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Showing metabocard for Docosahexaenoic acid (HMDB0002183)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
enzymes (5) Show 5 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:40 UTC
Update Date2022-03-07 02:49:13 UTC
HMDB IDHMDB0002183
Secondary Accession Numbers
  • HMDB0062579
  • HMDB02183
  • HMDB62579
Metabolite Identification
Common NameDocosahexaenoic acid
Descriptiontrue
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for HMDB0002183 (Docosahexaenoic acid)

Not Available

3D MOL for HMDB0002183 (Docosahexaenoic acid)

Not Available

3D SDF for HMDB0002183 (Docosahexaenoic acid)

Not Available

3D-SDF for HMDB0002183 (Docosahexaenoic acid)

Not Available

PDB for HMDB0002183 (Docosahexaenoic acid)

Not Available

3D PDB for HMDB0002183 (Docosahexaenoic acid)

Not Available

SMILES for HMDB0002183 (Docosahexaenoic acid)

Not Available

INCHI for HMDB0002183 (Docosahexaenoic acid)

Not Available
View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC22H32O2
Average Molecular Weight328.4883
Monoisotopic Molecular Weight328.240230268
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number6217-54-5
SMILESNot Available
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
ClassificationNot classified
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties
Predicted Molecular PropertiesNot Available
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Docosahexaenoic acidCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O4132.5Standard polar33892256
Docosahexaenoic acidCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O2242.9Standard non polar33892256
Docosahexaenoic acidCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O2521.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Docosahexaenoic acid,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C2562.9Semi standard non polar33892256
Docosahexaenoic acid,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C2809.9Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Adipose Tissue
  • Brain
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Retina
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal		 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
BloodDetected and Quantified128.5 +/- 46.1 uMAdult (>18 years old)Not Specified
Normal		 details
BloodDetected and Quantified103.504 +/- 30.442 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified100.460 +/- 24.354 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified66.973 +/- 21.310 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.00347 uMAdult (>18 years old)Not Specified
Normal		 details
BloodDetected and Quantified0.00391 uMAdult (>18 years old)Not Specified
Normal		 details
BloodDetected and Quantified0.00414 uMAdult (>18 years old)Not Specified
Normal		 details
BloodDetected and Quantified0.00461 uMAdult (>18 years old)Not Specified
Normal		 details
BloodDetected and Quantified60.885 +/- 12.177 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified154.252 +/- 47.155 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified165.607 +/- 68.496 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified189.352 +/- 70.0177 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified255.260 +/- 75.162 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified420 +/- 110 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.15 +/- 0.015 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified5.5 +/- 6.3 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
BloodDetected and Quantified20.66 uMNewborn (0-30 days old)Female
Peroxisomal biogenesis disorder		 details
BloodDetected and Quantified122.36 uMInfant (0-1 year old)Male
Peroxisomal biogenesis disorder		 details
BloodDetected and Quantified135.43 uMNewborn (0-30 days old)Female
Rhizomelic chondrodysplasia punctata		 details
BloodDetected and Quantified144.700-160.300 uMChildren (1-13 years old)Female
Peroxisomal biogenesis disorder		 details
BloodDetected and Quantified64.3 +/- 28.5 uMAdult (>18 years old)Not Specified
Isovaleric acidemia		 details
BloodDetected and Quantified146.733 +/- 61.798 uMAdult (>18 years old)BothDepression details
Cerebrospinal Fluid (CSF)Detected and Quantified1.43 +/- 0.3 uMAdult (>18 years old)Both
Stroke		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified4.4 +/- 9.4 umol/mmol creatinineAdult (>18 years old)BothThyroid cancer details
Associated Disorders and Diseases
Disease References
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. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
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. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Major depressive disorder
  1. Sublette ME, Segal-Isaacson CJ, Cooper TB, Fekri S, Vanegas N, Galfalvy HC, Oquendo MA, Mann JJ: Validation of a food frequency questionnaire to assess intake of n-3 polyunsaturated fatty acids in subjects with and without major depressive disorder. J Am Diet Assoc. 2011 Jan;111(1):117-123.e1-2. doi: 10.1016/j.jada.2010.10.007. [PubMed:21185973 ]
Rhizomelic chondrodysplasia punctata
  1. Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ]
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
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. [PubMed:12967724 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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. [PubMed:14643447 ]
Associated OMIM IDs
External LinksNot Available
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)Not Available
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. [PubMed: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. [PubMed:10319360 ]
  3. Sanders TA: Polyunsaturated fatty acids in the food chain in Europe. Am J Clin Nutr. 2000 Jan;71(1 Suppl):176S-8S. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:9746226 ]
  10. Gordon N: Nutrition and cognitive function. Brain Dev. 1997 Apr;19(3):165-70. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:15777760 ]
  17. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  18. 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. [PubMed:16902246 ]
  19. 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. [PubMed:17374880 ]
  20. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  21. 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. [PubMed:32033212 ]
  22. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details
1. Cytosolic acyl coenzyme A thioester hydrolase
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
Enzyme Details
2. Acyl-coenzyme A thioesterase 2, mitochondrial
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
Enzyme Details
3. Acyl-coenzyme A thioesterase 4
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
Enzyme Details
4. Cytochrome P450 2U1
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
Enzyme Details
5. Acyl-coenzyme A thioesterase 1
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