Page last updated: 2024-11-11

docosapentaenoic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

docosapentaenoic acid : Any straight-chain, C22 fatty acid having five C=C double bonds. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

(7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid : The all-cis-isomer of a C22 polyunsaturated fatty acid having five double bonds in the 7-, 10-, 13-, 16- and 19-positions. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5497182
CHEMBL ID496634
CHEBI ID53488
SCHEMBL ID20748
MeSH IDM0086338

Synonyms (66)

Synonym
(all z)-7,10,13,16,19-docosapentaenoic acid
7,10,13,16,19-docosapentaenoic acid, (all z)-
7,10,13,16,19-docasapentaenoic acid, (all-z)-
cis-7,10,13,16,19-docosapentaenoic acid
LMFA04000044
osbond's acid
clupanodonic acid
BSPBIO_001300
244880-45-3
all-cis-7,10,13,16,19-docosapentaenoic acid ,
7z,10z,13z,16z,19z-docosapentaenoic acid
7,10,13,16,19-docosapentaenoic acid, (all-z)- (8ci)
7,10,13,16,19-docosapentaenoic acid, (7z,10z,13z,16z,19z)-
(all-z)-7,10,13,16,19-docosapentaenoic acid
delta7,10,13,16,19-docosapentaenoic acid
7,10,13,16,19-docosapentaenoic acid, (7z,10z,13z,16z,19z)- (9ci)
all-cis-7,10,13,16,19-docosapentaenoic acid, synthetic, >=97%
c22:5n-3,6,9,12,15
IDI1_033770
NCGC00161353-01
NCGC00161353-02
NCGC00161353-03
24880-45-3
(7z,10z,13z,16z,19z)-docosa-7,10,13,16,19-pentaenoic acid
(7z,10z,13z,16z,19z)-docosapentaenoic acid
docosapentaenoic acid
fa 22:5
HMS1989A22
BML3-C02
HMS1791A22
HMS1361A22
bdbm50269224
docosa-7z,10z,13z,16z,19z-pentaenoic acid
docosa-7c,10c,13c,16c,19c-pentaensaeure
CHEBI:53488 ,
CHEMBL496634 ,
unii-ns3ozt14qt
ns3ozt14qt ,
docosapentaenoic acid (c22:5 n3)
(all-z)-7, 10, 13, 16, 19-docosapentaenoic acid
SCHEMBL20748
22:5 n-3
c22:5 (n-3)
docosapentaenoic acid [who-dd]
HMS3402A22
HMS3649F13
DTXSID6074758
AKOS027382354
docosapentaenoic acid 22n-3
docosapentaenoic acid (cis-7,10,13,16,19), 500 mug/ml in ethanol, certified reference material
docosapentaenoic acid (22n-3)
7,10,13,16,19-docosapentaenoate
clupanodonate
(7z,10z,13z,16z,19z)-docosa 7,10,13,16,19-pentaenoate
(7z,10z,13z,16z,19z)-docosa 7,10,13,16,19-pentaenoic acid
J-015716
Q3278345
7,10,13,16,19-docosapentaenoicacid,(7z,10z,13z,16z,19z)-
(all-cis)-7,10,13,16,19-docosapentaenoic acid
sr-01000946652
SR-01000946652-1
HY-113159
CS-0062313
fa(22:5(7z,10z,13z,16z,19z))
docosapentaenoic
(7z,10z,13z,16z,19z)-docosa-7,10,13,16,19-pentaenoicacid

Research Excerpts

Overview

Docosapentaenoic acid (DPA) is a minor omega-3 fatty acid (FA) which has been frequently overlooked in lipid research. DPA exists in two isomeric forms (n-3 and n-6), which differ in their physiological behaviors.

ExcerptReferenceRelevance
"Docosapentaenoic acid (DPA) is a minor omega-3 fatty acid (FA) which has been frequently overlooked in lipid research. "( n - 3 Docosapentaenoic acid: the iceberg n - 3 fatty acid.
Cameron-Smith, D; Ghasemi Fard, S; Sinclair, AJ, 2021
)
2.54
"Docosapentaenoic acid (DPA) is a long-chain n-3 polyunsaturated fatty acid that is intermediary between eicosapentaenoic acid and docosahexaenoic acid in the n-3 synthesis pathway. "( Short update on docosapentaenoic acid: a bioactive long-chain n-3 fatty acid.
Guo, XF; Kaur, G; Sinclair, AJ, 2016
)
2.22
"Docosapentaenoic acid (DPA) is a unique fatty acid that exists in two isomeric forms (n-3 and n-6), which differ in their physiological behaviors. "( LC/ESR/MS study of pH-dependent radical generation from 15-LOX-catalyzed DPA peroxidation.
Gu, Y; Kang, JX; Kelavkar, U; Law, B; Purwaha, P; Qian, SY; Wu, E, 2011
)
1.81

Bioavailability

ExcerptReferenceRelevance
" The objective of this work was to determine whether the source of dietary LC-PUFA affects the bioavailability in full-term infants."( The source of long-chain PUFA in formula supplements does not affect the fatty acid composition of plasma lipids in full-term infants.
Campoy, C; Castellote, AI; López-Sabater, MC; Rivero, M; Rodriguez-Palmero, M; Sala-Vila, A, 2004
)
0.32
" Unlike fish-sourced oils, the bioavailability of DHA from vegetarian-sourced (algal) oils has not been formally assessed."( Bioequivalence of Docosahexaenoic acid from different algal oils in capsules and in a DHA-fortified food.
Arterburn, LM; Bailey-Hall, E; Chung, G; Hamersley, J; Hoffman, JP; McCarthy, D; Oken, HA; Rom, D, 2007
)
0.34
"This randomized, single-blind, crossover trial assessed the bioavailability of eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), and docosapentaenoic acid (DPA) from two different sources, each examined over a 12h period following consumption of a single serving and after 2-weeks of daily supplementation."( Bioavailability of long chain omega-3 polyunsaturated fatty acids from phospholipid-rich herring roe oil in men and women with mildly elevated triacylglycerols.
Berger, A; Cook, CM; Hallaråker, H; Innis, SM; Kelley, KM; Maki, KC; Sanoshy, KD; Sæbø, PC, 2016
)
0.64

Dosage Studied

ExcerptRelevanceReference
" On D28, the patients were randomized into 2 groups: 18 received the drug (fish oil: 30% n-3 PUFA) and 19 received the placebo (olive oil containing only 1% of n-3 PUFA) at a daily dosage of 6 g (i."( Pilot study on n-3 polyunsaturated fatty acids in the treatment of human experimental gingivitis.
Campan, P; Duran, D; Planchand, PO, 1997
)
0.3
" Thus, on a per dosage basis, the total amounts of n-3 and n-6 end products accreted in plasma were considerably greater for C20 EFA precursors relative to C18."( In vivo conversion of 18- and 20-C essential fatty acids in rats using the multiple simultaneous stable isotope method.
Lin, YH; Salem, N, 2005
)
0.33
" Thus, a concentration of 1 mM of both indolamines was sufficient to inhibit in approximately 70% of the light emission in mitochondria, whereas a greater dosage of 10 times (10 mM) was necessary to produce the same effect in microsomes."( Relative efficacies of alpha-tocopherol, N-acetyl-serotonin, and melatonin in reducing non-enzymatic lipid peroxidation of rat testicular microsomes and mitochondria.
Catalá, A; Gavazza, M, 2009
)
0.35
" Although flax oil may decrease severity of illness in children and adolescents with bipolar disorder who have meaningful increases in serum EPA percent levels and/or decreased AA and DPA n-6 levels, individual variations in conversion of alpha-LNA to EPA and docosahexaenoic acid as well as dosing burden favor the use of fish oil both for clinical trials and clinical practice."( Randomized, placebo-controlled trial of flax oil in pediatric bipolar disorder.
Chirieac, MC; Costescu, S; Finucane, TL; Gracious, BL; Hibbeln, JR; Youngstrom, EA, 2010
)
0.36
" In addition, the reproductive system may be more sensitive to exposure of CTD even earlier in development (prenatal and early postnatal), and therefore it could be expected that more severe effects could also be observed at the NOAEL dose levels, if dosing had occurred in utero or early postnatal."( Effects of clothianidin exposure on sperm quality, testicular apoptosis and fatty acid composition in developing male rats.
Bal, R; Baydaş, G; Etem, E; Kuloğlu, T; Naziroğlu, M; Türk, G; Yılmaz, Ö, 2012
)
0.38
" We also characterized the dose-response effects of n-3 fatty acid supplementation on RBC n-3 DPA after five months of supplementation with fish oil (Study 1: 0, 300, 600, 900, and 1800 mg/day EPA + DHA) and eight weeks of prescription n-3 ethyl esters (Study 2: 0, 850, and 3400 mg/day EPA + DHA)."( Red Blood Cell Docosapentaenoic Acid (DPA n-3) is Inversely Associated with Triglycerides and C-reactive Protein (CRP) in Healthy Adults and Dose-Dependently Increases Following n-3 Fatty Acid Supplementation.
Flock, MR; Harris, WS; Kris-Etherton, PM; Richter, CK; Skulas-Ray, AC; West, SG, 2015
)
0.77
" Future research will include better identification of the determinants of variation of responses to increased intake of EPA and DHA; more in-depth dose-response studies of the effects of EPA and DHA; clearer identification of the specific roles of EPA, docosapentaenoic acid and DHA; testing strategies to enhance delivery of n-3 fatty acids to the bloodstream; and exploration of sustainable alternatives to fish-derived very long-chain n-3 fatty acids."( Very long-chain n-3 fatty acids and human health: fact, fiction and the future.
Calder, PC, 2018
)
0.66
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
algal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
docosapentaenoic acidAny straight-chain, C22 fatty acid having five C=C double bonds.
omega-3 fatty acidA family of polyunsaturated fatty acids that have in common a final carbon-carbon double bond in the omega-3 position, i.e., the third bond from the methyl end of the fatty acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (3)

PathwayProteinsCompounds
Alpha Linolenic Acid and Linoleic Acid Metabolism517
Omega-3 / omega-6 fatty acid synthesis038
Elongation of (very) long chain fatty acids345

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
phosphopantetheinyl transferaseBacillus subtilisPotency0.39810.141337.9142100.0000AID1490
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency39.81070.011212.4002100.0000AID1030
regulator of G-protein signaling 4Homo sapiens (human)Potency21.19230.531815.435837.6858AID504845
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency3.98110.035520.977089.1251AID504332
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency79.43280.354828.065989.1251AID504847
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AromataseHomo sapiens (human)IC50 (µMol)16.80000.00001.290410.0000AID376617
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (15)

Processvia Protein(s)Taxonomy
negative regulation of chronic inflammatory responseAromataseHomo sapiens (human)
steroid biosynthetic processAromataseHomo sapiens (human)
estrogen biosynthetic processAromataseHomo sapiens (human)
androgen catabolic processAromataseHomo sapiens (human)
syncytium formationAromataseHomo sapiens (human)
negative regulation of macrophage chemotaxisAromataseHomo sapiens (human)
sterol metabolic processAromataseHomo sapiens (human)
female genitalia developmentAromataseHomo sapiens (human)
mammary gland developmentAromataseHomo sapiens (human)
uterus developmentAromataseHomo sapiens (human)
prostate gland growthAromataseHomo sapiens (human)
testosterone biosynthetic processAromataseHomo sapiens (human)
positive regulation of estradiol secretionAromataseHomo sapiens (human)
female gonad developmentAromataseHomo sapiens (human)
response to estradiolAromataseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
iron ion bindingAromataseHomo sapiens (human)
steroid hydroxylase activityAromataseHomo sapiens (human)
electron transfer activityAromataseHomo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenAromataseHomo sapiens (human)
oxygen bindingAromataseHomo sapiens (human)
heme bindingAromataseHomo sapiens (human)
aromatase activityAromataseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
endoplasmic reticulumAromataseHomo sapiens (human)
endoplasmic reticulum membraneAromataseHomo sapiens (human)
membraneAromataseHomo sapiens (human)
endoplasmic reticulumAromataseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID376618Inhibition of aromatase in human SKBR3 cells at 100 uM relative to control2006Journal of natural products, Apr, Volume: 69, Issue:4
Interference by naturally occurring fatty acids in a noncellular enzyme-based aromatase bioassay.
AID376617Inhibition of aromatase in human placental microsomes by radiometric method2006Journal of natural products, Apr, Volume: 69, Issue:4
Interference by naturally occurring fatty acids in a noncellular enzyme-based aromatase bioassay.
AID376615Inhibition of aromatase in human placental microsomes at 20 ug/ml by radiometric method relative to control2006Journal of natural products, Apr, Volume: 69, Issue:4
Interference by naturally occurring fatty acids in a noncellular enzyme-based aromatase bioassay.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (406)

TimeframeStudies, This Drug (%)All Drugs %
pre-199019 (4.68)18.7374
1990's44 (10.84)18.2507
2000's95 (23.40)29.6817
2010's201 (49.51)24.3611
2020's47 (11.58)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 45.73

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index45.73 (24.57)
Research Supply Index6.15 (2.92)
Research Growth Index5.07 (4.65)
Search Engine Demand Index72.70 (26.88)
Search Engine Supply Index2.07 (0.95)

This Compound (45.73)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials53 (12.71%)5.53%
Reviews27 (6.47%)6.00%
Case Studies0 (0.00%)4.05%
Observational4 (0.96%)0.25%
Other333 (79.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]