Showing Compound 4-Chloro-1H-indole-3-acetic acid (FDB010921)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:22 UTC

Update date

2019-11-26 03:04:18 UTC

Primary ID

FDB010921

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Chloro-1H-indole-3-acetic acid

Description

4-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 has been detected, but not quantified in, several different foods, such as broad beans (Vicia faba), common peas (Pisum sativum), grass peas (Lathyrus sativus), lentils (Lens culinaris), and pulses. This could make 4-chloro-1H-indole-3-acetic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Chloro-1H-indole-3-acetic acid.

CAS Number

2519-61-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
(4-chloro-1H-indol-3-yl)Acetic acid	HMDB
(4-chloro-1H-indol-3-yl)acetic acid	biospider
1H-Indole-3-acetic acid, 4-chloro-	biospider
4-Chloro-1H-indole-3-acetate	Generator
4-chloro-1H-Indole-3-acetate	Generator
4-Chloro-1H-indole-3-acetic acid	ChEBI
4-chloro-IAA	HMDB
4-Chloro-IAA	biospider
4-Chloroindole-3-acetate	MeSH
4-Chloroindole-3-acetic acid	HMDB

Showing 1 to 10 of 15 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.42 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.31	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.14	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	53.26 m³·mol⁻¹	ChemAxon
Polarizability	19.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H8ClNO2

IUPAC name

2-(4-chloro-1H-indol-3-yl)acetic acid

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 Key

WNCFBCKZRJDRKZ-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CC1=CNC2=C1C(Cl)=CC=C2

Average Molecular Weight

209.629

Monoisotopic Molecular Weight

209.024356212

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.

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

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

chloroindole-3-acetic acid (CHEBI:20339 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Fabaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 57.30%; H 3.85%; Cl 16.91%; N 6.68%; O 15.26%	DFC
Melting Point	Mp 179-180°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	4-Chloro-1H-indole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-1900000000-3922803bd06d2468d32a	Spectrum
Predicted GC-MS	4-Chloro-1H-indole-3-acetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-044l-9820000000-7728d95ae08fd2588ef4	Spectrum
Predicted GC-MS	4-Chloro-1H-indole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0960000000-168499bd4020d259da9c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-77a8bd835dc1059aea6a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0iki-0900000000-ca0bc348782168f55e7a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-0590000000-a56d2dc53b14f9a0fde1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-0960000000-ddd2eb9f7541cc7be4bb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-2900000000-4a31f8dad8052191d458	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0390000000-41ac911cd3a259411637	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0890000000-9eb02ddbf1db8c55f80d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0900000000-91cf71df32929b2aeb22	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dl-0910000000-0185da37ee5f7812414b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9400000000-9d44442fbf8681f35afa	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03e9-3900000000-8bad02e39d3466d9776a	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

90727

ChEMBL ID

CHEMBL309993

KEGG Compound ID

Not Available

Pubchem Compound ID

100413

Pubchem Substance ID

Not Available

ChEBI ID

20339

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB32936

CRC / DFC (Dictionary of Food Compounds) ID

FVS94-I:FVS94-I

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00000102

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound 4-Chloro-1H-indole-3-acetic acid (FDB010921)

Structure for FDB010921 (4-Chloro-1H-indole-3-acetic acid)