacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Carbonyl group
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Endogenous |
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| Cellular Locations | - Cytoplasm
- Extracellular
- Mitochondria
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| Biofluid Locations | Not Available |
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| Tissue Locations | - Brain
- Central Nervous System
- Fibroblasts
- Hippocampus
- Hypothalamus
- Kidney
- Liver
- Platelet
- Spinal Cord
- Striatum
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| Pathways | |
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| Applications | Not Available |
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| Biological Roles | |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 168.5°C | | Boiling Point | Not Available | | Solubility | 1.5 mg/mL | | LogP | 1.41 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0udi-0391000000-7581f14fe5be5b2b2954 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0udi-0691000000-de9ac4f748d50db109ea | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0udi-0591000000-9687f83d1372abe23c3c | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0udi-1793100000-7c78003038436ec5a902 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-00ai-7910000000-4aa7b8244f32048c76bc | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0fk9-9250000000-a5f931fc3292056dba65 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-001i-1920000000-f0ecee61454a589493af | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0udi-1692000000-ce863a1ca2a657cb41d5 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-003r-0900000000-1edcb4977a52155bc130 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-0391000000-7581f14fe5be5b2b2954 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-0691000000-de9ac4f748d50db109ea | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-0591000000-9687f83d1372abe23c3c | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-1793100000-7c78003038436ec5a902 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00ai-7910000000-4aa7b8244f32048c76bc | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fk9-9250000000-a5f931fc3292056dba65 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-001i-1920000000-f0ecee61454a589493af | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udi-1692000000-ce863a1ca2a657cb41d5 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-0691000000-f6073f8f35a6930b5aac | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0059-1900000000-ab74ec83b16ac0b97d12 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-001i-7920000000-8dab2ad22251c9fbd21c | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00e9-0900000000-187b48f2258823cbc6a2 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-001i-0900000000-30b7a73fa446d0e3c8d3 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-0900000000-bbe0fb5a48f89ea6e383 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-004i-0900000000-97850f400d80de278334 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004i-0900000000-600545759ef108827b9e | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-001i-0900000000-b735e95cb23091491c2e | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00e9-0900000000-187b48f2258823cbc6a2 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-001i-0900000000-7dd685d97c3fa897c28f | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0900000000-5e0acffe0e3e18677dbe | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0900000000-97850f400d80de278334 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0900000000-600545759ef108827b9e | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-001i-0900000000-b735e95cb23091491c2e | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0900000000-f6dbb01a35af3042d126 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-0900000000-2ae231b7d0e2cd50aed8 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004i-6900000000-9eae14faa16b8f8259da | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-003r-0900000000-1edcb4977a52155bc130 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0kxr-5900000000-ba2eed29832f9ee48921 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-004l-5900000000-a0b30710f83e53b6f3db | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-001i-9500000000-146ac0a20f9d53e76291 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-053r-9600000000-d9258b3c6b5c6f748f6e | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-004i-9300000000-b59628beb41b424daf4a | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (UPLC Waters, Quattro Ultima Pt Micromass) , Positive (Annotated) | splash10-004i-0900000000-755373c9248cfb6425fc | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-004i-0900000000-2b3df7a1dd85faea6705 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-003r-0900000000-9522ab089ab89b64f96a | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-001i-0900000000-45eab4ddd1395448f757 | JSpectraViewer | MoNA | | MS | Mass Spectrum (Electron Ionization) | splash10-001i-1900000000-3ffc47eb6c977956ad93 | JSpectraViewer | MoNA | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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| Toxicity Profile |
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| Route of Exposure | Endogenous, Ingestion, Dermal (contact) |
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| Mechanism of Toxicity | Uremic toxins such as indole-3-acetic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (4). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (5) |
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| Metabolism | Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. 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. |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Naturally produced by the body (endogenous). Also a plant growth hormone (auxin). |
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| Minimum Risk Level | Not Available |
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| Health Effects | Indoleacetic acid is listed in its MSDS as potentially mutagenic to mammalian somatic cells. It is also identified as a potential skin, eye, and respiratory irritant, and users are warned not to ingest it. Acute exposure to Indoleacetic acid can lead to some mild skin and eye irritation. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Chronically high levels of Indoleacetic acid are associated with the inborn error of metabolism known as Hartnup disease. |
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| Symptoms | As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. |
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| Treatment | Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB07950 |
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| HMDB ID | HMDB00197 |
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| PubChem Compound ID | 802 |
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| ChEMBL ID | CHEMBL82411 |
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| ChemSpider ID | 780 |
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| KEGG ID | C00954 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 16411 |
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| BioCyc ID | Not Available |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | IAC |
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| ACToR ID | Not Available |
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| Wikipedia Link | Indoleacetic acid |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Link |
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| General References | - WEISSBACH H, KING W, SJOERDSMA A, UDENFRIEND S: Formation of indole-3-acetic acid and tryptamine in animals: a method for estimation of indole-3-acetic acid in tissues. J Biol Chem. 1959 Jan;234(1):81-6. [13610897 ]
- Folkes LK, Wardman P: Oxidative activation of indole-3-acetic acids to cytotoxic species- a potential new role for plant auxins in cancer therapy. Biochem Pharmacol. 2001 Jan 15;61(2):129-36. [11163327 ]
- Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [22626821 ]
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- Young GH, Wu VC: KLOTHO methylation is linked to uremic toxins and chronic kidney disease. Kidney Int. 2012 Apr;81(7):611-2. doi: 10.1038/ki.2011.461. [22419041 ]
- Carpenter LL, Anderson GM, Siniscalchi JM, Chappell PB, Price LH: Acute changes in cerebrospinal fluid 5-HIAA following oral paroxetine challenge in healthy humans. Neuropsychopharmacology. 2003 Feb;28(2):339-47. [12589387 ]
- Owens MJ, Nemeroff CB: Role of serotonin in the pathophysiology of depression: focus on the serotonin transporter. Clin Chem. 1994 Feb;40(2):288-95. [7508830 ]
- Tu JB, Wong CY: Serotonin metabolism in normal and abnormal infants during the perinatal period. Biol Neonate. 1976;29(3-4):187-93. [133735 ]
- Blennow K, Wallin A, Gottfries CG, Mansson JE, Svennerholm L: Concentration gradients for monoamine metabolites in lumbar cerebrospinal fluid. J Neural Transm Park Dis Dement Sect. 1993;5(1):5-15. [7679905 ]
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
- Morgan WW, Grant RW: Increased rate of disappearance of serum probenecid in barbital dependent rats. Eur J Pharmacol. 1976 Dec;40(2):349-57. [1033074 ]
- Jellinger K, Riederer P: Brain monoamines in metabolic (endotoxic) coma. A preliminary biochemical study in human postmortem material. J Neural Transm. 1977;41(4):275-86. [925688 ]
- Sarrias MJ, Cabre P, Martinez E, Artigas F: Relationship between serotoninergic measures in blood and cerebrospinal fluid simultaneously obtained in humans. J Neurochem. 1990 Mar;54(3):783-6. [1689378 ]
- Kema IP, Meijer WG, Meiborg G, Ooms B, Willemse PH, de Vries EG: Profiling of tryptophan-related plasma indoles in patients with carcinoid tumors by automated, on-line, solid-phase extraction and HPLC with fluorescence detection. Clin Chem. 2001 Oct;47(10):1811-20. [11568091 ]
- Bai F, Jones DC, Lau SS, Monks TJ: Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase. Chem Res Toxicol. 2001 Jul;14(7):863-70. [11453733 ]
- Ridges AP, Bishop FM, Lawton K, Goldberg IJ: Amine metabolism, thyroid function and response to clomipramine and maprotiline medication in depression. Postgrad Med J. 1980;56 Suppl 1:37-41. [6156444 ]
- Raghuram TC, Krishnaswamy K: Serotonin metabolism is pellagra. Arch Neurol. 1975 Oct;32(10):708-10. [1180737 ]
- Carling RS, Degg TJ, Allen KR, Bax ND, Barth JH: Evaluation of whole blood serotonin and plasma and urine 5-hydroxyindole acetic acid in diagnosis of carcinoid disease. Ann Clin Biochem. 2002 Nov;39(Pt 6):577-82. [12564839 ]
- Taniguchi K, Okatani Y, Sagara Y: Serotonin metabolism in the fetus in preeclampsia. Asia Oceania J Obstet Gynaecol. 1994 Mar;20(1):77-86. [7513511 ]
- Russo S, Boon JC, Kema IP, Willemse PH, den Boer JA, Korf J, de Vries EG: Patients with carcinoid syndrome exhibit symptoms of aggressive impulse dysregulation. Psychosom Med. 2004 May-Jun;66(3):422-5. [15184706 ]
- Igari T, Shimamura T: Serotonin metabolism and its enzymic activities in joint diseases. Clin Orthop Relat Res. 1979 Mar-Apr;(139):232-49. [455840 ]
- Bearcroft CP, Perrett D, Farthing MJ: Postprandial plasma 5-hydroxytryptamine in diarrhoea predominant irritable bowel syndrome: a pilot study. Gut. 1998 Jan;42(1):42-6. [9505884 ]
- Ilkhanizadeh B, Owji AA, Tavangar SM, Vasei M, Tabei SM: Spot urine 5-hydroxy indole acetic acid and acute appendicitis. Hepatogastroenterology. 2001 May-Jun;48(39):609-13. [11462886 ]
- Igari T, Tsuchizawa M, Shimamura T: Alteration of tryptophan metabolism in the synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Tohoku J Exp Med. 1987 Oct;153(2):79-86. [3500530 ]
- Apak S, Kazez A, Ozel SK, Ustundag B, Akpolat N, Kizirgil A: Spot urine 5-hydroxyindoleacetic acid levels in the early diagnosis of acute appendicitis. J Pediatr Surg. 2005 Sep;40(9):1436-9. [16150345 ]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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