FComEx: Prostaglandin E1 (PC000899)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:18 UTC

Update date

2017-01-19 02:36:40 UTC

FoodComEx ID

PC000899

FoodDB Record

FDB022625

Chemical Information

Name

Prostaglandin E1

Description

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. Mechanisms of hepatic cytopotection of PGE1: inhibitory effects on T-cell mediated cytotoxicity, enhance DNA synthesis of injured liver after partial hepatectomy by stimulating cyclic AMP production and increasing ATP level in hepatic tissue, and could accelerate the recovery of mitochondrial respiratory functio n after reperfusion, stabilization of membrane microviscosity. PGE1 is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (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, 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 signaling pathways. [HMDB]

CAS Number

745-65-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(-)-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
(+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoate	hmdb
(+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoic acid	hmdb
(11a,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate	Generator
(11a,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid	Generator
(11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate	Generator
(11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid	ChEBI
(11α,13e,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oate	Generator
(11α,13e,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oic acid	Generator
(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)-11,15-dihydroxy-9-oxoprost-13-enoate	hmdb
(13E)-(15S)-11,15-dihydroxy-9-oxoprost-13-enoic acid	hmdb
(13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate	Generator
(13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid	Generator
(13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoate	hmdb
(13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoic acid	hmdb
(13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoate	Generator
(13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoic acid	Generator
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
11a,15a-Dihydroxy-9-oxo-13-trans-prostenoate	Generator
11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acid	Generator
11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoate	Generator
11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid	ChEBI
11α,15α-dihydroxy-9-oxo-13-trans-prostenoate	Generator
11α,15α-dihydroxy-9-oxo-13-trans-prostenoic acid	Generator
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
Alprostadilum	ChEBI
Befar	hmdb
Befar (TN)	hmdb
Caverject	hmdb
EDEX	hmdb
l-Prostaglandin E1	hmdb
MUSE	hmdb
PGE-1	ChEBI
PGE1	hmdb
Prink	hmdb
Prink (TN)	hmdb
prostaglandin E1	hmdb
Prostin VR	hmdb

Chemical Formula

C20H34O5

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

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