Record Information
Creation date2015-10-09 22:33:18 UTC
Update date2017-01-19 02:36:40 UTC
FoodComEx IDPC000901
FoodDB RecordFDB022602
Chemical Information
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. [HMDB]
CAS Number41598-07-6
(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,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)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acidhmdb
(5Z,13E)-(15S)-9,15-dihydroxy-11-oxoprosta-5,13-dienoic acidhmdb
(5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidhmdb
(5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidhmdb
(5Z,13e)-(15S)-9α,15-dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(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 F2-aGenerator
11-Dehydroprostaglandin F2-alphahmdb
11-Dehydroprostaglandin F2-αGenerator
11-Dehydroprostaglandin F2alphahmdb
9S,15S-dihydroxy-11-oxo-5Z,13E-prostadienoic acidhmdb
prostaglandin d2hmdb
Chemical FormulaC20H32O5
IUPAC name7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
InChI IdentifierInChI=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)/t15-,16+,17+,18-/m0/s1
Isomeric SMILES[H]C(=C[C@@]1([H])C(=O)C[C@]([H])(O)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCC
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
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
  • 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 DescriptorsNot Available
Physico-Chemical Properties - Experimental
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 5 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
AKSci 2004AH
Cayman Chemical 10007202
Cayman Chemical 12010
Toronto Research Chemicals P838575