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

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 3D-SDF PDB SMILES InChI View 3D Structure

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

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid

Traditional Name

docosahexaenoic acid

CAS Registry Number

6217-54-5

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O

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

Property	Value	Source
logP	6.83	ALOGPS
logP	6.75	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	4.89	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	14	ChemAxon
Refractivity	111.39 m³·mol⁻¹	ChemAxon
Polarizability	38.63 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 - GC-MS (1 TMS)	splash10-004l-9800000000-86f34228f9e92b6da2c6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-9800000000-86f34228f9e92b6da2c6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0690-5590000000-145821d84e425eec8f98	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9363000000-db2668be2bbd1dbdd562	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0190000000-e6566b5aff7cefa4ae5d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0069000000-c76c91e0abd1895adb8b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001r-0069000000-a25e6a700612620a1217	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ab9-9321000000-6b36fbd84ed730000eac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-9642000000-5ecff42b9082b57b5be6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0389000000-737691a3fc2f16b3c59e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-9510000000-8e81381f5f447b18e9fc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-071caf7af6bdab525160	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1669000000-4e72cfd5cc68b32bd371	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1179000000-289993a223b524e7c74f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0019000000-aa9263466508c9f2e65c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-7389000000-4e6afa18acb803f01d23	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-9442000000-c452e1856fb3038c7f1e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1569000000-4e72cfd5cc68b32bd371	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0139000000-7f2351e9d6b367bd3e6d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-3592000000-10365ee2a8e305e24bd4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ktf-8960000000-6382301474f6f5630982	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0019000000-f498ba345a6e0d89ae44	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1069000000-be6f83d34620dceb650e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9130000000-abfb63ab3950fe4edf48	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fr-1439000000-c5fd83b4d4f8531d17e2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-3922000000-a59c9fe862e58a93dd03	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o3-7900000000-c8cfc5620efa939690bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-abcf527af18f1147a0aa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-1119000000-fbe7758a1c75272194e2	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-002f-9400000000-60bd7bfd4de9015476c7	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer

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)