| Record Information |
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| Version | 5.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2006-05-22 14:17:40 UTC |
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| Update Date | 2022-03-07 02:49:13 UTC |
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| HMDB ID | HMDB0002183 |
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| Secondary Accession Numbers | - HMDB0062579
- HMDB02183
- HMDB62579
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| Metabolite Identification |
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| Common Name | Docosahexaenoic acid |
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| Description | true |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C22H32O2 |
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| Average Molecular Weight | 328.4883 |
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| Monoisotopic Molecular Weight | 328.240230268 |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 6217-54-5 |
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| SMILES | Not Available |
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| 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- |
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| InChI Key | MBMBGCFOFBJSGT-KUBAVDMBSA-N |
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| Chemical Taxonomy |
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| Classification | Not classified |
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| Ontology |
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| Not Available | Not Available |
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| Physical Properties |
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| State | Liquid |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Experimental Chromatographic Properties |
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| Predicted Molecular Properties | Not Available |
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| Predicted Chromatographic Properties | Predicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 5.72 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 28.9229 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 1.6 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 43.3 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 3465.4 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 638.4 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 278.4 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 559.8 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 816.0 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 1354.4 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 660.9 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 94.9 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 2651.5 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 929.9 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 2083.2 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 1007.2 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 616.5 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 499.1 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 652.0 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 8.8 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized |
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| Spectra |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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| Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Urine
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| Tissue Locations | - Adipose Tissue
- Brain
- Epidermis
- Erythrocyte
- Fibroblasts
- Intestine
- Kidney
- Liver
- Neuron
- Pancreas
- Placenta
- Platelet
- Prostate
- Retina
- Skeletal Muscle
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 100.460 +/- 24.354 uM | Adult (>18 years old) | Male | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 128.5 +/- 46.1 uM | Adult (>18 years old) | Not Specified | Normal | | details | | Blood | Detected and Quantified | 420 +/- 110 uM | Adult (>18 years old) | Male | Normal | | details | | Blood | Detected and Quantified | 255.260 +/- 75.162 uM | Adult (>18 years old) | Female | Normal | | details | | Blood | Detected and Quantified | 189.352 +/- 70.0177 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 165.607 +/- 68.496 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 154.252 +/- 47.155 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 60.885 +/- 12.177 uM | Adult (>18 years old) | Male | Normal | | details | | Blood | Detected and Quantified | 0.00461 uM | Adult (>18 years old) | Not Specified | Normal | | details | | Blood | Detected and Quantified | 0.00414 uM | Adult (>18 years old) | Not Specified | Normal | | details | | Blood | Detected and Quantified | 0.00391 uM | Adult (>18 years old) | Not Specified | Normal | | details | | Blood | Detected and Quantified | 0.00347 uM | Adult (>18 years old) | Not Specified | Normal | | details | | Blood | Detected and Quantified | 66.973 +/- 21.310 uM | Adult (>18 years old) | Male | Normal | | details | | Blood | Detected and Quantified | 103.504 +/- 30.442 uM | Adult (>18 years old) | Male | Normal | | details | | Blood | Detected and Quantified | 98.7 +/- 41.0 uM | Adult (>18 years old) | Female | Normal | | details | | Blood | Detected and Quantified | 1.777 +/- 0.796 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 2.3 +/- 1.2 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 0.9 +/- 0.3 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 94.2 +/- 31.3 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 90.9 +/- 21.6 uM | Adult (>18 years old) | Male | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Normal | | details | | Blood | Detected and Quantified | 0.990 +/- 0.009 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 4.66 +/- 3.3 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.15 +/- 0.015 uM | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 5.5 +/- 6.3 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected and Quantified | 64.7 +/- 39.2 uM | Adult (>18 years old) | Both | Hypertension | | details | | Blood | Detected and Quantified | 56.6 +/- 36.7 uM | Adult (>18 years old) | Male | Essential hypertension | | details | | Blood | Detected and Quantified | 83.0 +/- 39.0 uM | Adult (>18 years old) | Female | Essential hypertension | | details | | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal adenoma | | details | | Blood | Detected and Quantified | 146.733 +/- 61.798 uM | Adult (>18 years old) | Both | Depression | | details | | Blood | Detected and Quantified | 20.66 uM | Newborn (0-30 days old) | Female | Peroxisomal biogenesis disorder | | details | | Blood | Detected and Quantified | 122.36 uM | Infant (0-1 year old) | Male | Peroxisomal biogenesis disorder | | details | | Blood | Detected and Quantified | 135.43 uM | Newborn (0-30 days old) | Female | Rhizomelic chondrodysplasia punctata | | details | | Blood | Detected and Quantified | 144.700-160.300 uM | Children (1-13 years old) | Female | Peroxisomal biogenesis disorder | | details | | Blood | Detected and Quantified | 64.3 +/- 28.5 uM | Adult (>18 years old) | Not Specified | Isovaleric acidemia | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 1.43 +/- 0.3 uM | Adult (>18 years old) | Both | Stroke | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | | Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Not Specified | Premature neonates | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | | Urine | Detected and Quantified | 4.4 +/- 9.4 umol/mmol creatinine | Adult (>18 years old) | Both | Thyroid cancer | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Hypertension |
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- 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 |
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- 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 |
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- 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 |
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- 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 |
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- 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 |
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- 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 |
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- 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 ]
- 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 ]
- 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 |
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- 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 ]
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| Associated OMIM IDs | |
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| External Links |
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| External Links | Not Available |
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| References |
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| Synthesis Reference | 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. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - 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 ]
- 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 ]
- Sanders TA: Polyunsaturated fatty acids in the food chain in Europe. Am J Clin Nutr. 2000 Jan;71(1 Suppl):176S-8S. [PubMed:10617968 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Gordon N: Nutrition and cognitive function. Brain Dev. 1997 Apr;19(3):165-70. [PubMed:9134186 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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