Indoleacetic Acid
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
Common Name | Indoleacetic Acid(F05239) |
2D Structure | |
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. (A3268, A3269). |
FRCD ID | F05239 |
CAS Number | 87-51-4 |
PubChem CID | 802 |
Formula | C10H9NO2 |
IUPAC Name | 2-(1H-indol-3-yl)acetic acid |
InChI Key | SEOVTRFCIGRIMH-UHFFFAOYSA-N |
InChI | 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) |
Canonical SMILES | C1=CC=C2C(=C1)C(=CN2)CC(=O)O |
Isomeric SMILES | C1=CC=C2C(=C1)C(=CN2)CC(=O)O |
Wikipedia | Indoleacetic Acid |
Synonyms | indole-3-acetic acid 1H-indol-3-ylacetic acid 87-51-4 3-Indoleacetic acid Heteroauxin indoleacetic acid 1H-Indole-3-acetic acid 2-(1H-Indol-3-yl)acetic acid Rhizopin Indol-3-ylacetic acid |
Classifies | Predicted: Pesticide |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organoheterocyclic compounds |
Class | Indoles and derivatives |
Subclass | Indolyl carboxylic acids and derivatives |
Intermediate Tree Nodes | Not available |
Direct Parent | Indole-3-acetic acid derivatives |
Alternative Parents | |
Molecular Framework | Aromatic heteropolycyclic compounds |
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 |
Description | This compound belongs to the class of organic compounds known as indole-3-acetic acid derivatives. These are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 175.187 |
Hydrogen Bond Donor Count | 2 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 2 |
Complexity | 205 |
Monoisotopic Mass | 175.063 |
Exact Mass | 175.063 |
XLogP | 1.4 |
Formal Charge | 0 |
Heavy Atom Count | 13 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9852 |
Human Intestinal Absorption | HIA+ | 0.9958 |
Caco-2 Permeability | Caco2- | 0.5130 |
P-glycoprotein Substrate | Non-substrate | 0.7220 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9876 |
Non-inhibitor | 0.9699 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8884 |
Distribution | ||
Subcellular localization | Mitochondria | 0.4539 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8233 |
CYP450 2D6 Substrate | Non-substrate | 0.8064 |
CYP450 3A4 Substrate | Non-substrate | 0.7535 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8579 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9120 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9426 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.8916 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9593 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9374 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9762 |
Non-inhibitor | 0.9541 | |
AMES Toxicity | Non AMES toxic | 0.9519 |
Carcinogens | Non-carcinogens | 0.9318 |
Fish Toxicity | High FHMT | 0.7617 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.7148 |
Honey Bee Toxicity | Low HBT | 0.5000 |
Biodegradation | Not ready biodegradable | 0.5445 |
Acute Oral Toxicity | III | 0.6531 |
Carcinogenicity (Three-class) | Non-required | 0.6421 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -2.0073 | LogS |
Caco-2 Permeability | 0.7939 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.9929 | LD50, mol/kg |
Fish Toxicity | 1.9787 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.4270 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E... | 0154010 | European Union | 0.1* | 16/08/2016 | |
Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou... | 0251040 | European Union | 0.1* | 16/08/2016 | |
Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L... | 0256080 | European Union | 0.1* | 16/08/2016 | |
Celery leaves (Angelica (leaves and stems), Burnet, Caraway leaves, Coriander leaves, Culantro/false coriander leaves, Dill leaves, Fennel leaves, Fenugreek leaves, Herb of grace/rue, Lovage leaves... | 0256030 | European Union | 0.1* | 16/08/2016 | |
FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.1* | 16/08/2016 | |
Citrus fruits | 0110000 | European Union | 0.1* | 16/08/2016 | |
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.1* | 16/08/2016 | |
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.1* | 16/08/2016 | |
Others (2) | 0154990 | European Union | 0.1* | 16/08/2016 | |
Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.1* | 16/08/2016 | |
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.1* | 16/08/2016 | |
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.1* | 16/08/2016 | |
Others (2) | 0110990 | European Union | 0.1* | 16/08/2016 | |
Tree nuts | 0120000 | European Union | 0.1* | 16/08/2016 | |
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.1* | 16/08/2016 | |
Brazil nuts | 0120020 | European Union | 0.1* | 16/08/2016 | |
Cashew nuts | 0120030 | European Union | 0.1* | 16/08/2016 | |
Chestnuts | 0120040 | European Union | 0.1* | 16/08/2016 | |
Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.1* | 16/08/2016 | |
Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.1* | 16/08/2016 |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Does Low-Protein Diet Influence the Uremic Toxin Serum Levels From the Gut Microbiota in Nondialysis Chronic Kidney Disease Patients? | J Ren Nutr | 2018 May | 29439931 |
CuO and ZnO Nanoparticles Modify Interkingdom Cell Signaling Processes Relevantto Crop Production. | J Agric Food Chem | 2018 Jul 5 | 28481096 |
Carbon nanomaterials alter plant physiology and soil bacterial community composition in a rice-soil-bacterial ecosystem. | Environ Pollut | 2018 Jan | 28947315 |
Impacts of exogenous pollutant bisphenol A on characteristics of soybeans. | Ecotoxicol Environ Saf | 2018 Aug 15 | 29655848 |
Plant architecture, auxin homeostasis and phenol content in Arabidopsis thaliana grown in cadmium- and zinc-enriched media. | J Plant Physiol | 2017 Sep | 28704702 |
Multiple metabolic pathways for metabolism of l-tryptophan in Fusarium graminearum. | Can J Microbiol | 2017 Nov | 28926717 |
Reduced abscisic acid content is responsible for enhanced sucrose accumulation bypotassium nutrition in vegetable soybean seeds. | J Plant Res | 2017 May | 28247062 |
Isolation and evaluation of endophytic Streptomyces endus OsiSh-2 with potential application for biocontrol of rice blast disease. | J Sci Food Agric | 2017 Mar | 27293085 |
Isolation of As-tolerant bacteria and their potentials of reducing As and Cdaccumulation of edible tissues of vegetables in metal(loid)-contaminated soils. | Sci Total Environ | 2017 Feb 1 | 27839757 |
Metabolism-mediated induction of zinc tolerance in Brassica rapa by Burkholderia cepacia CS2-1. | J Microbiol | 2017 Dec | 29214486 |
Indole-3-acetic acid in Fusarium graminearum: Identification of biosynthetic pathways and characterization of physiological effects. | Fungal Biol | 2016 Sep | 27567719 |
Abscisic acid and sucrose regulate tomato and strawberry fruit ripening throughthe abscisic acid-stress-ripening transcription factor. | Plant Biotechnol J | 2016 Oct | 27005823 |
Characterization of plant growth promoting traits of bacterial isolates from the rhizosphere of barley (Hordeum vulgare L.) and tomato (Solanum lycopersicon L.)grown under Fe sufficiency and deficiency. | Plant Physiol Biochem | 2016 Oct | 27295343 |
Anti-neuroinflammatory activities of indole alkaloids from kanjang (Korean fermented soy source) in lipopolysaccharide-induced BV2 microglial cells. | Food Chem | 2016 Dec 15 | 27451156 |
Transcriptome Analysis of Cadmium-Treated Roots in Maize (Zea mays L.). | Front Plant Sci | 2016 | 27630647 |
The contribution of endophytic bacteria to Albizia lebbeck-mediatedphytoremediation of tannery effluent contaminated soil. | Int J Phytoremediation | 2016 | 26147743 |
Isolation of Pantoea ananatis from sugarcane and characterization of its potential for plant growth promotion. | Genet Mol Res | 2015 Nov 30 | 26634494 |
Response difference of transgenic and conventional rice (Oryza sativa) tonanoparticles (γFe₂O₃). | Environ Sci Pollut Res Int | 2015 Nov | 26154040 |
Detection and characterization of broad-spectrum antipathogen activity of novelrhizobacterial isolates and suppression of Fusarium crown and root rot disease oftomato. | J Appl Microbiol | 2015 Mar | 25512025 |
Root architecture and morphometric analysis of Arabidopsis thaliana grown in Cd/Cu/Zn-gradient agar dishes: A new screening technique for studying plant response to metals. | Plant Physiol Biochem | 2015 Jun | 25839424 |