Identification

Name
Prostaglandin D2
Accession Number
DB02056  (EXPT02562, DB08863)
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
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
Categories
Not Available
UNII
RXY07S6CZ2
CAS number
41598-07-6
Weight
Average: 352.4651
Monoisotopic: 352.224974134
Chemical Formula
C20H32O5
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][[email protected]](O)(CCCCC)\C=C\[[email protected]@]1([H])C(=O)C[[email protected]]([H])(O)[[email protected]]1([H])C\C=C/CCCC(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAldo-keto reductase family 1 member C3Not AvailableHuman
UProstaglandin D2 receptor 2Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Lornoxicam Action PathwayDrug action
Phenylbutazone Action PathwayDrug action
Salsalate Action PathwayDrug action
Acetaminophen Action PathwayDrug action
Ketorolac Action PathwayDrug action
Suprofen Action PathwayDrug action
Valdecoxib Action PathwayDrug action
Diflunisal Action PathwayDrug action
Leukotriene C4 Synthesis DeficiencyDisease
Trisalicylate-choline Action PathwayDrug action
Arachidonic Acid MetabolismMetabolic
Meloxicam Action PathwayDrug action
Mefenamic Acid Action PathwayDrug action
Fc Epsilon Receptor I Signaling in Mast CellsSignaling
Magnesium salicylate Action PathwayDrug action
Nepafenac Action PathwayDrug action
Salicylate-sodium Action PathwayDrug action
Etodolac Action PathwayDrug action
Ibuprofen Action PathwayDrug action
Diclofenac Action PathwayDrug action
Bromfenac Action PathwayDrug action
Intracellular Signalling Through PGD2 receptor and Prostaglandin D2Signaling
Antipyrine Action PathwayDrug action
Antrafenine Action PathwayDrug action
Fenoprofen Action PathwayDrug action
Flurbiprofen Action PathwayDrug action
Lumiracoxib Action PathwayDrug action
Tenoxicam Action PathwayDrug action
Salicylic Acid Action PathwayDrug action
Piroxicam Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01403
KEGG Compound
C00696
PubChem Compound
448457
PubChem Substance
46504574
ChemSpider
395250
BindingDB
21544
ChEBI
15555
ChEMBL
CHEMBL1235252
HET
PG2
PDB Entries
1ry0

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.086 mg/mLALOGPS
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
Polarizability40.78 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9815
Blood Brain Barrier+0.8704
Caco-2 permeable+0.5245
P-glycoprotein substrateSubstrate0.5554
P-glycoprotein inhibitor INon-inhibitor0.9202
P-glycoprotein inhibitor IINon-inhibitor0.8983
Renal organic cation transporterNon-inhibitor0.9064
CYP450 2C9 substrateNon-substrate0.8211
CYP450 2D6 substrateNon-substrate0.8834
CYP450 3A4 substrateNon-substrate0.5292
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9502
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9725
Ames testNon AMES toxic0.9387
CarcinogenicityNon-carcinogens0.9201
BiodegradationReady biodegradable0.6056
Rat acute toxicity2.9631 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9087
hERG inhibition (predictor II)Non-inhibitor0.9138
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-005i-4920000000-0865a8f516450183b07c
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-0040-4920000000-7b37e8b3ecc2583f0fdc
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-005i-4920000000-0865a8f516450183b07c
GC-MS Spectrum - GC-MSGC-MSsplash10-0040-4920000000-7b37e8b3ecc2583f0fdc
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00yr-0494000000-005f78cb3131ac258d23
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 25V, NegativeLC-MS/MSsplash10-00dr-0592000000-3541be2f7c29b70b97a4
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00dr-0691000000-a08a3850e6fbf73fe539
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 35V, NegativeLC-MS/MSsplash10-00dr-0690000000-395bf1624fb183650268
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0079-0980000000-a0d1eacded9a909d2d07
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 45V, NegativeLC-MS/MSsplash10-000i-0960000000-982ce65a71003d3086b1
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0079-0930000000-15446e0930a7e4e23eff
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 55V, NegativeLC-MS/MSsplash10-00di-0920000000-5f7db7776dd0364029d7
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 60V, NegativeLC-MS/MSsplash10-00dj-0900000000-16cfbecd58e5a59ab631
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00yr-0494000000-65af63dd6c30ad10793d
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00dr-0592000000-3541be2f7c29b70b97a4
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00dr-0691000000-a08a3850e6fbf73fe539
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00dr-0690000000-fef454d771f83be8e0b4
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0079-0980000000-a0d1eacded9a909d2d07
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-000i-0960000000-982ce65a71003d3086b1
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0079-0930000000-15446e0930a7e4e23eff
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00di-0920000000-5f7db7776dd0364029d7
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00dj-0900000000-88efef42e905aa15039f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00y0-0493000000-654476042b0ee0709ced
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Prostaglandin skeleton / Long-chain fatty acid / Hydroxy fatty acid / Cyclopentanol / Fatty acid / Unsaturated fatty acid / Cyclic alcohol / Ketone / Cyclic ketone / Secondary alcohol
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
prostaglandins D (CHEBI:15555) / Prostaglandins (C00696) / Prostaglandins (LMFA03010004)

Targets

Kind
Protein
Organism
Human
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:16256979]
  2. 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. [PubMed:9579725]

Transporters

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:8787677]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:09