Iloprost (CED0003879)

Record Information

Version

1.0

Creation Date

2016-05-22 04:30:19 UTC

Update Date

2026-08-22 10:18:33 UTC

SynCED ID

CED0003879

Secondary Accession Numbers

CHEM017633

Identification

Common Name

Iloprost

Class

Small Molecule

Description

Iloprost is an organic compound with the chemical formula C30H38O5 and an average molecular weight of 478.62 g/mol. Iloprost belongs to the eicosanoids, a subclass of fatty acyls within the organic compounds. This compound is found in or released from three recorded sources, including antithrombotic agents within healthcare, pharmaceuticals, and veterinary products, as well as household cleaning and consumer products specifically related to tobacco pipes and pipe accessories. Recorded exposure routes for the substance include respiratory and intravenous administration. Iloprost interacts with nine recorded protein targets. It acts as an agonist, inducer, or otherwise interacts with the prostacyclin receptor (PTGIR), tissue-type plasminogen activator (PLAT), 3',5'-cyclic-AMP phosphodiesterase 4A (PDE4A), and 3',5'-cyclic-AMP phosphodiesterase 4B (PDE4B), in addition to five other proteins.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Iloprost-pe	HMDB
2-oxo-2-Phenylethyl 5-[(2Z)-5-hydroxy-4-[(1E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoic acid	HMDB
Iloprost phenacyl ester	HMDB

Chemical Formula

C₃₀H₃₈O₅

Average Molecular Mass

478.620 g/mol

Monoisotopic Mass

478.272 g/mol

CAS Registry Number

78919-13-8

IUPAC Name

2-oxo-2-phenylethyl 5-[(2Z)-5-hydroxy-4-[(1E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoate

Traditional Name

iloprost

SMILES

CC#CCC(C)C(O)\C=C\C1C(O)CC2C\C(CC12)=C\CCCC(=O)OCC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H38O5/c1-3-4-10-21(2)27(31)16-15-25-26-18-22(17-24(26)19-28(25)32)11-8-9-14-30(34)35-20-29(33)23-12-6-5-7-13-23/h5-7,11-13,15-16,21,24-28,31-32H,8-10,14,17-20H2,1-2H3/b16-15+,22-11-

InChI Key

CZUMMMDKQYRZDP-JCAXBLPDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Alkyl-phenylketone
Aromatic monoterpenoid
Monoterpenoid
Bicyclic monoterpenoid
Phenylketone
Fatty alcohol
Benzoyl
Aryl alkyl ketone
Aryl ketone
Fatty acid ester
Alpha-acyloxy ketone
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Ketone
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	5.04	ALOGPS
logP	4.94	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.72	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	139.85 m³·mol⁻¹	ChemAxon
Polarizability	55.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-3953200000-b443b1bda7d785ac5d30	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-1900210000-4e1ef34a133a2751758b	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fu-0002900000-6a96f6c0e27208aa18ae	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01yc-5455900000-87ae1678bc484e678de9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-057i-9483100000-98e240ce9fc267005932	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004l-0105900000-bd6afd767ba75381c69a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-056u-5509500000-2084dc240e0f75394853	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9413000000-b2178e58ccb54de33168	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0017900000-5e1366159937b37e0b05	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0aor-5308900000-271908350c9d4b1e9c90	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udu-9204300000-168e9fb8385284dbfa8a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-056r-0102900000-10e1eb3ea58023970cd4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-7903300000-97e90a9cce893500efab	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-054k-7194400000-f7eb359410db7895850e	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2705.0 Log mg/kg [1500:4800]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000273	Antithrombotic agents?Antithrombotic agents are synthetic chemicals designed to prevent blood clot formation, commonly used in the treatment and management of cardiovascular diseases.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	Not Available
CEDs000562	Pipe Accessories?Pipe accessories, such as fittings, connectors, and seals, are components used in plumbing systems to facilitate the flow of liquids and gases.	Household cleaning & consumer products	Not Available
CEDs000566	Tobacco Pipes?Tobacco pipes, often made from materials such as plastic, wood, or metal, can serve as sources of synthetic chemical contamination due to the residues left by tobacco products.	Household cleaning & consumer products	Not Available
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	Not Available
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	Not Available
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	Not Available
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	Not Available
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	Not Available
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	Not Available
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	Not Available
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	Not Available
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	Not Available
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	Not Available
CEDs000732	Spectacle Cases?Spectacle cases can serve as a source of synthetic chemical contamination due to the materials used in their production, such as polycarbonate, PVC, and various plastics, which may leach harmful substances over time.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	Not Available
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	Not Available

Pathways

2 pathwaysPathway Source: PathBank

Iloprost Action Pathway

Iloprost Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Prostacyclin receptor	P43119	Humans	Predicted (SEA)	Prediction Confidence Score 0.37 Applicability Domain 0.722 Statistical Significance 6.10e-04 Supporting Reference Compounds 63 E-value 4.7488
Click to view 3D structure	Prostaglandin E2 receptor EP3 subtype	P43115	Humans	Predicted (SEA)	Prediction Confidence Score 0.368 Applicability Domain 0.722 Statistical Significance 0.0016 Supporting Reference Compounds 102 E-value 12.6116
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	P43116	Humans	Predicted (SEA)	Prediction Confidence Score 0.359 Applicability Domain 0.722 Statistical Significance 0.0012 Supporting Reference Compounds 95 E-value 9.03051
Click to view 3D structure	Prostaglandin E2 receptor EP1 subtype	P34995	Humans	Predicted (SEA)	Prediction Confidence Score 0.343 Applicability Domain 0.722 Statistical Significance 0.0019 Supporting Reference Compounds 78 E-value 14.5578
Click to view 3D structure	Prostaglandin D2 receptor	Q13258	Humans	Predicted (SEA)	Prediction Confidence Score 0.333 Applicability Domain 0.722 Statistical Significance 0.0017 Supporting Reference Compounds 81 E-value 13.1565
Click to view 3D structure	Prostaglandin F2-alpha receptor	P43088	Humans	Predicted (SEA)	Prediction Confidence Score 0.276 Applicability Domain 0.309 Statistical Significance 0.004 Supporting Reference Compounds 50 E-value 31.4511
Click to view 3D structure	Prostacyclin receptor	P43253	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.266 Applicability Domain 0.722 Statistical Significance 2.40e-04 Supporting Reference Compounds 7 E-value 1.86838
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	P35408	Humans	Predicted (SEA)	Prediction Confidence Score 0.264 Applicability Domain 0.309 Statistical Significance 0.0157 Supporting Reference Compounds 92 E-value 122.223
Click to view 3D structure	Prostaglandin E2 receptor EP3 subtype	P30557	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.258 Applicability Domain 0.263 Low confidence Statistical Significance 0.0067 Supporting Reference Compounds 32 E-value 52.0811
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	P32240	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.258 Applicability Domain 0.263 Low confidence Statistical Significance 0.0071 Supporting Reference Compounds 29 E-value 55.1172
Click to view 3D structure	Prostaglandin F2-alpha receptor	P37289	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.255 Applicability Domain 0.326 Statistical Significance 4.30e-04 Supporting Reference Compounds 6 E-value 3.34752
Click to view 3D structure	Prostaglandin E2 receptor EP1 subtype	P35375	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.263 Low confidence Statistical Significance 0.0064 Supporting Reference Compounds 24 E-value 50.057
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	Q62053	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.263 Low confidence Statistical Significance 0.0049 Supporting Reference Compounds 25 E-value 38.4575
Click to view 3D structure	Solute carrier organic anion transporter family member 2A1	Q92959	Humans	Predicted (SEA)	Prediction Confidence Score 0.247 Applicability Domain 0.292 Low confidence Statistical Significance 5.80e-04 Supporting Reference Compounds 4 E-value 4.51525
Click to view 3D structure	Solute carrier organic anion transporter family member 2B1	Q9JHI3	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.243 Applicability Domain 0.25 Low confidence Statistical Significance 8.90e-04 Supporting Reference Compounds 2 E-value 6.92858
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	Q28691	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.24 Applicability Domain 0.24 Low confidence Statistical Significance 8.50e-04 Supporting Reference Compounds 1 E-value 6.61718
Click to view 3D structure	Thromboxane A2 receptor	P21731	Humans	Predicted (SEA)	Prediction Confidence Score 0.234 Applicability Domain 0.265 Low confidence Statistical Significance 0.0728 Supporting Reference Compounds 96 E-value 566.509
Click to view 3D structure	Solute carrier organic anion transporter family member 2A1	Q9EPT5	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.233 Applicability Domain 0.25 Low confidence Statistical Significance 0.0011 Supporting Reference Compounds 2 E-value 8.87481
Click to view 3D structure	Prostaglandin F2-alpha receptor	P43117	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.215 Applicability Domain 0.25 Low confidence Statistical Significance 0.0092 Supporting Reference Compounds 10 E-value 71.6991
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.21 Applicability Domain 0.216 Low confidence Statistical Significance 0.7319 Supporting Reference Compounds 955 E-value 5697.71
Click to view 3D structure	Protein-glutamine gamma-glutamyltransferase	Q7M0F8	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.209 Applicability Domain 0.232 Low confidence Statistical Significance 0.0282 Supporting Reference Compounds 2 E-value 219.379
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	P43114	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.208 Applicability Domain 0.255 Low confidence Statistical Significance 0.0362 Supporting Reference Compounds 16 E-value 281.97
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.206 Applicability Domain 0.216 Low confidence Statistical Significance 0.7686 Supporting Reference Compounds 1103 E-value 5983.72
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	Prediction Confidence Score 0.205 Applicability Domain 0.216 Low confidence Statistical Significance 0.6146 Supporting Reference Compounds 385 E-value 4784.69
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	Prediction Confidence Score 0.205 Applicability Domain 0.216 Low confidence Statistical Significance 0.4861 Supporting Reference Compounds 266 E-value 3784.41