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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:50 UTC
HMDB IDHMDB0001335
Secondary Accession Numbers
  • HMDB01335
Metabolite Identification
Common NameProstaglandin I2
DescriptionProstaglandin I2 or prostacyclin (or PGI2) is a member of the family of lipid molecules known as eicosanoids. It is produced in endothelial cells from prostaglandin H2 (PGH2) by the action of the enzyme prostacyclin synthase. It is a powerful vasodilator and inhibits platelet aggregation. Prostaglandin I2 is the main prostaglandin synthesized by the blood vessel wall. This suggests that it may play an important role in limiting platelet-mediated thrombosis. In particular, prostacyclin (PGI2) chiefly prevents formation of the platelet plug involved in primary hemostasis (a part of blood clot formation). The sodium salt (known as epoprostenol) has been used to treat primary pulmonary hypertension. Prostacyclin (PGI2) is released by healthy endothelial cells and performs its function through a paracrine signaling cascade that involves G protein-coupled receptors on nearby platelets and endothelial cells. The platelet Gs protein-coupled receptor (prostacyclin receptor) is activated when it binds to PGI2. This activation, in turn, signals adenylyl cyclase to produce cAMP. cAMP goes on to inhibit any undue platelet activation (in order to promote circulation) and also counteracts any increase in cytosolic calcium levels which would result from thromboxane A2 (TXA2) binding (leading to platelet activation and subsequent coagulation). PGI2 also binds to endothelial prostacyclin receptors and in the same manner raise cAMP levels in the cytosol. This cAMP then goes on to activate protein kinase A (PKA). PKA then continues the cascade by inhibiting myosin light-chain kinase which leads to smooth muscle relaxation and vasodilation. Notably, PGI2 and TXA2 work as antagonists. PGI2 is stable in basic buffers (pH=8), but it is rapidly hydrolyzed to 6-keto PGF1alpha in neutral or acidic solutions. The half-life is short both in vivo and in vitro, ranging from 30 seconds to a few minutes. PGI2 is administered by continuous infusion in humans for the treatment of idiopathic pulmonary hypertension.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 signaling pathways.
Structure
Thumb
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
EpoprostanolMeSH
Epoprostenol sodiumMeSH
Epoprostenol sodium salt, (5Z,9alpha,11alpha,13E,15S)-isomerMeSH
Prostaglandin I(2)MeSH
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
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
CAS Registry Number35121-78-9
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=O
InChI Identifier
InChI=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
DescriptionThis compound 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 DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

  Cell and elements:

    Cell:

    Element:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-5693000000-d4cdd32893c86bb9479aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ug0-9253570000-9f0d8bdb642b0c32f40bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0029000000-6c6186798558c5d1611fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-1093000000-eacafc8768142dba71daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00du-9450000000-e3b550dcd32e28648707View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-34a4a3eaa1abb59e8245View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-2139000000-efe90037816a750cfeeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9871000000-f961005fef0ef2363ce4View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid LocationsNot Available
Tissue Location
  • Adipose Tissue
  • Bladder
  • Blood
  • Brain
  • Fibroblasts
  • Kidney
  • Liver
  • Nerve Cells
  • Placenta
  • Platelet
Pathways
NameSMPDB/PathwhizKEGG
Acetaminophen Action PathwayPw000687Pw000687 greyscalePw000687 simpleNot Available
Acetylsalicylic Acid PathwayPw000128Pw000128 greyscalePw000128 simpleNot Available
Antipyrine Action PathwayPw000669Pw000669 greyscalePw000669 simpleNot Available
Antrafenine Action PathwayPw000670Pw000670 greyscalePw000670 simpleNot Available
Arachidonic Acid MetabolismPw000044Pw000044 greyscalePw000044 simpleMap00590
Displaying entries 1 - 5 of 42 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022560
KNApSAcK IDNot Available
Chemspider ID4445566
KEGG Compound IDC01312
BioCyc ID5Z13E-15S-69-ALPHA-EPOXY-11-ALPHA
BiGG ID37333
Wikipedia LinkEpoprostenol
METLIN ID778
PubChem Compound5282411
PDB IDNot Available
ChEBI ID15552
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:10381779 ]
  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. [PubMed:8179173 ]
  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. [PubMed:14975458 ]
  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. [PubMed:14729378 ]
  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. [PubMed:11980586 ]
  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. [PubMed:11997386 ]
  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. [PubMed:16087791 ]
  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. [PubMed:16810757 ]
  9. Nadar S, Lip GY: Platelet activation in the hypertensive disorders of pregnancy. Expert Opin Investig Drugs. 2004 May;13(5):523-9. [PubMed:15155127 ]
  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. [PubMed:10494782 ]
  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. [PubMed:11964481 ]
  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. [PubMed:11258611 ]
  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. [PubMed:10806831 ]
  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. [PubMed:1330499 ]
  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. [PubMed:10784307 ]
  16. Axelrod L: Insulin, prostaglandins, and the pathogenesis of hypertension. Diabetes. 1991 Oct;40(10):1223-7. [PubMed:1936584 ]
  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. [PubMed:11126272 ]
  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. [PubMed:2147814 ]
  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. [PubMed:11672751 ]
  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. [PubMed:15630490 ]

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:
PTGIS
Uniprot ID:
Q16647
Molecular weight:
57103.385
Reactions
Prostaglandin H2 → Prostaglandin I2details
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostacyclin (prostaglandin I2 or PGI2). The activity of this receptor is mediated by G(s) proteins which activate adenylate cyclase
Gene Name:
PTGIR
Uniprot ID:
P43119
Molecular weight:
40955.5