Prostaglandin I2 (CED0002604)

Record Information
Version1.0
Creation Date2016-05-26 05:33:01 UTC
Update Date2026-05-14 16:59:02 UTC
Accession NumberCHEM035175
Identification
Common NameProstaglandin I2
ClassSmall Molecule
Description
Prostaglandin I2 is an organic compound with the formula C20H32O5 and an average molecular weight of 352.47 g/mol. Prostaglandin I2 belongs to the eicosanoids, a subclass of fatty acyls within the organic compounds. It is classified under the superclass of lipids and lipid-like molecules. The compound is found in or released from healthcare, pharmaceuticals, and veterinary products, specifically as antithrombotic agents, and is administered via intravenous exposure. Prostaglandin I2 interacts with three recorded protein targets: the prostacyclin receptor (PTGIR), prostacyclin synthase (PTGIS), and the P2Y purinoceptor 12 (P2RY12), for which it acts as an agonist or inducer.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoateChEBI
(5Z,9alpha,11alpha,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acidChEBI
EpoprostenolChEBI
FlolanChEBI
PGI2ChEBI
PGXChEBI
ProstacyclinChEBI
Prostaglandin XChEBI
VasocyclinChEBI
(5Z,13E)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-6,9Α-epoxy-11α,15-dihydroxyprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-6,9Α-epoxy-11α,15-dihydroxyprosta-5,13-dienoic acidGenerator
(5Z,9a,11a,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-OateGenerator
(5Z,9a,11a,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acidGenerator
(5Z,9alpha,11alpha,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-OateGenerator
(5Z,9Α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-OateGenerator
(5Z,9Α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acidGenerator
(5Z,13E)-(15S)-6,9-alpha-Epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoateHMDB
(5Z,13E)-(15S)-6,9-alpha-Epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoic acidHMDB
(5Z,13E)-(15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dienoateHMDB
(5Z,13E)-(15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dienoic acidHMDB
(5Z,13E,15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoateHMDB
(5Z,13E,15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoic acidHMDB
ProstacyclineHMDB
EpoprostanolHMDB
Epoprostenol sodiumHMDB
Epoprostenol sodium salt, (5Z,9alpha,11alpha,13E,15S)-isomerHMDB
Prostaglandin I(2)HMDB
VeletriMeSH
Chemical FormulaC20H32O5
Average Molecular Mass352.465 g/mol
Monoisotopic Mass352.225 g/mol
CAS Registry Number35121-78-9
IUPAC Name5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid
Traditional Nameepoprostenol
SMILESCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=O
InChI IdentifierInChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1
InChI KeyKAQKFAOMNZTLHT-OZUDYXHBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Fatty alcohol
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Cyclic alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP3.83ALOGPS
logP2.42ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.43ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity99.01 m³·mol⁻¹ChemAxon
Polarizability41.47 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0159-5693000000-d4cdd32893c86bb9479aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0ug0-9253570000-9f0d8bdb642b0c32f40bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0029000000-6c6186798558c5d1611fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00y0-1093000000-eacafc8768142dba71daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00du-9450000000-e3b550dcd32e28648707Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-34a4a3eaa1abb59e8245Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-2139000000-efe90037816a750cfeeeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a59-9871000000-f961005fef0ef2363ce4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-39b83b5b9b932bb2f6a1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-0089000000-7141693b6303cf4e2e29Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003s-2391000000-22e55e30c5e2afce8cc2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0009000000-fcc9a31a4c60d564196fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-6359000000-d638f048af6abdb45cbfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05tf-9610000000-8baf1f1acd84f0ed7ba8Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
626.0Log mg/kg[350:1100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
273Antithrombotic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
1 pathway
Epoprostenol Drug Metabolism Action Pathway
Epoprostenol Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSolute carrier organic anion transporter family member 2B1Q9JHI3Rattus norvegicusPredicted (SEA)0.0778492
Prostacyclin receptor structureClick to view 3D structureProstacyclin receptorP43119HumansPredicted (SEA)1.55698
Click to view 3D structureSolute carrier organic anion transporter family member 2A1Q9EPT5Mus musculusPredicted (SEA)0.155698
Prostaglandin E2 receptor EP2 subtype structureClick to view 3D structureProstaglandin E2 receptor EP2 subtypeP43116HumansPredicted (SEA)1.55698
Prostaglandin E2 receptor EP4 subtype structureClick to view 3D structureProstaglandin E2 receptor EP4 subtypeP35408HumansPredicted (SEA)0.934191
Click to view 3D structureProstaglandin E2 receptor EP1 subtypeP35375Mus musculusPredicted (SEA)2.17978
Click to view 3D structureProstaglandin E2 receptor EP3 subtypeP30557Mus musculusPredicted (SEA)2.72472
Click to view 3D structureProstaglandin E2 receptor EP4 subtypeP32240Mus musculusPredicted (SEA)2.33548
Click to view 3D structureProstaglandin E2 receptor EP2 subtypeQ62053Mus musculusPredicted (SEA)2.02408
Prostaglandin E2 receptor EP3 subtype structureClick to view 3D structureProstaglandin E2 receptor EP3 subtypeP43115HumansPredicted (SEA)3.11397
Prostaglandin F2-alpha receptor structureClick to view 3D structureProstaglandin F2-alpha receptorP43088HumansPredicted (SEA)3.81461
Click to view 3D structureNuclear receptor subfamily 4 group A member 2Q07917Rattus norvegicusPredicted (SEA)0.311397
Click to view 3D structureProstaglandin E2 receptor EP1 subtypeP34995HumansPredicted (SEA)4.51525
Solute carrier organic anion transporter family member 2A1 structureClick to view 3D structureSolute carrier organic anion transporter family member 2A1Q92959HumansPredicted (SEA)0.467095
Click to view 3D structureProstaglandin D2 receptorQ13258HumansPredicted (SEA)7.94062
Click to view 3D structureProstaglandin E2 receptor EP4 subtypeP43114Rattus norvegicusPredicted (SEA)1.79053
Click to view 3D structureProstaglandin E2 receptor EP2 subtypeQ62928Rattus norvegicusPredicted (SEA)1.40129
Click to view 3D structureProstaglandin F2-alpha receptorP37289Bos taurusPredicted (SEA)0.622794
Thromboxane A2 receptor structureClick to view 3D structureThromboxane A2 receptorP21731HumansPredicted (SEA)13.5458
Click to view 3D structureProstaglandin F2-alpha receptorP43117Mus musculusPredicted (SEA)1.24559
Click to view 3D structureProstaglandin E2 receptor EP4 subtypeQ28691Oryctolagus cuniculusPredicted (SEA)0.0778492
Click to view 3D structureSolute carrier organic anion transporter family member 2A1Q00910Rattus norvegicusPredicted (SEA)0.0778492
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)93.4191
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)127.206
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)85.7898
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0001335
FooDB IDFDB022560
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID37333
BioCyc IDNot Available
METLIN ID778
PDB IDNot Available
Wikipedia LinkProstacyclin
Chemspider ID4445566
ChEBI ID15552
PubChem Compound ID5282411
Kegg Compound IDC01312
YMDB IDNot Available
ECMDB IDM2MDB005560
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Walsh SW, Wang Y, Killian A: AA-2414, an antioxidant and thromboxane receptor blocker, completely inhibits peroxide-induced vasoconstriction in the human placenta. J Pharmacol Exp Ther. 1999 Jul;290(1):220-6.
2. Brinkmann A, Seeling W, Wolf CF, Kneitinger E, Junger S, Rockemann M, Oettinger W, Georgieff M: [The effect of thoracic epidural anesthesia on the pathophysiology of the eventration syndrome]. Anaesthesist. 1994 Apr;43(4):235-44.
3. Kearney D, Byrne A, Crean P, Cox D, Fitzgerald DJ: Optimal suppression of thromboxane A(2) formation by aspirin during percutaneous transluminal coronary angioplasty: no additional effect of a selective cyclooxygenase-2 inhibitor. J Am Coll Cardiol. 2004 Feb 18;43(4):526-31.
4. De La Cruz JP, Arrebola MM, Villalobos MA, Pinacho A, Guerrero A, Gonzalez-Correa JA, Sanchez de la Cuesta F: Influence of glucose concentration on the effects of aspirin, ticlopidine and clopidogrel on platelet function and platelet-subendothelium interaction. Eur J Pharmacol. 2004 Jan 19;484(1):19-27.
5. Cruz-Gervis R, Stecenko AA, Dworski R, Lane KB, Loyd JE, Pierson R, King G, Brigham KL: Altered prostanoid production by fibroblasts cultured from the lungs of human subjects with idiopathic pulmonary fibrosis. Respir Res. 2002;3:17. Epub 2002 Feb 23.
6. den Dekker E, Gorter G, Heemskerk JW, Akkerman JW: Development of platelet inhibition by cAMP during megakaryocytopoiesis. J Biol Chem. 2002 Aug 9;277(32):29321-9. Epub 2002 May 7.
7. McAdam BF, Byrne D, Morrow JD, Oates JA: Contribution of cyclooxygenase-2 to elevated biosynthesis of thromboxane A2 and prostacyclin in cigarette smokers. Circulation. 2005 Aug 16;112(7):1024-9. Epub 2005 Aug 8.
8. Hei ZQ, Huang HQ, Luo CF, Li SR, Luo GJ: Changes of nitric oxide and endothelin, thromboxane A2 and prostaglandin in cirrhotic patients undergoing liver transplantation. World J Gastroenterol. 2006 Jul 7;12(25):4049-51.
9. Nadar S, Lip GY: Platelet activation in the hypertensive disorders of pregnancy. Expert Opin Investig Drugs. 2004 May;13(5):523-9.
10. Fruzzetti F, Giannessi D, Ricci C, Bernini W, Puntoni R, Genazzani AR, De Caterina R: Platelet-vessel wall interactions with third-generation oral contraceptives: no evidence of detrimental effects. Thromb Haemost. 1999 Sep;82(3):1164-70.
11. Cheng Y, Austin SC, Rocca B, Koller BH, Coffman TM, Grosser T, Lawson JA, FitzGerald GA: Role of prostacyclin in the cardiovascular response to thromboxane A2. Science. 2002 Apr 19;296(5567):539-41.
12. Okamoto M, Abe T, Shouno M, Kitabata Y, Narukawa N, Kobata H, Akizawa T: A case of thrombotic thrombocytopenic purpura refractory to plasma exchange. Ther Apher. 2001 Feb;5(1):49-53.
13. Li J, Dai G, Feng Z, Wang C, Yang Y, Wei W, Zhou B: Effect of low HDL combined with hypertriglyceridemia in coronary artery disease patients on PGI2 biological activity in relation to lipid regulating treatment. J Tongji Med Univ. 1998;18(2):87-9, 93.
14. Vassaux G, Gaillard D, Darimont C, Ailhaud G, Negrel R: Differential response of preadipocytes and adipocytes to prostacyclin and prostaglandin E2: physiological implications. Endocrinology. 1992 Nov;131(5):2393-8.
15. Haraldsson A, Kieler-Jensen N, Wadenvik H, Ricksten SE: Inhaled prostacyclin and platelet function after cardiac surgery and cardiopulmonary bypass. Intensive Care Med. 2000 Feb;26(2):188-94.
16. Axelrod L: Insulin, prostaglandins, and the pathogenesis of hypertension. Diabetes. 1991 Oct;40(10):1223-7.
17. Lehmann C, Taymoorian K, Wauer H, Krausch D, Birnbaum J, Kox WJ: Effects of the stable prostacyclin analogue iloprost on the plasma disappearance rate of indocyanine green in human septic shock. Intensive Care Med. 2000 Oct;26(10):1557-60.
18. Dickinson JE, Meyer BA, Brath PC, Chmielowiec S, Walsh SW, Parisi VM, Palmer SM: Placental thromboxane and prostacyclin production in an ovine diabetic model. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 1):1831-5.
19. Watanabe T, Kishi Y, Numano F, Isobe M: Enhanced platelet sensitivity to prostacyclin in patients in an active stage of Takayasu arteritis. Thromb Res. 2001 Oct 15;104(2):77-83.
20. Harada N, Okajima K, Yuksel M, Isobe H: Contribution of capsaicin-sensitive sensory neurons to antithrombin-induced reduction of ischemia/reperfusion-induced liver injury in rats. Thromb Haemost. 2005 Jan;93(1):48-56.