Basic Info

Common NameIndoleacetic 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 IDF05239
CAS Number87-51-4
PubChem CID802
FormulaC10H9NO2
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

WikipediaIndoleacetic 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 DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassIndoles and derivatives
SubclassIndolyl carboxylic acids and derivatives
Intermediate Tree NodesNot available
Direct ParentIndole-3-acetic acid derivatives
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsIndole-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
DescriptionThis 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 NameProperty Value
Molecular Weight175.187
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Complexity205
Monoisotopic Mass175.063
Exact Mass175.063
XLogP1.4
Formal Charge0
Heavy Atom Count13
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9852
Human Intestinal AbsorptionHIA+0.9958
Caco-2 PermeabilityCaco2-0.5130
P-glycoprotein SubstrateNon-substrate0.7220
P-glycoprotein InhibitorNon-inhibitor0.9876
Non-inhibitor0.9699
Renal Organic Cation TransporterNon-inhibitor0.8884
Distribution
Subcellular localizationMitochondria0.4539
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8233
CYP450 2D6 SubstrateNon-substrate0.8064
CYP450 3A4 SubstrateNon-substrate0.7535
CYP450 1A2 InhibitorNon-inhibitor0.8579
CYP450 2C9 InhibitorNon-inhibitor0.9120
CYP450 2D6 InhibitorNon-inhibitor0.9426
CYP450 2C19 InhibitorNon-inhibitor0.8916
CYP450 3A4 InhibitorNon-inhibitor0.9593
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9374
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9762
Non-inhibitor0.9541
AMES ToxicityNon AMES toxic0.9519
CarcinogensNon-carcinogens0.9318
Fish ToxicityHigh FHMT0.7617
Tetrahymena Pyriformis ToxicityHigh TPT0.7148
Honey Bee ToxicityLow HBT0.5000
BiodegradationNot ready biodegradable0.5445
Acute Oral ToxicityIII0.6531
Carcinogenicity (Three-class)Non-required0.6421

Model Value Unit
Absorption
Aqueous solubility-2.0073LogS
Caco-2 Permeability0.7939LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9929LD50, mol/kg
Fish Toxicity1.9787pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.4270pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
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...0154010European Union0.1*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...0251040European Union0.1*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...0256080European Union0.1*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...0256030European Union0.1*16/08/2016
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.1*16/08/2016
Citrus fruits0110000European Union0.1*16/08/2016
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.1*16/08/2016
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.1*16/08/2016
Others (2)0154990European Union0.1*16/08/2016
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.1*16/08/2016
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.1*16/08/2016
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.1*16/08/2016
Others (2)0110990European Union0.1*16/08/2016
Tree nuts0120000European Union0.1*16/08/2016
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.1*16/08/2016
Brazil nuts0120020European Union0.1*16/08/2016
Cashew nuts0120030European Union0.1*16/08/2016
Chestnuts0120040European Union0.1*16/08/2016
Coconuts (Areca nuts/betel nuts,)0120050European Union0.1*16/08/2016
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.1*16/08/2016

References

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Reduced abscisic acid content is responsible for enhanced sucrose accumulation bypotassium nutrition in vegetable soybean seeds.J Plant Res2017 May28247062
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Metabolism-mediated induction of zinc tolerance in Brassica rapa by Burkholderia cepacia CS2-1.J Microbiol2017 Dec29214486
Indole-3-acetic acid in Fusarium graminearum: Identification of biosynthetic pathways and characterization of physiological effects.Fungal Biol2016 Sep27567719
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Detection and characterization of broad-spectrum antipathogen activity of novelrhizobacterial isolates and suppression of Fusarium crown and root rot disease oftomato.J Appl Microbiol2015 Mar25512025
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 Biochem2015 Jun25839424