Page last updated: 2024-11-04

arachidonic acid 5-hydroperoxide

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

Description

5(S)-HPETE : An icosatetraenoic acid in which the double bonds are located at the 6-7, 8-9, 11-12, and 14-15 positions and have E, Z, Z, and Z geometry, respectively, and in which the pro-S hydrogen is substituted by a hydroperoxy group. [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]

arachidonic acid 5-hydroperoxide: 5-HPETE is used inconsistently in literature as syn for cpds with various tetraene locants; RN given refers to (6,8,11,14)-isomer; RN in CA Vol 91 Form Index for (E,Z,Z,Z)-isomer: 70968-82-0; RN for (5,8,11,13)-isomer: 71133-12-5; in Merck, arachidonic acid is the (5,8,11,14)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5-HPETE : A HPETE that consists of (6E,8Z,11Z,14Z)-icosatetraenoic acid in which the hydroperoxy group is located at position 5. [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 CID5280778
CHEMBL ID1743204
CHEBI ID15632
SCHEMBL ID1394974
MeSH IDM0084579
PubMed CID5283171
CHEBI ID91268
SCHEMBL ID3903801
MeSH IDM0084579

Synonyms (64)

Synonym
(s)-5-hpete
5(s)-hydroperoxy-6(e),8(z),11(z),14(z)-eicosatetraenoic acid
(5s,6e,8z,11z,14z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid
(5s,6e,8z,11z,14z)-5-hydroperoxyeicosa-6,8,11,14-tetraenoic acid
71774-08-8
5(s)-hydroxyperoxy-6e,8z,11z,14z-icosatetraenoic acid
5s-hpete
CHEBI:15632 ,
5-hydroperoxy-6,8,11,14-eicosatetraenoic acid
6,8,11,14-eicosatetraenoic acid, 5-hydroperoxy-, (s-(e,z,z,z))-
5(s)-hydroperoxyeicosatetraenoic acid
BSPBIO_001445
LMFA03060012
5s-hydroperoxy-6e,8z,11z,14z-eicosatetraenoic acid
(6e,8z,11z,14z)-(5s)-5-hydroperoxyeicosa-6,8,11,14-tetraenoic acid
C05356
5(s)-hpete
5(s)-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid
(6e,8z,11z,14z)-(5s)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
NCGC00161249-01
NCGC00161249-02
IDI1_033915
NCGC00161249-03
5-(s)-hydroperoxyeicosatetraenoic acid
gtpl2483
HMS1989I07
BML1-C04
HMS1791I07
HMS1361I07
CHEMBL1743204
6,8,11,14-eicosatetraenoicacid, 5-hydroperoxy-, (5s,6e,8z,11z,14z)-
SCHEMBL1394974
JNUUNUQHXIOFDA-JGKLHWIESA-N
HMS3402I07
(5s)-5-hydroperoxy-(e,z,z,z)-6,8,11,14-eicosatetraenoic acid
5-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid
5-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate
Q2823231
sr-01000946955
SR-01000946955-1
DTXSID701017279
(5s,6e,8z,11z,14z)-5-hydroperoxy-6,8,11,14-eicosatetraenoic acid
HY-125770
5(s)?-?hpete
CS-0099281
5(s)-hpete lipid maps(r) ms standard
AKOS040758309
5-hpete
arachidonic acid 5-hydroperoxide
6,8,11,14-eicosatetraenoic acid 5-hydroperoxide
74581-83-2
6,8,11,14-eicosatetraenoic acid, 5-hydroperoxy-
cis,trans-5-hydroperoxy-6,8,11,14-eicosatetraenoic acid
(6e,8z,11z,14z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid
SCHEMBL3903801
5-hydroperoxy-(6e,8z,11z,14z)-eicosatetraenoic acid
(6e,8z,11z,14z)-5-hydroperoxyicosatetraenoic acid
CHEBI:91268
5-hydroperoxy-(6e,8z,11z,14z)-icosatetraenoic acid
5-hydroperoxyeicosa-6e,8z,1z1,14z-tetraenoic acid
(s,6e,8z,11z,)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid
LMFA03060108
5(s)-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate
Q27163174

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Dose-response studies indicated that 5-HPETE was a potent (IC25 = 10(-8) M) inhibitor of Na+, K(+)-ATPase activity."( 5-HPETE is a potent inhibitor of neuronal Na+, K(+)-ATPase activity.
Foley, TD, 1997
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human xenobiotic metaboliteAny human metabolite produced by metabolism of a xenobiotic compound in humans.
[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
5-HPETEA HPETE that consists of (6E,8Z,11Z,14Z)-icosatetraenoic acid in which the hydroperoxy group is located at position 5.
HPETEMono-hydroperoxy (e)icosatetraenoic acids (HPETEs) are the primary products of lipoxygenase-catalysed oxygenation of arachidonic 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 (59)

PathwayProteinsCompounds
Metabolism14961108
Metabolism of lipids500463
Fatty acid metabolism113203
Arachidonic acid metabolism3682
Synthesis of Leukotrienes (LT) and Eoxins (EX)1329
Synthesis of 5-eicosatetraenoic acids615
Biosynthesis of specialized proresolving mediators (SPMs)13107
Synthesis of Lipoxins (LX)616
Prostaglandin and Leukotriene metabolism ( Prostaglandin and Leukotriene metabolism )2223
Leukotriene metabolic pathway219
Folic acid network070
Eicosanoid metabolism via lipoxygenases (LOX)040
Selenium micronutrient network095
Eicosanoid synthesis026
Arachidonic Acid Metabolism2966
Leukotriene C4 Synthesis Deficiency2966
Piroxicam Action Pathway2967
Acetylsalicylic Acid Action Pathway2967
Etodolac Action Pathway2967
Ketoprofen Action Pathway2967
Ibuprofen Action Pathway5076
Rofecoxib Action Pathway2967
Diclofenac Action Pathway2967
Sulindac Action Pathway2967
Celecoxib Action Pathway3573
Ketorolac Action Pathway2967
Suprofen Action Pathway2967
Bromfenac Action Pathway2967
Indomethacin Action Pathway3067
Mefenamic Acid Action Pathway2967
Oxaprozin Action Pathway2967
Nabumetone Action Pathway2967
Naproxen Action Pathway2967
Diflunisal Action Pathway2967
Meloxicam Action Pathway2967
Valdecoxib Action Pathway2967
Antipyrine Action Pathway2967
Antrafenine Action Pathway2967
Carprofen Action Pathway2967
Etoricoxib Action Pathway2967
Fenoprofen Action Pathway2967
Flurbiprofen Action Pathway2967
Magnesium Salicylate Action Pathway2967
Lumiracoxib Action Pathway2967
Lornoxicam Action Pathway2967
Phenylbutazone Action Pathway2967
Nepafenac Action Pathway2967
Trisalicylate-Choline Action Pathway2967
Tolmetin Action Pathway2967
Tiaprofenic Acid Action Pathway2967
Tenoxicam Action Pathway2967
Salsalate Action Pathway2967
Salicylate-Sodium Action Pathway2967
Salicylic Acid Action Pathway2967
Acetaminophen Action Pathway2967
Metabolism of alpha-linolenic acid615
Eicosanoid metabolism via lipooxygenases (LOX)040
Prostaglandin and leukotriene metabolism in senescence619
Arachidonic acid (AA, ARA) oxylipin metabolism076
Relationship between glutathione and NADPH036

Protein Targets (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
regulator of G-protein signaling 4Homo sapiens (human)Potency8.43680.531815.435837.6858AID504845
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay IDTitleYearJournalArticle
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.
AID1346064Human OXE receptor (Leukotriene receptors)2005Biochemical and biophysical research communications, Sep-09, Volume: 334, Issue:4
TG1019/OXE, a Galpha(i/o)-protein-coupled receptor, mediates 5-oxo-eicosatetraenoic acid-induced chemotaxis.
AID1346643Rat TRPV1 (Transient Receptor Potential channels)2000Proceedings of the National Academy of Sciences of the United States of America, May-23, Volume: 97, Issue:11
Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (141)

TimeframeStudies, This Drug (%)All Drugs %
pre-199068 (48.23)18.7374
1990's49 (34.75)18.2507
2000's15 (10.64)29.6817
2010's6 (4.26)24.3611
2020's3 (2.13)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews10 (7.09%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
Other131 (92.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]