Milk Composition Database: Showing metabocard for Valeric acid (BMDB0000892)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2016-09-30 22:38:10 UTC

Update Date

2020-06-04 21:21:22 UTC

MCDB ID

BMDB0000892

Secondary Accession Numbers

BMDB00892

Metabolite Identification

Common Name

Valeric acid

Description

Pentanoic acid, also known as valerate or N-pentanoate, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Pentanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Pentanoic acid exists in all living species, ranging from bacteria to humans. Pentanoic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Butanecarboxylic acid	ChEBI
CH3-[CH2]3-COOH	ChEBI
N-BuCOOH	ChEBI
N-Pentanoate	ChEBI
N-Pentanoic acid	ChEBI
N-Valeric acid	ChEBI
Pentanoate	ChEBI
Pentanoic acid	ChEBI
Pentoic acid	ChEBI
Propylacetic acid	ChEBI
Valerate	ChEBI
Valerianic acid	ChEBI
Valeriansaeure	ChEBI
Valeric acid, normal	ChEBI
1-Butanecarboxylate	Generator
N-Valerate	Generator
Pentoate	Generator
Propylacetate	Generator
Valerianate	Generator
Valerate, normal	Generator
1-Pentanoate	HMDB
1-Pentanoic acid	HMDB
Butanecarboxylate	HMDB
Butanecarboxylic acid	HMDB
Kyselina valerova	HMDB
N-C4H9COOH	HMDB
Valeriansaure	HMDB
Valeric acid normal	HMDB
N-Pentanoic acid, ammonium salt	HMDB
N-Pentanoic acid, potassium salt	HMDB
N-Pentanoic acid, sodium salt	HMDB
N-Pentanoic acid, zinc salt	HMDB
N-Pentanoic acid, maganese (+2) salt	HMDB
N-Pentanoic acid, 11C-labeled	HMDB
Lithium pentanoate	HMDB
N-Pentanoic acid, 11C-labeled sodium salt	HMDB
Valeric acid	KEGG

Chemical Formula

C₅H₁₀O₂

Average Molecular Weight

102.1317

Monoisotopic Molecular Weight

102.068079564

IUPAC Name

pentanoic acid

Traditional Name

N-valeric acid

CAS Registry Number

109-52-4

SMILES

CCCCC(O)=O

InChI Identifier

InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)

InChI Key

NQPDZGIKBAWPEJ-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:17418 )
short-chain fatty acid (CHEBI:17418 )
Straight chain fatty acids (C00803 )
Saturated fatty acids (C00803 )
Straight chain fatty acids (LMFA01010005 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-34 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	24 mg/mL	Not Available
LogP	1.39	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.34	ALOGPS
logP	1.37	ChemAxon
logS	-0.4	ALOGPS
pKa (Strongest Acidic)	5.01	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	3	ChemAxon
Refractivity	26.47 m³·mol⁻¹	ChemAxon
Polarizability	11.23 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03fr-9000000000-5ef705125c3c70ad3df3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9000000000-2160417549a364f722df	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03fr-9000000000-5ef705125c3c70ad3df3	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9000000000-2160417549a364f722df	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9000000000-317b810c8d610eaf0188	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05dr-9200000000-cfee4e723931c0c4882e	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0kdi-9200000000-68de4edfab1763d25290	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-5807dc032b484168ad7f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-6815adcb2b82e3f1f29f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-03fr-9000000000-5ef705125c3c70ad3df3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03di-9000000000-90144d1440b06340fe7e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-99bad9fba8cf3bc081e3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-95b1b8722cad92c490e7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0udi-2900000000-d6ebac4ebed40b98b291	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0udi-9000000000-94459eb26bcb7c315bcd	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-e212c5cbe08c4eb40b95	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-99bad9fba8cf3bc081e3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-95b1b8722cad92c490e7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-2900000000-d6ebac4ebed40b98b291	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-9000000000-94459eb26bcb7c315bcd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-e212c5cbe08c4eb40b95	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-3900000000-dd2e8ada707700a86c15	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-9700000000-3b6086e299b180404c66	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4u-9100000000-1c4280d0a9143e3d48d0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-bc80b097ba0f51c3ca40	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-a4de42a48fe44ac339fa	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-9800000000-543e60b2b278c1d51c48	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-6b15e313e3ee4ada68aa	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9100000000-e626913b2548db6c8608	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-a5c7e6b5fe910559a628	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-890b839f8e2f9ac3fd83	2021-09-21	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-9246123374d3104316a3	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	9 +/- 2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	4.9 +/- 0.3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	5 +/- 1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	6 +/- 3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	7 +/- 2.84 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	5.44 +/- 2.61 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	7 +/- 3.2 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	0.1 (0 - 0.4) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	0.2 (0.1 - 0.5) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	0.3 (0.1 - 0.6) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	1.5 (0.7 - 2.7) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	1.8 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	4.0 +/- 0.2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	4.18 +/- 0.03 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	4.91 +/- 0.13 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000892

DrugBank ID

DB02406

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Valeric acid

METLIN ID

110

PubChem Compound

7991

PDB ID

Not Available

ChEBI ID

17418

References

Synthesis Reference

Ruiz, Maria Olga; Cabezas, Jose Luis; Escudero, Isabel; Coca, Jose. Valeric acid extraction with tri-n-butyl phosphate impregnated in a macroporous resin: II. Studies in fixed bed columns. Journal of Chemical Technology and Biotechnology (2006), 81(3), 275-281.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
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.

Showing metabocard for Valeric acid (BMDB0000892)

Structure for BMDB0000892 (Valeric acid)