Prostaglandin G2

Identification

Name
Prostaglandin G2
Accession Number
DB03866  (EXPT02577)
Type
Small Molecule
Groups
Experimental
Description

A cyclic endoperoxide intermediate produced by the action of CYCLOOXYGENASE on ARACHIDONIC ACID. It is further converted by a series of specific enzymes to the series 2 prostaglandins. [PubChem]

Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 368.4645
Monoisotopic: 368.219888756
Chemical Formula
C20H32O6
InChI Key
SGUKUZOVHSFKPH-YNNPMVKQSA-N
InChI
InChI=1S/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
IUPAC Name
(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
SMILES
[H][C@@](CCCCC)(OO)\C=C\[C@@]1([H])[C@@]2([H])C[C@]([H])(OO2)[C@]1([H])C\C=C/CCCC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProstaglandin G/H synthase 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
Arachidonic Acid MetabolismMetabolic
Meloxicam Action PathwayDrug action
Mefenamic Acid Action PathwayDrug action
Magnesium salicylate Action PathwayDrug action
Nepafenac Action PathwayDrug action
Salicylate-sodium Action PathwayDrug action
Diclofenac Action PathwayDrug action
Indomethacin Action PathwayDrug action
Meloxicam Action PathwayDrug action
Nabumetone Action PathwayDrug action
Naproxen Action PathwayDrug action
Etoricoxib Action PathwayDrug action
Arachidonic Acid MetabolismMetabolic
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
Piroxicam Action PathwayDrug action
Sulindac Action PathwayDrug action
Celecoxib Action PathwayDrug action
Bromfenac Action PathwayDrug action
Antrafenine Action PathwayDrug action
Magnesium salicylate Action PathwayDrug action
Lornoxicam Action PathwayDrug action
Acetaminophen Action PathwayDrug action
Etodolac Action PathwayDrug action
Ibuprofen Action PathwayDrug action
Diclofenac Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with (4R)-limonene.
AceclofenacThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Acetylsalicylic acid.
AlclofenacThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Alclofenac.
AlminoprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Alminoprofen.
AndrographolideThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Andrographolide.
AnisodamineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Anisodamine.
AntipyrineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Antipyrine.
ApocyninThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Apocynin.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0003235
KEGG Compound
C05956
PubChem Compound
5280883
PubChem Substance
46509030
ChemSpider
4444406
ChEBI
27647
HET
PGX
Wikipedia
Prostaglandin_G2
PDB Entries
1ddx

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 Solubility0.0264 mg/mLALOGPS
logP4.31ALOGPS
logP4.41ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity99.39 m3·mol-1ChemAxon
Polarizability40.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.859
Blood Brain Barrier+0.8659
Caco-2 permeable-0.5826
P-glycoprotein substrateSubstrate0.607
P-glycoprotein inhibitor INon-inhibitor0.7556
P-glycoprotein inhibitor IINon-inhibitor0.9371
Renal organic cation transporterNon-inhibitor0.8993
CYP450 2C9 substrateNon-substrate0.818
CYP450 2D6 substrateNon-substrate0.8386
CYP450 3A4 substrateNon-substrate0.5401
CYP450 1A2 substrateNon-inhibitor0.7686
CYP450 2C9 inhibitorNon-inhibitor0.8485
CYP450 2D6 inhibitorNon-inhibitor0.9119
CYP450 2C19 inhibitorNon-inhibitor0.7986
CYP450 3A4 inhibitorNon-inhibitor0.8137
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8634
Ames testNon AMES toxic0.6094
CarcinogenicityNon-carcinogens0.9048
BiodegradationNot ready biodegradable0.6704
Rat acute toxicity2.9740 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7324
hERG inhibition (predictor II)Non-inhibitor0.8095
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0119000000-06893304af83e030a39b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zmr-3369000000-b1d0f67eea930b11ae4c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-1003-9400000000-7fbd48d8b1a086fc44d2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0019000000-4a1c6a9bb1b35fe201ef
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00r2-2149000000-16bc14c91731cdc79586
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9162000000-ad0929ccdcab78d69a99

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 / Hydroperoxy fatty acids / Heterocyclic fatty acids / Unsaturated fatty acids / 1,2-dioxanes / Allylic hydroperoxides / 1,2-dioxolanes / Dialkyl peroxides / Peroxols / Oxacyclic compounds
show 5 more
Substituents
Prostaglandin skeleton / Long-chain fatty acid / Hydroperoxy fatty acid / Heterocyclic fatty acid / Ortho-dioxane / Fatty acid / Unsaturated fatty acid / Allylic hydroperoxide / Ortho-dioxolane / Dialkyl peroxide
show 14 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
prostaglandins G (CHEBI:27647) / Prostaglandins (C05956) / Prostaglandins (LMFA03010009)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. 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]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 05:12