MiMeDB: Showing metabocard for 2,4,5-trihydroxyphenylacetic acid (MMDBc0055299)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:48:39 UTC

Update Date

2025-10-07 16:09:03 UTC

Metabolite ID

MMDBc0055299

Metabolite Identification

Common Name

2,4,5-trihydroxyphenylacetic acid

Description

2,4,5-trihydroxyphenylacetic acid is a phenolic compound classified as a metabolite. Its chemical structure features a phenyl ring with three hydroxyl groups located at the 2, 4, and 5 positions, along with an acetic acid side chain. This compound is involved in various biochemical pathways, particularly in the context of redox reactions where it can form a semiquinonic radical, which has been unambiguously attributed to its structure (PMID:27414279 ). The presence of multiple hydroxyl groups enhances its reactivity and potential interactions with biological molecules, suggesting a role in oxidative stress and signaling pathways. As a metabolite, it may also participate in the degradation of phenolic compounds, contributing to the overall metabolic processes in organisms. The understanding of its chemical properties and biological interactions is crucial for elucidating its role in metabolic pathways and potential implications in health and disease.

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    4    6                                                       
CONECT    2    4    8                                                       
CONECT    3    5    7                                                       
CONECT    4    1    2    5                                                  
CONECT    5    3    4    9                                                  
CONECT    6    1    7   10                                                  
CONECT    7    3    6   11                                                  
CONECT    8    2   12   13                                                  
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Synonyms

Value	Source
2,4,5-Trihydroxyphenylacetic acid	Generator

Molecular Formula

C₈H₇O₅

Average Mass

183.14

Monoisotopic Mass

183.029896905

IUPAC Name

2-(carboxymethyl)-4,5-dihydroxybenzen-1-olate

Traditional Name

2-(carboxymethyl)-4,5-dihydroxybenzenolate

CAS Registry Number

Not Available

SMILES

OC(=O)CC1=CC(O)=C(O)C=C1[O-]

InChI Identifier

InChI=1S/C8H8O5/c9-5-3-7(11)6(10)1-4(5)2-8(12)13/h1,3,9-11H,2H2,(H,12,13)/p-1

InChI Key

FKWSAXDBQYTQDO-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-2-unsubstituted benzenoid
Phenoxide
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic anion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	0.7	ChemAxon
pKa (Strongest Acidic)	3.28	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.86 m³·mol⁻¹	ChemAxon
Polarizability	16.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

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	292.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	116.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	233.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	281.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	343.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	304.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	944.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	438.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	643.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	158.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	301.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	165.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	79.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	398.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	551.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	61.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	221.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	945.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	630.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_1	C[Si](C)(C)OC(=O)CC1=CC(O)=C(O)C=C1[O-]	standard non polar	2025-10-24	1952.19
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_2	C[Si](C)(C)OC1=CC(CC(=O)O)=C([O-])C=C1O	standard non polar	2025-10-24	2332.49
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_3	C[Si](C)(C)OC1=CC([O-])=C(CC(=O)O)C=C1O	standard non polar	2025-10-24	1922.8
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_4	C[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C)=C(O)C=C1[O-]	standard non polar	2025-10-24	1790.82
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_5	C[Si](C)(C)OC(=O)CC1=CC(O)=C(O[Si](C)(C)C)C=C1[O-]	standard non polar	2025-10-24	2067.56
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_6	C[Si](C)(C)OC1=CC([O-])=C(CC(=O)O)C=C1O[Si](C)(C)C	standard non polar	2025-10-24	2341.07
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_7	C[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1[O-]	standard non polar	2025-10-24	1754.68
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_1	C[Si](C)(C)OC(=O)CC1=CC(O)=C(O)C=C1[O-]	standard polar	2025-10-24	2181.72
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_2	C[Si](C)(C)OC1=CC(CC(=O)O)=C([O-])C=C1O	standard polar	2025-10-24	2086.72
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_3	C[Si](C)(C)OC1=CC([O-])=C(CC(=O)O)C=C1O	standard polar	2025-10-24	2344.12
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_4	C[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C)=C(O)C=C1[O-]	standard polar	2025-10-24	2230.78
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_5	C[Si](C)(C)OC(=O)CC1=CC(O)=C(O[Si](C)(C)C)C=C1[O-]	standard polar	2025-10-24	1576.52
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_6	C[Si](C)(C)OC1=CC([O-])=C(CC(=O)O)C=C1O[Si](C)(C)C	standard polar	2025-10-24	2427.3
Gas Chromatography	2,4,5-trihydroxyphenylacetic acid_TMS_7	C[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1[O-]	standard polar	2025-10-24	1837.92

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
Eukaryota/Fungi	Ascomycota	1	Human feces

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

76962417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129626790

PDB ID

Not Available

ChEBI ID

138056

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 2,4,5-trihydroxyphenylacetic acid (MMDBc0055299)

MOL for #<Metabolite:0x00007f2e3a499908>

3D MOL for #<Metabolite:0x00007f2e3a499908>

3D SDF for #<Metabolite:0x00007f2e3a499908>

3D-SDF for #<Metabolite:0x00007f2e3a499908>

PDB for #<Metabolite:0x00007f2e3a499908>

3D PDB for #<Metabolite:0x00007f2e3a499908>

SMILES for #<Metabolite:0x00007f2e3a499908>

INCHI for #<Metabolite:0x00007f2e3a499908>

Structure for #<Metabolite:0x00007f2e3a499908>

3D Structure for #<Metabolite:0x00007f2e3a499908>