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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-03-02 21:26:34 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameProstaglandin D2
DescriptionProstaglandin D2 (or PGD2) is a prostaglandin that is actively produced in various organs such as the brain, spleen, thymus, bone marrow, uterus, ovary, oviduct, testis, prostate and epididymis, and is involved in many physiological events. PGD2 binds to the prostaglandin D2 receptor (PTGDR) which is a G-protein-coupled receptor. Its activity is mainly mediated by G-S proteins that stimulate adenylate cyclase resulting in an elevation of intracellular cAMP and Ca2+. PGD2 promotes sleep; regulates body temperature, olfactory function, hormone release, and nociception in the central nervous system; prevents platelet aggregation; and induces vasodilation and bronchoconstriction. PGD2 is also released from mast cells as an allergic and inflammatory mediator. Prostaglandin H2 is an unstable intermediate formed from PGG2 by the action of cyclooxygenase (COX) in the arachidonate cascade. In mammalian systems, it is efficiently converted into more stable arachidonate metabolites, such as PGD2, PGE2, PGF2a by the action of three groups of enzymes, PGD synthases (PGDS), PGE synthases and PGF synthases, respectively. PGDS catalyzes the isomerization of PGH2 to PGD2. Two types of PGD2 synthase are known. Lipocalin-type PGD synthase is present in cerebrospinal fluid, seminal plasma and may play an important role in male reproduction. Another PGD synthase, hematopoietic PGD synthase is present in the spleen, fallopian tube, endometrial gland cells, extravillous trophoblasts and villous trophoblasts, and perhaps plays an important role in female reproduction. Recent studies demonstrate that PGD2 is probably involved in multiple aspects of inflammation through its dual receptor systems, DP and CRTH2. (PMID: 12148545 )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.
11-Dehydroprostaglandin F2-alphaChEBI
(5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
11-Dehydroprostaglandin F2-aGenerator
11-Dehydroprostaglandin F2-αGenerator
(5Z,13E)-(15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidHMDB
(5Z,13E)-(15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidHMDB
(5Z,13E,15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidHMDB
(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dien-1-Oic acidHMDB
(5Z,9-alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oic acidHMDB
(5Z,9alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oic acidHMDB
11-Dehydroprostaglandin F2alphaHMDB
9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoic acidHMDB
F2alpha, 11-DehydroprostaglandinMeSH
11 Dehydroprostaglandin F2alphaMeSH
11 Dehydroprostaglandin F2 alphaMeSH
D2, ProstaglandinMeSH
F2 alpha, 11-DehydroprostaglandinMeSH
alpha, 11-Dehydroprostaglandin F2MeSH
11-Dehydroprostaglandin F2 alphaMeSH
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
Traditional Nameprostaglandin D2
CAS Registry Number41598-07-6
InChI Identifier
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
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Component of Prostaglandin and leukotriene metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
Experimental Properties
Melting Point56 - 57 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.086 mg/mLALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.44 m3·mol-1ChemAxon
Polarizability40.78 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-005i-4920000000-0865a8f516450183b07cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0040-4920000000-7b37e8b3ecc2583f0fdcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 20V, Negativesplash10-00yr-0494000000-005f78cb3131ac258d23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 25V, Negativesplash10-00dr-0592000000-3541be2f7c29b70b97a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 30V, Negativesplash10-00dr-0691000000-a08a3850e6fbf73fe539View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 35V, Negativesplash10-00dr-0690000000-395bf1624fb183650268View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 40V, Negativesplash10-0079-0980000000-a0d1eacded9a909d2d07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 45V, Negativesplash10-000i-0960000000-982ce65a71003d3086b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 50V, Negativesplash10-0079-0930000000-15446e0930a7e4e23effView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 55V, Negativesplash10-00di-0920000000-5f7db7776dd0364029d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 60V, Negativesplash10-00dj-0900000000-16cfbecd58e5a59ab631View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00yr-0494000000-65af63dd6c30ad10793dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0690000000-fef454d771f83be8e0b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dj-0900000000-88efef42e905aa15039fView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Adipose Tissue
  • Brain
  • Liver
  • Mast Cell
  • Neuron
  • Platelet
  • Skin
  • Smooth Muscle
  • Spleen
Acetaminophen Action PathwaySMP00710Not Available
Acetylsalicylic Acid PathwaySMP00083Not Available
Antipyrine Action PathwaySMP00692Not Available
Antrafenine Action PathwaySMP00693Not Available
Arachidonic Acid MetabolismSMP00075map00590
Bromfenac PathwaySMP00102Not Available
Carprofen Action PathwaySMP00694Not Available
Celecoxib PathwaySMP00096Not Available
Diclofenac PathwaySMP00093Not Available
Diflunisal PathwaySMP00289Not Available
Etodolac PathwaySMP00084Not Available
Etoricoxib Action PathwaySMP00695Not Available
Fc Epsilon Receptor I Signaling in Mast CellsSMP00358Not Available
Fenoprofen Action PathwaySMP00696Not Available
Flurbiprofen Action PathwaySMP00697Not Available
Ibuprofen PathwaySMP00086Not Available
Indomethacin PathwaySMP00104Not Available
Intracellular Signalling Through PGD2 receptor and Prostaglandin D2SMP00343Not Available
Ketoprofen PathwaySMP00085Not Available
Ketorolac PathwaySMP00098Not Available
Leukotriene C4 Synthesis DeficiencySMP00353Not Available
Lornoxicam Action PathwaySMP00700Not Available
Lumiracoxib Action PathwaySMP00699Not Available
Magnesium salicylate Action PathwaySMP00698Not Available
Mefanamic Acid PathwaySMP00109Not Available
Meloxicam PathwaySMP00106Not Available
Nabumetone PathwaySMP00114Not Available
Naproxen PathwaySMP00120Not Available
Nepafenac Action PathwaySMP00702Not Available
Oxaprozin PathwaySMP00113Not Available
Phenylbutazone Action PathwaySMP00701Not Available
Piroxicam PathwaySMP00077Not Available
Rofecoxib PathwaySMP00087Not Available
Salicylate-sodium Action PathwaySMP00708Not Available
Salicylic Acid Action PathwaySMP00709Not Available
Salsalate Action PathwaySMP00707Not Available
Sulindac PathwaySMP00094Not Available
Suprofen PathwaySMP00101Not Available
Tenoxicam Action PathwaySMP00706Not Available
Tiaprofenic Acid Action PathwaySMP00705Not Available
Tolmetin Action PathwaySMP00704Not Available
Trisalicylate-choline Action PathwaySMP00703Not Available
Valdecoxib PathwaySMP00116Not Available
Normal Concentrations
BloodDetected and Quantified0.0002 +/- 6.5E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000306 +/- 0.000355 uMAdult (>18 years old)Both
BloodDetected and Quantified0.0000726 +/- 0.0000058 uMAdult (>18 years old)Both
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
Abnormal Concentrations
Cerebrospinal Fluid (CSF)Detected and Quantified0.000165 (0.000159-0.000170) uMNot SpecifiedNot Specifiedclosed head injury details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000511 uMNot SpecifiedNot Specifiedgunshot wound details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000142 +/- 0.000133 uMNot SpecifiedNot Specifiedhydrocephalus details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000384 (0.000108-0.000880) uMNot SpecifiedNot Specifiedmeningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00321 uMNot SpecifiedNot Specifiedsubarachnoid hemorrhage with cerebral vasospasm details
Cerebrospinal Fluid (CSF)Detected and Quantified1844.18 (595.8-3092.5) uMAdult (>18 years old)Not SpecifiedSubarachnoid Aneurysmal Hemorrhage details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00131 +/- 0.000159 uMNot SpecifiedNot Specifiedsubarachnoid hemorrhage without cerebral vasospasm details
Associated Disorders and Diseases
Disease References
Subarachnoid hemorrhage
  1. Gaetani P, Rodriguez y Baena R, Vigano T, Crivellari MT: [Prostaglandin D2 in subarachnoid hemorrhage. Biological and diagnostic implications]. Riv Patol Nerv Ment. 1983 Jul-Aug;104(4):171-7. [PubMed:6598516 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022602
KNApSAcK IDNot Available
Chemspider ID395250
KEGG Compound IDC00696
BiGG ID35725
Wikipedia LinkProstaglandin D2
NuGOwiki LinkHMDB01403
Metagene LinkHMDB01403
PubChem Compound448457
ChEBI ID15555
Synthesis ReferenceOgawa, Yuji; Nunomoto, Makoto; Shibasaki, Masakatsu. A novel synthesis of prostaglandin D2. Journal of Organic Chemistry (1986), 51(9), 1625-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. O'Sullivan S, Dahlen B, Dahlen SE, Kumlin M: Increased urinary excretion of the prostaglandin D2 metabolite 9 alpha, 11 beta-prostaglandin F2 after aspirin challenge supports mast cell activation in aspirin-induced airway obstruction. J Allergy Clin Immunol. 1996 Aug;98(2):421-32. [PubMed:8757220 ]
  2. Parsons WG 3rd, Roberts LJ 2nd: Transformation of prostaglandin D2 to isomeric prostaglandin F2 compounds by human eosinophils: a potential mast cell-eosinophil interaction. Adv Prostaglandin Thromboxane Leukot Res. 1989;19:499-502. [PubMed:2526527 ]
  3. Parsons WG 3rd, Roberts LJ 2nd: Transformation of prostaglandin D2 to isomeric prostaglandin F2 compounds by human eosinophils. A potential mast cell-eosinophil interaction. J Immunol. 1988 Oct 1;141(7):2413-9. [PubMed:3139758 ]
  4. Cooper B: Diminished platelet adenylate cyclase activation by prostaglandin D2 in acute thrombosis. Blood. 1979 Sep;54(3):684-93. [PubMed:380688 ]
  5. Bushfield M, McNicol A, MacIntyre DE: Inhibition of platelet-activating-factor-induced human platelet activation by prostaglandin D2. Differential sensitivity of platelet transduction processes and functional responses to inhibition by cyclic AMP. Biochem J. 1985 Nov 15;232(1):267-71. [PubMed:3002327 ]
  6. Awad JA, Morrow JD, Roberts LJ 2nd: Detection of the major urinary metabolite of prostaglandin D2 in the circulation: demonstration of elevated levels in patients with disorders of systemic mast cell activation. J Allergy Clin Immunol. 1994 May;93(5):817-24. [PubMed:8182221 ]
  7. Wolfe LS, Rostworowski K, Pellerin L, Sherwin A: Metabolism of prostaglandin D2 by human cerebral cortex into 9 alpha, 11 beta-prostaglandin F2 by an active NADPH-dependent 11-ketoreductase. J Neurochem. 1989 Jul;53(1):64-70. [PubMed:2723663 ]
  8. Cutler LS, Christian CP, Feinstein MB: Cytochemical localization of adenylate cyclase in the dense tubule system of human blood platelets stimulated by forskolin, prostacyclin and prostaglandin D2. Biochim Biophys Acta. 1985 Jun 30;845(3):403-10. [PubMed:3890960 ]
  9. Murray JJ, Tonnel AB, Brash AR, Roberts LJ 2nd, Gosset P, Workman R, Capron A, Oates JA: Release of prostaglandin D2 into human airways during acute antigen challenge. N Engl J Med. 1986 Sep 25;315(13):800-4. [PubMed:3462506 ]
  10. Liston TE, Roberts LJ 2nd: Transformation of prostaglandin D2 to 9 alpha, 11 beta-(15S)-trihydroxyprosta-(5Z,13E)-dien-1-oic acid (9 alpha, 11 beta-prostaglandin F2): a unique biologically active prostaglandin produced enzymatically in vivo in humans. Proc Natl Acad Sci U S A. 1985 Sep;82(18):6030-4. [PubMed:3862115 ]
  11. Haberl C, Hultner L, Flugel A, Falk M, Geuenich S, Wilmanns W, Denzlinger C: Release of prostaglandin D2 by murine mast cells: importance of metabolite formation for antiproliferative activity. Mediators Inflamm. 1998;7(2):79-84. [PubMed:9836493 ]
  12. Bate C, Kempster S, Williams A: Prostaglandin D2 mediates neuronal damage by amyloid-beta or prions which activates microglial cells. Neuropharmacology. 2006 Feb;50(2):229-37. Epub 2005 Nov 11. [PubMed:16289250 ]
  13. Nishizawa EE, Miller WL, Gorman RR, Bundy GL, Svensson J, Hamberg M: Prostaglandin d2 as a potential antithrombotic agent. Prostaglandins. 1975 Jan;9(1):109-21. [PubMed:806102 ]
  14. Fuller RW, Dixon CM, Dollery CT, Barnes PJ: Prostaglandin D2 potentiates airway responsiveness to histamine and methacholine. Am Rev Respir Dis. 1986 Feb;133(2):252-4. [PubMed:3511806 ]
  15. Lewis RA, Soter NA, Diamond PT, Austen KF, Oates JA, Roberts LJ 2nd: Prostaglandin D2 generation after activation of rat and human mast cells with anti-IgE. J Immunol. 1982 Oct;129(4):1627-31. [PubMed:6809826 ]
  16. Gresele P, Deckmyn H, Huybrechts E, Vermylen J: Serum albumin enhances the impairment of platelet aggregation with thromboxane synthase inhibition by increasing the formation of prostaglandin D2. Biochem Pharmacol. 1984 Jul 1;33(13):2083-8. [PubMed:6430299 ]
  17. VanderEnde DS, Morrow JD: Release of markedly increased quantities of prostaglandin D2 from the skin in vivo in humans after the application of cinnamic aldehyde. J Am Acad Dermatol. 2001 Jul;45(1):62-7. [PubMed:11423836 ]
  18. Downard CD, Roberts LJ 2nd, Morrow JD: Topical benzoic acid induces the increased biosynthesis of prostaglandin D2 in human skin in vivo. Clin Pharmacol Ther. 1995 Apr;57(4):441-5. [PubMed:7712673 ]
  19. Morrow JD, Minton TA, Awad JA, Roberts LJ: Release of markedly increased quantities of prostaglandin D2 from the skin in vivo in humans following the application of sorbic acid. Arch Dermatol. 1994 Nov;130(11):1408-12. [PubMed:7979442 ]
  20. Morrow JD, Awad JA, Oates JA, Roberts LJ 2nd: Identification of skin as a major site of prostaglandin D2 release following oral administration of niacin in humans. J Invest Dermatol. 1992 May;98(5):812-5. [PubMed:1373750 ]
  21. Saito S, Tsuda H, Michimata T: Prostaglandin D2 and reproduction. Am J Reprod Immunol. 2002 May;47(5):295-302. [PubMed:12148545 ]


General function:
Involved in glutathione transferase activity
Specific function:
Bifunctional enzyme which catalyzes both the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation, and the conjugation of glutathione with a wide range of aryl halides and organic isothiocyanates. Also exhibits low glutathione-peroxidase activity towards cumene hydroperoxide.
Gene Name:
Uniprot ID:
Molecular weight:
Prostaglandin H2 → Prostaglandin D2details
General function:
Involved in binding
Specific function:
Catalyzes the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation. Involved in a variety of CNS functions, such as sedation, NREM sleep and PGE2-induced allodynia, and may have an anti-apoptotic role in oligodendrocytes. Binds small non-substrate lipophilic molecules, including biliverdin, bilirubin, retinal, retinoic acid and thyroid hormone, and may act as a scavenger for harmful hydrophopic molecules and as a secretory retinoid and thyroid hormone transporter. Possibly involved in development and maintenance of the blood-brain, blood-retina, blood-aqueous humor and blood-testis barrier. It is likely to play important roles in both maturation and maintenance of the central nervous system and male reproductive system.
Gene Name:
Uniprot ID:
Molecular weight:
Prostaglandin H2 → Prostaglandin D2details
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostaglandin D2 (PGD2). The activity of this receptor is mainly mediated by G(s) proteins that stimulate adenylate cyclase, resulting in an elevation of intracellular cAMP. A mobilization of calcium is also observed, but without formation of inositol 1,4,5-trisphosphate
Gene Name:
Uniprot ID:
Molecular weight: