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Showing metabocard for Ethylmethylacetic acid (HMDB0002176)

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enzymes (1) Show 1 protein
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:39 UTC
Update Date2023-02-21 17:16:14 UTC
HMDB IDHMDB0002176
Secondary Accession Numbers
  • HMDB02176
Metabolite Identification
Common NameEthylmethylacetic acid
DescriptionEthylmethylacetic acid, also known as alpha-methyl butyric acid or a-methyl butyrate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Ethylmethylacetic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1676999774
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002176 (Ethylmethylacetic acid)


  Mrv1652304272018562D          

  7  6  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
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3D MOL for HMDB0002176 (Ethylmethylacetic acid)

HMDB0002176
     RDKit          3D
Ethylmethylacetic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.7818   -0.6211    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8987    0.5489    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646    0.1752   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1588    1.4535   -0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1892   -0.7934    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666   -0.5540    0.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -2.0300    0.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8698   -0.3950    0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7034   -0.8270    1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5397   -1.5308   -0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4456    1.2751   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978    1.1009    1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1408   -0.2781   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    1.6441   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445    1.3819   -0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6506    2.3330   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381   -2.8832    0.1038 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
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3D SDF for HMDB0002176 (Ethylmethylacetic acid)


  Mrv1652304272018562D          

  7  6  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002176

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)

> <INCHI_KEY>
WLAMNBDJUVNPJU-UHFFFAOYSA-N

> <FORMULA>
C5H10O2

> <MOLECULAR_WEIGHT>
102.1317

> <EXACT_MASS>
102.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
10.98492198543893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylbutanoic acid

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.464745076

> <ALOGPS_LOGS>
-0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.969194504225091

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
26.446099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.72e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-2-methylbutyrate

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0002176 (Ethylmethylacetic acid)

HMDB0002176
     RDKit          3D
Ethylmethylacetic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.7818   -0.6211    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8987    0.5489    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646    0.1752   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1588    1.4535   -0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1892   -0.7934    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666   -0.5540    0.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -2.0300    0.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8698   -0.3950    0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7034   -0.8270    1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5397   -1.5308   -0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4456    1.2751   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978    1.1009    1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1408   -0.2781   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    1.6441   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445    1.3819   -0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6506    2.3330   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381   -2.8832    0.1038 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
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PDB for HMDB0002176 (Ethylmethylacetic acid)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    4                                                       
CONECT    4    2    3    5                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0002176 (Ethylmethylacetic acid)

COMPND    HMDB0002176
HETATM    1  C1  UNL     1       1.782  -0.621   0.515  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.899   0.549   0.232  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.365   0.175  -0.506  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.159   1.453  -0.724  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.189  -0.793   0.261  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.367  -0.554   0.631  1.00  0.00           O  
HETATM    7  O2  UNL     1      -0.654  -2.030   0.597  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.870  -0.395   0.338  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.703  -0.827   1.623  1.00  0.00           H  
HETATM   10  H3  UNL     1       1.540  -1.531  -0.037  1.00  0.00           H  
HETATM   11  H4  UNL     1       1.446   1.275  -0.395  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.598   1.101   1.157  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.141  -0.278  -1.482  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.330   1.644  -1.800  1.00  0.00           H  
HETATM   15  H8  UNL     1      -2.144   1.382  -0.213  1.00  0.00           H  
HETATM   16  H9  UNL     1      -0.651   2.333  -0.301  1.00  0.00           H  
HETATM   17  H10 UNL     1      -0.838  -2.883   0.104  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4    5   13
CONECT    4   14   15   16
CONECT    5    6    6    7
CONECT    7   17
END
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SMILES for HMDB0002176 (Ethylmethylacetic acid)

CCC(C)C(O)=O
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INCHI for HMDB0002176 (Ethylmethylacetic acid)

InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Methybutyric acidChEBI
alpha-Methyl butyric acidChEBI
alpha-Methylbutyric acidChEBI
Butane-2-carboxylic acidChEBI
Methylethylacetic acidChEBI
2-Methylbutyric acidKegg
2-MethybutyrateGenerator
a-Methyl butyrateGenerator
a-Methyl butyric acidGenerator
alpha-Methyl butyrateGenerator
Α-methyl butyrateGenerator
Α-methyl butyric acidGenerator
a-MethylbutyrateGenerator
a-Methylbutyric acidGenerator
alpha-MethylbutyrateGenerator
Α-methylbutyrateGenerator
Α-methylbutyric acidGenerator
Butane-2-carboxylateGenerator
MethylethylacetateGenerator
2-MethylbutyrateGenerator
EthylmethylacetateGenerator
(+/-)-2-methylbutyrateHMDB
(+/-)-2-methylbutyric acidHMDB
2-EthylpropionateHMDB
2-Ethylpropionic acidHMDB
2-Methyl butyrateHMDB
2-Methyl butyric acidHMDB
2-MethylbutanoateHMDB, Generator
2-Methylbutanoic acidHMDB
D-2-Methyl butyrateHMDB
D-2-Methyl butyric acidHMDB
DL-2-Methy butyrateHMDB
DL-2-Methy butyric acidHMDB
DL-2-MethylbutyrateHMDB
DL-2-Methylbutyric acidHMDB
2-Methylbutyrate, (+-)-isomerMeSH, HMDB
2-Methylbutyrate, sodium saltMeSH, HMDB
RS-2-MethylbutyrateMeSH, HMDB
Ethylmethylacetic acidChEBI
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Name2-methylbutanoic acid
Traditional Name(+-)-2-methylbutyrate
CAS Registry Number116-53-0
SMILES
CCC(C)C(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)
InChI KeyWLAMNBDJUVNPJU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
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 Point176.00 to 177.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility45 mg/mL at 20 °CNot Available
LogP1.18HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility57.2 g/LALOGPS
logP1.47ALOGPS
logP1.46ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.45 m³·mol⁻¹ChemAxon
Polarizability10.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+120.6731661259
DarkChem[M-H]-115.54831661259
DeepCCS[M+H]+129.88930932474
DeepCCS[M-H]-127.0930932474
DeepCCS[M-2H]-163.52830932474
DeepCCS[M+Na]+138.12230932474
AllCCS[M+H]+126.332859911
AllCCS[M+H-H2O]+122.032859911
AllCCS[M+NH4]+130.332859911
AllCCS[M+Na]+131.532859911
AllCCS[M-H]-127.032859911
AllCCS[M+Na-2H]-131.032859911
AllCCS[M+HCOO]-135.332859911

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, 2022.2.72 minutes32390414
Predicted by Siyang on May 30, 202211.3424 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.36 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid66.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1391.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid400.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid121.4 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid247.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid91.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid395.9 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 Acid463.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)126.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid805.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid337.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1031.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid266.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid308.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate464.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA346.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water122.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethylmethylacetic acidCCC(C)C(O)=O1615.3Standard polar33892256
Ethylmethylacetic acidCCC(C)C(O)=O829.3Standard non polar33892256
Ethylmethylacetic acidCCC(C)C(O)=O863.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethylmethylacetic acid,1TMS,isomer #1CCC(C)C(=O)O[Si](C)(C)C938.5Semi standard non polar33892256
Ethylmethylacetic acid,1TBDMS,isomer #1CCC(C)C(=O)O[Si](C)(C)C(C)(C)C1154.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethylmethylacetic acid EI-B (Non-derivatized)splash10-05i3-9000000000-0aaa78177c0a6f4e0f302017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethylmethylacetic acid EI-B (Non-derivatized)splash10-05i3-9000000000-0aaa78177c0a6f4e0f302018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethylmethylacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-2909ffab0f5a63851edf2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethylmethylacetic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05dr-9200000000-d03c368f82e8aafbbf2e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethylmethylacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethylmethylacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-05i0-9000000000-5202133990304f535e3e2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethylmethylacetic acid EI-B (HITACHI M-80B) , Positive-QTOFsplash10-05i3-9000000000-1b5a036458bffab2edb22012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 10V, Positive-QTOFsplash10-0udr-9500000000-015593bb5625d47062e02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 20V, Positive-QTOFsplash10-0a4r-9100000000-9cefc93a02ed409afaa72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-4c09f00d4b395429c15f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 10V, Positive-QTOFsplash10-0udr-9500000000-015593bb5625d47062e02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 20V, Positive-QTOFsplash10-0a4r-9100000000-9cefc93a02ed409afaa72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-4c09f00d4b395429c15f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 10V, Negative-QTOFsplash10-0udi-2900000000-91099c4563c2a38048c72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 20V, Negative-QTOFsplash10-0pb9-9500000000-614d914711126947b2cc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-0c48b735fe7cb3bd438f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 10V, Negative-QTOFsplash10-0udi-2900000000-91099c4563c2a38048c72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 20V, Negative-QTOFsplash10-0pb9-9500000000-614d914711126947b2cc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-0c48b735fe7cb3bd438f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 10V, Negative-QTOFsplash10-0udi-0900000000-4c159e60dacc58e6ba982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 20V, Negative-QTOFsplash10-0udi-2900000000-3de63f631f358f44d6632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-49980d35bd5bcf94041b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 10V, Positive-QTOFsplash10-0zg0-9500000000-ebceed22ebf0c3f30cbf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 20V, Positive-QTOFsplash10-0a4i-9000000000-ee8b144eb008ebfb745c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylmethylacetic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-b0c600bc4b289c4f5f6d2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart 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 Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified735.913 +/- 226.276 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified80-2120 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified8.04 +/- 7.66 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
UrineDetected and Quantified0.0097 nmol/mmol creatinineChildren (1-13 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Treated celiac disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  3. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  4. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008135
KNApSAcK IDC00029461
Chemspider ID8012
KEGG Compound IDC18319
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6528
PubChem Compound8314
PDB IDNot Available
ChEBI ID37070
Food Biomarker OntologyNot Available
VMH ID2MBUT
MarkerDB IDNot Available
Good Scents IDrw1056421
References
Synthesis ReferenceBueding, Ernest; Yale, Helen W. Production of a-methylbutyric acid by bacteria-free Ascaris lumbricoides. Journal of Biological Chemistry (1951), 193 411-23.
Material Safety Data Sheet (MSDS)Download (PDF)
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. Schatowitz B, Gercken G: Simultaneous determination of C2-C22 non-esterified fatty acids and other metabolically relevant carboxylic acids in biological material by gas chromatography of their benzyl esters. J Chromatogr. 1988 Mar 18;425(2):257-68. [PubMed:3372640 ]

Enzymes

Enzyme Details
1. 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
Ethylmethylacetic acid → 3,4,5-trihydroxy-6-[(2-methylbutanoyl)oxy]oxane-2-carboxylic aciddetails