General Information of MET (ID: META00423)
Name Prostaglandin D2
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(5Z,13E)-(15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dienoate; (5Z,13E)-(15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid; (5Z,13E)-(15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate; (5Z,13E)-(15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid; (5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoate; (5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid; (5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate; (5Z,13E,15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate; (5Z,13E,15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid; (5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dien-1-Oate; (5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dien-1-Oic acid; (5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoate; (5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid; (5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate; (5Z,9-alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oate; (5Z,9-alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oic acid; (5Z,9alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oate; (5Z,9alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oic acid; 11 Dehydroprostaglandin F2 alpha; 11 Dehydroprostaglandin F2alpha; 11-Dehydroprostaglandin F2 alpha; 11-Dehydroprostaglandin F2-alpha; 11-Dehydroprostaglandin F2alpha; 9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoate; 9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoic acid; D2, Prostaglandin; F2 alpha, 11-Dehydroprostaglandin; F2alpha, 11-Dehydroprostaglandin; PGD2; alpha, 11-Dehydroprostaglandin F2
Source Endogenous;Fatty acyls;Food;Drug
Structure Type   Eicosanoids  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Eicosanoids
PubChem CID
448457
HMDB ID
HMDB0001403
Formula
C20H32O5
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00696
DrugBank ID
DB02056
ChEBI ID
15555
FooDB ID
FDB022602
ChemSpider ID
395250
METLIN ID
6221
Physicochemical Properties Molecular Weight 352.5 Topological Polar Surface Area 94.8
XlogP 2.6 Complexity 469
Heavy Atom Count 25 Rotatable Bond Count 12
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Function
Prostaglandin 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. 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 signalling pathways.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Group 10 secretory phospholipase A2 (PLA2G10) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of Pla2g10
                      Induced Change Prostaglandin D2 concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Inflammatory bowel disease [ICD-11: DD72]
                      Details It is reported that overexpression of Pla2g10 leads to the increase of prostaglandin D2 levels compared with control group.
References
1 Group X Secreted Phospholipase A2 Releases 3 Polyunsaturated Fatty Acids, Suppresses Colitis, and Promotes Sperm Fertility. J Biol Chem. 2016 Mar 25;291(13):6895-911.

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