MiMeDB: Showing metabocard for 3-Phenylbutyric acid (MMDBc0048022)

Microbial

Human

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-19 21:49:55 UTC

Update Date

2025-09-17 19:36:31 UTC

Metabolite ID

MMDBc0048022

Metabolite Identification

Common Name

3-Phenylbutyric acid

Description

3-Phenylbutyric acid, also known as 3-phenylbutyrate or (RS)-3-phenylbutanoate, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Adverse effects Nearly 1/4 women may experience an adverse effect of amenorrhea or menstrual dysfunction. Sodium phenylbutyrate can act as a chemical chaperone, stabilising the mutant CFTR in the endoplasmic reticulum and allowing it to reach the cell surface. A 5g tablet or powder of sodium phenylbutyrate taken by mouth can be detected in the blood within 15 minutes, and reaches peak concentration in the bloodstream within an hour.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Phenylbutyrate	Generator
3-Phenylbutiric acid	HMDB
3-Phenylbutirate	HMDB
(RS)-3-Phenylbutanoate	HMDB
(RS)-3-Phenylbutanoic acid	HMDB
3-Phenylbutanoate	HMDB
3-Phenylbutanoic acid	HMDB
b-Methylbenzenepropanoate	HMDB
b-Methylbenzenepropanoic acid	HMDB
b-Methylhydrocinnamate	HMDB
b-Methylhydrocinnamic acid	HMDB
b-Phenyl-N-butyrate	HMDB
b-Phenyl-N-butyric acid	HMDB
b-Phenylbutyrate	HMDB
b-Phenylbutyric acid	HMDB
beta-Methylbenzenepropanoate	HMDB
beta-Methylbenzenepropanoic acid	HMDB
beta-Methylhydrocinnamate	HMDB
beta-Methylhydrocinnamic acid	HMDB
beta-Phenyl-N-butyrate	HMDB
beta-Phenyl-N-butyric acid	HMDB
beta-Phenylbutyrate	HMDB
beta-Phenylbutyric acid	HMDB
3-PB	HMDB
3-Phenylbutyric acid	MeSH

Molecular Formula

C₁₀H₁₂O₂

Average Mass

164.2011

Monoisotopic Mass

164.083729628

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C10H12O2/c1-8(7-10(11)12)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)

InChI Key

ZZEWMYILWXCRHZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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

Membrane

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

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Reference
MMDBr0012786	3-Phenylbutyric acid	Phenylpropanoate	Not Available	omega-oxidation and decarboxylation	7118830
MMDBr0012787	Phenylpropanoate	Phenylacetic acid	Not Available	Alpha-oxidation	7118830
MMDBr0012788	Phenylacetic acid	Benzoic acid	Not Available	Alpha-oxidation	7118830

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Parkinson's disease	increased	Association	Human urine	PubMed	25271123
Anti-microbial		Microbial culture	culture	PubMed	23727774

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	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0001955

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022762

KNApSAcK ID

Not Available

Chemspider ID

19513

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sodium phenylbutyrate

METLIN ID

6399

PubChem Compound

20724

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Landeghem AA, Somers-Pijnenburg YT, Somers WJ, Stokwielder C, de Bruyn W, van den Berg GB: Adsorption of small hydroxy acids on glass: a pitfall in quantitative urinary organic acid analysis by GC-MS. J Inherit Metab Dis. 1999 May;22(3):293-6. doi: 10.1023/a:1005527315019. [PubMed:10384390 ]
Ki KR, Lee J, Ha D, Kim JH: Configurational analysis of chiral acids as O-trifluoroacetylated (-)-menthyl esters by achiral dual-capillary column gas chromatography. J Chromatogr A. 2000 Sep 8;891(2):257-66. doi: 10.1016/s0021-9673(00)00690-7. [PubMed:11043786 ]

Showing metabocard for 3-Phenylbutyric acid (MMDBc0048022)

MOL for #<Metabolite:0x00007f9a9dac36d8>

3D MOL for #<Metabolite:0x00007f9a9dac36d8>

3D SDF for #<Metabolite:0x00007f9a9dac36d8>

3D-SDF for #<Metabolite:0x00007f9a9dac36d8>

PDB for #<Metabolite:0x00007f9a9dac36d8>

3D PDB for #<Metabolite:0x00007f9a9dac36d8>

SMILES for #<Metabolite:0x00007f9a9dac36d8>

INCHI for #<Metabolite:0x00007f9a9dac36d8>

Structure for #<Metabolite:0x00007f9a9dac36d8>

3D Structure for #<Metabolite:0x00007f9a9dac36d8>