Showing metabocard for Isobutyric acid (BMDB0001873)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:48:27 UTC
Update Date2020-06-04 21:13:48 UTC
BMDB IDBMDB0001873
Secondary Accession Numbers
  • BMDB01873
Metabolite Identification
Common NameIsobutyric acid
DescriptionIsobutanoic acid, also known as isobutyrate or 2,2-dimethylacetate, 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. Isobutanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Isobutanoic acid exists in all living species, ranging from bacteria to humans. Isobutanoic acid has been found to be associated with several diseases known as nonalcoholic fatty liver disease, eosinophilic esophagitis, crohn's disease, and early preeclampsia; also isobutanoic acid has been linked to the inborn metabolic disorders including celiac disease.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-46 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility167 mg/mL at 20 °CNot Available
LogP0.94SANGSTER (1993)
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4c977a2f823cde05363aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e8e4dc7f7f3f492ec19cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4c977a2f823cde05363aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e8e4dc7f7f3f492ec19cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-d3c10d617448ce79a5a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0076-9100000000-80d574b59e1edc9d7535View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00dr-9000000000-67f1d07ca106199c76d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-d5e7b5664f34e843b614View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f79-9200000000-b18c55d6aa937214dca2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-688272ebde48c146c6d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-f1d1211c63775f704d72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-d5f9008f8738e9ee1206View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-3b1bc720943b7b4b9b7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-af791f98a192fc352a65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-d5f9008f8738e9ee1206View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-3b1bc720943b7b4b9b7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-af791f98a192fc352a65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-b9f811f5e57b3eeeb842View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-eabd518990089acf84caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-9ec563a3b4f50dc2aaafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-eee01af90e21c20eb584View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4952a01442de6ea6ecfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-23cf7c0a08ac346b6bfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00rl-9000000000-7ca1184fbf16cfe0b735View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4b3590a18d40d4d58a01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-4b3590a18d40d4d58a01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-97afb40e14188e82aee9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-82e9a26713840d90625eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-f007a4a376085ff3e56aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-17c0b668153fbfe212cbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-ce74765d5e4785841363View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Fibroblasts
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified15.87 +/- 20.47 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.3 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.0 +/- 0.4 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.3 +/- 0.2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.2 +/- 0.4 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.10 +/- 4.79 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified14.45 +/- 15.29 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified1420 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified719 +/- 226 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Ruminal FluidDetected and Quantified1100-4100 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified1429.07 +/- 228.2 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified708-1100 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified1283 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified1216 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified1430 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified590 +/- 50 uMNot SpecifiedBothNormal details
Ruminal FluidDetected and Quantified1280 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified1450 +/- 180 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified1670 +/- 530 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified1815 +/- 194 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified1430 +/- 228 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified1450 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified1670 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified1810 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Treated with growth-promoting hormones		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Mycobacterium avium subsp. paratuberculosis infection		 details
Ruminal FluidDetected and Quantified1815.2 +/- 187.74 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
 details
HMDB IDHMDB0001873
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
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)Not Available
General References
  1. Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. [PubMed:25599412 ]
  2. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  3. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.