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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:45 UTC
Update Date2019-07-23 06:12:08 UTC
HMDB IDHMDB0032936
Secondary Accession Numbers
  • HMDB32936
Metabolite Identification
Common Name4-Chloro-1H-indole-3-acetic acid
Description4-Chloro-1H-indole-3-acetic acid, also known as 4-CL-iaa or 4-chloroindolyl-3-acetate, 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. 4-Chloro-1H-indole-3-acetic acid is a weakly acidic compound (based on its pKa). Outside of the human body, 4-Chloro-1H-indole-3-acetic acid has been detected, but not quantified in, several different foods, such as broad beans, common pea, grass pea, lentils, and pulses. This could make 4-chloro-1H-indole-3-acetic acid a potential biomarker for the consumption of these foods.
Structure
Data?1563862328
Synonyms
ValueSource
4-Chloroindolyl-3-acetic acidChEBI
4-CL-IAAChEBI
4-Chloroindolyl-3-acetateGenerator
4-Chloro-1H-indole-3-acetateGenerator
(4-Chloro-1H-indol-3-yl)acetic acidHMDB
4-Chloro-iaaHMDB
4-Chloroindole-3-acetateHMDB
4-Chloroindole-3-acetic acidHMDB
4-Chloro-1H-indole-3-acetic acidChEBI
Chemical FormulaC10H8ClNO2
Average Molecular Weight209.629
Monoisotopic Molecular Weight209.024356212
IUPAC Name2-(4-chloro-1H-indol-3-yl)acetic acid
Traditional Name4-chloroindole-3-acetic acid
CAS Registry Number2519-61-1
SMILES
OC(=O)CC1=CNC2=C1C(Cl)=CC=C2
InChI Identifier
InChI=1S/C10H8ClNO2/c11-7-2-1-3-8-10(7)6(5-12-8)4-9(13)14/h1-3,5,12H,4H2,(H,13,14)
InChI KeyWNCFBCKZRJDRKZ-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndole-3-acetic acid derivatives
Alternative Parents
Substituents
  • Indole-3-acetic acid derivative
  • 3-alkylindole
  • Indole
  • Aryl chloride
  • Aryl halide
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point179 - 180 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP2.3ALOGPS
logP2.31ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.26 m³·mol⁻¹ChemAxon
Polarizability19.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1900000000-3922803bd06d2468d32aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-044l-9820000000-7728d95ae08fd2588ef4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0960000000-168499bd4020d259da9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-77a8bd835dc1059aea6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0iki-0900000000-ca0bc348782168f55e7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-0590000000-a56d2dc53b14f9a0fde1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-0960000000-ddd2eb9f7541cc7be4bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-2900000000-4a31f8dad8052191d458Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010921
KNApSAcK IDC00000102
Chemspider ID90727
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound100413
PDB IDNot Available
ChEBI ID20339
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .