Prostaglandin F2-alpha

Athanor · official

C₂₀H₃₄O₅ · 354.5 g/mol

IUPAC name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid

Also called PGF2a, dinoprost

Hormones Lipids

Open in Athanor

Drawn from its SMILES with RDKit

DangerHarmful if swallowed · Causes serious eye irritation · May damage fertility or the unborn child · Causes damage to organs · Causes damage to organs through prolonged or repeated exposure

Names and identifiers

IUPAC name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
Synonyms: PGF2a, dinoprost, prostaglandin F2alpha
+ 36 more
PGF2alpha, Prostaglandin F2a, amoglandin, Enzaprost, panacelan, Dinoprosta, Protamodin, l-PGF2-alpha, PGF-2alpha, PGF2-alpha, Dinoprostum, Prosmon, l-Prostaglandin F2-alpha, Prostarmon F, Prostin F2alpha, Prostin F2-alpha, cyclosin, Prostaglandin F2 alpha, 9alpha,11alpha-PGF2, U-14583, (+)-Prostaglandin F2a, PGF2 alpha, CCRIS 4253, DTXSID9022946, HSDB 3315, PGF2, Dinoprostum [INN-Latin], U 14583, Dinoprosta [INN-Spanish], UNII-B7IN85G1HY, (+)-Prostaglandin F2alpha, B7IN85G1HY, Prostin F 2 alpha, BRN 2225571, U-14,583, 9a,11a-PGF2
Molecular formula: C₂₀H₃₄O₅
Empirical formula: C₂₀H₃₄O₅
Molecular weight: 354.5 g/mol
Exact mass: 354.24062
CAS number: 551-11-1
PubChem CID: 5280363
Canonical SMILES: CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O
InChI: 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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
InChIKey: PXGPLTODNUVGFL-YNNPMVKQSA-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): 0.75
H-bond donors: 4
H-bond acceptors: 4 computed here · PubChem 5
Rotatable bonds: 12
TPSA (Å²): 98
Formal charge: 0
XLogP3: 2.7 PubChem
Complexity: 432 PubChem
Stereocenters: 5 definedCIP: C6: S · C10: R · C11: R · C14: S · 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

C67.77%
H9.67%
O22.57%

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: 3.04 Crippen (Wildman and Crippen 1999)
log S (water solubility): -3.16 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 3.98 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 354.49
log P ≤ 5 (Crippen): 3.04
H-bond donors ≤ 5: 4
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: 39 company reports to ECHA. Source [2].

Harmful or irritant
Health hazard

H302Harmful if swallowed
H319Causes serious eye irritation (89.7% of reports)
H360May damage fertility or the unborn child (97.4% of reports)
H370Causes damage to organs (89.7% of reports)
H372Causes damage to organs through prolonged or repeated exposure (89.7% of reports)

Precautionary statements: P203, P260, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P308+P316, P318, P319, P321, P330, P337+P317, P405, P501

Safety data sheets on the supplier’s page: Alfa Chemistry, CymitQuimica, Key Organics/BIONET.

Always read the supplier’s safety data sheet before working with it.

Spectra

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]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
[2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[5]MassBank of North America (MoNA) · CC BY 4.0 · 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.