Showing Compound 2-Ethylhydracrylic acid (FDB022014)

Record Information

Version

1.0

Creation date

2011-09-21 00:07:00 UTC

Update date

2015-07-21 06:56:56 UTC

Primary ID

FDB022014

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Ethylhydracrylic acid

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 (PMID 15615815) 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). (PMID: 1016232) [HMDB]

CAS Number

4374-62-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-(Hydroxymethyl)-butyrate	Generator
2-(hydroxymethyl)-Butyrate	hmdb
2-(Hydroxymethyl)-butyric acid	ChEBI
2-(hydroxymethyl)-Butyric acid	hmdb
2-(Hydroxymethyl)butyrate	HMDB
2-(Hydroxymethyl)butyric acid	HMDB
2-Ethyl-3-hydroxypropionate	HMDB
2-Ethyl-3-hydroxypropionic acid	HMDB
2-Ethyl-hydracrylate	HMDB
2-Ethylhydracrylate	Generator

Showing 1 to 10 of 27 entries

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C5H10O3

IUPAC name

2-(hydroxymethyl)butanoic acid

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

Isomeric SMILES

CCC(CO)C(O)=O

Average Molecular Weight

118.1311

Monoisotopic Molecular Weight

118.062994186

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Biofluid and excreta:

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	2-Ethylhydracrylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-9100000000-59a6eea0d0e7113fac3b	Spectrum
Predicted GC-MS	2-Ethylhydracrylic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00ds-9520000000-fe0d3d2aa8e758f26b61	Spectrum
Predicted GC-MS	2-Ethylhydracrylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Ethylhydracrylic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Ethylhydracrylic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Ethylhydracrylic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Ethylhydracrylic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Ethylhydracrylic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d329b2816688175f0721	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-22531cd4192cb58bffc8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-28513bb053ccf9cda074	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-3900000000-f4f29b39d6efac6dea03	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-9500000000-033bb7e1b24d83c3260e	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f9809158ef0031b0966e	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-7900000000-2b7594fdf2745541476d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00rl-9000000000-15a1a560605b3560b3c5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e23602be1497f191e28f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0lk9-8900000000-7d190d86968d376f371f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-d13a71b7a126b5b4db40	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-187afb47dc1fef8de486	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-7900000000-9c57f47a79d94aa41b40	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xs-9000000000-7eb9835e7021f42ca784	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-ebe207f16b68bd130a7c	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

164207

ChEMBL ID

CHEMBL1160011

KEGG Compound ID

Not Available

Pubchem Compound ID

188979

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00396

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 2-Ethylhydracrylic acid (FDB022014)

Structure for FDB022014 (2-Ethylhydracrylic acid)