Showing metabocard for Docosahexaenoic acid (BMDB0002183)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:52:14 UTC
Update Date2020-06-04 21:14:09 UTC
MCDB ID BMDB0002183
Secondary Accession Numbers
  • BMDB0063579
  • BMDB02183
  • BMDB63579
Metabolite Identification
Common NameDocosahexaenoic acid
DescriptionDocosahexaenoic 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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acidChEBI
22:6(N-3)ChEBI
22:6-4, 7,10,13,16,19ChEBI
4,7,10,13,16,19-Docosahexaenoic acidChEBI
all-cis-4,7,10,13,16,19-Docosahexaenoic acidChEBI
all-cis-DHAChEBI
Cervonic acidChEBI
DHAChEBI
DoconexentChEBI
DOCOSA-4,7,10,13,16,19-hexaenoIC ACIDChEBI
DocosahexaenoateKegg
4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoic acidKegg
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acidKegg
(4Z,7Z,10Z,13Z,16Z,19Z)-DocosahexaenoateGenerator
4,7,10,13,16,19-DocosahexaenoateGenerator
all-cis-4,7,10,13,16,19-DocosahexaenoateGenerator
CervonateGenerator
DOCOSA-4,7,10,13,16,19-hexaenoateGenerator
4Z,7Z,10Z,13Z,16Z,19Z-DocosahexaenoateGenerator
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoateGenerator
all-Z-DocosahexaenoateHMDB
all-Z-Docosahexaenoic acidHMDB
cis-4,7,10,13,16,19-DocosahexanoateHMDB
cis-4,7,10,13,16,19-Docosahexanoic acidHMDB
DoconexentoHMDB
DoconexentumHMDB
DoxonexentHMDB
Acids, docosahexaenoicHMDB
Acids, docosahexenoicHMDB
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-isomerHMDB
EfalexHMDB
(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acidHMDB
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexenoic acidHMDB
(all-Z)-4,7,10,13,16,19-Docosahexaenoic acidHMDB
4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-Docosahexaenoic acidHMDB
FA(22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
FA(22:6n3)HMDB
delta4,7,10,13,16,19-Docosahexaenoic acidHMDB
Δ4,7,10,13,16,19-docosahexaenoic acidHMDB
Docosahexaenoic acidHMDB
Choline docosahexaenoateHMDB
Choline docosahexaenoic acidHMDB
DocosahexaenoylcholineHMDB
Chemical FormulaC22H32O2
Average Molecular Weight328.4883
Monoisotopic Molecular Weight328.240230268
IUPAC Name(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
Traditional Namedocosahexaenoic acid
CAS Registry Number6217-54-5
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 KeyMBMBGCFOFBJSGT-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.83ALOGPS
logP6.75ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity111.39 m³·mol⁻¹ChemAxon
Polarizability38.63 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004l-9800000000-86f34228f9e92b6da2c62014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-9800000000-86f34228f9e92b6da2c62017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0690-5590000000-145821d84e425eec8f982017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9363000000-db2668be2bbd1dbdd5622017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0190000000-e6566b5aff7cefa4ae5d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0069000000-c76c91e0abd1895adb8b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-0069000000-a25e6a700612620a12172017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9321000000-6b36fbd84ed730000eac2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9642000000-5ecff42b9082b57b5be62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0389000000-737691a3fc2f16b3c59e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00l6-9510000000-8e81381f5f447b18e9fc2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-071caf7af6bdab5251602021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-1669000000-4e72cfd5cc68b32bd3712021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0059-1179000000-289993a223b524e7c74f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-aa9263466508c9f2e65c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-7389000000-4e6afa18acb803f01d232021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9442000000-c452e1856fb3038c7f1e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-1569000000-4e72cfd5cc68b32bd3712021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0139000000-7f2351e9d6b367bd3e6d2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3592000000-10365ee2a8e305e24bd42016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktf-8960000000-6382301474f6f56309822016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-f498ba345a6e0d89ae442016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1069000000-be6f83d34620dceb650e2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-abfb63ab3950fe4edf482016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-1439000000-c5fd83b4d4f8531d17e22021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-3922000000-a59c9fe862e58a93dd032021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o3-7900000000-c8cfc5620efa939690bb2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-abcf527af18f1147a0aa2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1119000000-fbe7758a1c75272194e22021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-002f-9400000000-60bd7bfd4de9015476c72015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified1035 +/- 426 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified882 +/- 304 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected but not QuantifiedNot Applicable details
Detected and Quantified183 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
Detected and Quantified304 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
Detected and Quantified1218 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
Detected and Quantified1827 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0002183
DrugBank IDDB03756
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003003
KNApSAcK IDNot Available
Chemspider ID393183
KEGG Compound IDC06429
BioCyc IDCPD-10244
BiGG ID1586190
Wikipedia LinkDocosahexaenoic_acid
METLIN ID3457
PubChem Compound445580
PDB IDNot Available
ChEBI ID28125
References
Synthesis ReferenceWright, 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)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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.
  5. 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.