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Record Information
Version3.6
Creation Date2006-05-22 14:17:40 UTC
Update Date2016-02-11 01:05:25 UTC
HMDB IDHMDB02183
Secondary Accession NumbersNone
Metabolite Identification
Common NameDocosahexaenoic acid
DescriptionDocosahexaenoic 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 humans, which may reduce the risk of heart disease. (wikipedia).
Structure
Thumb
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
Docosahexaenoic acidChEBI
(4Z,7Z,10Z,13Z,16Z,19Z)-DocosahexaenoateGenerator
all-cis-Docosa-4,7,10,13,16,19-hexaenoateGenerator
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
DocosahexaenoateGenerator
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
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 KeyInChIKey=MBMBGCFOFBJSGT-KUBAVDMBSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000186 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity111.39 m3·mol-1ChemAxon
Polarizability38.63 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004l-9800000000-86f34228f9e92b6da2c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
MSMass Spectrum (Electron Ionization)splash10-002f-9400000000-60bd7bfd4de9015476c7View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Brain
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Myelin
  • Nervous Tissues
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Retina
  • Skeletal Muscle
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018map00592
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified94.2 +/- 31.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified4.66 +/- 3.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified90.9 +/- 21.6 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified98.7 +/- 41.0 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.3 +/- 1.2 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.9 +/- 0.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.777 +/- 0.796 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.990 +/- 0.009 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.15 +/- 0.015 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified5.5 +/- 6.3 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified64.7 +/- 39.2 uMAdult (>18 years old)Both
Hypertension
details
BloodDetected and Quantified56.6 +/- 36.7 uMAdult (>18 years old)MaleEssential hypertension details
BloodDetected and Quantified83.0 +/- 39.0 uMAdult (>18 years old)FemaleEssential hypertension details
Cerebrospinal Fluid (CSF)Detected and Quantified1.43 +/- 0.3 uMAdult (>18 years old)Both
Stroke
details
UrineDetected and Quantified4.4 +/- 9.4 umol/mmol creatinineAdult (>18 years old)BothThyroid cancer details
Associated Disorders and Diseases
Disease References
Thyroid cancer
  1. Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [14643447 ]
Essential hypertension
  1. Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. [18633173 ]
Hypertension
  1. Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. [18633173 ]
Stroke
  1. Pilitsis JG, Coplin WM, O'Regan MH, Wellwood JM, Diaz FG, Fairfax MR, Michael DB, Phillis JW: Measurement of free fatty acids in cerebrospinal fluid from patients with hemorrhagic and ischemic stroke. Brain Res. 2003 Sep 26;985(2):198-201. [12967724 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003003
KNApSAcK IDNot Available
Chemspider ID393183
KEGG Compound IDC06429
BioCyc IDD-HEXOSE-6-PHOSPHATE
BiGG ID1586190
Wikipedia LinkDocosahexaenoic acid
NuGOwiki LinkHMDB02183
Metagene LinkHMDB02183
METLIN ID3457
PubChem Compound445580
PDB IDHXA
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. 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. [12482554 ]
  2. 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. [10319360 ]
  3. Sanders TA: Polyunsaturated fatty acids in the food chain in Europe. Am J Clin Nutr. 2000 Jan;71(1 Suppl):176S-8S. [10617968 ]
  4. 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. [15097041 ]
  5. 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. [2975919 ]
  6. 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. [16303609 ]
  7. 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. [15576068 ]
  8. 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. [11345178 ]
  9. 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. [9746226 ]
  10. Gordon N: Nutrition and cognitive function. Brain Dev. 1997 Apr;19(3):165-70. [9134186 ]
  11. Martinez M: Severe deficiency of docosahexaenoic acid in peroxisomal disorders: a defect of delta 4 desaturation? Neurology. 1990 Aug;40(8):1292-8. [2143272 ]
  12. 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. [10094448 ]
  13. 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. [10419087 ]
  14. 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. [8171289 ]
  15. 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. [9300779 ]
  16. 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. [15777760 ]

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:
ACOT7
Uniprot ID:
O00154
Molecular weight:
40454.945
Reactions
Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:
ACOT2
Uniprot ID:
P49753
Molecular weight:
53218.02
Reactions
Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Molecular weight:
46326.09
Reactions
Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic aciddetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the hydroxylation of arachidonic acid, docosahexaenoic acid and other long chain fatty acids. May modulate the arachidonic acid signaling pathway and play a role in other fatty acid signaling processes.
Gene Name:
CYP2U1
Uniprot ID:
Q7Z449
Molecular weight:
61986.525
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:
ACOT1
Uniprot ID:
Q86TX2
Molecular weight:
46276.96
Reactions
Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic aciddetails