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Showing metabocard for Isobutyric acid (HMDB0001873)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-23 12:29:19 UTC
Update Date2023-02-21 17:15:53 UTC
HMDB IDHMDB0001873
Secondary Accession Numbers
  • HMDB0003151
  • HMDB01873
  • HMDB03151
Metabolite Identification
Common NameIsobutyric acid
DescriptionIsobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell. Small amount of isobutyrate is generated via microbial (gut) metabolism. Small amounts may also be found in certain foods or fermented beverages. There is anosmia (genetic inability to smell) for the odor of isobutyric acid with a frequency of about 2.5%. (OMIM 207000 ). Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents. Isobutyric acid can affect people if breathed in and may be absorbed through the skin. Contact can irritate and burn the skin and eyes. Breathing Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath.
Structure
Data?1676999753
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001873 (Isobutyric acid)


  Mrv1652303262019152D          

  6  5  0  0  0  0            999 V2000
   -4.4864    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2008    0.4464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4864    1.6839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719   -0.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
Download

3D MOL for HMDB0001873 (Isobutyric acid)

HMDB0001873
     RDKit          3D
Isobutyric acid
 14 13  0  0  0  0  0  0  0  0999 V2000
   -0.2790    1.2326    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441    0.2385   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217   -0.8103   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -0.3754   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8922   -0.2231   -1.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190   -1.1073    0.5413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.7974    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733    2.1877    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    1.3541    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    0.7661   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -1.0172    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -1.7558   -0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793   -0.3619   -0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -0.9254    0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
M  END
Download

3D SDF for HMDB0001873 (Isobutyric acid)


  Mrv1652303262019152D          

  6  5  0  0  0  0            999 V2000
   -4.4864    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2008    0.4464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4864    1.6839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719   -0.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001873

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)

> <INCHI_KEY>
KQNPFQTWMSNSAP-UHFFFAOYSA-N

> <FORMULA>
C4H8O2

> <MOLECULAR_WEIGHT>
88.1051

> <EXACT_MASS>
88.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.116588155592677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpropanoic acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
1.020176411

> <ALOGPS_LOGS>
0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.866878196732949

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
21.845100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isobutyric acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0001873 (Isobutyric acid)

HMDB0001873
     RDKit          3D
Isobutyric acid
 14 13  0  0  0  0  0  0  0  0999 V2000
   -0.2790    1.2326    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441    0.2385   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217   -0.8103   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -0.3754   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8922   -0.2231   -1.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190   -1.1073    0.5413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.7974    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733    2.1877    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    1.3541    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    0.7661   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -1.0172    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -1.7558   -0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793   -0.3619   -0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -0.9254    0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
M  END
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PDB for HMDB0001873 (Isobutyric acid)

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0      -8.375   1.603   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.708   0.833   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -8.375   3.143   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -7.041   0.833   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.041  -0.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.707   1.603   0.000  0.00  0.00           C+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0001873 (Isobutyric acid)

COMPND    HMDB0001873
HETATM    1  C1  UNL     1      -0.279   1.233   0.663  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.144   0.239  -0.467  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.222  -0.810  -0.272  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.202  -0.375  -0.516  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.892  -0.223  -1.555  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.719  -1.107   0.541  1.00  0.00           O  
HETATM    7  H1  UNL     1       0.257   0.797   1.536  1.00  0.00           H  
HETATM    8  H2  UNL     1       0.173   2.188   0.354  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.333   1.354   0.897  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.375   0.766  -1.399  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.406  -1.017   0.812  1.00  0.00           H  
HETATM   12  H6  UNL     1      -0.988  -1.756  -0.802  1.00  0.00           H  
HETATM   13  H7  UNL     1      -2.179  -0.362  -0.655  1.00  0.00           H  
HETATM   14  H8  UNL     1       2.683  -0.925   0.861  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4   10
CONECT    3   11   12   13
CONECT    4    5    5    6
CONECT    6   14
END
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SMILES for HMDB0001873 (Isobutyric acid)

CC(C)C(O)=O
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INCHI for HMDB0001873 (Isobutyric acid)

InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,2-Dimethylacetic acidChEBI
2-METHYL-propionIC ACIDChEBI
2-MethylpropanoateChEBI
2-Methylpropanoic acidChEBI
2-MethylpropionsaeureChEBI
alpha-Isobutyric acidChEBI
alpha-Methylpropanoic acidChEBI
alpha-Methylpropionic acidChEBI
Dimethylacetic acidChEBI
Iso-butyric acidChEBI
Iso-C3H7COOHChEBI
IsobutanoateChEBI
Isobutanoic acidChEBI
IsobuttersaeureChEBI
IsobutyrateChEBI
Isopropylformic acidChEBI
2,2-DimethylacetateGenerator
2-METHYL-propionateGenerator
a-IsobutyrateGenerator
a-Isobutyric acidGenerator
alpha-IsobutyrateGenerator
Α-isobutyrateGenerator
Α-isobutyric acidGenerator
a-MethylpropanoateGenerator
a-Methylpropanoic acidGenerator
alpha-MethylpropanoateGenerator
Α-methylpropanoateGenerator
Α-methylpropanoic acidGenerator
a-MethylpropionateGenerator
a-Methylpropionic acidGenerator
alpha-MethylpropionateGenerator
Α-methylpropionateGenerator
Α-methylpropionic acidGenerator
DimethylacetateGenerator
Iso-butyrateGenerator
IsopropylformateGenerator
2-MethylpropionateHMDB
2-Methylpropionic acidHMDB
I-butyrateHMDB
I-butyric acidHMDB
Ammonium isobutyrateHMDB
Isobutyric acid, ammonium saltHMDB
Isobutyric acid, sodium saltHMDB
2-Methpropanoic acidHMDB
Isobutyric acid, hemiammoniateHMDB
Sodium isobutyrateHMDB
Isobutyric acid, calcium saltHMDB
Isobutyric acid, nickel saltHMDB
Isobutyric acid, potassium saltHMDB
Isobutyric acid, sodium salt, 11C-labeledHMDB
Isobutyric acid, sodium salt, 14C-labeledHMDB
Isobutyric acidKEGG
Chemical FormulaC4H8O2
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
IUPAC Name2-methylpropanoic acid
Traditional Nameisobutyric acid
CAS Registry Number79-31-2
SMILES
CC(C)C(O)=O
InChI Identifier
InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
InChI KeyKQNPFQTWMSNSAP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • 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
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-46 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility167 mg/mL at 20 °CNot Available
LogP0.94SANGSTER (1993)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility197 g/LALOGPS
logP0.78ALOGPS
logP1.02ChemAxon
logS0.35ALOGPS
pKa (Strongest Acidic)4.87ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.85 m³·mol⁻¹ChemAxon
Polarizability9.12 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]+116.50231661259
DarkChem[M-H]-110.72331661259
AllCCS[M+H]+124.06732859911
AllCCS[M-H]-126.18532859911
DeepCCS[M+H]+129.46830932474
DeepCCS[M-H]-126.67130932474
DeepCCS[M-2H]-163.22930932474
DeepCCS[M+Na]+137.64530932474
AllCCS[M+H]+124.132859911
AllCCS[M+H-H2O]+119.732859911
AllCCS[M+NH4]+128.132859911
AllCCS[M+Na]+129.332859911
AllCCS[M-H]-126.232859911
AllCCS[M+Na-2H]-130.932859911
AllCCS[M+HCOO]-136.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isobutyric acidCC(C)C(O)=O1526.0Standard polar33892256
Isobutyric acidCC(C)C(O)=O719.9Standard non polar33892256
Isobutyric acidCC(C)C(O)=O759.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isobutyric acid,1TMS,isomer #1CC(C)C(=O)O[Si](C)(C)C835.7Semi standard non polar33892256
Isobutyric acid,1TBDMS,isomer #1CC(C)C(=O)O[Si](C)(C)C(C)(C)C1057.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Isobutyric acid EI-B (Non-derivatized)splash10-0006-9000000000-4c977a2f823cde05363a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isobutyric acid EI-B (Non-derivatized)splash10-0006-9000000000-e8e4dc7f7f3f492ec19c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isobutyric acid EI-B (Non-derivatized)splash10-0006-9000000000-4c977a2f823cde05363a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isobutyric acid EI-B (Non-derivatized)splash10-0006-9000000000-e8e4dc7f7f3f492ec19c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-d3c10d617448ce79a5a12016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyric acid GC-MS (1 TMS) - 70eV, Positivesplash10-0076-9100000000-80d574b59e1edc9d75352017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-ce74765d5e47858413632015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00dr-9000000000-67f1d07ca106199c76d32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-d5e7b5664f34e843b6142012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0f79-9200000000-b18c55d6aa937214dca22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-0006-9000000000-688272ebde48c146c6d72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0006-9000000000-f1d1211c63775f704d722012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-000i-9000000000-d5f9008f8738e9ee12062012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-000i-9000000000-3b1bc720943b7b4b9b7b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-000i-9000000000-af791f98a192fc352a652012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-d5f9008f8738e9ee12062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-3b1bc720943b7b4b9b7b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-af791f98a192fc352a652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isobutyric acid 35V, Negative-QTOFsplash10-000i-9000000000-b9f811f5e57b3eeeb8422021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 10V, Positive-QTOFsplash10-000i-9000000000-eabd518990089acf84ca2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 20V, Positive-QTOFsplash10-0006-9000000000-9ec563a3b4f50dc2aaaf2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 40V, Positive-QTOFsplash10-0006-9000000000-eee01af90e21c20eb5842016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 10V, Negative-QTOFsplash10-000i-9000000000-4952a01442de6ea6ecfe2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 20V, Negative-QTOFsplash10-000i-9000000000-23cf7c0a08ac346b6bfe2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 40V, Negative-QTOFsplash10-00rl-9000000000-7ca1184fbf16cfe0b7352016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 10V, Negative-QTOFsplash10-000i-9000000000-4b3590a18d40d4d58a012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 20V, Negative-QTOFsplash10-000i-9000000000-4b3590a18d40d4d58a012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 40V, Negative-QTOFsplash10-000f-9000000000-97afb40e14188e82aee92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 10V, Positive-QTOFsplash10-0006-9000000000-82e9a26713840d90625e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 20V, Positive-QTOFsplash10-0006-9000000000-f007a4a376085ff3e56a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyric acid 40V, Positive-QTOFsplash10-0006-9000000000-17c0b668153fbfe212cb2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart 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
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.3 (0.7-4.4) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.8 (0-3.6) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 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 QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified2200 (700-3800) nmol/g wet fecesAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified1710 +/- 1050 nmol/g wet fecesAdult (>18 years old)Female
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 and Quantified80-2260 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified0-25991.685 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified116.73 +/- 107.44 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SalivaDetected and Quantified885.0 (10.0-1760.0) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.929 +/- 1.157 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified3.9 umol/mmol creatinineAdult (>18 years old)Not Specified
Normal
    • Shaykhutdinov RA,...
 details
UrineDetected and Quantified0.02-1.05 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.06(0.02-0.98) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0.06(0.02-1.07) umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected and Quantified2.82 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
 details
UrineDetected and Quantified15.0 (12.0-27.0) umol/mmol creatinineInfant (0-1 year old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified39.0 (9.0-122.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.5 (1.2-9.0) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified8.4 +/- 1.9 uMAdult (>18 years old)BothHeart Transplant details
BloodDetected and Quantified38.0 (14.0) uMAdult (>18 years old)FemaleDown syndrome pregnancy details
BloodDetected and Quantified35.2 (15.4) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified6.77 +/- 2.5 uMAdult (>18 years old)Female
Pregnancy with fetuses with trisomy 18		 details
BloodDetected and Quantified5.6 +/- 4.7 uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified6.3 (2.1) uMAdult (>18 years old)FemaleEarly preeclampsia details
BloodDetected and Quantified6.3 (2.1) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified4.59 (1.89) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified4.65 (2.06) uMAdult (>18 years old)FemalePregnancy details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 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 QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected and Quantified0-82477.253 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified2.44 +/- 1.584 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Early preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
  2. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ]
  3. Bahado-Singh RO, Akolekar R, Chelliah A, Mandal R, Dong E, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester trisomy 18 detection. Am J Obstet Gynecol. 2013 Jul;209(1):65.e1-9. doi: 10.1016/j.ajog.2013.03.028. Epub 2013 Mar 25. [PubMed:23535240 ]
  4. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
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 ]
Ulcerative colitis
  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 ]
  2. 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 ]
  3. 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 ]
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 ]
Colorectal cancer
  1. Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ]
  2. Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]
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 ]
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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB02531
Phenol Explorer Compound IDNot Available
FooDB IDFDB003277
KNApSAcK IDC00029462
Chemspider ID6341
KEGG Compound IDC02632
BioCyc IDISOBUTYRATE
BiGG IDNot Available
Wikipedia LinkIsobutyric_acid
METLIN ID106
PubChem Compound6590
PDB IDNot Available
ChEBI ID16135
Food Biomarker OntologyNot Available
VMH IDISOBUT
MarkerDB IDMDB00000349
Good Scents IDNot Available
References
Synthesis ReferenceWang, Hengxiu; Chen, Weibin; Zhao, Dehua; Zhang, Jianbin. Preparation of isobutyric acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  2. Hoverstad T, Fausa O, Bjorneklett A, Bohmer T: Short-chain fatty acids in the normal human feces. Scand J Gastroenterol. 1984 May;19(3):375-81. [PubMed:6740214 ]
  3. Mix KS, Coon CI, Rosen ED, Suh N, Sporn MB, Brinckerhoff CE: Peroxisome proliferator-activated receptor-gamma-independent repression of collagenase gene expression by 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid and prostaglandin 15-deoxy-delta(12,14) J2: a role for Smad signaling. Mol Pharmacol. 2004 Feb;65(2):309-18. [PubMed:14742672 ]
  4. Faed EM, McQueen EG: Separation of two conjugates of clofibric acid (CPIB) found in the urine of subjects taking clofibrate. Clin Exp Pharmacol Physiol. 1978 Mar-Apr;5(2):195-8. [PubMed:648038 ]

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
Isobutyric acid → 3,4,5-trihydroxy-6-[(2-methylpropanoyl)oxy]oxane-2-carboxylic aciddetails