Record Information
Version1.0
Creation date2010-04-08 22:09:22 UTC
Update date2019-11-26 03:04:18 UTC
Primary IDFDB010921
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). 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.
CAS Number2519-61-1
Structure
Thumb
Synonyms
SynonymSource
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
(4-chloro-1H-indol-3-yl)acetic acidbiospider
1H-Indole-3-acetic acid, 4-chloro-biospider
4-chloro-1H-Indole-3-acetateGenerator
4-Chloro-IAAbiospider
4-chloroindolyl-3-acetic acidbiospider
4-Cl-Iaabiospider
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H8ClNO2
IUPAC name2-(4-chloro-1H-indol-3-yl)acetic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)CC1=CNC2=C1C(Cl)=CC=C2
Average Molecular Weight209.629
Monoisotopic Molecular Weight209.024356212
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.30%; H 3.85%; Cl 16.91%; N 6.68%; O 15.26%DFC
Melting PointMp 179-180°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1900000000-3922803bd06d2468d32aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-044l-9820000000-7728d95ae08fd2588ef4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0960000000-168499bd4020d259da9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-77a8bd835dc1059aea6aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0iki-0900000000-ca0bc348782168f55e7aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-0590000000-a56d2dc53b14f9a0fde1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-0960000000-ddd2eb9f7541cc7be4bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-2900000000-4a31f8dad8052191d458JSpectraViewer
ChemSpider ID90727
ChEMBL IDCHEMBL309993
KEGG Compound IDNot Available
Pubchem Compound ID100413
Pubchem Substance IDNot Available
ChEBI ID20339
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32936
CRC / DFC (Dictionary of Food Compounds) IDFVS94-I:FVS94-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000102
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.