Prostaglandin G2

Identification

Generic Name

Prostaglandin G2

DrugBank Accession Number

DB03866

Background

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]

Type

Small Molecule

Groups

Experimental

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Prostaglandin G2 (DB03866)

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Weight

Average: 368.4645
Monoisotopic: 368.219888756

Chemical Formula

C₂₀H₃₂O₆

Synonyms

Not Available

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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
UProstaglandin G/H synthase 2	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

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Toxicity

Not Available

Pathways

Pathway	Category
Piroxicam Action Pathway	Drug action
Rofecoxib Action Pathway	Drug action
Diclofenac Action Pathway	Drug action
Sulindac Action Pathway	Drug action
Nabumetone Action Pathway	Drug action
Valdecoxib Action Pathway	Drug action
Antipyrine Action Pathway	Drug action
Flurbiprofen Action Pathway	Drug action
Nepafenac Action Pathway	Drug action
Arachidonic Acid Metabolism	Metabolic
Acetylsalicylic Acid Action Pathway	Drug action
Ketorolac Action Pathway	Drug action
Bromfenac Action Pathway	Drug action
Meloxicam Action Pathway	Drug action
Mefenamic Acid Action Pathway	Drug action
Oxaprozin Action Pathway	Drug action
Naproxen Action Pathway	Drug action
Carprofen Action Pathway	Drug action
Etoricoxib Action Pathway	Drug action
Lumiracoxib Action Pathway	Drug action
Phenylbutazone Action Pathway	Drug action
Salsalate Action Pathway	Drug action
Salicylate-Sodium Action Pathway	Drug action
Acetaminophen Action Pathway	Drug action
Etodolac Action Pathway	Drug action
Ketoprofen Action Pathway	Drug action
Ibuprofen Action Pathway	Drug action
Celecoxib Action Pathway	Drug action
Suprofen Action Pathway	Drug action
Indomethacin Action Pathway	Drug action

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Aceclofenac	The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Aceclofenac.
Acemetacin	The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Acemetacin.
Acetylsalicylic acid	The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Acetylsalicylic acid.
Alclofenac	The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Alclofenac.
Aminophenazone	The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Aminophenazone.

Food Interactions

Not Available

Categories

Drug Categories

• Anions
• Autacoids
• Biological Factors
• Eicosanoids
• Electrolytes
• Fatty Acids
• Fatty Acids, Unsaturated
• Free Radicals
• Inflammation Mediators
• Ions
• Lipids
• Oxides
• Oxygen Compounds
• Peroxides
• Prostaglandin Endoperoxides
• Prostaglandins
• Reactive Oxygen Species

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 / Hydroperoxy fatty acids / Heterocyclic fatty acids / Unsaturated fatty acids / 1,2-dioxanes / Allylic hydroperoxides / 1,2-dioxolanes / Dialkyl peroxides / Peroxols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Alkyl hydroperoxides / Hydrocarbon derivatives / Carbonyl compounds

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Substituents

Aliphatic heteropolycyclic compound / Alkyl hydroperoxide / Allylic hydroperoxide / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkyl peroxide / Fatty acid / Heterocyclic fatty acid / Hydrocarbon derivative / Hydroperoxide / Hydroperoxy fatty acid / Long-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organooxygen compound / Ortho-dioxane / Ortho-dioxolane / Oxacycle / Peroxol / Prostaglandin skeleton / Unsaturated fatty acid

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Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

prostaglandins G (CHEBI:27647) / Prostaglandins (C05956) / Prostaglandins (LMFA03010009)

Affected organisms

Not Available

Chemical Identifiers

UNII

AZ87DUD2Y8

CAS number

Not Available

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

References

General References

Not Available

External Links

Human Metabolome Database

HMDB0003235

KEGG Compound

C05956

PubChem Compound

5280883

PubChem Substance

46509030

ChemSpider

4444406

ChEBI

27647

ZINC

ZINC000008220097

PDBe Ligand

PGX

Wikipedia

Prostaglandin_G2

PDB Entries

1ddx

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	0.0264 mg/mL	ALOGPS
logP	4.31	ALOGPS
logP	4.41	Chemaxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.36	Chemaxon
pKa (Strongest Basic)	-4.2	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	85.22 Å2	Chemaxon
Rotatable Bond Count	13	Chemaxon
Refractivity	99.39 m3·mol-1	Chemaxon
Polarizability	40.85 Å3	Chemaxon
Number of Rings	2	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	+	0.859
Blood Brain Barrier	+	0.8659
Caco-2 permeable	-	0.5826
P-glycoprotein substrate	Substrate	0.607
P-glycoprotein inhibitor I	Non-inhibitor	0.7556
P-glycoprotein inhibitor II	Non-inhibitor	0.9371
Renal organic cation transporter	Non-inhibitor	0.8993
CYP450 2C9 substrate	Non-substrate	0.818
CYP450 2D6 substrate	Non-substrate	0.8386
CYP450 3A4 substrate	Non-substrate	0.5401
CYP450 1A2 substrate	Non-inhibitor	0.7686
CYP450 2C9 inhibitor	Non-inhibitor	0.8485
CYP450 2D6 inhibitor	Non-inhibitor	0.9119
CYP450 2C19 inhibitor	Non-inhibitor	0.7986
CYP450 3A4 inhibitor	Non-inhibitor	0.8137
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8634
Ames test	Non AMES toxic	0.6094
Carcinogenicity	Non-carcinogens	0.9048
Biodegradation	Not ready biodegradable	0.6704
Rat acute toxicity	2.9740 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7324
hERG inhibition (predictor II)	Non-inhibitor	0.8095

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-006x-5293000000-4f6f219630c974fad684
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0gb9-0009000000-fa8aaf9b3d16b82204b4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0009000000-3bf4906569364c75a5a8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0019-0019000000-cd8b0cdbce3257cf755a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014r-2379000000-d3aa6159664b84197d60
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-040s-2196000000-b229797b3d5183b95b81
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000f-9830000000-d349a2c46ad04a620fce
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	223.2530617	predicted	DarkChem Lite v0.1.0
[M-H]-	198.73991	predicted	DeepCCS 1.0 (2019)
[M+H]+	222.9631617	predicted	DarkChem Lite v0.1.0
[M+H]+	200.61024	predicted	DeepCCS 1.0 (2019)
[M+Na]+	224.0817617	predicted	DarkChem Lite v0.1.0
[M+Na]+	206.21674	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Prostaglandin G/H synthase 2

Kind

Protein

Organism

Humans

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. [Article]

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Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52