Prostaglandin E2
Athanor · official
C20H32O5 · 352.5 g/mol
IUPAC name: (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
Also called PGE2, dinoprostone, prostaglandin, Cervidil
DangerHarmful if swallowed · May damage fertility or the unborn childNames and identifiers
- IUPAC name
- (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
- Synonyms
- PGE2, dinoprostone, prostaglandin
+ 37 more
Cervidil, Dinoprostone, Prostin E2, Prepidil, Minprostin E2, Propess, Minprositin E2, Dinoproston, Dinoprostonum, Cerviprost, Dinoprostona, Enzaprost E, Cerviprime, Prostenone, PGE2alpha, U-12062, (5Z,11alpha,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid, Prostaglandin E2alpha, (E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid, DTXSID4022947, U 12062, K7Q1JQR04M, Prostaglandin E(2), (Z)-7-[(1R,2R,3R)-3-Hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid, (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid, NSC-165560, NSC-196514, (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate, Dinoprostone beta-Cyclodextrin Clathrate, 5-Heptenoic acid, 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-, Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11alpha,13E,15S)-, DTXCID002947, (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate, CHEBI:15551, U-12,062, Prosta-5,13-dien-1-oic acid, (5Z,11-alpha,13E,15S)-11,15-dihydroxy-9-oxo-, PGE2 alpha
- Molecular formula
- C20H32O5
- Empirical formula
- C20H32O5
- Molecular weight
- 352.5 g/mol
- Exact mass
- 352.22497
- CAS number
- 363-24-6
- PubChem CID
- 5280360
- Canonical SMILES
- CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
- Isomeric SMILES
- CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O
- InChI
- InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
- InChIKey
- XEYBRNLFEZDVAW-ARSRFYASSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 25
- Rings
- 1
- Aromatic rings
- 0
- Fraction sp³ carbons (Fsp3)
- 0.7
- H-bond donors
- 3
- H-bond acceptors
- 4 computed here · PubChem 5
- Rotatable bonds
- 12
- TPSA (Ų)
- 94.8
- Formal charge
- 0
- XLogP3
- 2.8 PubChem
- Complexity
- 469 PubChem
- Stereocenters
- 4 definedCIP: C6: S · C10: R · C11: R · C16: R
- Double-bond geometry
- C8=C9: E · C18=C19: Z
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C68.15%
- H9.15%
- O22.70%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- 3.25 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -3.28 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.87 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 352.47
- log P ≤ 5 (Crippen): 3.25
- H-bond donors ≤ 5: 3
- H-bond acceptors ≤ 10: 4
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
Danger
Most widely reported: 79 company reports to ECHA. Source [1].
- Harmful or irritant
- Health hazard
- H302Harmful if swallowed
- H360May damage fertility or the unborn child (94.9% of reports)
Precautionary statements: P203, P264, P270, P280, P301+P317, P318, P330, P405, P501
Safety data sheets on the supplier’s page: Alfa Chemistry, SHANDONG OCTAGON CHEMICALS LIMITED, InvivoChem.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 1H NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · 100%_DMSO)
- 1H-13C NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · 100%_DMSO)
- GC-MSHuman Metabolome Database (HMDB) (GC-MS) · MassBank of North America (MoNA) (GC-MS)
- MS-MSHuman Metabolome Database (HMDB) (LC-ESI-QIT · negative) · Human Metabolome Database (HMDB) (LC-ESI-QIT · negative) · Human Metabolome Database (HMDB) (LC-ESI-QIT · negative) · Human Metabolome Database (HMDB) (LC-ESI-QIT · negative) · Human Metabolome Database (HMDB) (LC-ESI-QIT · negative) · Human Metabolome Database (HMDB) (LC-ESI-QIT · negative)
- LC-MSMassBank Europe (Agilent 6560 QTOF · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Agilent 6560 QTOF · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Agilent 6560 QTOF · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Agilent 6560 QTOF · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Agilent 6560 QTOF · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (Agilent 6560 QTOF · LC-ESI-QTOF · NEGATIVE)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [2]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [3]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- [4]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- [5]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.