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    Also known as: Doconexent, Cervonic acid, 6217-54-5, Cis-4,7,10,13,16,19-docosahexaenoic acid, Docosahexaenoate, (4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoic acid
    Molecular Formula
    C22H32O2
    Molecular Weight
    328.5  g/mol
    InChI Key
    MBMBGCFOFBJSGT-KUBAVDMBSA-N
    FDA UNII
    ZAD9OKH9JC
    DHA
    C22-unsaturated fatty acids found predominantly in FISH OILS.
    1 2D Structure

    DHA

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
    2.1.2 InChI
    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-
    2.1.3 InChI Key
    MBMBGCFOFBJSGT-KUBAVDMBSA-N
    2.1.4 Canonical SMILES
    CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O
    2.1.5 Isomeric SMILES
    CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    ZAD9OKH9JC
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Acid, Docosahexaenoic

    2. Acids, Docosahexaenoic

    3. Acids, Docosahexenoic

    4. Docosahexaenoate

    5. Docosahexaenoic Acid (all-z Isomer)

    6. Docosahexaenoic Acid Dimer (all-z Isomer)

    7. Docosahexaenoic Acid, 3,6,9,12,15,18-isomer

    8. Docosahexaenoic Acid, 4,7,10,13,16,19-(all-z-isomer)

    9. Docosahexaenoic Acid, 4,7,10,13,16,19-(all-z-isomer), Cerium Salt

    10. Docosahexaenoic Acid, 4,7,10,13,16,19-(all-z-isomer), Cesium Salt

    11. Docosahexaenoic Acid, 4,7,10,13,16,19-(all-z-isomer), Potassium Salt

    12. Docosahexaenoic Acid, 4,7,10,13,16,19-(z,z,z,z,z,e-isomer)

    13. Docosahexaenoic Acid, 4,7,10,13,16,19-isomer

    14. Docosahexaenoic Acid, 4,7,10,13,16,19-isomer, Sodium Salt

    15. Docosahexaenoic Acid, Sodium Salt

    16. Docosahexaenoic Acids

    17. Docosahexenoic Acids

    2.3.2 Depositor-Supplied Synonyms

    1. Doconexent

    2. Cervonic Acid

    3. 6217-54-5

    4. Cis-4,7,10,13,16,19-docosahexaenoic Acid

    5. Docosahexaenoate

    6. (4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoic Acid

    7. All-cis-dha

    8. Doconexento

    9. Doconexentum

    10. Doxonexent

    11. Aquagrow Advantage

    12. All-z-docosahexaenoic Acid

    13. Doconexent [inn]

    14. Martek Dha Hm

    15. Ropufa 60

    16. All-cis-4,7,10,13,16,19-docosahexaenoic Acid

    17. (4z,7z,10z,13z,16z,19z)-docosahexaenoic Acid

    18. Docosaheaenoic-acid

    19. Docosahexaenoic Acid (all-z)

    20. Ccris 7670

    21. All-cis-docosa-4,7,10,13,16,19-hexaenoic Acid

    22. Zad9okh9jc

    23. Docosahexanoic Acid

    24. (all-z)-4,7,10,13,16,19-docosahexaenoic Acid

    25. Docosa-4,7,10,13,16,19-hexaenoic Acid

    26. (4z,7z,10z,13z,16z,19z)-4,7,10,13,16,19-docosahexaenoic Acid

    27. Chembl367149

    28. Docosahexaenoic Acid(dha)

    29. Chebi:28125

    30. Delta4,7,10,13,16,19-docosahexaenoic Acid

    31. 4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-docosahexaenoic Acid

    32. 4z,7z,10z,13z,16z,19z-docosahexaenoic Acid

    33. Docosahexaenoic Acid (c22:6 N3)

    34. Omega-3 Marine Triglycerides

    35. Mfcd00065722

    36. 4,7,10,13,16,19-docosahexaenoic Acid, (all-z)-

    37. Fa 22:6

    38. Efalex

    39. Ncgc00161345-04

    40. C22:6 (n-3)

    41. Docosahexaenoic Acid (22:6 N-3)

    42. 22:6 N-3

    43. 22:6(n-3)

    44. Cis-4,7,10,13,16,19-docosahexanoic Acid

    45. 4,7,10,13,16,19-docosahexaenoic Acid

    46. C22:6n-3,6,9,12,15,18

    47. Monolife 50

    48. Marinol D 50tg

    49. Sr-05000002130

    50. Unii-zad9okh9jc

    51. Doconexentum [inn-latin]

    52. Doconexento [inn-spanish]

    53. Dha-[21,21,22,22,22-d5]

    54. Cervonate

    55. Dtxsid5040465

    56. 1fdq

    57. Algal Dha

    58. Docohexanenoic Acid

    59. Docosahexanenoic Acid

    60. Omega 3 Fatty Acid

    61. All-z-docosahexaenoate

    62. Spectrum5_002062

    63. Docosahexaenoic Acid (6ci)

    64. Dsstox_cid_20465

    65. Dsstox_rid_79498

    66. Dsstox_gsid_40465

    67. Schembl19577

    68. Bspbio_001298

    69. Docoshexaenoic Acid (powder)

    70. Mls004773950

    71. Bml3-b02

    72. Gtpl1051

    73. Retriacyl (proposed Trade Name)

    74. Bcbcmap01_000145

    75. Docosahexaenoic Acid [mi]

    76. Hms1361a20

    77. Hms1791a20

    78. Hms1989a20

    79. Hms3402a20

    80. Hms3649j15

    81. Docosahexaenoic Acid [inci]

    82. Hy-b2167

    83. Zinc4474564

    84. Docosahexaenoic Acid [vandf]

    85. Tox21_111992

    86. Bdbm50210259

    87. Docosahexaenoic Acid [mart.]

    88. Lmfa01030185

    89. Docosahexaenoic Acid [usp-rs]

    90. Docosahexaenoic Acid [who-dd]

    91. Akos015962159

    92. Ac-1010

    93. Ccg-207958

    94. Ccg-208135

    95. Cs-6261

    96. Db03756

    97. Kl-0761

    98. Idi1_033768

    99. 4,7,10,13,16,19-docosahexaenoate

    100. Ncgc00161345-01

    101. Ncgc00161345-02

    102. Ncgc00161345-03

    103. Ncgc00161345-05

    104. Ncgc00161345-07

    105. All Cis- Docosahexaenoic Acid (cis-dha)

    106. Smr001881493

    107. Cas-6217-54-5

    108. Cis-4,7,10,13,16,19-docosahexanoate

    109. D2226

    110. S6454

    111. C06429

    112. H10987

    113. Ab01563379_01

    114. Docosahexaenoic Acid (dha) (c22:6 N3)

    115. Docosahexaenoic Acid-rich Single Cell Oil

    116. 217d545

    117. Q423345

    118. Sr-05000002130-1

    119. Sr-05000002130-4

    120. Brd-k39965020-001-02-6

    121. 4,7,10,13,16,19-docosahexaenoic Acid, (all Cis)-

    122. A320050000

    123. Cis-4,7,10,13,16,19-docosahexaenoic Acid, >=98%

    124. Fa(22:6(4z,7z,10z,13z,16z,19z))

    125. Z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoic Acid

    126. (all-z)-4,7,10,13,16,19-docosahexaenoic Acid, Dha

    127. 800e8e72-bbf4-46f7-a60b-b8f2b54669c7

    128. C22h32o2 (cis-4,7,10,13,16,19-docosahexaenoic Acid)

    129. 4,7,10,13,16,19-docosahexaenoic Acid, (all-z)- (8ci)

    130. Cis-4,7,10,13,16,19-docosahexaenoic Acid, Analytical Standard

    131. Docosa-4z,7z,10z,13z,16z,19z-hexaenoic Acid (22:6, N-3)

    132. (4z,7z,10z,13z,16z, 19z)-docosa-4,7,10,13,16,19-hexaenoic Acid

    133. (4z,7z,10z,13z,16z,19z)-docosa-4, 7,10,13,16,19-hexaenoic Acid

    134. (4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19- Hexaenoic Acid

    135. Cis-4,7,13,16,19-docosahexaenoic Acid (stabilized With Vitamine E)

    136. 4,7,10,13,16,19-docosahexaenoic Acid, (4z,7z,10z,13z,16z,19z)- (9ci)

    137. Docosahexaenoic Acid (dha) (c22:6) (constituent Of Krill Oil) [dsc]

    138. 1024594-51-1

    139. Cis-4,7,10,13,16,19-docosahexaenoic Acid, 500 Mug/ml In Ethanol, Certified Reference Material

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 328.5 g/mol
    Molecular Formula C22H32O2
    XLogP36.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count14
    Exact Mass328.240230259 g/mol
    Monoisotopic Mass328.240230259 g/mol
    Topological Polar Surface Area37.3 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity462
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count6
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Used as a high-docosahexaenoic acid (DHA) oral supplement.

    Treatment of Retinitis Pigmentosa

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    DHA in the central nervous system is found in the phospholipid bilayers where it modulates the physical environment and increase the free volume within the membrane bilayer. It influences the G-protein coupled receptor activity and affects transmembrane transport and cell interaction with the exterior world. It is also reported to promote apoptosis, neuronal differentiation and ion channel activity. Like other polyunsaturated fatty acids, DHA acts as a ligand at PPARs that plays an anti-inflammatory effect and regulate inflammatory gene expression and NFB activation. DHA also gives rise to resolvins and related compounds (e.g., protectins) through pathways involving cyclooxygenase and lipoxygenase enzymes to resolve the inflammatory responses.

    5.2 Absorption, Distribution and Excretion

    Absorption

    Like other omega-3 fatty acids, DHA is hydrolyzed from the intestines and delivered through the lymphatic circulation. Plasma DHA concentrations increase in a dose-dependent and saturable manner.

    Volume of Distribution

    DHA is the most abundant n3 fatty acid in membranes and is present in all organs. It is also the most variable among organs and is particularly abundant in neural tissue, such as brain and retina, where it is several hundred-fold more abundant than EPA.

    5.3 Metabolism/Metabolites

    DHA can be metabolized into DHA-derived specialized pro-resolving mediators (SPMs), DHA epoxides, electrophilic oxo-derivatives (EFOX) of DHA, neuroprostanes, ethanolamines, acylglycerols, docosahexaenoyl amides of amino acids or neurotransmitters, and branched DHA esters of hydroxy fatty acids, among others. It is converted to 17-hydroperoxy-DHA derivatives via COX-2 and 15-LOX and 5-LOX activity. These derivatives are further converted into D-series resolvins and protectins with potent anti-inflammatory potential and potent neuroprotective effect. DHA may also be metabolized to 19,20-epoxydocosapentaenoic acids (EDPs) and isomers via CYP2C9 activity. Epoxy metabolites are reported to mediate anti-tumor activity by inhibiting angiogenesis, tumor growth, and metastasis.

    5.4 Biological Half-Life

    Approximately 20 hours.

    5.5 Mechanism of Action

    DHA and its conversion to other lipid signalling moleccules compete with the arachidonic acid cascade from endogenous phospholipids and shift the inflammatory state to being more anti-inflammatory. DHA inhibits endotoxin-stimulated production of IL-6 and IL-8 in human endothelial cells. Derivatives of DHA are anti-inflammatory lipid mediators. Lipid mediators resolvin D1 and protectin D1 all inhibit transendothelial migration of neutrophils, so preventing neutrophilic infiltration at sites of inflammation, resolvin D1 inhibits IL-1 production, and protectin D1 inhibits TNF and IL-1 production. Monoxydroxy derivative of DHA converted by LOX inhibit thromboxane-induced platelet aggregation. DHA supplementation has also shown to reduce the levels of serum C-reactive protein (CRP) and other circulating markers of inflammation such as neutrophils in hypertriglyceridemic men. DHA acts as a ligand at peroxisome proliferator-activated receptor (PPAR) gamma and alpha that regulate lipid signalling molecule-mediated transduction pathways and modulate inflammation. As a natural ligand, DHA induces a protective effect in retinal tissues by activating retinoid x receptors and subsequent ERK/MAPK signaling pathway in photoreceptors to promote their survival and differentiation, stimulating the expression of antiapoptotic proteins such as Bcl-2 and preserving mitochondrial membrane potential.

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    31-Mar-2021
    28-Jul-2024
    KGS
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