MiMeDB: Showing metabocard for Hydroxyphenylacetylglycine (MMDBc0048019)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-19 21:49:50 UTC

Update Date

2025-09-17 19:36:32 UTC

Metabolite ID

MMDBc0048019

Metabolite Identification

Common Name

Hydroxyphenylacetylglycine

Description

Hydroxyphenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Hydroxyphenylacetylglycine is an endogenous human metabolite. It can be originated from the metabolism of tyramine, itself is a monoamine compound derived from the amino acid tyrosine. Hydroxyphenylacetylglycine can also be derived from the metabolism of 3,4-dihydroxyphenylalanine (L-DOPA). In the metabolism of tyrosine, this compound is involved in the reaction Hydroxyphenylacetyl-CoA + Glycine <=> Hydroxyphenylacetylglycine + CoA, catalyzed by acyltransferase enzymes (EC 2.3.1.-). Hydroxyphenylacetylglycine has been identified in human biofluids. (PMID: 14201174 , 912020 , 716472 , 7096501 , 7438429 , 7438430 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
p-Hydroxyphenylacetylglycine	ChEBI
4-Hydroxyphenylacetylglycine	Kegg
N-[(4-Hydroxyphenyl)acetyl]-glycine	HMDB
N-[(p-Hydroxyphenyl)acetyl]-glycine	HMDB
[[(4-Hydroxyphenyl)acetyl]amino]acetate	HMDB
[[(4-Hydroxyphenyl)acetyl]amino]acetic acid	HMDB

Molecular Formula

C₁₀H₁₁NO₄

Average Mass

209.1986

Monoisotopic Mass

209.068807845

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C10H11NO4/c12-8-3-1-7(2-4-8)5-9(13)11-6-10(14)15/h1-4,12H,5-6H2,(H,11,13)(H,14,15)

InChI Key

CPPDWYIPKSSNNM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Phenylacetamide
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:28595 )
monocarboxylic acid amide (CHEBI:28595 )
N-acylglycine (CHEBI:28595 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	<0.0025‚Äì0.0048	umol/mmol creatinine	Adult (25-30 years old)	Both		HMDB	23062437
Human Urine	Detected and Quantified	<0.0025‚Äì0.0079	umol/mmol creatinine	Adult (25-30 years old)	Both		HMDB	23062437
Human Urine	Detected and Quantified	<0.0025‚Äì0.0097	umol/mmol creatinine	Adult (25-30 years old)	Both		HMDB	23062437
Human Urine	Detected but not Quantified			NULL	NULL	Normal	HMDB	21543078
Human Urine	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000735

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022212

KNApSAcK ID

Not Available

Chemspider ID

389604

KEGG Compound ID

C05596

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440732

PDB ID

Not Available

ChEBI ID

28595

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Goodwin BL, Ruthven CR, King GS, Sandler M: Metabolism of 3, 4-dihydroxyphenylalanine, its metabolites and analogues in vivo in the rat: urinary excretion pattern. Xenobiotica. 1978 Oct;8(10):629-51. doi: 10.3109/00498257809069575. [PubMed:716472 ]
Ramsdell HS, Baretz BH, Tanaka K: Mass spectrometric studies of twenty-one metabolically important acylglycines. Biomed Mass Spectrom. 1977 Aug;4(4):220-5. doi: 10.1002/bms.1200040406. [PubMed:912020 ]
Tanaka K, Hine DG: Compilation of gas chromatographic retention indices of 163 metabolically important organic acids, and their use in detection of patients with organic acidurias. J Chromatogr. 1982 Apr 30;239:301-22. doi: 10.1016/s0021-9673(00)81990-1. [PubMed:7096501 ]
Tanaka K, Hine DG, West-Dull A, Lynn TB: Gas-chromatographic method of analysis for urinary organic acids. I. Retention indices of 155 metabolically important compounds. Clin Chem. 1980 Dec;26(13):1839-46. [PubMed:7438429 ]
Tanaka K, West-Dull A, Hine DG, Lynn TB, Lowe T: Gas-chromatographic method of analysis for urinary organic acids. II. Description of the procedure, and its application to diagnosis of patients with organic acidurias. Clin Chem. 1980 Dec;26(13):1847-53. [PubMed:7438430 ]
NAKAJIMA T, SANO I: NEW METABOLITES OF P-TYRAMINE FROM THE URINE OF RATS. Biochim Biophys Acta. 1964 Jul 15;90:37-44. doi: 10.1016/0304-4165(64)90116-3. [PubMed:14201174 ]

Showing metabocard for Hydroxyphenylacetylglycine (MMDBc0048019)

MOL for #<Metabolite:0x00007f8ae8732038>

3D MOL for #<Metabolite:0x00007f8ae8732038>

3D SDF for #<Metabolite:0x00007f8ae8732038>

3D-SDF for #<Metabolite:0x00007f8ae8732038>

PDB for #<Metabolite:0x00007f8ae8732038>

3D PDB for #<Metabolite:0x00007f8ae8732038>

SMILES for #<Metabolite:0x00007f8ae8732038>

INCHI for #<Metabolite:0x00007f8ae8732038>

Structure for #<Metabolite:0x00007f8ae8732038>

3D Structure for #<Metabolite:0x00007f8ae8732038>