Identification
- Generic Name
- Indoleacetic acid
- DrugBank Accession Number
- DB07950
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Indoleacetic acid (DB07950)
- Weight
- Average: 175.184
Monoisotopic: 175.063328537 - Chemical Formula
- C10H9NO2
- Synonyms
- (Indol-3-yl)acetate
- (indol-3-yl)acetic acid
- 2-(indol-3-yl)ethanoic acid
- 3-Indolylessigsäure
- heteroauxin
- IAA
- IES
- Indole-3-acetic acid
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGroup IIE secretory phospholipase A2 Not Available Humans US-phase kinase-associated protein 1 Not Available Humans UKynurenine--oxoglutarate transaminase 1 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Tryptophan Metabolism Metabolic - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Indolyl carboxylic acids and derivatives
- Direct Parent
- Indole-3-acetic acid derivatives
- Alternative Parents
- 3-alkylindoles / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides show 2 more
- Substituents
- 3-alkylindole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Indole show 10 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- monocarboxylic acid, indole-3-acetic acids (CHEBI:16411) / Indole alkaloids, Auxins (C00954)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 6U1S09C61L
- CAS number
- 87-51-4
- 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)
- IUPAC Name
- 2-(1H-indol-3-yl)acetic acid
- SMILES
- OC(=O)CC1=CNC2=CC=CC=C12
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000197
- KEGG Compound
- C00954
- PubChem Compound
- 802
- PubChem Substance
- 99444421
- ChemSpider
- 780
- BindingDB
- 50201883
- ChEBI
- 16411
- ChEMBL
- CHEMBL82411
- ZINC
- ZINC000000083860
- PDBe Ligand
- IAC
- Wikipedia
- Indole-3-acetic_acid
- PDB Entries
- 2oyf / 2p1p / 2p1q / 3fvu / 3o97 / 3snm / 4hm0 / 4pgp / 5aog / 5iuw … show 20 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.38 mg/mL ALOGPS logP 1.87 ALOGPS logP 1.71 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 4.66 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 53.09 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 48.45 m3·mol-1 Chemaxon Polarizability 17.74 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9958 Blood Brain Barrier + 0.9852 Caco-2 permeable - 0.513 P-glycoprotein substrate Non-substrate 0.722 P-glycoprotein inhibitor I Non-inhibitor 0.9876 P-glycoprotein inhibitor II Non-inhibitor 0.9699 Renal organic cation transporter Non-inhibitor 0.8884 CYP450 2C9 substrate Non-substrate 0.8233 CYP450 2D6 substrate Non-substrate 0.8064 CYP450 3A4 substrate Non-substrate 0.7535 CYP450 1A2 substrate Non-inhibitor 0.8579 CYP450 2C9 inhibitor Non-inhibitor 0.912 CYP450 2D6 inhibitor Non-inhibitor 0.9426 CYP450 2C19 inhibitor Non-inhibitor 0.8916 CYP450 3A4 inhibitor Non-inhibitor 0.9593 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9374 Ames test Non AMES toxic 0.9519 Carcinogenicity Non-carcinogens 0.9318 Biodegradation Not ready biodegradable 0.5445 Rat acute toxicity 1.9929 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9762 hERG inhibition (predictor II) Non-inhibitor 0.9541
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Phospholipase a2 activity
- Specific Function
- PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
- Gene Name
- PLA2G2E
- Uniprot ID
- Q9NZK7
- Uniprot Name
- Group IIE secretory phospholipase A2
- Molecular Weight
- 15988.525 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin-protein transferase activity
- Specific Function
- Essential component of the SCF (SKP1-CUL1-F-box protein) ubiquitin ligase complex, which mediates the ubiquitination of proteins involved in cell cycle progression, signal transduction and transcri...
- Gene Name
- SKP1
- Uniprot ID
- P63208
- Uniprot Name
- S-phase kinase-associated protein 1
- Molecular Weight
- 18657.86 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transaminase activity
- Specific Function
- Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to ...
- Gene Name
- CCBL1
- Uniprot ID
- Q16773
- Uniprot Name
- Kynurenine--oxoglutarate transaminase 1
- Molecular Weight
- 47874.765 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:27 / Updated at May 05, 2022 15:59