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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-23 12:29:19 UTC
Update Date2020-11-09 23:16:07 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?1585246595
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial 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)
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 Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available116.50231661259
DarkChem[M-H]-PredictedNot Available110.72331661259
AllCCS[M+H]+PredictedNot Available124.06732859911
AllCCS[M-H]-PredictedNot Available126.18532859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Isobutyric acid,1TMS,#1835.7037https://arxiv.org/abs/1905.12712
Isobutyric acid,1TBDMS,#11057.0016https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4c977a2f823cde05363a2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e8e4dc7f7f3f492ec19c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4c977a2f823cde05363a2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e8e4dc7f7f3f492ec19c2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-d3c10d617448ce79a5a12016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0076-9100000000-80d574b59e1edc9d75352017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-ce74765d5e47858413632015-03-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00dr-9000000000-67f1d07ca106199c76d32012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-d5e7b5664f34e843b6142012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f79-9200000000-b18c55d6aa937214dca22012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-688272ebde48c146c6d72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-f1d1211c63775f704d722012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-d5f9008f8738e9ee12062012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-3b1bc720943b7b4b9b7b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-af791f98a192fc352a652012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-d5f9008f8738e9ee12062017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-3b1bc720943b7b4b9b7b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-af791f98a192fc352a652017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-b9f811f5e57b3eeeb8422021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-eabd518990089acf84ca2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-9ec563a3b4f50dc2aaaf2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-eee01af90e21c20eb5842016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4952a01442de6ea6ecfe2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-23cf7c0a08ac346b6bfe2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00rl-9000000000-7ca1184fbf16cfe0b7352016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4b3590a18d40d4d58a012021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-97afb40e14188e82aee92021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-82e9a26713840d90625e2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-f007a4a376085ff3e56a2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-17c0b668153fbfe212cb2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-4b3590a18d40d4d58a012021-09-09View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)2015-03-12View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View 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
    • Mordechai, Hien, ...
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
    • López Hernández Y...
details
UrineDetected and Quantified0.06(0.02-0.98) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.06(0.02-1.07) umol/mmol creatinineNewborn (0-30 days old)MaleNormal
    • López Hernández Y...
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
    • Mordechai, Hien, ...
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. (). Mordechai, Hien, and David S. Wishart. .
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
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. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]

Enzymes

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