PGF3alpha
Basic information
- CAS
745-64-2- Standard SMILES
CC/C=C\C[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O- InChIKey
SAKGBZWJAIABSY-SAMSIYEGSA-N- Molecular formula
- C20H32O5
- Average molar mass
- 352.5 g/mol
- Monoisotopic mass
- 352.22497412
Overview
Prostaglandin F3alpha is a prostaglandin Falpha that is prosta-5,13,17-trien-1-oic acid carrying three hydroxy substituents at positions 9alpha, 11alpha and 15. It is a conjugate acid of a prostaglandin F3alpha(1-).
Names & identifiers
- Preferred name
- PGF3alpha
- IUPAC
- (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dienyl]cyclopentyl]hept-5-enoic acid
- English name
- PROSTAGLANDIN F3ALPHA
- Molecular formula
- C20H32O5
- Molecular weight
- 352.47
Names & synonyms
Prostaglandin F3alphaPGF3alpha745-64-2Prostaglandin F3 alpha9S,11R,15S-trihydroxy-5Z,13E,17Z-prostatrienoic acidCHEBI:36075Prosta-5,13,17-trien-1-oic acid, 9,11,15-trihydroxy-, (5Z,9alpha,11alpha,13E,15S,17Z)-RefChem:176616Prostaglandin F3|A(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dienyl]cyclopentyl]hept-5-enoic acidPROSTAGLANDINF3ALPHA(5Z,13E,15S,17Z)-9alpha,11alpha,15-trihydroxyprosta-5,13,17-trien-1-oic acid
Show more names
PGF3αProstaglandin F3α9ALPHA,11ALPHA,15S-TRIHYDROXY-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID(5Z,13E,15S,17Z)-9α,11α,15-Trihydroxyprosta-5,13,17-trien-1-oic acid(5Z,9S,11R,13E,15S,17Z)-9,11,15-Trihydroxy-5,13,17-prostatriene-1-oic acidProsta-5,13,17-trien-1-oicacid, 9,11,15-trihydroxy-, (5Z,9a,11a,13E,15S,17Z)-Prosta-5,13,17-trien-1-oic acid, 9,11,15-trihydroxy-, (5Z,9α,11α,13E,15S,17Z)-
Prostaglandin F3aDTXSID101357815PGF3.alpha.(5Z,13E,15S,17Z)-9alpha,11alpha,15-trihydroxyprosta-5,13,17-trien-1-oateProstaglandin F3I+/-Prostaglandin F3.alpha.9S,11R,15S-trihydroxy-5Z,13E,17Z-prostatrienoateorb3133179
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 98 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 11
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 469
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 541.7 · 541.7±50.0 °C(Predicted)
- Density
- 1.171 · 1.171±0.06 g/cm3(Predicted)
- solubility
- 10 mM · 10 mM Na2CO3: >6.5 mg/ml (from PGF2a); DMF: >100 mg/ml (from PGF2a); DMSO: >100 mg/ml (from PGF2a); Ethanol: >100 mg/ml (from PGF2a); PBS pH 7.2: >10 mg/ml (from PGF2a)
- pka
- 4.76 · 4.76±0.10(Predicted)
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
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)
- GHS02,GHS07
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
UsesProstaglandin F3α (PGF3α) is an eicosapentaenoic acid (EPA)-derived bioactive lipid mediator that has anti-cancer and anti-inflammatory effects. Prostaglandin F3α is a substrate of ABCC4 with a Km of 12.1 μM. Prostaglandin F3α can be used for the research of diabetes[1][2].
Additional notes
DefinitionChEBI: Prostaglandin F3alpha is a prostaglandin Falpha that is prosta-5,13,17-trien-1-oic acid carrying three hydroxy substituents at positions 9alpha, 11alpha and 15. It is a conjugate acid of a prostaglandin F3alpha(1-).
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