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8-Epi-prostaglandin F2alpha

HCID 5282263
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
27415-26-5
Standard SMILES
CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O
InChIKey
PXGPLTODNUVGFL-NAPLMKITSA-N
Molecular formula
C20H34O5
Average molar mass
354.5 g/mol
Monoisotopic mass
354.24062418

Overview

8-epi-prostaglandin F2alpha is an isoprostane that is prostaglandin F2alpha having inverted stereochemistry at the 8-position. It has a role as a bronchoconstrictor agent, a vasoconstrictor agent and a biomarker. It is functionally related to a prostaglandin F2alpha. It is a conjugate acid of an 8-epi-prostaglandin F2alpha(1-).

Names & identifiers

Preferred name
8-Epi-prostaglandin F2alpha
IUPAC
(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
English name
8-epi-Prostaglandin F2α
Molecular formula
C20H34O5
Molecular weight
354.48

Names & synonyms

8-Epi-prostaglandin F2alpha27415-26-58-Isoprostaglandin F2alpha8-epi-PGF2alpha8-iso-PGF2alpha8-Epiprostaglandin F2alpha15-F2t-Isoprostane8-iso-PGF2a9,11,15-Trihydroxy-prosta-5,13-dien-1-oic acidCHEBI:34505Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-, (5Z,8beta,9alpha,11alpha,13E,15S)-8-epi-PGF2 alpha
Show more names
8-epi-PGF2α8-Isoprostaglandin F2α-d9(5Z,8β,9α,11α,13E,15S)-9,11,15-trihydroxyprosta-5,13-dien-1-oic Acid8-Iso-PGF2αIPF2ALPHA-III15-F2t-IsoP-d98-epi-PGF2α-d98-Iso-PGF2α-d9
8-F(2t)-isoprostane8-iso-PGF(2alpha)15-F(2t)-isoprostaneisoprostaglandin F2alpha type-IIIRefChem:91455215-F(2t)-IsoP8-Isoprostane15-F2t-IsoP

Database identifiers

CAS
27415-26-5

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
98 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
5
Rotatable bonds
12
Heavy atoms
25
Formal charge
0
Complexity
432

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Isoprostanes [FA0311]
LogP2.183
Physical DescriptionSolid
Collision Cross Section · 3 items

194.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]

199.03 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

197.8 Ų [M+Na]+

Physicochemical properties

Boiling point
531 · 531.0±50.0 °C(Predicted)
Density
1.153 · 1.153±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
solubility
100 mg/ml; · DMF: >100 mg/ml; DMSO: >100 mg/ml; Ethanol: >100 mg/ml; PBS pH 7.2: 3 mg/ml
form
A crystalline solid
pka
4.76 · 4.76±0.10(Predicted)
color
White to off-white

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

Signal word
Danger
Symbol(GHS)
GHS07,GHS08
Hazard statements
H302-H360
Precautionary statements
P201-P202-P264-P270-P280-P301+P312-P330-P308+P313-P405-P501

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationDrugs used to cause constriction of the blood vessels.
Cellular LocationsExtracellular
Applications · 4 items

Description8-iso PGF2α is an isoprostane produced by the non-enzymatic peroxidation of arachidonic acid in membrane phospholipids. It is present in human plasma in two distinct forms - esterified in phospholipids and as the free acid. The ratio of these two forms is approximately 2:1, with a total plasma 8-iso PGF2α level of about 150 pg/ml in normal volunteers. In normal human urine, 8-iso PGF2α levels are about 180-200 pg/mg of creatinine. 8-iso PGF2α is a weak TP receptor agonist in vascular smooth muscle. Conversely, 8-iso PGF2α inhibits platelet aggregation induced by U-46619 (10−6 M) and I-BOP (3 x 10−7 M) with IC50 values of 1.6 x 10−6 M and 1.8 x 10−6 M, respectively.

Description8-iso Prostaglandin F2α (8-iso PGF2α) is an isoprostane produced by the non-enzymatic peroxidation of arachidonic acid in membrane phospholipids. It is present in human plasma in two distinct forms - esterified in phospholipids and as the free acid. The ratio of these two forms is approximately 2:1, with a total plasma 8-iso PGF2α level of about 150 pg/ml in normal volunteers. In normal human urine, 8-iso PGF2α levels are about 180-200 pg/mg of creatinine. 8-iso PGF2α is a weak TP receptor agonist in vascular smooth muscle. Conversely, 8-iso PGF2α inhibits platelet aggregation induced by U-46619 (10−6 M) and I-BOP (3 x 10−7 M) with IC50 values of 1.6 x 10−6 M and 1.8 x 10−6 M, respectively. 8-iso Prostaglandin F2α MaxSpec® standard is a quantitative grade standard of 8-iso Prostaglandin F2α that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This 8-iso Prostaglandin F2α MaxSpec® standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.

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Related reactions

2 records
New reaction record
HRID 868799 reaction equation
HRID 868799As productuspto-grants-2015_03
HRID 1873483 reaction equation
HRID 1873483As productuspto-grants-2012_11

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
5282263
DTXSID
DTXSID10959353
ChEMBL
CHEMBL1592632
ChEBI
CHEBI:34505
UNII
W83YE66SBY
Nikkaji
J493.589F
FDA UNII
83 YE66SBY · W83YE66SBY
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Danger
Hazard statements
302 · H302-H360
Precautionary statements
201 · P201-P202-P264-P270-P280-P301+P312-P330-P308+P313-P405-P501

Uses(8-epi-prostaglandin F2a) A major metabolite of PGF2α. A prostaglandin derivative used as a biomarker in the diagnosis and treatment of cardiovascular-related diseases as well as biomarkers of total body oxidative stress.

UsesA major metabolite of PGF2α. A prostaglandin derivative used as a biomarker in the diagnosis and treatment of cardiovascular-related diseases as well as biomarkers of total body oxidative stress.

Additional notes

DefinitionChEBI: A prostanoid that is prostaglandin F2alpha having inverted stereochemistry at the 8-position.