Livestock Metabolome Database: Showing metabocard for Butyric acid (LMDB00013)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:27 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00013

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Butyric acid

Description

Butyric acid, a four-carbon fatty acid, is formed in the animal colon by bacterial fermentation of carbohydrates (including dietary fiber), and putatively suppresses colorectal cancer (CRC). Butyrate has diverse and apparently paradoxical effects on cellular proliferation, apoptosis and differentiation that may be either pro-neoplastic or anti-neoplastic, depending upon factors such as the level of exposure, availability of other metabolic substrate and the intracellular milieu. In animals, the relationship between luminal butyrate exposure and CRC has been examined only indirectly in case-control studies, by measuring fecal butyrate concentrations, although this may not accurately reflect effective butyrate exposure during carcinogenesis. Perhaps not surprisingly, results of these investigations have been mutually contradictory. The direct effect of butyrate on tumorigenesis has been assessed in a no. of in vivo animal models, which have also yielded conflicting results. In part, this may be explained by methodology: differences in the amount and route of butyrate administration, which are likely to significantly influence delivery of butyrate to the distal colon. (PMID: 16460475 ) Butyric acid is a carboxylic acid found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. Interestingly, low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes. As a consequence, they find use as food and perfume additives. Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Butanoic acid	ChEBI
1-Butyric acid	ChEBI
1-Propanecarboxylic acid	ChEBI
4:0	ChEBI
Acide butanoique	ChEBI
Acide butyrique	ChEBI
Butanic acid	ChEBI
Butanoate	ChEBI
Butanoic acid	ChEBI
Butoic acid	ChEBI
Buttersaeure	ChEBI
C4:0	ChEBI
CH3-[CH2]2-COOH	ChEBI
Ethylacetic acid	ChEBI
N-Butanoic acid	ChEBI
N-Butyric acid	ChEBI
Propanecarboxylic acid	ChEBI
Propylformic acid	ChEBI
Butyrate	Kegg
1-Butanoate	Generator
1-Butyrate	Generator
1-Propanecarboxylate	Generator
Butanate	Generator
Butoate	Generator
Ethylacetate	Generator
N-Butanoate	Generator
N-Butyrate	Generator
Propanecarboxylate	Generator
Propylformate	Generator
Honey robber	HMDB
Kyselina maselna	HMDB
Butyrate, magnesium	HMDB
Magnesium butyrate	HMDB
Acid, butyric	HMDB
Butyrate, sodium	HMDB
Dibutyrate, magnesium	HMDB
Magnesium dibutyrate	HMDB
Sodium butyrate	HMDB
Acid, butanoic	HMDB
Butyric acid magnesium salt	HMDB
Butyric acid, sodium salt	HMDB
FA(4:0)	HMDB
Butyric acid	KEGG

Chemical Formula

C₄H₈O₂

Average Molecular Weight

88.1051

Monoisotopic Molecular Weight

88.0524295

IUPAC Name

butanoic acid

Traditional Name

butyric acid

CAS Registry Number

107-92-6

SMILES

CCCC(O)=O

InChI Identifier

InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)

InChI Key

FERIUCNNQQJTOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Straight chain fatty acids

Alternative Parents

Substituents

Straight chain 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 Framework

Aliphatic acyclic compounds

External Descriptors

straight-chain saturated fatty acid (CHEBI:30772 )
short-chain fatty acid (CHEBI:30772 )
Straight chain fatty acids (C00246 )
Saturated fatty acids (C00246 )
Straight chain fatty acids (LMFA01010004 )

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	0.92	ChemAxon
logS	0.43	ALOGPS
pKa (Strongest Acidic)	4.91	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	2	ChemAxon
Refractivity	21.87 m³·mol⁻¹	ChemAxon
Polarizability	9.22 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)	splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-032fc35b394786b5896a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-032fc35b394786b5896a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-a7792b54320e7c859731	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9100000000-d125b331c4a6d37648a1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-7f461db56bfd8568ec71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000i-9000000000-66f857fa612f773837bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000i-9000000000-e6689b2e6bf21570b934	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-03dl-9000000000-b2ffa7d67b2466dea94f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03dl-9000000000-7467bf19c64fd3f51105	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-9ae015043b014b3c93d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-e30b3c6bd6218b9b49e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-efbb0e35a19a1713240b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-9ae015043b014b3c93d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-e30b3c6bd6218b9b49e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-efbb0e35a19a1713240b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-acb5cf0017a9ee680dd8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-812e24462a71dccb0fec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f9d30338ca1ee9409964	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-9d749b6b6cf2f93a8f85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ku-9000000000-ee742730266fb4997777	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-88fc445cddcb726e93d8	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	splash10-014r-9000000000-140190568a3f2b3c6f01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-1f7dab1fbd0179ef6d17	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9000000000-020fcfb652dc5a6f3036	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-3e4b1bc1291a3fbf86c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1f57e9adb6de1499caf5	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-5338ff8a9c4e59150aba	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
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

Colostrum
Feces
Meat
Milk
Plasma
Rumen
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	22417363	details
Feces	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	22417363	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	20855010	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23497994	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23182357	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	14168161	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Ovine	14168161	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	14168161	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Equine	14168161	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Porcine	14168161	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25108860	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Ovine	5829180	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25087032	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Lawrence K. Cream...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Ovine	Park, Y. W; Juáre...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Lawrence K. Cream...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	H. Steinshamn, R....	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	H. Steinshamn, R....	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	H. Steinshamn, R....	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	H. Steinshamn, R....	details
Milk	Detected and Quantified	11.8 mol/100 mol	Not Available	Bovine	1779072	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22675387	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Rumen	Detected but not Quantified	Not Applicable	Not Available	Bovine	Hanne Christine B...	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	24617926	details
Ruminal Fluid	Detected and Quantified	10800 +/- 1100 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	8040 +/- 600 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	9780 +/- 500 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	5350 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	8790 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	10710 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	11600 +/- 1500 uM	Not Available	Caprine	22706048	details
Ruminal Fluid	Detected and Quantified	15,131 +/- 2,957 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	7,400 +/- 800 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	8,100 +/- 1,350 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	8,103 +/- 1,631 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	9,386 +/- 1,367 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	9,386 +/- 1,367 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	8030 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	8100 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	9380 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	15130 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	6420 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	6890 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	7970 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	19300 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	70000 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Ruminal Fluid	Detected and Quantified	70000-81000 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Ruminal Fluid	Detected and Quantified	72000-82000 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Serum	Detected and Quantified	3.0387 +/- 2.9374 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.0791 +/- 8.4071 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.3913 +/- 5.7894 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	17.8696 +/- 14.113 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.6386 +/- 3.9046 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.8981 +/- 6.644 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.0618 +/- 8.6142 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.9805 +/- 3.509 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.0511 +/- 8.6429 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.2601 +/- 9.0284 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.3387 +/- 4.2438 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	19.1873 +/- 12.5917 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	9.5919 +/- 4.8489 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	17.7182 +/- 14.3086 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.7024 +/- 4.4172 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.7413 +/- 5.6497 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.5558 +/- 6.965 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.5011 +/- 8.1624 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	22.1396 +/- 18.0034 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.053 +/- 4.6869 uM	Normal	Ovine	Goldansaz et al.,...	details