Docosahexaenoic acid (CHEM017546)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:27:19 UTC
Update Date2016-10-28 10:02:20 UTC
Accession NumberCHEM017546
Identification
Common NameDocosahexaenoic acid
ClassSmall Molecule
DescriptionA mixture of fish oil and primrose oil, Docosahexaenoic acid is used as a high-docosahexaenoic acid (DHA) supplement. Docosahexaenoic acid is a 22 carbon chain with 6 cis double bonds with anti-inflammatory effects. It can be biosythesized from alpha-linolenic acid or commercially manufactured from microalgae. It is an omega-3 fatty acid and primary structural component of the human brain, cerebral cortex, skin, and retina thus plays an important role in their development and function. The amino-phospholipid Docosahexaenoic acid is found at a high concentration across several brain subcellular fractions, including nerve terminals, microsomes, synaptic vesicles, and synaptosomal plasma membranes .
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical 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 Mass328.488 g/mol
Monoisotopic Mass328.240 g/mol
CAS Registry Number6217-54-5
IUPAC Name(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
Traditional Namedocosahexaenoic acid
SMILESCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004l-9800000000-86f34228f9e92b6da2c6Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-9800000000-86f34228f9e92b6da2c6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0690-5590000000-145821d84e425eec8f98Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9363000000-db2668be2bbd1dbdd562Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0190000000-e6566b5aff7cefa4ae5dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0069000000-c76c91e0abd1895adb8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-0069000000-a25e6a700612620a1217Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9321000000-6b36fbd84ed730000eacSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9642000000-5ecff42b9082b57b5be6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0389000000-737691a3fc2f16b3c59eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00l6-9510000000-8e81381f5f447b18e9fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-071caf7af6bdab525160Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-1669000000-4e72cfd5cc68b32bd371Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0059-1179000000-289993a223b524e7c74fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-aa9263466508c9f2e65cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-7389000000-4e6afa18acb803f01d23Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9442000000-c452e1856fb3038c7f1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-1569000000-4e72cfd5cc68b32bd371Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0139000000-7f2351e9d6b367bd3e6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3592000000-10365ee2a8e305e24bd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktf-8960000000-6382301474f6f5630982Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-f498ba345a6e0d89ae44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1069000000-be6f83d34620dceb650eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-abfb63ab3950fe4edf48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-1439000000-c5fd83b4d4f8531d17e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-3922000000-a59c9fe862e58a93dd03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o3-7900000000-c8cfc5620efa939690bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-abcf527af18f1147a0aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1119000000-fbe7758a1c75272194e2Spectrum
MSMass Spectrum (Electron Ionization)splash10-002f-9400000000-60bd7bfd4de9015476c7Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03756
HMDB IDHMDB0002183
FooDB IDFDB003003
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID1586190
BioCyc IDCPD-10244
METLIN ID3457
PDB IDNot Available
Wikipedia LinkDocosahexaenoic_acid
Chemspider ID393183
ChEBI ID28125
PubChem Compound ID445580
Kegg Compound IDC06429
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
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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.
3. 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
4. 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
5. 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.
6. Watanabe A, Saito S, Tsuchida T, Higuchi K, Okita M: Low plasma levels of docosahexaenoic acid in patients with liver cirrhosis and its correction with a polyunsaturated fatty acid-enriched soft oil capsule. Nutrition. 1999 Apr;15(4):284-8.
7. Sanders TA: Polyunsaturated fatty acids in the food chain in Europe. Am J Clin Nutr. 2000 Jan;71(1 Suppl):176S-8S.
8. Gomez de Segura IA, Valderrabano S, Vazquez I, Vallejo-Cremades MT, Gomez-Garcia L, Sanchez M, de Miguel E: Protective effects of dietary enrichment with docosahexaenoic acid plus protein in 5-fluorouracil-induced intestinal injury in the rat. Eur J Gastroenterol Hepatol. 2004 May;16(5):479-85.
9. Woodman RJ, Mori TA, Burke V, Puddey IB, Barden A, Watts GF, Beilin LJ: Effects of purified eicosapentaenoic acid and docosahexaenoic acid on platelet, fibrinolytic and vascular function in hypertensive type 2 diabetic patients. Atherosclerosis. 2003 Jan;166(1):85-93.
10. Shingu T, Karanian JW, Kim HY, Yergey JA, Salem N Jr: Discovery of novel brain lipoxygenase products formed from docosahexaenoic acid (22:6w3). Adv Alcohol Subst Abuse. 1988;7(3-4):235-40.
11. Hong S, Tjonahen E, Morgan EL, Lu Y, Serhan CN, Rowley AF: Rainbow trout (Oncorhynchus mykiss) brain cells biosynthesize novel docosahexaenoic acid-derived resolvins and protectins-Mediator lipidomic analysis. Prostaglandins Other Lipid Mediat. 2005 Dec;78(1-4):107-16. Epub 2005 Jun 13.
12. Hibbeln JR, Bissette G, Umhau JC, George DT: Omega-3 status and cerebrospinal fluid corticotrophin releasing hormone in perpetrators of domestic violence. Biol Psychiatry. 2004 Dec 1;56(11):895-7.
13. Jorgensen MH, Hernell O, Hughes E, Michaelsen KF: Is there a relation between docosahexaenoic acid concentration in mothers' milk and visual development in term infants? J Pediatr Gastroenterol Nutr. 2001 Mar;32(3):293-6.
14. Crabtree JT, Gordon MJ, Campbell FM, Dutta-Roy AK: Differential distribution and metabolism of arachidonic acid and docosahexaenoic acid by human placental choriocarcinoma (BeWo) cells. Mol Cell Biochem. 1998 Aug;185(1-2):191-8.
15. Gordon N: Nutrition and cognitive function. Brain Dev. 1997 Apr;19(3):165-70.
16. Martinez M: Severe deficiency of docosahexaenoic acid in peroxisomal disorders: a defect of delta 4 desaturation? Neurology. 1990 Aug;40(8):1292-8.
17. Bohles H, Arndt S, Ohlenschlager U, Beeg T, Gebhardt B, Sewell AC: Maternal plasma homocysteine, placenta status and docosahexaenoic acid concentration in erythrocyte phospholipids of the newborn. Eur J Pediatr. 1999 Mar;158(3):243-6.
18. Crawford MA, Bloom M, Broadhurst CL, Schmidt WF, Cunnane SC, Galli C, Gehbremeskel K, Linseisen F, Lloyd-Smith J, Parkington J: Evidence for the unique function of docosahexaenoic acid during the evolution of the modern hominid brain. Lipids. 1999;34 Suppl:S39-47.
19. Andersson L, Sternby B, Nilsson A: Hydrolysis of phosphatidylethanolamine by human pancreatic phospholipase A2. Effect of bile salts. Scand J Gastroenterol. 1994 Feb;29(2):182-7.
20. Brossard N, Croset M, Normand S, Pousin J, Lecerf J, Laville M, Tayot JL, Lagarde M: Human plasma albumin transports [13C]docosahexaenoic acid in two lipid forms to blood cells. J Lipid Res. 1997 Aug;38(8):1571-82.
21. Berry CB, Hayes D, Murphy A, Wiessner M, Rauen T, McBean GJ: Differential modulation of the glutamate transporters GLT1, GLAST and EAAC1 by docosahexaenoic acid. Brain Res. 2005 Mar 10;1037(1-2):123-33.
22. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
23. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
24. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
25. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
26. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
27. The lipid handbook with CD-ROM
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=12359365
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=12538082
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=17291553
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=18072818
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=18220672
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