Bovine Metabolome Database: Showing metabocard for Capric acid (BMDB0000511)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:31:54 UTC

Update Date

2020-06-04 22:42:01 UTC

BMDB ID

BMDB0000511

Secondary Accession Numbers

BMDB00511

Metabolite Identification

Common Name

Capric acid

Description

Capric acid, also known as decanoate or 10:0, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Capric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Capric acid exists in all living species, ranging from bacteria to humans. Capric acid participates in a number of enzymatic reactions, within cattle. In particular, Capric acid can be biosynthesized from trans-dec-2-enoic acid through its interaction with the enzyme fatty acid synthase. enoyl reductase domain. In addition, Capric acid and malonic acid can be converted into 3-oxododecanoic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, capric acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Capric acid is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Nonanecarboxylic acid	ChEBI
10:0	ChEBI
C10:0	ChEBI
Caprinic acid	ChEBI
CH3-[CH2]8-COOH	ChEBI
Decanoate	ChEBI
Decoic acid	ChEBI
Decylic acid	ChEBI
Dekansaeure	ChEBI
Kaprinsaeure	ChEBI
N-Capric acid	ChEBI
N-Decanoic acid	ChEBI
N-Decoic acid	ChEBI
N-Decylic acid	ChEBI
1-Nonanecarboxylate	Generator
Caprinate	Generator
Decanoic acid	Generator
Decoate	Generator
Decylate	Generator
N-Caprate	Generator
N-Decanoate	Generator
N-Decoate	Generator
N-Decylate	Generator
Caprate	Generator
Caprynate	HMDB
Caprynic acid	HMDB
Emery 659	HMDB
Lunac 10-95	HMDB
Lunac 10-98	HMDB
Prifac 2906	HMDB
Prifac 296	HMDB
Decanoic acid, sodium salt	HMDB
Sodium caprate	HMDB
Sodium decanoate	HMDB
FA(10:0)	HMDB

Chemical Formula

C₁₀H₂₀O₂

Average Molecular Weight

172.2646

Monoisotopic Molecular Weight

172.146329884

IUPAC Name

decanoic acid

Traditional Name

capric acid

CAS Registry Number

334-48-5

SMILES

CCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)

InChI Key

GHVNFZFCNZKVNT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
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

medium-chain fatty acid (CHEBI:30813 )
straight-chain saturated fatty acid (CHEBI:30813 )
Straight chain fatty acids (C01571 )
Saturated fatty acids (C01571 )
Straight chain fatty acids (LMFA01010010 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	31.9 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0618 mg/mL	Not Available
LogP	4.09	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	3.93	ALOGPS
logP	3.59	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.95	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	8	ChemAxon
Refractivity	49.48 m³·mol⁻¹	ChemAxon
Polarizability	21.61 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

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Blood
Epidermis
Liver
Milk
Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
Fatty Acid Biosynthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Laura Evans, Stua...	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Milk	Detected and Quantified	10.1 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	20.66 +/- 5.75 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	14.3 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	12.7 +/- 0.2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	11.4 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	2670.31 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	2322.01 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	522.452 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1393.206 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	522.452 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	6269.43 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	5921.12 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	5514.77 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	20 +/- 3 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	19 +/- 6 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	23 +/- 2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	25 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	18.26 +/- 2.36 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 11913692	details
Milk	Detected and Quantified	19.76 +/- 2.58 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	6.87 +/- 0.86 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	5.16 +/- 0.86 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	17.01 +/- 0.05 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 1779072	details
Milk	Detected and Quantified	8127.0136 +/- 3483.00583 uM	Not Specified	Not Specified	Normal	PMID: 16899705	details
Milk	Detected and Quantified	21.885 +/- 0.18 uM	Not Specified	Not Specified	Normal	Catrienus De Jong...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	23.59 +/- 7.41 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	6791.861 +/- 2031.753 uM	Not Specified	Not Specified	Normal	M. Ferrand et al....	details
Milk	Detected and Quantified	6385.511 +/- 1741.503 uM	Not Specified	Not Specified	Normal	M. Ferrand et al....	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Lawrence K. Cream...	details
Milk	Detected and Quantified	19.89 +/- 5.74 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	31347.125 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	37152.148 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	38893.655 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	45279.181 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000511

DrugBank ID

DB03600

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Decanoic acid

METLIN ID

336

PubChem Compound

2969

PDB ID

Not Available

ChEBI ID

30813

References

Synthesis Reference

Wang, Qin; Ni, Xindi; Shi, Jianying. Manufacturing technology of capric acid and hydroxyalkyl amide from Litsea cubeba nucleolus oil. Huaxue Shijie (1993), 34(2), 84-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
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 ]
van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock 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.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities as an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: Q71SP7
Molecular weight:: 274554.0

Reactions

trans-Dec-2-enoic acid → Capric acid	details
Capric acid + Malonic acid → 3-Oxododecanoic acid	details

Enzyme Details

2. G-protein coupled receptor 84

General function:: Involved in G-protein coupled receptor activity
Specific function:: Receptor for medium-chain free fatty acid (FFA) with carbon chain lengths of C9 to C14. Capric acid (C10:0), undecanoic acid (C11:0) and lauric acid (C12:0) are the most potent agonists. Not activated by short-chain and long-chain saturated and unsaturated FFAs. Activation by medium-chain free fatty acid is coupled to a pertussis toxin sensitive G(i/o) protein pathway. May have important roles in processes from fatty acid metabolism to regulation of the immune system (By similarity).
Gene Name:: GPR84
Uniprot ID:: Q2KI97
Molecular weight:: 43517.0

Showing metabocard for Capric acid (BMDB0000511)

Structure for BMDB0000511 (Capric acid)

Enzymes

Reactions