Prostaglandin G2

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Prostaglandin G2

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Prostaglandin G₂
Names

IUPAC name (5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-Hydroperoxy-1-octen-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}-5-heptenoic acid
Identifiers
CAS Number	51982-36-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27647
ChemSpider	4444406
EC Number	200-662-2
KEGG	C05956
PubChem CID	5280883
UNII	AZ87DUD2Y8^Y
CompTox Dashboard (EPA)	DTXSID00866229
InChI InChI=1S/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1 Key: SGUKUZOVHSFKPH-YNNPMVKQSA-N InChI=1/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1 Key: SGUKUZOVHSFKPH-YNNPMVKQBO
SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H]2C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)OO2)OO
Properties
Chemical formula	C₂₀H₃₂O₆
Molar mass	368.470 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Prostaglandin G₂ (PGG₂) is an organic peroxide belonging to the family of prostaglandins.^[1] The compound has been isolated as a solid, although it is usually used in vivo. It quickly converts into prostaglandin H₂, a process catalyzed by the enzyme cyclooxygenase (COX).

Prostaglandin G₂ is produced from the fatty acid arachidonic acid. The reaction, a double oxygenation, requires the enzyme COX, which inserts two molecules of O₂ into the C-H bonds of the substrate acid.^[2]^[1]^[3]

References

[edit]

^ ^a ^b Wilfred van der Donk; Tsai Ah-Lim; Kulmacz Richard J. (2002). "The cyclooxygenase reaction mechanism". Biochemistry. 41 (52): 15451–8. doi:10.1021/bi026938h. PMID 12501173.
^ Rouzer, Carol A.; Marnett, Lawrence J. (2003). "Mechanism of Free Radical Oxygenation of Polyunsaturated Fatty Acids by Cyclooxygenases". Chemical Reviews. 103 (6): 2239–2304. doi:10.1021/cr000068x. PMID 12797830.
^ "Prostaglandin G2". Santa cruz biotechnology, inc. Retrieved 27 April 2015.

Prostanoid signaling modulators

Receptor
(ligands)

DP (D₂)

DP₁Tooltip Prostaglandin D2 receptor 1	Agonists: Prostaglandin D₂ Treprostinil Antagonists: Asapiprant Laropiprant Vidupiprant
DP₂Tooltip Prostaglandin D2 receptor 2	Agonists: Indometacin Prostaglandin D₂ Antagonists: ADC-3680 AZD-1981 Bay U3405 Fevipiprant MK-1029 MK-7246 QAV-680 Ramatroban Setipiprant Timapiprant TM30089 Vidupiprant

EP (E₂)

EP₁Tooltip Prostaglandin EP1 receptor	Agonists: Beraprost Enprostil Iloprost (ciloprost) Latanoprost Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Sulprostone Antagonists: AH-6809 ONO-8130 SC-19220 SC-51089 SC-51322
EP₂Tooltip Prostaglandin EP2 receptor	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155
EP₃Tooltip Prostaglandin EP3 receptor	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Ricinoleic acid Sulprostone Antagonists: L-798106
EP₄Tooltip Prostaglandin EP4 receptor	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: Grapiprant GW-627368 L-161982 ONO-AE3-208
Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)

IP (I₂)

Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I₂, epoprostenol)
Prostaglandin E₁ (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil

Antagonists: RO1138452

TP (TX_A2)

Agonists: Carbocyclic thromboxane A₂
I-BOP
Thromboxane A₂
U-46619
Vapiprost

Unsorted

Enzyme
(inhibitors)

COX (PTGS)	Salicylic acids: Aloxiprin Aspirin (acetylsalicylic acid) Benorilate (benorylate) Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine (5-aminosalicylic acid) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate (salicylic acid) Salsalate Sodium salicylate Triflusal; Acetic acids: Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin (indomethacin) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac; Propionic acids: Alminoprofen Benoxaprofen Bucloxic acid (blucloxate) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid (tiaprofenate) Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate) Floctafenic acid (floctafenate) Flufenamic acid (flufenamate) Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Morniflumic acid (morniflumate) Niflumic acid (niflumate) Talinflumic acid (talinflumate) Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone; Enolic acids (oxicams): Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam; 4-Aminoquinolines: Antrafenine Floctafenine Glafenine; Quinazolines: Fluproquazone Proquazone; Aminonicotinic acids: Clonixeril Clonixin Flunixin; Sulfonanilides: Flosulide Nimesulide; Aminophenols (anilines): Acetanilide AM-404 (N-arachidonoylaminophenol) Bucetin Paracetamol (acetaminophen) Parapropamol Phenacetin Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib; Others/unsorted: Anitrazafen Clobuzarit Curcumin DuP-697 FK-3311 Flumizole FR-122047 Glimepiride Hyperforin Itazigrel L-655240 L-670596 Licofelone Menatetrenone (vitamin K₂) NCX-466 NCX-4040 NS-398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC-236 SC-560 SC-58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin
PGD₂STooltip Prostaglandin D synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
PGESTooltip Prostaglandin E synthase	HQL-79
PGFSTooltip Prostaglandin F synthase	Bimatoprost
PGI₂STooltip Prostacyclin synthase	Tranylcypromine
TXASTooltip Thromboxane A synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Receptor/signaling modulators; Leukotriene signaling modulators

Aryl hydrocarbon receptor modulators

AhR

Agonists: Arachidonic acid metabolites (e.g., lipoxin A4, prostaglandin G2)
Dietary carotenoids
Flutamide
Halogenated aromatic hydrocarbons (e.g., polychlorinated dibenzodioxins (e.g., TCDD), dibenzofurans, biphenyls)
ΙΤΕ
Modified low-density lipoproteins
Polycyclic aromatic hydrocarbons (e.g., 3-methylcholanthrene, benzo[a]pyrene, benzanthracenes, benzoflavones (e.g., β-naphthoflavone))
Tapinarof (benvitimod)
Tetrapyrroles (e.g., bilirubin)
Tryptophan derivatives (e.g., indigo dye, indirubin)

See also: Receptor/signaling modulators

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