MiMeDB: Showing metabocard for 3-chlorocatechol (MMDBc0054219)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:59:40 UTC

Update Date

2025-10-07 16:08:25 UTC

Metabolite ID

MMDBc0054219

Metabolite Identification

Common Name

3-chlorocatechol

Description

3-chlorocatechol is a chlorinated phenolic compound belonging to the chemical class of catechols. Its chemical structure features a benzene ring with two hydroxyl groups and one chlorine substituent, specifically at the 3-position of the catechol moiety. In microbial biochemistry, 3-chlorocatechol plays a crucial role in the degradation pathways of chlorinated aromatic compounds. It is produced from the metabolism of 3-chlorobenzoate, with genes responsible for this conversion located on chromosomes 2 and 1 (PMID:38488372 ). The compound is further processed through the clcABCDE operon, which is integral to the 3-chlorocatechol degradation pathway (PMID:36965871 ). Enzymatic activity involving 3-chlorocatechol includes its conversion into 2-chloromucounate by specific dioxygenases (PMID:35625452 ) and its participation in various oxidation reactions catalyzed by engineered monooxygenases (PMID:35736230 ). Additionally, 3-chlorocatechol has been shown to exhibit significant differences in inactivation across various substrates, highlighting its biochemical versatility (PMID:35906995 ). Overall, 3-chlorocatechol serves as an important intermediate in the microbial breakdown of chlorinated compounds, illustrating its relevance in environmental biochemistry.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Chloropyrocatechol	ChEBI
3-Chlorocatechol	MeSH

Molecular Formula

C₆H₅ClO₂

Average Mass

144.556

Monoisotopic Mass

143.997807111

IUPAC Name

3-chlorobenzene-1,2-diol

Traditional Name

3-chlorocatechol

CAS Registry Number

Not Available

SMILES

OC1=CC=CC(Cl)=C1O

InChI Identifier

InChI=1S/C6H5ClO2/c7-4-2-1-3-5(8)6(4)9/h1-3,8-9H

InChI Key

GQKDZDYQXPOXEM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-chlorocatechols. These are chlorocatechols with the chlorine atom attached at position C3 of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

3-chlorocatechol
3-halophenol
2-halophenol
2-chlorophenol
3-chlorophenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:27715 )
chlorocatechol (CHEBI:27715 )
a chloroaromatic compound (CPD-9151 )
a catechol (CPD-9151 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	26.4 g/L	ALOGPS
logP	1.67	ALOGPS
logP	1.97	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	8.12	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	34.82 m³·mol⁻¹	ChemAxon
Polarizability	12.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-6c131ce9611205ed376b	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-7158ca561a105f6634d3	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-3e5824107e74f17f553d	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-7a157dce7f8ebf6bbfad	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-f9d305eb8f03f21f4e2a	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9700000000-7a8fe9039c5270aeae87	2019-02-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	306.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	81.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	376.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	509.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	503.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	423.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1349.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	301.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	686.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	300.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	286.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	287.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	150.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	227.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	671.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	291.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	359.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1096.7
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	939.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3-chlorocatechol_TMS_1	C[Si](C)(C)OC1=CC=CC(Cl)=C1O	standard non polar	2025-10-24	1999.46
Gas Chromatography	3-chlorocatechol_TMS_2	C[Si](C)(C)OC1=C(O)C=CC=C1Cl	standard non polar	2025-10-24	1926.89
Gas Chromatography	3-chlorocatechol_TMS_3	C[Si](C)(C)OC1=CC=CC(Cl)=C1O[Si](C)(C)C	standard non polar	2025-10-24	1770.12
Gas Chromatography	3-chlorocatechol_TMS_1	C[Si](C)(C)OC1=CC=CC(Cl)=C1O	standard polar	2025-10-24	1782.13
Gas Chromatography	3-chlorocatechol_TMS_2	C[Si](C)(C)OC1=C(O)C=CC=C1Cl	standard polar	2025-10-24	1838.22
Gas Chromatography	3-chlorocatechol_TMS_3	C[Si](C)(C)OC1=CC=CC(Cl)=C1O[Si](C)(C)C	standard polar	2025-10-24	1479.75

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human
Bacteria	Proteobacteria	2	Human

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05618

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

19928

PDB ID

Not Available

ChEBI ID

27715

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 3-chlorocatechol (MMDBc0054219)

MOL for #<Metabolite:0x00007f9ac4c6cb20>

3D MOL for #<Metabolite:0x00007f9ac4c6cb20>

3D SDF for #<Metabolite:0x00007f9ac4c6cb20>

3D-SDF for #<Metabolite:0x00007f9ac4c6cb20>

PDB for #<Metabolite:0x00007f9ac4c6cb20>

3D PDB for #<Metabolite:0x00007f9ac4c6cb20>

SMILES for #<Metabolite:0x00007f9ac4c6cb20>

INCHI for #<Metabolite:0x00007f9ac4c6cb20>

Structure for #<Metabolite:0x00007f9ac4c6cb20>

3D Structure for #<Metabolite:0x00007f9ac4c6cb20>