Identification
- Generic Name
- Prostaglandin D2
- DrugBank Accession Number
- DB02056
- Background
The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Prostaglandin D2 (DB02056)
- Weight
- Average: 352.4651
Monoisotopic: 352.224974134 - Chemical Formula
- C20H32O5
- Synonyms
- (5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate
- (5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate
- 11-Dehydroprostaglandin F2-alpha
- PGD2
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UProstaglandin D2 receptor 2 Not Available Humans UAldo-keto reductase family 1 member C3 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAceclofenac The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Acemetacin. Acetylsalicylic acid The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Acetylsalicylic acid. Alclofenac The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Alclofenac. Aminophenazone The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Aminophenazone. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Eicosanoids
- Direct Parent
- Prostaglandins and related compounds
- Alternative Parents
- Long-chain fatty acids / Hydroxy fatty acids / Unsaturated fatty acids / Cyclopentanols / Cyclic ketones / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic alcohol / Cyclic ketone / Cyclopentanol / Fatty acid / Hydrocarbon derivative
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- prostaglandins D (CHEBI:15555) / Prostaglandins (C00696) / Prostaglandins (LMFA03010004)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- RXY07S6CZ2
- CAS number
- 41598-07-6
- InChI Key
- BHMBVRSPMRCCGG-OUTUXVNYSA-N
- InChI
- 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
- IUPAC Name
- (5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
- SMILES
- [H][C@](O)(CCCCC)\C=C\[C@@]1([H])C(=O)C[C@]([H])(O)[C@]1([H])C\C=C/CCCC(O)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001403
- KEGG Compound
- C00696
- PubChem Compound
- 448457
- PubChem Substance
- 46504574
- ChemSpider
- 395250
- BindingDB
- 21544
- ChEBI
- 15555
- ChEMBL
- CHEMBL1235252
- ZINC
- ZINC000085994848
- PDBe Ligand
- PG2
- Wikipedia
- Prostaglandin_D2
- PDB Entries
- 1ry0
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.086 mg/mL ALOGPS logP 3.12 ALOGPS logP 3.23 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 4.4 Chemaxon pKa (Strongest Basic) -1.6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 94.83 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 99.44 m3·mol-1 Chemaxon Polarizability 40.78 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9815 Blood Brain Barrier + 0.8704 Caco-2 permeable + 0.5245 P-glycoprotein substrate Substrate 0.5554 P-glycoprotein inhibitor I Non-inhibitor 0.9202 P-glycoprotein inhibitor II Non-inhibitor 0.8983 Renal organic cation transporter Non-inhibitor 0.9064 CYP450 2C9 substrate Non-substrate 0.8211 CYP450 2D6 substrate Non-substrate 0.8834 CYP450 3A4 substrate Non-substrate 0.5292 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9502 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9725 Ames test Non AMES toxic 0.9387 Carcinogenicity Non-carcinogens 0.9201 Biodegradation Ready biodegradable 0.6056 Rat acute toxicity 2.9631 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9087 hERG inhibition (predictor II) Non-inhibitor 0.9138
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 217.0592855 predictedDarkChem Lite v0.1.0 [M-H]- 222.0547855 predictedDarkChem Lite v0.1.0 [M-H]- 220.4431855 predictedDarkChem Lite v0.1.0 [M-H]- 199.17653 predictedDeepCCS 1.0 (2019) [M+H]+ 217.3015855 predictedDarkChem Lite v0.1.0 [M+H]+ 220.9717855 predictedDarkChem Lite v0.1.0 [M+H]+ 221.6941855 predictedDarkChem Lite v0.1.0 [M+H]+ 201.5721 predictedDeepCCS 1.0 (2019) [M+Na]+ 217.3613855 predictedDarkChem Lite v0.1.0 [M+Na]+ 200.3500932 predictedDarkChem Standard v0.1.0 [M+Na]+ 220.6121855 predictedDarkChem Lite v0.1.0 [M+Na]+ 208.76962 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Prostaglandin j receptor activity
- Specific Function
- Receptor for prostaglandin D2 (PGD2). Coupled to the G(i)-protein. Receptor activation may result in pertussis toxin-sensitive decreases in cAMP levels and Ca(2+) mobilization. PI3K signaling is al...
- Gene Name
- PTGDR2
- Uniprot ID
- Q9Y5Y4
- Uniprot Name
- Prostaglandin D2 receptor 2
- Molecular Weight
- 43267.15 Da
References
- Sugimoto H, Shichijo M, Okano M, Bacon KB: CRTH2-specific binding characteristics of [3H]ramatroban and its effects on PGD2-, 15-deoxy-Delta12, 14-PGJ2- and indomethacin-induced agonist responses. Eur J Pharmacol. 2005 Nov 7;524(1-3):30-7. Epub 2005 Oct 27. [Article]
- Wright DH, Metters KM, Abramovitz M, Ford-Hutchinson AW: Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist. Br J Pharmacol. 1998 Apr;123(7):1317-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function
- Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
- Gene Name
- AKR1C3
- Uniprot ID
- P42330
- Uniprot Name
- Aldo-keto reductase family 1 member C3
- Molecular Weight
- 36852.89 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
- Gene Name
- SLCO2A1
- Uniprot ID
- Q92959
- Uniprot Name
- Solute carrier organic anion transporter family member 2A1
- Molecular Weight
- 70043.33 Da
References
- Lu R, Kanai N, Bao Y, Schuster VL: Cloning, in vitro expression, and tissue distribution of a human prostaglandin transporter cDNA(hPGT). J Clin Invest. 1996 Sep 1;98(5):1142-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52