Indolepropionic acid
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Overview
- DrugBank ID
- DB02758
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 1
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
Identification
- Generic Name
- Indolepropionic acid
- DrugBank Accession Number
- DB02758
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 189.2105
Monoisotopic: 189.078978601 - Chemical Formula
- C11H11NO2
- Synonyms
- 1H-Indole-3-propionic acid
- 3-(3-Indole)propionic acid
- 3-(3-Indolyl)propanoic acid
- 3-(3-Indolyl)propionic acid
- 3-(Indol-3-yl)propionic acid
- 3-indolepropionic acid
- beta-Indolylpropionate
- Indole-3-propionic acid
- Indolylpropionic acid
- External IDs
- VP 20629
- VP-20629
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGroup IIE secretory phospholipase A2 Not Available Humans UAspartate aminotransferase Not Available Escherichia coli (strain K12) UAromatic-amino-acid aminotransferase Not Available Paracoccus denitrificans - 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. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- 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 indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Indolyl carboxylic acids and derivatives
- Direct Parent
- Indolyl carboxylic acids and 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
- indol-3-yl carboxylic acid (CHEBI:43580)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- JF49U1Q7KN
- CAS number
- 830-96-6
- InChI Key
- GOLXRNDWAUTYKT-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)
- IUPAC Name
- 3-(1H-indol-3-yl)propanoic acid
- SMILES
- OC(=O)CCC1=CNC2=CC=CC=C12
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0002302
- PubChem Compound
- 3744
- PubChem Substance
- 46507621
- ChemSpider
- 3613
- BindingDB
- 31879
- ChEBI
- 43580
- ChEMBL
- CHEMBL207225
- ZINC
- ZINC000000007700
- PDBe Ligand
- IOP
- Wikipedia
- 3-Indolepropionic_acid
- PDB Entries
- 1ahf / 2ay5 / 2oli / 4ejk / 4ejl / 5o0f / 6f7f / 6fal / 6qmg / 7kh3
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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 0.727 mg/mL ALOGPS logP 2.04 ALOGPS logP 2.15 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 4.8 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 3 Chemaxon Refractivity 53.05 m3·mol-1 Chemaxon Polarizability 20 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 + 0.9934 Blood Brain Barrier + 0.9789 Caco-2 permeable - 0.5427 P-glycoprotein substrate Non-substrate 0.7023 P-glycoprotein inhibitor I Non-inhibitor 0.9863 P-glycoprotein inhibitor II Non-inhibitor 0.9534 Renal organic cation transporter Non-inhibitor 0.8472 CYP450 2C9 substrate Non-substrate 0.8162 CYP450 2D6 substrate Non-substrate 0.8075 CYP450 3A4 substrate Non-substrate 0.7305 CYP450 1A2 substrate Non-inhibitor 0.7261 CYP450 2C9 inhibitor Non-inhibitor 0.8397 CYP450 2D6 inhibitor Non-inhibitor 0.947 CYP450 2C19 inhibitor Non-inhibitor 0.8916 CYP450 3A4 inhibitor Non-inhibitor 0.9402 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9181 Ames test Non AMES toxic 0.9559 Carcinogenicity Non-carcinogens 0.9566 Biodegradation Ready biodegradable 0.5241 Rat acute toxicity 2.0347 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9491 hERG inhibition (predictor II) Non-inhibitor 0.9446
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 146.3877579 predictedDarkChem Lite v0.1.0 [M-H]- 146.6929579 predictedDarkChem Lite v0.1.0 [M-H]- 146.3856579 predictedDarkChem Lite v0.1.0 [M-H]- 134.31526 predictedDeepCCS 1.0 (2019) [M+H]+ 137.8646 predictedDeepCCS 1.0 (2019) [M+Na]+ 147.08914 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsGroup IIE secretory phospholipase A2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Secretory calcium-dependent phospholipase A2 that primarily targets extracellular phospholipids (PubMed:10681567, PubMed:11922621, PubMed:28883454). Hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity), releasing various unsaturated fatty acids including oleoate, linoleoate, arachidonate, docosahexaenoate and lysophosphatidylethanolamines in preference to lysophosphatidylcholines (PubMed:10681567, PubMed:28883454). In response to high-fat diet, hydrolyzes minor lipoprotein phospholipids including phosphatidylserines, phosphatidylinositols and phosphatidylglycerols, altering lipoprotein composition and fat storage in adipose tissue and liver (By similarity). May act in an autocrine and paracrine manner (PubMed:11922621). Contributes to lipid remodeling of cellular membranes and generation of lipid mediators involved in pathogen clearance. Cleaves sn-2 fatty acyl chains of phosphatidylglycerols and phosphatidylethanolamines, which are major components of membrane phospholipids in bacteria (PubMed:11922621). Acts as a hair follicle phospholipase A2. Selectively releases lysophosphatidylethanolamines (LPE) and various unsaturated fatty acids in skin to regulate hair follicle homeostasis (By similarity). May regulate the inflammatory response by releasing arachidonate, a precursor of prostaglandins and leukotrienes (PubMed:11922621). Upon allergen exposure, may participate in allergic inflammatory response by enhancing leukotriene C4 synthesis and degranulation in mast cells (By similarity)
- Specific Function
- calcium ion binding
- 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]
2. DetailsAspartate aminotransferase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- identical protein binding
- Gene Name
- aspC
- Uniprot ID
- P00509
- Uniprot Name
- Aspartate aminotransferase
- Molecular Weight
- 43572.965 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- 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]
3. DetailsAromatic-amino-acid aminotransferase
- Kind
- Protein
- Organism
- Paracoccus denitrificans
- Pharmacological action
- Unknown
- General Function
- Shows activities toward both dicarboxylic and aromatic substrates.
- Specific Function
- identical protein binding
- Gene Name
- tyrB
- Uniprot ID
- P95468
- Uniprot Name
- Aromatic-amino-acid aminotransferase
- Molecular Weight
- 42731.635 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52