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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-08-05 20:05:53 UTC
HMDB IDHMDB01403
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.
Structure
Thumb
Synonyms
  1. (5Z,13E)-(15S)-9,15-dihydroxy-11-oxoprosta-5,13-dienoate
  2. (5Z,13E)-(15S)-9,15-dihydroxy-11-oxoprosta-5,13-dienoic acid
  3. (5z,13e)-(15S)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
  4. (5z,13e)-(15S)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid
  5. (5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoate
  6. (5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid
  7. (5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
  8. (5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid
  9. (5Z,13E,15S)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
  10. (5Z,13E,15S)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid
  11. (5Z,13E,15S)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oate
  12. (5Z,13E,15S)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic acid
  13. (5Z,9-alpha,13E,15S)-9,15-dihydroxy-11-oxo-Prosta-5,13-dien-1-oate
  14. (5Z,9-alpha,13E,15S)-9,15-dihydroxy-11-oxo-Prosta-5,13-dien-1-oic acid
  15. (5Z,9alpha,13E,15S)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oate
  16. (5Z,9alpha,13E,15S)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oic acid
  17. 11-Dehydroprostaglandin F2-alpha
  18. 11-Dehydroprostaglandin F2alpha
  19. 9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoate
  20. 9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoic acid
  21. PGD2
  22. Prostaglandin d2
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
SMILES
CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O
InChI Identifier
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
InChI KeyBHMBVRSPMRCCGG-OUTUXVNYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassProstaglandins and related compounds
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Carbocyclic Fatty Acids
  • Keto Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Cyclic Alcohol
  • Ketone
  • Secondary Alcohol
Direct ParentProstaglandins and related compounds
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Prostaglandin and leukotriene metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point56 - 57 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.086ALOGPS
logP3.12ALOGPS
logP3.23ChemAxon
logS-3.6ALOGPS
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
Polarizability40.73 Å3ChemAxon
Spectra
SpectraGC-MSLC-MS1D NMR2D NMR
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
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0002 +/- 6.5E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000306 +/- 0.000355 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0000726 +/- 0.0000058 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Not Specified
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
BioCyc ID5Z13E-15S-9-ALPHA15-DIHYDROXY-11-O
BiGG ID35725
Wikipedia LinkProstaglandin D2
NuGOwiki LinkHMDB01403
Metagene LinkHMDB01403
METLIN ID6221
PubChem Compound448457
PDB IDPG2
ChEBI ID15555
References
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

Enzymes

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:
HPGDS
Uniprot ID:
O60760
Molecular weight:
23343.65
Reactions
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:
PTGDS
Uniprot ID:
P41222
Molecular weight:
21028.665
Reactions
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:
PTGDR
Uniprot ID:
Q13258
Molecular weight:
40270.1