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Showing metabocard for 2-Ethylhydracrylic acid (HMDB0000396)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:47 UTC
HMDB IDHMDB0000396
Secondary Accession Numbers
  • HMDB0002321
  • HMDB00396
  • HMDB02321
Metabolite Identification
Common 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 ). 2-Ethylhydracrylic acid has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1676999687
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000396 (2-Ethylhydracrylic acid)


  Mrv0541 02231218302D          

  8  7  0  0  0  0            999 V2000
   13.2458   -8.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1037   -8.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3893   -7.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6748   -8.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9603   -8.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6748   -9.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9603  -10.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3893   -8.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
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3D MOL for HMDB0000396 (2-Ethylhydracrylic acid)

HMDB0000396
     RDKit          3D
2-Ethylhydracrylic acid
 18 17  0  0  0  0  0  0  0  0999 V2000
    2.1758   -0.0795    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040   -0.6013   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3187   -0.1737    0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -0.7845   -0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6665   -0.4470   -0.1075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3988    1.3212    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5490    1.9917    1.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073    2.0023   -0.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9725   -0.8565    0.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9198    0.2349    1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5739    0.8022    0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0240   -0.2936   -1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944   -1.7269   -0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068   -0.5429    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -0.4478   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104   -1.8874   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150   -1.2635    0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    2.7522   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
M  END
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3D SDF for HMDB0000396 (2-Ethylhydracrylic acid)


  Mrv0541 02231218302D          

  8  7  0  0  0  0            999 V2000
   13.2458   -8.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1037   -8.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3893   -7.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6748   -8.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9603   -8.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6748   -9.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9603  -10.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3893   -8.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000396

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C5H10O3

> <MOLECULAR_WEIGHT>
118.1311

> <EXACT_MASS>
118.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
11.898270599053731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)butanoic acid

> <ALOGPS_LOGP>
0.03

> <JCHEM_LOGP>
0.18397391933333335

> <ALOGPS_LOGS>
0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.51028800103905

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5138551197178725

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6964607220213894

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
28.2208

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.87e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ethylhydracrylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000396 (2-Ethylhydracrylic acid)

HMDB0000396
     RDKit          3D
2-Ethylhydracrylic acid
 18 17  0  0  0  0  0  0  0  0999 V2000
    2.1758   -0.0795    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040   -0.6013   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3187   -0.1737    0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -0.7845   -0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6665   -0.4470   -0.1075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3988    1.3212    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5490    1.9917    1.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073    2.0023   -0.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9725   -0.8565    0.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9198    0.2349    1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5739    0.8022    0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0240   -0.2936   -1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944   -1.7269   -0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068   -0.5429    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -0.4478   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104   -1.8874   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150   -1.2635    0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    2.7522   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
M  END
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PDB for HMDB0000396 (2-Ethylhydracrylic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      24.725 -16.661   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.060 -16.661   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      28.727 -14.351   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      27.393 -16.661   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.059 -15.891   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.393 -18.201   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.059 -18.971   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.727 -15.891   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4    5    6    8                                                  
CONECT    5    1    4                                                       
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    2    3    4                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0000396 (2-Ethylhydracrylic acid)

COMPND    HMDB0000396
HETATM    1  C1  UNL     1       2.176  -0.079   0.561  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.004  -0.601  -0.214  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.319  -0.174   0.351  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.398  -0.785  -0.547  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.667  -0.447  -0.108  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.399   1.321   0.323  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.549   1.992   1.374  1.00  0.00           O  
HETATM    8  O3  UNL     1      -0.307   2.002  -0.879  1.00  0.00           O  
HETATM    9  H1  UNL     1       2.973  -0.857   0.607  1.00  0.00           H  
HETATM   10  H2  UNL     1       1.920   0.235   1.590  1.00  0.00           H  
HETATM   11  H3  UNL     1       2.574   0.802   0.001  1.00  0.00           H  
HETATM   12  H4  UNL     1       1.024  -0.294  -1.284  1.00  0.00           H  
HETATM   13  H5  UNL     1       0.994  -1.727  -0.243  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.507  -0.543   1.369  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.208  -0.448  -1.575  1.00  0.00           H  
HETATM   16  H8  UNL     1      -1.210  -1.887  -0.514  1.00  0.00           H  
HETATM   17  H9  UNL     1      -3.115  -1.264   0.218  1.00  0.00           H  
HETATM   18  H10 UNL     1      -0.985   2.752  -1.032  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4    6   14
CONECT    4    5   15   16
CONECT    5   17
CONECT    6    7    7    8
CONECT    8   18
END
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SMILES for HMDB0000396 (2-Ethylhydracrylic acid)

CCC(CO)C(O)=O
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INCHI for HMDB0000396 (2-Ethylhydracrylic acid)

InChI=1S/C5H10O3/c1-2-4(3-6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
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
Chemical FormulaC5H10O3
Average Molecular Weight118.1311
Monoisotopic Molecular Weight118.062994186
IUPAC Name2-(hydroxymethyl)butanoic acid
Traditional Name2-ethylhydracrylic acid
CAS Registry Number4374-62-3
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 KeyZMZQVAUJTDKQGE-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.
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.63331661259
DarkChem[M-H]-121.26831661259
AllCCS[M+H]+129.02132859911
AllCCS[M-H]-124.83632859911
DeepCCS[M+H]+135.7530932474
DeepCCS[M-H]-132.98830932474
DeepCCS[M-2H]-169.56330932474
DeepCCS[M+Na]+144.24530932474
AllCCS[M+H]+129.032859911
AllCCS[M+H-H2O]+124.832859911
AllCCS[M+NH4]+133.032859911
AllCCS[M+Na]+134.132859911
AllCCS[M-H]-124.832859911
AllCCS[M+Na-2H]-128.132859911
AllCCS[M+HCOO]-131.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.09 minutes32390414
Predicted by Siyang on May 30, 20229.612 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.48 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid170.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid980.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid330.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid74.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid194.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid68.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid291.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid299.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)187.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid641.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid187.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid896.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid207.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid248.5 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate501.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA263.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water244.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Ethylhydracrylic acidCCC(CO)C(O)=O2224.8Standard polar33892256
2-Ethylhydracrylic acidCCC(CO)C(O)=O1029.3Standard non polar33892256
2-Ethylhydracrylic acidCCC(CO)C(O)=O1088.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Ethylhydracrylic acid,1TMS,isomer #1CCC(CO[Si](C)(C)C)C(=O)O1159.9Semi standard non polar33892256
2-Ethylhydracrylic acid,1TMS,isomer #2CCC(CO)C(=O)O[Si](C)(C)C1105.2Semi standard non polar33892256
2-Ethylhydracrylic acid,2TMS,isomer #1CCC(CO[Si](C)(C)C)C(=O)O[Si](C)(C)C1221.9Semi standard non polar33892256
2-Ethylhydracrylic acid,1TBDMS,isomer #1CCC(CO[Si](C)(C)C(C)(C)C)C(=O)O1381.4Semi standard non polar33892256
2-Ethylhydracrylic acid,1TBDMS,isomer #2CCC(CO)C(=O)O[Si](C)(C)C(C)(C)C1336.5Semi standard non polar33892256
2-Ethylhydracrylic acid,2TBDMS,isomer #1CCC(CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1649.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylhydracrylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-9100000000-59a6eea0d0e7113fac3b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylhydracrylic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-9520000000-fe0d3d2aa8e758f26b612017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylhydracrylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylhydracrylic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylhydracrylic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylhydracrylic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylhydracrylic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylhydracrylic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Ethylhydracrylic acid 40V, Negative-QTOFsplash10-0006-9000000000-d329b2816688175f07212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Ethylhydracrylic acid 10V, Negative-QTOFsplash10-000i-9000000000-22531cd4192cb58bffc82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Ethylhydracrylic acid 20V, Negative-QTOFsplash10-000i-9000000000-28513bb053ccf9cda0742021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 10V, Positive-QTOFsplash10-0uxr-3900000000-f4f29b39d6efac6dea032016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 20V, Positive-QTOFsplash10-0zfr-9500000000-033bb7e1b24d83c3260e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-f9809158ef0031b0966e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 10V, Negative-QTOFsplash10-014i-7900000000-2b7594fdf2745541476d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 20V, Negative-QTOFsplash10-00rl-9000000000-15a1a560605b3560b3c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 40V, Negative-QTOFsplash10-0006-9000000000-e23602be1497f191e28f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 10V, Positive-QTOFsplash10-0lk9-8900000000-7d190d86968d376f371f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 20V, Positive-QTOFsplash10-0ab9-9000000000-d13a71b7a126b5b4db402021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-187afb47dc1fef8de4862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 10V, Negative-QTOFsplash10-014i-7900000000-9c57f47a79d94aa41b402021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 20V, Negative-QTOFsplash10-00xs-9000000000-7eb9835e7021f42ca7842021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylhydracrylic acid 40V, Negative-QTOFsplash10-014l-9000000000-ebe207f16b68bd130a7c2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified3.9 (0.1-14.5) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified4.3 (0.1-6.5) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified4.0 (1.0-13.3) umol/mmol creatinineChildren (1-13 years old)Both
Normal		 details
UrineDetected and Quantified4.6 (1.0-7.3) umol/mmol creatinineChildren (1-13 years old)Both
Normal		 details
UrineDetected and Quantified2.0 (1.2-6.4) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal		 details
UrineDetected and Quantified2.1(1.3-2.9) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified<2 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0-1.914 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified5 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified<2000 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal details
UrineDetected and Quantified0-0.4 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected and Quantified0-0.9 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected and Quantified0-2.2 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected and Quantified0-4.4 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1.914-30.626 umol/mmol creatinineChildren (1-13 years old)Not Specified3-methylglutaconic aciduria type II, X-linked details
UrineDetected and Quantified4-31 umol/mmol creatinineChildren (1-13 years old)Both2-Methylbutyryl-CoA dehydrogenase deficiency (SBACDD) details
UrineDetected and Quantified3700 umol/mmol creatinineChildren (1-13 years old)Male3-Methylglutaconic Aciduria (Type V) details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
3-methylglutaconic aciduria type II, X-linked
  1. Kelley RI, Cheatham JP, Clark BJ, Nigro MA, Powell BR, Sherwood GW, Sladky JT, Swisher WP: X-linked dilated cardiomyopathy with neutropenia, growth retardation, and 3-methylglutaconic aciduria. J Pediatr. 1991 Nov;119(5):738-47. [PubMed:1719174 ]
Short/branched chain acyl-CoA dehydrogenase deficiency
  1. Sass JO, Ensenauer R, Roschinger W, Reich H, Steuerwald U, Schirrmacher O, Engel K, Haberle J, Andresen BS, Megarbane A, Lehnert W, Zschocke J: 2-Methylbutyryl-coenzyme A dehydrogenase deficiency: functional and molecular studies on a defect in isoleucine catabolism. Mol Genet Metab. 2008 Jan;93(1):30-5. doi: 10.1016/j.ymgme.2007.09.002. Epub 2007 Oct 22. [PubMed:17945527 ]
3-Methylglutaconic Aciduria type V
  1. Ojala T, Polinati P, Manninen T, Hiippala A, Rajantie J, Karikoski R, Suomalainen A, Tyni T: New mutation of mitochondrial DNAJC19 causing dilated and noncompaction cardiomyopathy, anemia, ataxia, and male genital anomalies. Pediatr Res. 2012 Oct;72(4):432-7. doi: 10.1038/pr.2012.92. Epub 2012 Jul 13. [PubMed:22797137 ]
Associated OMIM IDs
  • 302060 (3-methylglutaconic aciduria type II, X-linked)
  • 610006 (Short/branched chain acyl-CoA dehydrogenase deficiency)
  • 610198 (3-Methylglutaconic Aciduria type V)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022014
KNApSAcK IDNot Available
Chemspider ID164207
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3785
PubChem Compound188979
PDB IDNot Available
ChEBI ID82956
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000156
Good Scents IDNot Available
References
Synthesis ReferencePrice, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:15615815 ]
  2. 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. [PubMed:8087979 ]
  3. 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. [PubMed:12829005 ]
  4. 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. [PubMed:1016232 ]
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details
1. Sulfotransferase family cytosolic 2B member 1
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
2-Ethylhydracrylic acid → 2-[(sulfooxy)methyl]butanoic aciddetails
Enzyme Details
2. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-Ethylhydracrylic acid → 6-(2-carboxy-2-ethylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-Ethylhydracrylic acid → 3,4,5-trihydroxy-6-{[2-(hydroxymethyl)butanoyl]oxy}oxane-2-carboxylic aciddetails