Prostaglandin E3
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Basic information
- CAS
802-31-3- Standard SMILES
CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O- InChIKey
CBOMORHDRONZRN-QLOYDKTKSA-N- Molecular formula
- C20H30O5
- Average molar mass
- 350.4 g/mol
- Monoisotopic mass
- 350.20932405
Overview
Prostaglandin E3 is a prostaglandins E. It has a role as a human metabolite. It is a conjugate acid of a prostaglandin E3(1-).
Names & identifiers
- Preferred name
- Prostaglandin E3
- IUPAC
- (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dienyl]-5-oxocyclopentyl]hept-5-enoic acid
- English name
- 9-OXO-11ALPHA,15S-DIHYDROXY-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID
- Molecular formula
- C20H30O5
- Molecular weight
- 350.45
Names & synonyms
prostaglandin E3PGE3802-31-3delta(17)-PGE1PGE1, delta(17)-delta(17)-Prostaglandin E1ZED6SBL53S9-oxo-11R,15S-dihydroxy-5Z,13E,17Z-prostatrienoic acid(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dienyl]-5-oxocyclopentyl]hept-5-enoic acidCHEBI:28031(5Z,13E,15S,17Z)-11alpha,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-oic acid(5Z,11alpha,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-oic acid
Show more names
Prostaglandin E3 (PGE3)Prostaglandin E3 Exclusive9-OXO-11ALPHA,15S-DIHYDROXY-PROSTA-5Z,13E,17Z-TRIEN-1-OIC ACID(5Z,13E,15S,17Z)-11α,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-oic acid(5Z,11a,13E,15S,17Z) 11,15-dihydroxy-9-oxo-prosta-5,13,17-trien-1-oic acidProsta-5,13,17-trien-1-oicacid, 11,15-dihydroxy-9-oxo-, (5Z,11a,13E,15S,17Z)-Prosta-5,13,17-trien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11α,13E,15S,17Z)-
Prosta-5,13,17-trien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11alpha,13E,15S,17Z)-(Z)-7-((1R,2R,3R)-3-hydroxy-2-((1E,3S,5Z)-3-hydroxyocta-1,5-dienyl)-5-oxocyclopentyl)hept-5-enoic acidProstaglandin E(3)RefChem:176611PGE(3)Prosta-5,13,17-trien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11.alpha.,13E,15S,17Z)-(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,1E,5Z)-3-hydroxyocta-1,5-dien-1-yl)-5-oxocyclopentyl)hept-5-enoic acidDTXSID301045731
Properties
Computed structural propertiesFilling in
- XLogP
- 2.3
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 11
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 506
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
Physical DescriptionSolid
Collision Cross Section185.0 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]
Physicochemical properties
- Melting point
- 84.5 · 84.5-85.5 °C
- Boiling point
- 541 · 541.0±50.0 °C(Predicted)
- Density
- 1.166 · 1.166±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 100 mg/ml · DMF: >100 mg/ml (from PGE2); DMSO: >100 mg/ml (from PGE2); Ethanol: >100 mg/ml (from PGE2); PBS pH 7.2: >5 mg/ml (from PGE2)
- form
- Liquid
- pka
- 4.75 · 4.75±0.10(Predicted)
- color
- Colorless to light yellow
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 E3 (PGE3) is formed via the cyclooxygenase (COX) metabolism of eicosapentaenoic acid. In human ocular tissue, it comprises 2.4% of the COX products formed. When applied to the eyes of a rabbit, a 1 μg dose of PGE3 decreases intraocular pressure from 21 mmHg to about 17 mmHg.
Additional notes
DefinitionChEBI: Prostaglandin E3 is a prostaglandins E. It has a role as a human metabolite. It is a conjugate acid of a prostaglandin E3(1-).
Related reactions
2 records
Compound notes
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