Bovine Metabolome Database: Showing metabocard for Propionic acid (BMDB0000237)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:11 UTC

Update Date

2020-06-04 22:29:10 UTC

BMDB ID

BMDB0000237

Secondary Accession Numbers

BMDB00237

Metabolite Identification

Common Name

Propionic acid

Description

Propionic acid, also known as propionate or acide propanoique, 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. Propionic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Propionic acid exists in all living species, ranging from bacteria to humans. Propionic acid is a potentially toxic compound. Propionic acid has been found to be associated with several diseases known as rheumatoid arthritis, irritable bowel syndrome, colorectal cancer, and ulcerative colitis; also propionic acid has been linked to the inborn metabolic disorders including propionic acidemia.

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

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-20.7 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000.0 mg/mL	Not Available
LogP	0.33	HANSCH,C ET AL. (1995)

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
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-51f674be972a6c17185b	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-691dcd080b30c9898350	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-51f674be972a6c17185b	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-691dcd080b30c9898350	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9000000000-abf322c73e6badb078bf	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9100000000-cbfe9e32208652e70047	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-9000000000-1af60fc458a7f351a9b0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-aa6e765fc867ac8be641	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-27e0b790e192d1304449	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-004i-9000000000-51f674be972a6c17185b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-004i-9000000000-90d9e0181596093a2f85	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-bdd7baa3d1bda886fb77	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9000000000-e73379c8765802cf3228	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-d6832c04c8b2ca0fdfa3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-9000000000-d0c93844dbfaed791bb0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-bdd7baa3d1bda886fb77	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-e73379c8765802cf3228	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-d6832c04c8b2ca0fdfa3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-d0c93844dbfaed791bb0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-47364fadf00a5a2b7e93	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-76fad523c005a6510264	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-a1c0234da57ff32c6e12	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-47364fadf00a5a2b7e93	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-76fad523c005a6510264	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-a1c0234da57ff32c6e12	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-db59da781a70634d2526	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-9000000000-bea4ff21e6ab6c664412	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-782832f8f5ab85f2ef4f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-db59da781a70634d2526	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-9000000000-bea4ff21e6ab6c664412	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-782832f8f5ab85f2ef4f	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-00b9-9000000000-0bb3297c4159bed2316e	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Adipose Tissue
Blood
Brain
Colostrum
Epidermis
Fibroblasts
Intestine
Milk
Muscle
Neuron
Platelet
Ruminal Fluid
Testis
Urine

Pathways

Name	SMPDB/Pathwhiz	KEGG
Vitamin K Metabolism		Not Available
Propanoate Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25372282	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected and Quantified	1.0 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	1.9 +/- 0.3 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	3 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	2.3 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	2 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	5.71 +/- 7.02 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	2.94 +/- 0.12 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	2.0 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	2.0 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	7.58 +/- 6.92 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	3.84 +/- 2.27 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	0.2 (0.1 - 0.6) uM	Not Specified	Not Specified	Normal	Harper, W. J., Go...	details
Milk	Detected and Quantified	0.2 (0.1 - 0.4) uM	Not Specified	Not Specified	Normal	Harper, W. J., Go...	details
Milk	Detected and Quantified	0.2 (0.1 - 0.5) uM	Not Specified	Not Specified	Normal	Harper, W. J., Go...	details
Milk	Detected and Quantified	0.5 (0.7 - 2.7) uM	Not Specified	Not Specified	Normal	Harper, W. J., Go...	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	16103 +/- 4550 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Ruminal Fluid	Detected and Quantified	1820 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	2260 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	3180 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	1680 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	14000-17000 uM	Not Specified	Not Specified	Normal	PMID: 22706048	details
Ruminal Fluid	Detected and Quantified	13196-21732 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Ruminal Fluid	Detected and Quantified	18210 +/- 3210 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	22630 +/- 8030 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	31835 +/- 6795 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	16860 +/- 5180 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24617926	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Hanne Christine B...	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22706048	details
Ruminal Fluid	Detected and Quantified	17900 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22706048	details
Ruminal Fluid	Detected and Quantified	18000 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22706048	details
Ruminal Fluid	Detected and Quantified	27600 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	15000 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	21340 +/- 2970 uM	Adult	Both	Normal	PMID: 18328751	details
Ruminal Fluid	Detected and Quantified	16855.86 +/- 5180.48 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22059599	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	All Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	High dose Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Low dose Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Commercial Product/bacterial growth on ground beef	PMID: 22417363	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Commercial Product/bacterial growth on ground beef	PMID: 22417363	details
Ruminal Fluid	Detected and Quantified	31831.51 +/- 6577.68 uM	Not Specified	Not Specified	Rumen acidosis	Fozia Saleem, Sou...	details

External Links

HMDB ID

HMDB0000237

DrugBank ID

DB03766

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30768

References

Synthesis Reference

Zhan, Jianghong; Meng, Wei; Gong, Tao; Huang, Fen-sheng. Preparation of propionic acid by propionaldehyde oxidation. Shihua Jishu Yu Yingyong (2005), 23(6), 421-423.

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
Brigitta Gaspardo, Giuseppe Procida, Saša Volarič, Sandy Sgorlon & Bruno Stefanon (2009). Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009. Italian Journal of Animal Science .
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.

Enzymes

Enzyme Details

1. Acyl-CoA synthetase short-chain family member 3, mitochondrial

General function:: Lipid transport and metabolism
Specific function:: Catalyzes the synthesis of acetyl-CoA from short-chain fatty acids (By similarity). Propionate is the preferred substrate but can also utilize acetate and butyrate with a much lower affinity.
Gene Name:: ACSS3
Uniprot ID:: A7MB45
Molecular weight:: 74805.0

Reactions

Propinol adenylate → Propionic acid + Adenosine monophosphate	details

Showing metabocard for Propionic acid (BMDB0000237)

Structure for BMDB0000237 (Propionic acid)

Enzymes

Reactions