Record Information
Creation date2011-09-21 00:16:44 UTC
Update date2015-10-09 22:33:18 UTC
Primary IDFDB022602
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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
Predicted Properties
Water Solubility0.086 g/LALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.44 m³·mol⁻¹ChemAxon
Polarizability40.52 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
SpectraNot Available
ChemSpider ID395250
KEGG Compound IDC00696
Pubchem Compound ID448457
Pubchem Substance IDNot Available
ChEBI ID15555
Phenol-Explorer IDNot Available
DrugBank IDDB02056
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35725
KNApSAcK IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDProstaglandin D2
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
NameGene NameUniProt ID
Hematopoietic prostaglandin D synthaseHPGDSO60760
Prostaglandin-H2 D-isomerasePTGDSP41222
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference