ChemFOnt: Showing chemical card for 13,14-Dihydro-15-keto PGF2a (CFc000002172)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:59 UTC

Chemfont ID

CFc000002172

Molecule Identification

Common Name

13,14-Dihydro-15-keto PGF2a

Definition

13,14-dihydro-15-keto PGF2a E1 is an isoprostane. The isoprostanes embody a vast family of novel prostaglandin-like lipids that are produced by nonenzymatic peroxidation of arachidonic acid (AA) in response to free radicals and reactive oxygen species. Although free AA is required for the formation of prostaglandins by cyclooxygenases, the isoprostanes can be generated nonenzymatically from esterified AA in membrane phospholipids before being released by a phospholipase(s). Another dissimilarity is that isoprostanes feature side chains that are almost exclusively orientated cis relative to the cyclopentane ring and are therefore distinct from the prostaglandins, which always have side chains in the trans configuration. Nevertheless, isoprostanes are isomeric with prostaglandins and have been given the prefix D-, E-, and F{alpha}- to denote the prostane ring shared with PGD2, PGE2, and PGF2{alpha} respectively. An additional level of complexity is that peroxidation of AA can occur at one of any of four carbon atoms producing regioisomers, the so-called 5-, 12-, 8-, and 15-series isoprostanes, each consisting of eight racemic diastereomers. Thus, a total of 64 isomers can be generated for each of the D-, E-, and F{alpha}-ring isoprostanes. (PMID: 15528403 ). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid

Traditional Name

7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid

CAS Registry Number

27376-76-7

SMILES

[H][C@@]1(O)C[C@]([H])(O)[C@]([H])(CC=CCCCC(O)=O)[C@@]1([H])CCC(=O)CCCCC

InChI Identifier

InChI=1S/C20H34O5/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/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/t16-,17-,18+,19-/m1/s1

InChI Key

VKTIONYPMSCHQI-AKHDSKFASA-N

Chemical Taxonomy

Description

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

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Hydroxy fatty acid
Cyclopentanol
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 3252730)

Cellular substructure

Extracellular (HMDB: HMDB0004685)
Membrane (HMDB: HMDB0004685)

Source

Exogenous

Exogenous (HMDB: HMDB0004685)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0004685)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Pregnancy (MarkerDB: MDB00013452)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.12	ALOGPS
logP	3.02	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.31	ChemAxon
pKa (Strongest Basic)	-2.9	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	13	ChemAxon
Refractivity	98.48 m³·mol⁻¹	ChemAxon
Polarizability	41.39 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023404

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

105046

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 13,14-Dihydro-15-keto PGF2a (CFc000002172)

MOL for CFc000002172 (13,14-Dihydro-15-keto PGF2a)

3D MOL for CFc000002172 (13,14-Dihydro-15-keto PGF2a)

3D SDF for CFc000002172 (13,14-Dihydro-15-keto PGF2a)

3D-SDF for CFc000002172 (13,14-Dihydro-15-keto PGF2a)

PDB for CFc000002172 (13,14-Dihydro-15-keto PGF2a)

3D PDB for CFc000002172 (13,14-Dihydro-15-keto PGF2a)

SMILES for CFc000002172 (13,14-Dihydro-15-keto PGF2a)

INCHI for CFc000002172 (13,14-Dihydro-15-keto PGF2a)

Structure for CFc000002172 (13,14-Dihydro-15-keto PGF2a)

3D Structure for CFc000002172 (13,14-Dihydro-15-keto PGF2a)