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Identification
NameProstaglandin G2
Accession NumberDB03866  (EXPT02577)
TypeSmall Molecule
GroupsExperimental
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
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 368.4645
Monoisotopic: 368.219888756
Chemical FormulaC20H32O6
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroperoxy fatty acid
  • Heterocyclic fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Ortho-dioxane
  • Ortho-dioxolane
  • Dialkyl peroxide
  • Hydroperoxide
  • Oxacycle
  • Organoheterocyclic compound
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Lornoxicam Action PathwayDrug actionSMP00700
Phenylbutazone Action PathwayDrug actionSMP00701
Salsalate Action PathwayDrug actionSMP00707
Acetaminophen Action PathwayDrug actionSMP00710
Arachidonic Acid MetabolismMetabolicSMP00075
Meloxicam Action PathwayDrug actionSMP00106
Mefenamic Acid Action PathwayDrug actionSMP00109
Magnesium salicylate Action PathwayDrug actionSMP00698
Nepafenac Action PathwayDrug actionSMP00702
Salicylate-sodium Action PathwayDrug actionSMP00708
Ketorolac Action PathwayDrug actionSMP00098
Suprofen Action PathwayDrug actionSMP00101
Valdecoxib Action PathwayDrug actionSMP00116
Diflunisal Action PathwayDrug actionSMP00289
Leukotriene C4 Synthesis DeficiencyDiseaseSMP00353
Trisalicylate-choline Action PathwayDrug actionSMP00703
Etodolac Action PathwayDrug actionSMP00084
Ibuprofen Action PathwayDrug actionSMP00086
Diclofenac Action PathwayDrug actionSMP00093
Bromfenac Action PathwayDrug actionSMP00102
Antipyrine Action PathwayDrug actionSMP00692
Antrafenine Action PathwayDrug actionSMP00693
Fenoprofen Action PathwayDrug actionSMP00696
Flurbiprofen Action PathwayDrug actionSMP00697
Lumiracoxib Action PathwayDrug actionSMP00699
Tenoxicam Action PathwayDrug actionSMP00706
Salicylic Acid Action PathwayDrug actionSMP00709
Piroxicam Action PathwayDrug actionSMP00077
Acetylsalicylic Acid Action PathwayDrug actionSMP00083
Ketoprofen Action PathwayDrug actionSMP00085
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0119000000-06893304af83e030a39bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zmr-3369000000-b1d0f67eea930b11ae4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1003-9400000000-7fbd48d8b1a086fc44d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-4a1c6a9bb1b35fe201efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r2-2149000000-16bc14c91731cdc79586View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9162000000-ad0929ccdcab78d69a99View in MoNA
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23