| Version |
2.5 |
| Creation Date |
2006-05-22 15:17:40 |
| Update Date |
2009-11-22 23:38:52 |
| Accession Number |
HMDB02183 |
| Secondary Accession Numbers |
Not Available |
| Common Name |
Docosahexaenoic acid |
| Description |
Docosahexaenoic 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) |
| Synonyms |
- 4,7,10,13,16,19-Docosahexaenoate
- 4,7,10,13,16,19-Docosahexaenoic acid
- Cervonate
- Cervonic acid
- Doconexent
- Doconexento
- Doconexentum
- Docosahexaenoate
- Docosahexaenoic acid
- Doxonexent
- all-Z-Docosahexaenoate
- all-Z-Docosahexaenoic acid
- cis-4,7,10,13,16,19-Docosahexanoate
- cis-4,7,10,13,16,19-Docosahexanoic acid
|
| Chemical IUPAC Name |
(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid |
| Chemical Formula |
C22H32O2 |
| Chemical Structure |
 |
| Chemical Taxonomy |
| Kingdom |
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| Super Class |
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| Class |
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| Sub Class |
|
| Family |
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| Species |
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| Biofunction |
| — |
| Application |
| — |
| Source |
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|
| Average Molecular Weight |
328.488 |
| Monoisotopic Molecular Weight |
328.240234 |
| Isomeric SMILES |
CCC=C/CC=C/CC=C/CC=C/CC=C/CC=C/CCC(O)=O |
| Canonical SMILES |
CCC=CCC=CCC=CCC=CCC=CCC=CCCC(O)=O |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
D-HEXOSE-6-PHOSPHATE  |
| BiGG ID |
1586190  |
| Wikipedia Link |
Docosahexaenoic acid  |
| NuGOwiki Link |
HMDB02183  |
| Metagene Link |
HMDB02183  |
| METLIN ID |
3457  |
| PubChem Compound |
6433873  |
| PubChem Substance |
174742  |
| ChEBI ID |
Not Available |
| CAS Registry Number |
6217-54-5 |
| InChI Identifier |
InChI=1/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- |
| 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. |
| Melting Point (Experimental) |
Not Available |
| Experimental Water Solubility |
Not Available
Source: PhysProp
|
| Predicted Water Solubility |
1.86e-04 mg/mL [Predicted by ALOGPS]
Calculated using ALOGPS
|
| Physiological Charge |
-1 |
| State |
Solid |
| Experimental LogP/Hydrophobicity |
Not Available
Source: PhysProp
|
| Predicted LogP/Hydrophobicity |
6.83 [Predicted by ALOGPS]; 6.723 [Predicted by PubChem via XLOGP]
Calculated using ALOGPS
|
| Material Safety Data Sheet (MSDS) |
|
| MOL File |
Show |
| SDF File |
Show |
| PDB File |
Show |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Experimental 1H NMR Spectrum |
Not Available |
| Experimental 13C NMR Spectrum |
Not Available |
| Experimental 13C HSQC Spectrum |
Not Available |
| Predicted 1H NMR Spectrum |
Show Image Show Peaklist
|
| Predicted 13C NMR Spectrum |
Show Image Show Peaklist
|
| Mass Spectrum |
Not Available |
| Simplified TOCSY Spectrum |
Not Available |
| BMRB Spectrum |
Not Available |
| Cellular Location |
|
| Biofluid Location |
- Blood
- Cerebrospinal Fluid
- Urine
|
| Tissue Location |
| Tissue |
References |
| Adipose Tissue |
— |
| Brain |
— |
| Epidermis |
— |
| Erythrocyte |
— |
| Fibroblasts |
— |
| Intestine |
— |
| Kidney |
— |
| Liver |
— |
| Myelin |
— |
| Nervous Tissues |
— |
| Neuron |
— |
| Pancreas |
— |
| Placenta |
— |
| Platelet |
— |
| Prostate |
— |
| Retina |
— |
| Skeletal Muscle |
— |
| Testes |
— |
|
| Concentrations (Normal) |
| Biofluid |
Blood |
| Value |
1.777 +/- 0.796 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Both |
| Patient information |
Normal |
| Comments |
Not Available |
| References |
- Nikolaos Psychogios, David D. Hau, Jun Peng, An Chi Guo, Rupasri Mandal, Souhaila Bouatra, Igor Sinelnikov, Ramanarayan Krishnamurthy, Roman Eisner, Bijaya Gautam, Nelson Young, Jinaguo Xia, Craig Knox, Ying Wei Dong, Paul Huang, Janet McManus, Theresa Pedersen, Fiona Bamforth, Russ Greiner, Bruce McManus, John Newman, David S. Wishart, The Human Serum Metabolome, PLoS ONE (Submitted).
- Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [PubMed
]
|
| Biofluid |
Blood |
| Value |
2.3 +/- 1.2 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Both |
| Patient information |
Fasted subjects |
| Comments |
Not Available |
| References |
- Kargas G, Rudy T, Spennetta T, Takayama K, Querishi N, Shrago E: Separation and quantitation of long-chain free fatty acids in human serum by high-performance liquid chromatography. J Chromatogr. 1990 Apr 6;526(2):331-40. [PubMed
]
|
| Biofluid |
Blood |
| Value |
0.9 +/- 0.3 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Both |
| Patient information |
Fed subjects |
| Comments |
Not Available |
| References |
- Kargas G, Rudy T, Spennetta T, Takayama K, Querishi N, Shrago E: Separation and quantitation of long-chain free fatty acids in human serum by high-performance liquid chromatography. J Chromatogr. 1990 Apr 6;526(2):331-40. [PubMed
]
|
| Biofluid |
Blood |
| Value |
94.2 +/- 31.3 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Both |
| Patient information |
Normal |
| Comments |
Not Available |
| References |
- 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. [PubMed
]
|
| Biofluid |
Blood |
| Value |
90.9 +/- 21.6 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Male |
| Patient information |
Normal |
| Comments |
Not Available |
| References |
- 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. [PubMed
]
|
| Biofluid |
Blood |
| Value |
98.7 +/- 41.0 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Female |
| Patient information |
Normal |
| Comments |
Not Available |
| References |
- 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. [PubMed
]
|
| Biofluid |
CSF |
| Value |
0.15 +/- 0.015 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Both |
| Patient information |
Normal |
| Comments |
Not Available |
| References |
- 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
]
|
| Biofluid |
Urine |
| Value |
5.5 +/- 6.3 umol/mmol creatinine |
| Age |
Adult:>18 yrs old |
| Sex |
Both |
| Patient information |
Normal |
| Comments |
Not Available |
| References |
- 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
]
|
|
| Concentrations (Abnormal) |
| Biofluid |
Blood |
| Value |
64.7 +/- 39.2 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Both |
| Condition |
Hypertension |
| Comments |
n=109
Essential hypertension |
| References |
- 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. [PubMed
]
|
| Biofluid |
Blood |
| Value |
56.6 +/- 36.7 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Male |
| Condition |
Essential hypertension |
| Comments |
Not Available |
| References |
- 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. [PubMed
]
|
| Biofluid |
Blood |
| Value |
83.0 +/- 39.0 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Female |
| Condition |
Essential hypertension |
| Comments |
Not Available |
| References |
- 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. [PubMed
]
|
| Biofluid |
CSF |
| Value |
1.43 +/- 0.3 uM |
| Age |
Adult:>18 yrs old |
| Sex |
Both |
| Condition |
Stroke |
| Comments |
Ischemic and/or hemorrhagic |
| References |
- 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
]
|
| Biofluid |
Urine |
| Value |
4.4 +/- 9.4 umol/mmol creatinine |
| Age |
Adult:>18 yrs old |
| Sex |
Both |
| Condition |
Thyroid cancer |
| Comments |
Not Available |
| References |
- 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
]
|
|
| Associated Disorders |
| Condition |
References |
| Essential hypertension |
- 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. [PubMed
]
|
| Hypertension |
- 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. [PubMed
]
|
| Stroke |
- 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
]
|
| Thyroid cancer |
- 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
]
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| OMIM ID |
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| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Alpha Linolenic Acid and Linoleic Acid Metabolism |
SMP00018  |
map00592  |
|
| General References |
- 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
]
- Sanders TA: Polyunsaturated fatty acids in the food chain in Europe. Am J Clin Nutr. 2000 Jan;71(1 Suppl):176S-8S. [PubMed
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- Gordon N: Nutrition and cognitive function. Brain Dev. 1997 Apr;19(3):165-70. [PubMed
]
- Martinez M: Severe deficiency of docosahexaenoic acid in peroxisomal disorders: a defect of delta 4 desaturation? Neurology. 1990 Aug;40(8):1292-8. [PubMed
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- Wikipedia

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| Metabolic Enzymes |
- Cytochrome P450 2U1
|