ContaminantDB: 2-Ethylhydracrylic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:07:34 UTC

Update Date

2026-04-06 14:06:17 UTC

Accession Number

CHEM003214

Identification

Common Name

2-Ethylhydracrylic acid

Class

Small Molecule

Description

Isolated excretion of 2-Ethylhydracrylic acid (2-methylbutyrylglycine; 2-MBG) is the hallmark of short/branched-chain acyl-CoA dehydrogenase deficiency (SBCADD), a defect in the proximal pathway of L-isoleucine oxidation Normal human urine contains small amounts (less than 4 mg/g of creatinine) of 2-ethylhydracrylic acid. Urinary excretion of 2-ethylhydracrylic acid is variably increased in defects of isoleucine oxidation at distal steps in the catabolic pathway (3-oxoacyl-CoA thiolase deficiency and methylmalonyl-CoA mutase deficiency) and is diminished when proximal steps of the oxidative pathway are blocked as in branched-chain oxo acid decarboxylase deficiency ('maple-syrup-urine' disease). (1, 2).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Animal Toxin
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(Hydroxymethyl)-butyric acid	ChEBI
3-Hydroxy-2-ethylpropanoic acid	ChEBI
beta-Hydroxy-alpha-ethylpropionic acid	ChEBI
2-(Hydroxymethyl)-butyrate	Generator
3-Hydroxy-2-ethylpropanoate	Generator
b-Hydroxy-a-ethylpropionate	Generator
b-Hydroxy-a-ethylpropionic acid	Generator
beta-Hydroxy-alpha-ethylpropionate	Generator
Β-hydroxy-α-ethylpropionate	Generator
Β-hydroxy-α-ethylpropionic acid	Generator
2-Ethylhydracrylate	Generator
2-(Hydroxymethyl)butyrate	HMDB
2-(Hydroxymethyl)butyric acid	HMDB
2-Ethyl-3-hydroxypropionate	HMDB
2-Ethyl-3-hydroxypropionic acid	HMDB
3-Hydroxy-2-ethylpropionate	HMDB
3-Hydroxy-2-ethylpropionic acid	HMDB
3-Hydroxy-propionic acid ethyl ester	HMDB
2-Ethyl-hydracrylate	HMDB
2-Ethylhydracrylic acid	MeSH

Chemical Formula

C₅H₁₀O₃

Average Molecular Mass

118.131 g/mol

Monoisotopic Mass

118.063 g/mol

CAS Registry Number

4374-62-3

IUPAC Name

Not Available

Traditional Name

2-ethylhydracrylic acid

SMILES

CCC(CO)C(O)=O

InChI Identifier

InChI=1S/C5H10O3/c1-2-4(3-6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)

InChI Key

ZMZQVAUJTDKQGE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Hydroxy fatty acid
Branched fatty acid
Beta-hydroxy acid
Hydroxy acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hydroxy fatty acid (CHEBI:82956 )
branched-chain saturated fatty acid (CHEBI:82956 )
short-chain fatty acid (CHEBI:82956 )
Hydroxy fatty acids (LMFA01050388 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency	SMP00137	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	387 g/L	ALOGPS
logP	0.03	ALOGPS
logP	0.18	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	4.51	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.22 m³·mol⁻¹	ChemAxon
Polarizability	11.9 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-9100000000-59a6eea0d0e7113fac3b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00ds-9520000000-fe0d3d2aa8e758f26b61	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d329b2816688175f0721	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-22531cd4192cb58bffc8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-28513bb053ccf9cda074	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-3900000000-f4f29b39d6efac6dea03	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-9500000000-033bb7e1b24d83c3260e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f9809158ef0031b0966e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-7900000000-2b7594fdf2745541476d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00rl-9000000000-15a1a560605b3560b3c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e23602be1497f191e28f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0lk9-8900000000-7d190d86968d376f371f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-d13a71b7a126b5b4db40	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-187afb47dc1fef8de486	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-7900000000-9c57f47a79d94aa41b40	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xs-9000000000-7eb9835e7021f42ca784	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-ebe207f16b68bd130a7c	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000396

FooDB ID

FDB022014

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

3785

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

164207

ChEBI ID

82956

PubChem Compound ID

188979

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Price, Charles C.; Cypher, George A.; Krishnamurti, I. V. Thermal reaction of formaldehyde with allyl cyanide. Journal of the American Chemical Society (1952), 74 2987-91.

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1016232

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15615815

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=4458986

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=759179

5. Price, Charles C.; Cypher, George A.; Krishnamurti, I. V. Thermal reaction of formaldehyde with allyl cyanide. Journal of the American Chemical Society (1952), 74 2987-91.

6. Mamer OA, Tjoa SS, Scriver CR, Klassen GA: Demonstration of a new mammalian isoleucine catabolic pathway yielding an Rseries of metabolites. Biochem J. 1976 Dec 15;160(3):417-26.

7. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6.

8. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30.

9. Korman SH, Andresen BS, Zeharia A, Gutman A, Boneh A, Pitt JJ: 2-ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation. Clin Chem. 2005 Mar;51(3):610-7. Epub 2004 Dec 22.

2-Ethylhydracrylic acid (CHEM003214)

Structure for CHEM003214: 2-Ethylhydracrylic acid