Classification Term: 168156

Isoprostanes [FA0311] (ontology term: 9b4795e201efa4a6967d6a0cf230e615)

Isoprostanes [FA0311]

found 29 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Eicosanoids [FA03]

Child Taxonomies: There is no child term of current ontology term.

8-Isoprostaglandin F2a

(5Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

C20H34O5 (354.24061140000003)


8-Isoprostaglandin F2a is an isoprostane and a potent renal vasoconstrictor. Isoprostanes are prostaglandin-like compounds that are produced in vivo in humans by a noncyclooxygenase mechanism involving free radical-catalyzed peroxidation of arachidonic acid. The formation of these prostanoids proceeds through bicyclic endoperoxide intermediates that are then reduced to form ring isoprostanes. Of considerable interest is that, in contradistinction to cyclooxygenase-derived prostaglandins, isoprostanes have been shown to be initially formed in situ, esterified to phospholipids, and subsequently released preformed, presumably by phospholipases. The fact that prostanoids are produced in vivo by a noncyclooxygenase mechanism is of considerable interest from a biochemical perspective. However, this may also be associated with biological ramifications since it has been shown that these compounds are capable of exerting potent biological activity. (PMID: 7825845, 17012140). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 8-iso-prostaglandin F2A is a biomarker for the consumption of offal meat. 8-Isoprostaglandin F2a is an isoprostane and a potent renal vasoconstrictor. Isoprostanes are prostaglandin-like compounds that are produced in vivo in humans by a noncyclooxygenase mechanism involving free radical-catalyzed peroxidation of arachidonic acid. The formation of these prostanoids proceeds through bicyclic endoperoxide intermediates that are then reduced to form ring isoprostanes. Of considerable interest is that, in contradistinction to cyclooxygenase-derived prostaglandins, isoprostanes have been shown to be initially formed in situ, esterified to phospholipids, and subsequently released preformed, presumably by phospholipases. The fact that prostanoids are produced in vivo by a noncyclooxygenase mechanism is of considerable interest from a biochemical perspective. However, this may also be associated with biological ramifications since it has been shown that these compounds are capable of exerting potent biological activity. (PMID: 7825845, 17012140). 8-iso-prostaglandin F2A is a biomarker for the consumption of offal meat. D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents

   

8-iso-PGE1

9-oxo-11R,15S-dihydroxy-13E-prostaenoic acid-cyclo[8S,12R]

C20H34O5 (354.24061140000003)


   

8-iso-PGF2alpha III-EA

N-([8S,12R]9S,11R,15S-trihydroxy-5Z,13E-prostadienoyl)-ethanolamine

C22H39NO5 (397.2828084)


   

5-F2t-IsoP

5S,9S,11R-trihydroxy-6E,14Z-prostadienoic acid-cyclo[8S,12R]

C20H34O5 (354.24061140000003)


   

8-F2t-IsoP

8S,12S,14R-trihydroxy-5Z,9E-prostadienoic acid-cyclo[11S,15R]

C20H34O5 (354.24061140000003)


   

8-D2c-IsoP

8S,12S-dihydroxy-14-oxo-5Z,9E-prostadienoic acid-cyclo[11R,15S]

C20H32O5 (352.2249622)


   

8-D2t-IsoP

8S,12S-dihydroxy-14-oxo-5Z,9E-prostadienoic acid-cyclo[11S,15R]

C20H32O5 (352.2249622)


   

8-J2-IsoP

8S-hydroxy-14-oxo-5Z,9E,12-prostatrienoic acid-cyclo[11R,15S]

C20H30O4 (334.214398)


   

5-D2t-IsoP

5S,9S-dihydroxy-11-oxo-6E,14Z-prostadienoic acid-cyclo[8S,12R]

C20H32O5 (352.2249622)


   

5-J2-IsoP

5S-hydroxy-11-oxo-6E,14Z,12-prostatrienoic acid-cyclo[8R,12S]

C20H30O4 (334.214398)


   

15-J2-IsoP

15S-hydroxy-11-oxo-5Z,9,13E-prostatrienoic acid-cyclo[8S,12S]

C20H30O4 (334.214398)


   

ent-PGE2

9-oxo-11S,15R-dihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12S]

C20H32O5 (352.2249622)


   

ent-PGD2

9R,15R-dihydroxy-11-oxo-5Z,13E-prostadienoic acid-cyclo[8S,12S]

C20H32O5 (352.2249622)


   

FA 20:4;O3

4-((1S,2S,5R)-5-hydroxy-2-((S,1E,5Z)-3-hydroxyundeca-1,5-dien-1-yl)-3-oxocyclopentyl)butanoic acid

C20H32O5 (352.2249622)


D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents

   

FA 18:3;O3

8-((1R,2S,3S)-3-hydroxy-2-((R,E)-3-hydroxypent-1-en-1-yl)-5-oxocyclopentyl)octanoic acid

C18H30O5 (326.209313)


   

FA 20:5;O2

4-((1R,5S)-5-((R,1E,5Z)-3-hydroxyundeca-1,5-dien-1-yl)-4-oxocyclopent-2-en-1-yl)butanoic acid

C20H30O4 (334.214398)


An oxylipin that is the (5S,6S)-epoxy-(15S)-hydroxy derivative of 7E,9E,11Z,13E-icosa-7,9,11,13-tetraenoic acid. D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000970 - Antineoplastic Agents

   

FA 20:4;O2

(5S,12R,6E,8Z,10E,14Z)-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid;(5S,6E,8Z,10E,12R,14Z)-5,12-dihydroxyeicosa-6,8,10,14-tetraenoic acid;(6E,8Z)-LTB4;5(S),12(R)-dihydroxy-6(E),8(Z),10(E),14(Z)-eicosatetraenoic acid;5(S),12(R)-dihydroxy-6(E),8(Z),10(E),14(Z)-icosatetraenoic acid;Delta(6)-trans,Delta(8)-cis-LTB4

C20H32O4 (336.2300472)


   

FA 20:6;O

9-oxo-5E,10Z,14Z-prostatrienoic acid-1,4R-lactone-cyclo[8S,12R]

C20H28O3 (316.2038338)


D007155 - Immunologic Factors

   

FA 20:3;O3

7-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid

C20H34O5 (354.24061140000003)


D012102 - Reproductive Control Agents > D000019 - Abortifacient Agents D012102 - Reproductive Control Agents > D010120 - Oxytocics

   

FA 20:5;O3

(5R,6E,8Z,10E,12E,14R,15R,17Z)-5,14,15-trihydroxyicosa-6,8,10,12,17-pentaenoic acid

C20H30O5 (350.209313)


   

FA 22:3;O3

1a,1b-dihomo-11S,13R,17S-trihydroxy-7Z,15E-prostadienoic acid-cyclo[10S,14R]

C22H38O5 (382.2719098)


   

FA 23:3;O3

1a,1b-dihomo-8,12,14-trihydroxy-5Z,9E-prostadienoic acid-cyclo[11,15]

C23H40O5 (396.28755900000004)


   

iPF2alpha-I

5,9S,11R-trihydroxy-6E,14Z-prostadienoic acid-cyclo[8S,12R]

C20H34O5 (354.24061140000003)


   

(+/-) 5-iPF2alpha-VI-(d11)

5,9S,11R-trihydroxy-6E,14Z-prostadienoic acid-cyclo[8S,12R]-(d11)

C20H23D11O5 (365.30966035800003)


   

5-E2t-IsoP

(S,E)-5-hydroxy-7-((1S,2R,3R)-3-hydroxy-2-((Z)-oct-2-en-1-yl)-5-oxocyclopentyl)hept-6-enoic acid

C20H32O5 (352.2249622)


   

12-A2-IsoP

4-((1R,2R)-2-((S,1E,5Z)-3-hydroxyundeca-1,5-dien-1-yl)-5-oxocyclopent-3-en-1-yl)butanoic acid

C20H30O4 (334.214398)


   

5-A2-IsoP

(S,E)-5-hydroxy-7-((1R,2R)-2-((Z)-oct-2-en-1-yl)-5-oxocyclopent-3-en-1-yl)hept-6-enoic acid

C20H30O4 (334.214398)


   

8-A2-IsoP

(S,5Z,9E)-8-hydroxy-10-((1R,5R)-2-oxo-5-pentylcyclopent-3-en-1-yl)deca-5,9-dienoic acid

C20H30O4 (334.214398)


   

8-Isoprostane

9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acid

C20H34O5 (354.24061140000003)


A prostanoid that is prostaglandin F2alpha having inverted stereochemistry at the 8-position. D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents