Record Information
Version1.0
Creation date2011-09-21 00:07:00 UTC
Update date2015-07-21 06:56:56 UTC
Primary IDFDB022014
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Ethylhydracrylic acid
DescriptionIsolated 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 Number4374-62-3
Structure
Thumb
Synonyms
SynonymSource
2-(Hydroxymethyl)-butyric acidChEBI
3-Hydroxy-2-ethylpropanoic acidChEBI
beta-Hydroxy-alpha-ethylpropionic acidChEBI
2-(Hydroxymethyl)-butyrateGenerator
3-Hydroxy-2-ethylpropanoateGenerator
b-Hydroxy-a-ethylpropionateGenerator
b-Hydroxy-a-ethylpropionic acidGenerator
beta-Hydroxy-alpha-ethylpropionateGenerator
Β-hydroxy-α-ethylpropionateGenerator
Β-hydroxy-α-ethylpropionic acidGenerator
2-EthylhydracrylateGenerator
2-(Hydroxymethyl)butyrateHMDB
2-(Hydroxymethyl)butyric acidHMDB
2-Ethyl-3-hydroxypropionateHMDB
2-Ethyl-3-hydroxypropionic acidHMDB
3-Hydroxy-2-ethylpropionateHMDB
3-Hydroxy-2-ethylpropionic acidHMDB
3-Hydroxy-propionic acid ethyl esterHMDB
2-Ethyl-hydracrylateHMDB
2-Ethylhydracrylic acidMeSH
2-(hydroxymethyl)-Butyratehmdb
2-(hydroxymethyl)-Butyric acidhmdb
3-hydroxy-2-ethylpropanoatehmdb
3-hydroxy-2-ethylpropanoic acidhmdb
3-hydroxy-propionic acid ethyl esterhmdb
β-hydroxy-α-ethylpropionateGenerator
β-hydroxy-α-ethylpropionic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility387 g/LALOGPS
logP0.03ALOGPS
logP0.18ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)4.51ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.22 m³·mol⁻¹ChemAxon
Polarizability11.9 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H10O3
IUPAC name2-(hydroxymethyl)butanoic acid
InChI IdentifierInChI=1S/C5H10O3/c1-2-4(3-6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)
InChI KeyZMZQVAUJTDKQGE-UHFFFAOYSA-N
Isomeric SMILESCCC(CO)C(O)=O
Average Molecular Weight118.1311
Monoisotopic Molecular Weight118.062994186
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-9100000000-59a6eea0d0e7113fac3bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-9520000000-fe0d3d2aa8e758f26b61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-3900000000-f4f29b39d6efac6dea03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-9500000000-033bb7e1b24d83c3260eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-f9809158ef0031b0966eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-7900000000-2b7594fdf2745541476dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00rl-9000000000-15a1a560605b3560b3c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e23602be1497f191e28fView in MoNA
ChemSpider ID164207
ChEMBL IDCHEMBL1160011
KEGG Compound IDNot Available
Pubchem Compound ID188979
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00396
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference