Prostacyclin (C20H32O5): structure, properties and hazards

Names and identifiers

IUPAC name: (5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid
Synonyms: PGI2, prostaglandin I2, epoprostenol
+ 36 more
Flolan, platelet inhibitor, Vasocyclin, Prostaglandin X, Epoprostenolum, ACT-385781A, DCR9Z582X0, U-53217, (5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid, (5Z,9alpha,11alpha,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid, U-53,217, DTXSID5022988, CHEBI:15552, 6,9S-epoxy-11R,15S-dihydoxy-5Z,13E-prostadienoic acid, Epoprostanol, (5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoate, Prosta-5,13-dien-1-oic acid, 6,9-epoxy-11,15-dihydroxy-, (5Z,9alpha,11alpha,13E,15S)-, Prostaglandin I(2), epoprostenolo, (5Z)-5-((3aR,4R,5R,6aS)-5-hydroxy-4-((E,3S)-3-hydroxyoct-1-enyl)-3,3a,4,5,6,6a-hexahydrocyclopenta(b)furan-2-ylidene)pentanoic acid, (5Z)-5-((3aR,4R,5R,6aS)-5-hydroxy-4-((E,3S)-3-hydroxyoct-1-enyl)-3,3a,4,5,6,6a-hexahydrocyclopenta(d)furan-2-ylidene)pentanoic acid, (5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[d]furan-2-ylidene]pentanoic acid, RefChem:57239, DTXCID602988, B01AC09, Epoprostenol Sodium Salt, (5Z,9alpha,11alpha,13E,15S)-, Prostacyclin I2, PGX, (Z)-5-((3aR,4R,5R,6aS)-5-hydroxy-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-ylidene)pentanoic acid, PG-I2, (5Z)-5-[(3Ar,4R,5R,6aR)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid, PGI(sub 2), Epoprostenol [USAN:INN], Prosta-5,13-dien-1-oicacid, 6,9-epoxy-11,15-dihydroxy-, (5Z,9a,11a,13E,15S)-, Epoprostenolum [INN-Latin], KB-IV-24
Molecular formula: C₂₀H₃₂O₅
Empirical formula: C₂₀H₃₂O₅
Molecular weight: 352.5 g/mol
Exact mass: 352.22497
CAS number: 35121-78-9
PubChem CID: 5282411
Canonical SMILES: CCCCCC(C=CC1C(CC2C1CC(=CCCCC(=O)O)O2)O)O
Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/O2)O)O
InChI: InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1
InChIKey: KAQKFAOMNZTLHT-OZUDYXHBSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms: 25
Rings: 2
Aromatic rings: 0
Fraction sp³ carbons (Fsp3): 0.75
H-bond donors: 3
H-bond acceptors: 4 computed here · PubChem 5
Rotatable bonds: 10
TPSA (Å²): 87
Formal charge: 0
XLogP3: 2.9 PubChem
Complexity: 484 PubChem
Stereocenters: 5 definedCIP: C6: S · C10: R · C11: R · C14: R · C16: S
Double-bond geometry: C8=C9: E · C17=C18: E
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: 3.41 Crippen (Wildman and Crippen 1999)
log S (water solubility): -3.51 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 5.1 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): 3.41
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

No GHS hazard classification was found in the sources.

Safety data sheets on the supplier’s page: BOC Sciences, RR Scientific, Smolecule.

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]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
[2]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[3]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.

Similar structures

Tanimoto similarity on Morgan fingerprints (radius 2) with RDKit 2026.09, at least 45%.