Bovine Metabolome Database: Showing metabocard for Docosahexaenoic acid (BMDB0002183)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:52:14 UTC

Update Date

2020-06-04 21:14:09 UTC

BMDB ID

BMDB0002183

Secondary Accession Numbers

BMDB0063579
BMDB02183
BMDB63579

Metabolite Identification

Common Name

Docosahexaenoic acid

Description

Docosahexaenoic acid, also known as all-cis-dha or doconexent, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Docosahexaenoic acid is a drug which is used as a high-docosahexaenoic acid (dha) oral supplement. . Docosahexaenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, docosahexaenoic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid	ChEBI
22:6(N-3)	ChEBI
22:6-4, 7,10,13,16,19	ChEBI
4,7,10,13,16,19-Docosahexaenoic acid	ChEBI
all-cis-4,7,10,13,16,19-Docosahexaenoic acid	ChEBI
all-cis-DHA	ChEBI
Cervonic acid	ChEBI
DHA	ChEBI
Doconexent	ChEBI
DOCOSA-4,7,10,13,16,19-hexaenoIC ACID	ChEBI
Docosahexaenoate	Kegg
4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoic acid	Kegg
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid	Kegg
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoate	Generator
4,7,10,13,16,19-Docosahexaenoate	Generator
all-cis-4,7,10,13,16,19-Docosahexaenoate	Generator
Cervonate	Generator
DOCOSA-4,7,10,13,16,19-hexaenoate	Generator
4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoate	Generator
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoate	Generator
all-Z-Docosahexaenoate	HMDB
all-Z-Docosahexaenoic acid	HMDB
cis-4,7,10,13,16,19-Docosahexanoate	HMDB
cis-4,7,10,13,16,19-Docosahexanoic acid	HMDB
Doconexento	HMDB
Doconexentum	HMDB
Doxonexent	HMDB
Acids, docosahexaenoic	HMDB
Acids, docosahexenoic	HMDB
Docosahexaenoic acid, 4,7,10,13,16,19-(all-Z-isomer)	HMDB
Docosahexaenoic acid (all-Z isomer)	HMDB
Docosahexaenoic acid, 4,7,10,13,16,19-isomer	HMDB
Efalex	HMDB
(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid	HMDB
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexenoic acid	HMDB
(all-Z)-4,7,10,13,16,19-Docosahexaenoic acid	HMDB
4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-Docosahexaenoic acid	HMDB
FA(22:6(4Z,7Z,10Z,13Z,16Z,19Z))	HMDB
FA(22:6n3)	HMDB
delta4,7,10,13,16,19-Docosahexaenoic acid	HMDB
Δ4,7,10,13,16,19-docosahexaenoic acid	HMDB
Docosahexaenoic acid	HMDB
Choline docosahexaenoate	HMDB
Choline docosahexaenoic acid	HMDB
Docosahexaenoylcholine	HMDB

Chemical Formula

C₂₂H₃₂O₂

Average Molecular Weight

328.4883

Monoisotopic Molecular Weight

328.240230268

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

6217-54-5

SMILES

Not Available

InChI Identifier

InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

InChI Key

MBMBGCFOFBJSGT-KUBAVDMBSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Unsaturated 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

omega-3 fatty acid (CHEBI:28125 )
docosahexaenoic acid (CHEBI:28125 )
Unsaturated fatty acids (C06429 )
Docosanoids (C06429 )
Polyunsaturated fatty acids (C06429 )
Unsaturated fatty acids (LMFA01030185 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Cytoplasm
Membrane
Myelin sheath

Physical Properties

State

Liquid

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

Not Available

Spectra

Spectrum Type	Description	Splash Key

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm
Membrane
Myelin sheath

Biospecimen Locations

Adipose Tissue
Brain
Epidermis
Erythrocyte
Fibroblasts
Intestine
Kidney
Liver
Milk
Neuron
Oocyte
Pancreas
Placenta
Platelet
Prostate Tissue
Retina
Skeletal Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Alpha Linolenic Acid and Linoleic Acid Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Detected and Quantified	20.0616 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	50.0474 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	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
Erythrocyte	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
Kidney	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 but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 11913692	details
Milk	Detected and Quantified	182.655 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	304.425 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	1217.699 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	1826.549 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 18522410	details
Milk	Detected and Quantified	1035.0454 +/- 426.195 uM	Not Specified	Not Specified	Normal	M. Ferrand et al....	details
Milk	Detected and Quantified	882.833 +/- 304.425 uM	Not Specified	Not Specified	Normal	M. Ferrand et al....	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Oocyte	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 10793638	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	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
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Retina	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002183

DrugBank ID

DB03756

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003003

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28125

References

Synthesis Reference

Wright, Stephen W.; Kuo, Elaine Y.; Corey, E. J. An effective process for the isolation of Docosahexaenoic acid in quantity from cod liver oil. Journal of Organic Chemistry (1987), 52(19), 4399-4401.

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
Lopez C, Briard-Bion V, Menard O, Rousseau F, Pradel P, Besle JM: Phospholipid, sphingolipid, and fatty acid compositions of the milk fat globule membrane are modified by diet. J Agric Food Chem. 2008 Jul 9;56(13):5226-36. doi: 10.1021/jf7036104. Epub 2008 Jun 4. [PubMed:18522410 ]
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.
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.

Showing metabocard for Docosahexaenoic acid (BMDB0002183)

Structure for BMDB0002183 (Docosahexaenoic acid)