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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:45 UTC

Update Date

2023-02-21 17:22:49 UTC

HMDB ID

HMDB0032936

Secondary Accession Numbers

HMDB32936

Metabolite Identification

Common 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv0541 02241219272D          

 14 15  0  0  0  0            999 V2000
   -0.5355    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955   -0.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380    1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955    1.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355    1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2880    1.4433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7830    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2880    0.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605   -0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9380   -0.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955   -0.8659    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6080   -1.6084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1  9  1  0  0  0  0
  2  3  2  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032936

> <DATABASE_NAME>
hmdb

> <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_KEY>
WNCFBCKZRJDRKZ-UHFFFAOYSA-N

> <FORMULA>
C10H8ClNO2

> <MOLECULAR_WEIGHT>
209.629

> <EXACT_MASS>
209.024356212

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.922565451006136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.3138007746666664

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.858821121357352

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.144646700106181

> <JCHEM_POLAR_SURFACE_AREA>
53.09

> <JCHEM_REFRACTIVITY>
53.25690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-chloroindole-3-acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.000   0.692   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.232  -0.076   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.618   0.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.618   2.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.232   3.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.000   2.232   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.538   2.694   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.462   1.462   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.538   0.232   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.000  -1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.540  -1.462   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.618  -0.384   0.000  0.00  0.00           O+0
HETATM   13 Cl   UNK     0      -2.232  -1.616   0.000  0.00  0.00          Cl+0
HETATM   14  O   UNK     0       3.002  -3.002   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11                                                            
CONECT   13    2                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Chloroindolyl-3-acetic acid	ChEBI
4-CL-IAA	ChEBI
4-Chloroindolyl-3-acetate	Generator
4-Chloro-1H-indole-3-acetate	Generator
4-Chloroindole-3-acetate	MeSH
(4-chloro-1H-indol-3-yl)Acetic acid	HMDB
4-chloro-IAA	HMDB
4-Chloroindole-3-acetic acid	HMDB
4-Chloro-1H-indole-3-acetic acid	ChEBI

Chemical Formula

C₁₀H₈ClNO₂

Average Molecular Weight

209.629

Monoisotopic Molecular Weight

209.024356212

IUPAC Name

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

Traditional Name

4-chloroindole-3-acetic acid

CAS Registry Number

2519-61-1

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 Key

WNCFBCKZRJDRKZ-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.

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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032936)
Cytoplasm (HMDB: HMDB0032936)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032936)

Source

Exogenous

Exogenous (HMDB: HMDB0032936)

Food

Food (HMDB: HMDB0032936)

Pulse

Lentil

Lentils (FooDB: FOOD00098)

Pea

Common pea (FooDB: FOOD00141)
Grass pea (FooDB: FOOD00096)

Bean

Broad bean (FooDB: FOOD00197)

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Fabaceae (HMDB: HMDB0032936)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032936)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	179 - 180 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1456 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	137.324	30932474
DeepCCS	[M-H]-	134.777	30932474
DeepCCS	[M-2H]-	170.606	30932474
DeepCCS	[M+Na]+	146.144	30932474
AllCCS	[M+H]+	142.8	32859911
AllCCS	[M+H-H2O]+	138.6	32859911
AllCCS	[M+NH4]+	146.7	32859911
AllCCS	[M+Na]+	147.8	32859911
AllCCS	[M-H]-	140.3	32859911
AllCCS	[M+Na-2H]-	140.5	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Chloro-1H-indole-3-acetic acid	OC(=O)CC1=CNC2=C1C(Cl)=CC=C2	3010.2	Standard polar	33892256
4-Chloro-1H-indole-3-acetic acid	OC(=O)CC1=CNC2=C1C(Cl)=CC=C2	1861.2	Standard non polar	33892256
4-Chloro-1H-indole-3-acetic acid	OC(=O)CC1=CNC2=C1C(Cl)=CC=C2	2132.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Chloro-1H-indole-3-acetic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=C[NH]C2=CC=CC(Cl)=C12	2097.7	Semi standard non polar	33892256
4-Chloro-1H-indole-3-acetic acid,1TMS,isomer #2	C[Si](C)(C)N1C=C(CC(=O)O)C2=C(Cl)C=CC=C21	2138.5	Semi standard non polar	33892256
4-Chloro-1H-indole-3-acetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12	2126.4	Semi standard non polar	33892256
4-Chloro-1H-indole-3-acetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC(Cl)=C12	2055.0	Standard non polar	33892256
4-Chloro-1H-indole-3-acetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=C[NH]C2=CC=CC(Cl)=C12	2361.6	Semi standard non polar	33892256
4-Chloro-1H-indole-3-acetic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CC(=O)O)C2=C(Cl)C=CC=C21	2382.5	Semi standard non polar	33892256
4-Chloro-1H-indole-3-acetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12	2585.1	Semi standard non polar	33892256
4-Chloro-1H-indole-3-acetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(Cl)=C12	2478.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Chloro-1H-indole-3-acetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-1900000000-3922803bd06d2468d32a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Chloro-1H-indole-3-acetic acid GC-MS (1 TMS) - 70eV, Positive	splash10-044l-9820000000-7728d95ae08fd2588ef4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Chloro-1H-indole-3-acetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 10V, Positive-QTOF	splash10-03dl-0960000000-168499bd4020d259da9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 20V, Positive-QTOF	splash10-03di-0900000000-77a8bd835dc1059aea6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 40V, Positive-QTOF	splash10-0iki-0900000000-ca0bc348782168f55e7a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 10V, Negative-QTOF	splash10-0bt9-0590000000-a56d2dc53b14f9a0fde1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 20V, Negative-QTOF	splash10-0bt9-0960000000-ddd2eb9f7541cc7be4bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 40V, Negative-QTOF	splash10-06tf-2900000000-4a31f8dad8052191d458	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 10V, Positive-QTOF	splash10-03di-0390000000-41ac911cd3a259411637	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 20V, Positive-QTOF	splash10-03di-0890000000-9eb02ddbf1db8c55f80d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 40V, Positive-QTOF	splash10-03di-0900000000-91cf71df32929b2aeb22	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 10V, Negative-QTOF	splash10-03dl-0910000000-0185da37ee5f7812414b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 20V, Negative-QTOF	splash10-001i-9400000000-9d44442fbf8681f35afa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-1H-indole-3-acetic acid 40V, Negative-QTOF	splash10-03e9-3900000000-8bad02e39d3466d9776a	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010921

KNApSAcK ID

C00000102

Chemspider ID

90727

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100413

PDB ID

Not Available

ChEBI ID

20339

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1832521

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Chloro-1H-indole-3-acetic acid (HMDB0032936)

MOL for HMDB0032936 (4-Chloro-1H-indole-3-acetic acid)

3D MOL for HMDB0032936 (4-Chloro-1H-indole-3-acetic acid)

3D SDF for HMDB0032936 (4-Chloro-1H-indole-3-acetic acid)

3D-SDF for HMDB0032936 (4-Chloro-1H-indole-3-acetic acid)

PDB for HMDB0032936 (4-Chloro-1H-indole-3-acetic acid)

3D PDB for HMDB0032936 (4-Chloro-1H-indole-3-acetic acid)

SMILES for HMDB0032936 (4-Chloro-1H-indole-3-acetic acid)

INCHI for HMDB0032936 (4-Chloro-1H-indole-3-acetic acid)

Structure for HMDB0032936 (4-Chloro-1H-indole-3-acetic acid)

3D Structure for HMDB0032936 (4-Chloro-1H-indole-3-acetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra