Livestock Metabolome Database: Showing metabocard for Propionic acid (LMDB00110)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:35 UTC

Update Date

2016-09-23 18:44:43 UTC

Lmdb

LMDB00110

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Propionic acid

Description

Propionic acid (PA) is widely used as an antifungal agent in food. It is present naturally at low levels in dairy products and occurs ubiquitously, together with other short-chain fatty acids (SCFA), in the gastro-intestinal tract of animals and other mammals as an end-product of the microbial digestion of carbohydrates. It has significant physiological activity in animals. PA is irritant but produces no acute systemic effects and has no demonstrable genotoxic potential. (PMID 1628870 ) Propionic aciduria is one of the most frequent organic acidurias, a disease that comprise many various disorders. The outcome of patients born with Propionic aciduria is poor intellectual development patterns, with 60% having an IQ less than 75 and requiring special education. Successful liver and/or renal transplantations, in a few patients, have resulted in better quality of life but have not necessarily prevented neurological and various visceral complications. These results emphasize the need for permanent metabolic follow-up whatever the therapeutic strategy. (PMID 15868474 ) Decreased early mortality, less severe symptoms at diagnosis, and more favorable short-term neurodevelopmental outcome were recorded in patients identified through expanded newborn screening. (PMID 16763906 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acide propanoique	ChEBI
Acide propionique	ChEBI
Carboxyethane	ChEBI
CH3-CH2-COOH	ChEBI
Ethanecarboxylic acid	ChEBI
Ethylformic acid	ChEBI
Metacetonic acid	ChEBI
Methylacetic acid	ChEBI
PA	ChEBI
Propanoic acid	ChEBI
Propioic acid	ChEBI
Propionsaeure	ChEBI
Propoic acid	ChEBI
Pseudoacetic acid	ChEBI
Propionate	Kegg
Ethanecarboxylate	Generator
Ethylformate	Generator
Metacetonate	Generator
Methylacetate	Generator
Propanoate	Generator
Propioate	Generator
Propoate	Generator
Pseudoacetate	Generator
Adofeed	HMDB
Antischim b	HMDB
Luprosil	HMDB
MonoProp	HMDB
Propanate	HMDB
Propcorn	HMDB
Propkorn	HMDB
Prozoin	HMDB
Toxi-check	HMDB
Propionic acid, zinc salt	HMDB
Potassium propionate	HMDB
Chromium propionate	HMDB
Lithium propanoate	HMDB
Zinc propionate	HMDB

Chemical Formula

C₃H₆O₂

Average Molecular Weight

74.0785

Monoisotopic Molecular Weight

74.036779436

IUPAC Name

propanoic acid

Traditional Name

propanoic acid

CAS Registry Number

79-09-4

SMILES

CCC(O)=O

InChI Identifier

InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)

InChI Key

XBDQKXXYIPTUBI-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

saturated fatty acid (CHEBI:30768 )
short-chain fatty acid (CHEBI:30768 )
Straight chain fatty acids (C00163 )
Saturated fatty acids (C00163 )
Straight chain fatty acids (LMFA01010003 )

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	0.31	ALOGPS
logP	0.48	ChemAxon
logS	0.68	ALOGPS
pKa (Strongest Acidic)	4.75	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	17.27 m³·mol⁻¹	ChemAxon
Polarizability	7.24 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)	splash10-004i-9000000000-51f674be972a6c17185b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-691dcd080b30c9898350	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-51f674be972a6c17185b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-691dcd080b30c9898350	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9000000000-abf322c73e6badb078bf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9100000000-cbfe9e32208652e70047	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 (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, Positive (Annotated)	splash10-004i-9000000000-1af60fc458a7f351a9b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-aa6e765fc867ac8be641	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-27e0b790e192d1304449	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-004i-9000000000-51f674be972a6c17185b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-004i-9000000000-90d9e0181596093a2f85	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-bdd7baa3d1bda886fb77	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9000000000-e73379c8765802cf3228	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-d6832c04c8b2ca0fdfa3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-9000000000-d0c93844dbfaed791bb0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-bdd7baa3d1bda886fb77	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-e73379c8765802cf3228	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-d6832c04c8b2ca0fdfa3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-d0c93844dbfaed791bb0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-47364fadf00a5a2b7e93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-76fad523c005a6510264	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-a1c0234da57ff32c6e12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-47364fadf00a5a2b7e93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-76fad523c005a6510264	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-a1c0234da57ff32c6e12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-db59da781a70634d2526	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-9000000000-bea4ff21e6ab6c664412	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-782832f8f5ab85f2ef4f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-db59da781a70634d2526	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-9000000000-bea4ff21e6ab6c664412	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-782832f8f5ab85f2ef4f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00b9-9000000000-0bb3297c4159bed2316e	Spectrum
1D NMR	13C NMR Spectrum	Not Available	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
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D 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
Plasma
Rumen
Ruminal Fluid
Serum
Urine

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
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22673149	details
Rumen	Detected but not Quantified	Not Applicable	Not Available	Bovine	Hanne Christine B...	details
Ruminal Fluid	Detected and Quantified	134000 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Ruminal Fluid	Detected and Quantified	146000-153000 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Ruminal Fluid	Detected and Quantified	156000-162000 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Ruminal Fluid	Detected and Quantified	16,000 +/- 2,000 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	16,860 +/- 5,180 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	16,860 +/- 5,180 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	18,210 +/- 3,210 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	22,630 +/- 8,030 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	31,835 +/- 6,795 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	15000 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	17900 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	18000 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	27600 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	24617926	details
Ruminal Fluid	Detected and Quantified	16800 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	18200 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	15200 +/- 1000 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	22600 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	15800 +/- 900 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	31800 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	15900 +/- 1300 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	12310 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	12770 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	14110 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	14700 +/- 300 uM	Not Available	Caprine	22706048	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	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
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	22059599	details

External Links

DrugBank ID

DB03766

HMDB ID

HMDB0000237

FooDB ID

FDB031132

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Harrison PT: Propionic acid and the phenomenon of rodent forestomach tumorigenesis: a review. Food Chem Toxicol. 1992 Apr;30(4):333-40. [1628870 ]
de Baulny HO, Benoist JF, Rigal O, Touati G, Rabier D, Saudubray JM: Methylmalonic and propionic acidaemias: management and outcome. J Inherit Metab Dis. 2005;28(3):415-23. [15868474 ]
Dionisi-Vici C, Deodato F, Roschinger W, Rhead W, Wilcken B: 'Classical' organic acidurias, propionic aciduria, methylmalonic aciduria and isovaleric aciduria: long-term outcome and effects of expanded newborn screening using tandem mass spectrometry. J Inherit Metab Dis. 2006 Apr-Jun;29(2-3):383-9. [16763906 ]

Showing metabocard for Propionic acid (LMDB00110)

Structure for LMDB00110 (Propionic acid)