Livestock Metabolome Database: Showing metabocard for Docosahexaenoic acid (LMDB00382)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:35 UTC

Update Date

2016-09-23 18:45:18 UTC

Lmdb

LMDB00382

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Docosahexaenoic acid

Description

Docosahexaenoic acid (DHA) is an omega-3 essential fatty acid. Chemically, DHA is a carboxylic acid with a 22-carbon chain and six cis double bonds with the first double bond is located at the third carbon from the omega end. DHA is most often found in fish oil. It is a major fatty acid in sperm and brain phospholipids, especially in the retina. Dietary DHA can reduce the level of blood triglycerides in animals, which may reduce the risk of heart disease. (wikipedia).

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

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004l-9800000000-86f34228f9e92b6da2c6	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-9800000000-86f34228f9e92b6da2c6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0690-5590000000-145821d84e425eec8f98	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9363000000-db2668be2bbd1dbdd562	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0190000000-e6566b5aff7cefa4ae5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0069000000-c76c91e0abd1895adb8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001r-0069000000-a25e6a700612620a1217	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ab9-9321000000-6b36fbd84ed730000eac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-9642000000-5ecff42b9082b57b5be6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0389000000-737691a3fc2f16b3c59e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-9510000000-8e81381f5f447b18e9fc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-071caf7af6bdab525160	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1669000000-4e72cfd5cc68b32bd371	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1179000000-289993a223b524e7c74f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0019000000-aa9263466508c9f2e65c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-7389000000-4e6afa18acb803f01d23	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-9442000000-c452e1856fb3038c7f1e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1569000000-4e72cfd5cc68b32bd371	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0139000000-7f2351e9d6b367bd3e6d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-3592000000-10365ee2a8e305e24bd4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ktf-8960000000-6382301474f6f5630982	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0019000000-f498ba345a6e0d89ae44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1069000000-be6f83d34620dceb650e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9130000000-abfb63ab3950fe4edf48	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fr-1439000000-c5fd83b4d4f8531d17e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-3922000000-a59c9fe862e58a93dd03	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o3-7900000000-c8cfc5620efa939690bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-abcf527af18f1147a0aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-1119000000-fbe7758a1c75272194e2	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002f-9400000000-60bd7bfd4de9015476c7	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Follicular Fluid
Milk
Oocyte
Oocyte (zona-intact oocytes)
Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected but not Quantified	Not Applicable	Not Available	Porcine	Warzych, E., Cies...	details
Milk	Detected and Quantified	60 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	100 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	400 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	600 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Oocyte	Detected but not Quantified	Not Applicable	Not Available	Ovine	10793638	details
Oocyte (zona-intact oocytes)	Detected but not Quantified	Not Applicable	Not Available	Bovine	10793638	details
Oocyte (zona-intact oocytes)	Detected but not Quantified	Not Applicable	Not Available	Porcine	10793638	details
Oocyte (zona-intact oocytes)	Detected but not Quantified	Not Applicable	Not Available	Porcine	10793638	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	Sun Ming-Qian, Li...	details