MiMeDB: Showing metabocard for 2-amino-5-chlorophenol (MMDBc0054158)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:56:29 UTC

Update Date

2025-10-07 16:08:23 UTC

Metabolite ID

MMDBc0054158

Metabolite Identification

Common Name

2-amino-5-chlorophenol

Description

2-amino-5-chlorophenol is a chlorinated aromatic amine that belongs to the class of phenolic compounds. Its chemical structure features an amino group and a chlorine substituent on a phenolic ring, which contributes to its reactivity and biological interactions. This compound is involved in several biochemical pathways, particularly in microbial metabolism, where it serves as a carbon source for certain strains, such as strain DL-8, which can transform chlorinated compounds into 2-amino-5-chlorophenol (PMID:27208123 ). Additionally, it is a product of enzymatic reactions catalyzed by toluene dioxygenase, indicating its role in the degradation of chlorinated nitrobenzenes (PMID:24064298 ). The compound is also a substrate for specific dioxygenases, which exhibit a higher affinity for it compared to other similar compounds, highlighting its significance in bioremediation processes (PMID:15580337 ). However, 2-amino-5-chlorophenol is also associated with nephrotoxicity, affecting renal cortical slices in experimental models, although the precise mechanisms of its toxicity remain to be fully elucidated (PMID:10558918 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxy-4-chloroaniline	ChEBI
4-Chloro-2-hydroxyaniline	ChEBI
5-Chloro-2-aminophenol	ChEBI
5-Chloro-O-aminophenol	ChEBI

Molecular Formula

C₆H₆ClNO

Average Mass

143.57

Monoisotopic Mass

143.0137915

IUPAC Name

2-amino-5-chlorophenol

Traditional Name

2-amino-5-chlorophenol

CAS Registry Number

Not Available

SMILES

NC1=C(O)C=C(Cl)C=C1

InChI Identifier

InChI=1S/C6H6ClNO/c7-4-1-2-5(8)6(9)3-4/h1-3,9H,8H2

InChI Key

FZCQMIRJCGWWCL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-chlorophenols. These are chlorophenols carrying a iodine at the C3 position of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Aminophenol
O-aminophenol
Aniline or substituted anilines
3-chlorophenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Amine
Organochloride
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:75051 )
primary amino compound (CHEBI:75051 )
monochlorobenzenes (CHEBI:75051 )
a chloroaromatic compound (CPD-9158 )
an arylamine (CPD-9158 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	12.8 g/L	ALOGPS
logP	1.53	ALOGPS
logP	1.44	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.54	ChemAxon
pKa (Strongest Basic)	3.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	37.54 m³·mol⁻¹	ChemAxon
Polarizability	13.4 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_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-c12e859749e20b000a42	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-c356e05d3d931a46c323	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udj-9100000000-be8a259cb52ef024fee2	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-2dd4027c506591ebdbbd	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-ab7b782fe09f57d097a5	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-7900000000-0304c9bd9a9d6f505e0a	2019-02-23	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	257.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	99.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	358.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	513.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	489.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	523.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1724.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	261.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	659.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	398.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	189.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	395.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	166.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	200.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	496.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	350.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	400.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1005.1
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1199.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	2-amino-5-chlorophenol_TMS_1	C[Si](C)(C)OC1=CC(Cl)=CC=C1N	standard non polar	2025-10-24	1805.35
Gas Chromatography	2-amino-5-chlorophenol_TMS_2	C[Si](C)(C)NC1=CC=C(Cl)C=C1O	standard non polar	2025-10-24	1845.22
Gas Chromatography	2-amino-5-chlorophenol_TMS_3	C[Si](C)(C)NC1=CC=C(Cl)C=C1O[Si](C)(C)C	standard non polar	2025-10-24	1736.79
Gas Chromatography	2-amino-5-chlorophenol_TMS_4	C[Si](C)(C)N(C1=CC=C(Cl)C=C1O)[Si](C)(C)C	standard non polar	2025-10-24	1958.16
Gas Chromatography	2-amino-5-chlorophenol_TMS_5	C[Si](C)(C)OC1=CC(Cl)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1873.21
Gas Chromatography	2-amino-5-chlorophenol_TMS_1	C[Si](C)(C)OC1=CC(Cl)=CC=C1N	standard polar	2025-10-24	1910.89
Gas Chromatography	2-amino-5-chlorophenol_TMS_2	C[Si](C)(C)NC1=CC=C(Cl)C=C1O	standard polar	2025-10-24	2181.54
Gas Chromatography	2-amino-5-chlorophenol_TMS_3	C[Si](C)(C)NC1=CC=C(Cl)C=C1O[Si](C)(C)C	standard polar	2025-10-24	2103.59
Gas Chromatography	2-amino-5-chlorophenol_TMS_4	C[Si](C)(C)N(C1=CC=C(Cl)C=C1O)[Si](C)(C)C	standard polar	2025-10-24	2010.29
Gas Chromatography	2-amino-5-chlorophenol_TMS_5	C[Si](C)(C)OC1=CC(Cl)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1988.9

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 ; Human supragingival plaque

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

Not Available

BioCyc ID

CPD-9158

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91591

PDB ID

Not Available

ChEBI ID

75051

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 2-amino-5-chlorophenol (MMDBc0054158)

MOL for #<Metabolite:0x00005624c9d71600>

3D MOL for #<Metabolite:0x00005624c9d71600>

3D SDF for #<Metabolite:0x00005624c9d71600>

3D-SDF for #<Metabolite:0x00005624c9d71600>

PDB for #<Metabolite:0x00005624c9d71600>

3D PDB for #<Metabolite:0x00005624c9d71600>

SMILES for #<Metabolite:0x00005624c9d71600>

INCHI for #<Metabolite:0x00005624c9d71600>

Structure for #<Metabolite:0x00005624c9d71600>

3D Structure for #<Metabolite:0x00005624c9d71600>