ChemFOnt: Showing chemical card for Prostaglandin E1 (CFc000001114)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:40 UTC

Chemfont ID

CFc000001114

Molecule Identification

Common Name

Prostaglandin E1

Definition

Prostaglandin E1 (PGE1) is a potent endogenous vasodilator agent that increases peripheral blood flow. It inhibits platelet aggregation and has many other biological effects such as bronchodilation, mediation of inflammation, and various protective functions. The protective action of PGE1 has been shown on both experimental animal models of liver injury and patients with fulminant viral hepatitis. PGE1-treated cirrhotic rats had less hepatosplenomegaly, lower serum alanine aminotransferase levels and portal pressures, and higher arterial pressure than placebo-treated cirrhotic rats. There are several mechanisms of PGE1 hepatic cytoprotection: inhibiting T-cell mediated cytotoxicity, enhancing DNA synthesis of the injured liver after partial hepatectomy by stimulating cyclic AMP production, increasing ATP level in hepatic tissue to accelerate the recovery of mitochondrial respiratory function after reperfusion, and stabilizing membrane microviscosity. PGE1 is a prostanoid. The term prostanoid collectively describes prostaglandins, prostacyclins, and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They are derived from C-20 polyunsaturated fatty acids, mainly dihomo-γ-linolenic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2) (PMID: 11819590 , 16986207 ). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent and are able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis through receptor-mediated G-protein linked signalling pathways.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate	HMDB
(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid	HMDB
(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate	HMDB
(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid	HMDB
(-)-Prostaglandin e1	HMDB
(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoate	HMDB
(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid	HMDB
(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoate	HMDB
(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoic acid	HMDB
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate	HMDB
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid	HMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oate	HMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid	HMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid (acd/name 4.0)	HMDB
3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate	HMDB
3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid	HMDB
Alprostadil	HMDB
Alprostadil prostoglandin e1	HMDB
Alprostadil(usan)	HMDB
Befar	HMDB
Caverject	HMDB
EDEX	HMDB
L-Prostaglandin e1	HMDB
MUSE	HMDB
PGE1	HMDB
Prink	HMDB
Prostin VR	HMDB
Abbott brand OF alprostadil	MeSH
Allphar brand OF alprostadil	MeSH
Astra brand OF alprostadil	MeSH
AstraZeneca brand OF alprostadil	MeSH
Hoyer brand OF alprostadil	MeSH
Janssen brand OF alprostadil	MeSH
lipo PGE1	MeSH
lipo-PGE1	MeSH
Minprog	MeSH
PGE1alpha	MeSH
Paladin brand OF alprostadil	MeSH
Pharmacia brand 1 OF alprostadil	MeSH
Pharmacia brand 2 OF alprostadil	MeSH
Prostaglandin e1alpha	MeSH
Prostavasin	MeSH
Prostine VR	MeSH
Schwarz brand OF alprostadil	MeSH
Schwarz pharma brand OF alprostadil	MeSH
Sugiran	MeSH
Vasaprostan	MeSH
Viridal	MeSH
Vivus brand OF alprostadil	MeSH

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

Traditional Name

alprostadil

CAS Registry Number

745-65-3

SMILES

[H][C@](O)(CCCCC)C=C[C@@]1([H])[C@]([H])(O)CC(=O)[C@]1([H])CCCCCCC(O)=O

InChI Identifier

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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/t15-,16+,17+,19+/m0/s1

InChI Key

GMVPRGQOIOIIMI-DODZYUBVSA-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
Long-chain fatty acid
Fatty alcohol
Hydroxy fatty acid
Cyclopentanol
Cyclic alcohol
Cyclic ketone
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8070511)

Cell

Fibroblasts (HMDB: HMDB0001442)
Neuron (HMDB: HMDB0001442)

Hematocyte

Platelet (HMDB: HMDB0001442)

Organ

Tissue

Epithelium

Epidermis (HMDB: HMDB0001442)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0001442)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0001442)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.079 g/L	ALOGPS
logP	3.04	ALOGPS
logP	3.59	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	98.32 m³·mol⁻¹	ChemAxon
Polarizability	42.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB00770

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022625

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Prostaglandin E1

METLIN ID

Not Available

PubChem Compound

149351

PDB ID

Not Available

ChEBI ID

92915

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Liang, Yong-tao; Wei, Feng-ping; Li, Gui-ying; Wang, En-si. Chemoenzymic synthesis of prostaglandin E1. Jilin Daxue Ziran Kexue Xuebao (2001), (2), 77-80.

Showing chemical card for Prostaglandin E1 (CFc000001114)

MOL for CFc000001114 (Prostaglandin E1)

3D MOL for CFc000001114 (Prostaglandin E1)

3D SDF for CFc000001114 (Prostaglandin E1)

3D-SDF for CFc000001114 (Prostaglandin E1)

PDB for CFc000001114 (Prostaglandin E1)

3D PDB for CFc000001114 (Prostaglandin E1)

SMILES for CFc000001114 (Prostaglandin E1)

INCHI for CFc000001114 (Prostaglandin E1)

Structure for CFc000001114 (Prostaglandin E1)

3D Structure for CFc000001114 (Prostaglandin E1)