Livestock Metabolome Database: Showing metabocard for Isobutyric acid (LMDB00357)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:02 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00357

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isobutyric acid

Description

Isobutyric 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,2-Dimethylacetic acid	ChEBI
2-METHYL-propionIC ACID	ChEBI
2-Methylpropanoate	ChEBI
2-Methylpropanoic acid	ChEBI
2-Methylpropionsaeure	ChEBI
alpha-Isobutyric acid	ChEBI
alpha-Methylpropanoic acid	ChEBI
alpha-Methylpropionic acid	ChEBI
Dimethylacetic acid	ChEBI
Iso-butyric acid	ChEBI
Iso-C3H7COOH	ChEBI
Isobutanoate	ChEBI
Isobutanoic acid	ChEBI
Isobuttersaeure	ChEBI
Isobutyrate	ChEBI
Isopropylformic acid	ChEBI
2,2-Dimethylacetate	Generator
2-METHYL-propionate	Generator
a-Isobutyrate	Generator
a-Isobutyric acid	Generator
alpha-Isobutyrate	Generator
Α-isobutyrate	Generator
Α-isobutyric acid	Generator
a-Methylpropanoate	Generator
a-Methylpropanoic acid	Generator
alpha-Methylpropanoate	Generator
Α-methylpropanoate	Generator
Α-methylpropanoic acid	Generator
a-Methylpropionate	Generator
a-Methylpropionic acid	Generator
alpha-Methylpropionate	Generator
Α-methylpropionate	Generator
Α-methylpropionic acid	Generator
Dimethylacetate	Generator
Iso-butyrate	Generator
Isopropylformate	Generator
2-Methylpropionate	HMDB
2-Methylpropionic acid	HMDB
I-butyrate	HMDB
I-butyric acid	HMDB
Ammonium isobutyrate	HMDB
Isobutyric acid, ammonium salt	HMDB
Isobutyric acid, sodium salt	HMDB
2-Methpropanoic acid	HMDB
Isobutyric acid, hemiammoniate	HMDB
Sodium isobutyrate	HMDB
Isobutyric acid, calcium salt	HMDB
Isobutyric acid, nickel salt	HMDB
Isobutyric acid, potassium salt	HMDB
Isobutyric acid, sodium salt, 11C-labeled	HMDB
Isobutyric acid, sodium salt, 14C-labeled	HMDB
Isobutyric acid	KEGG

Chemical Formula

C₄H₈O₂

Average Molecular Weight

88.1051

Monoisotopic Molecular Weight

88.0524295

IUPAC Name

2-methylpropanoic acid

Traditional Name

isobutyric acid

CAS Registry Number

79-31-2

SMILES

CC(C)C(O)=O

InChI Identifier

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

InChI Key

KQNPFQTWMSNSAP-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

branched-chain saturated fatty acid (CHEBI:16135 )
methyl-branched fatty acid (CHEBI:16135 )
short-chain fatty acid (CHEBI:16135 )
Branched fatty acids (LMFA01020071 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.78	ALOGPS
logP	1.02	ChemAxon
logS	0.35	ALOGPS
pKa (Strongest Acidic)	4.87	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	21.85 m³·mol⁻¹	ChemAxon
Polarizability	9.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-4c977a2f823cde05363a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e8e4dc7f7f3f492ec19c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-4c977a2f823cde05363a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e8e4dc7f7f3f492ec19c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-d3c10d617448ce79a5a1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0076-9100000000-80d574b59e1edc9d7535	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00dr-9000000000-67f1d07ca106199c76d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-d5e7b5664f34e843b614	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0f79-9200000000-b18c55d6aa937214dca2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-688272ebde48c146c6d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-f1d1211c63775f704d72	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-d5f9008f8738e9ee1206	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-3b1bc720943b7b4b9b7b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-af791f98a192fc352a65	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-d5f9008f8738e9ee1206	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-3b1bc720943b7b4b9b7b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-af791f98a192fc352a65	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9000000000-b9f811f5e57b3eeeb842	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-eabd518990089acf84ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-9ec563a3b4f50dc2aaaf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-eee01af90e21c20eb584	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4952a01442de6ea6ecfe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-23cf7c0a08ac346b6bfe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00rl-9000000000-7ca1184fbf16cfe0b735	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-97afb40e14188e82aee9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-82e9a26713840d90625e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-f007a4a376085ff3e56a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-17c0b668153fbfe212cb	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-ce74765d5e4785841363	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Plasma
Ruminal Fluid
Serum
Synovial Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23497994	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	22370585	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	21496096	details
Ruminal Fluid	Detected and Quantified	1216 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	1280 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	1283 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	1430 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	1420 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	1450 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	1670 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	1810 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	1,285 +/- 235 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	1,430 +/- 228 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	1,430 +/- 228 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	1,450 +/- 180 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	1,670 +/- 530 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	1,815 +/- 194 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	1320 +/- 200 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	1330 +/- 100 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	3610 +/- 400 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	1480 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	1630 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	1650 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	2260 +/- 300 uM	Not Available	Caprine	22706048	details
Ruminal Fluid	Detected and Quantified	5300 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Ruminal Fluid	Detected and Quantified	4400-6400 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Ruminal Fluid	Detected and Quantified	5500-6500 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Serum	Detected and Quantified	11.624 +/- 2.7566 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	23.8859 +/- 16.0335 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.0395 +/- 3.863 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	20.0066 +/- 8.5248 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.8054 +/- 4.8392 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	20.3948 +/- 14.0144 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.8864 +/- 4.4637 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	15.7323 +/- 8.0367 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	19.7439 +/- 7.621 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	9.21 +/- 3.54 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	12.9663 +/- 5.3542 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.023 +/- 9.4535 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.6897 +/- 7.8012 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.1171 +/- 3.6158 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected and Quantified	27.7467 +/- 14.6532 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	11.9959 +/- 3.2479 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.0123 +/- 3.0299 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	21.6144 +/- 13.0494 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.8933 +/- 5.852 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.0451 +/- 11.2862 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.8583 +/- 9.0948 uM	Normal	Ovine	Goldansaz et al.,...	details
Synovial Fluid	Detected but not Quantified	Not Applicable	Not Available	Ovine	25283885	details