Record Information
Version1.0
Creation date2011-09-21 00:17:03 UTC
Update date2015-10-09 22:33:18 UTC
Primary IDFDB022625
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProstaglandin E1
DescriptionProstaglandin 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 Number745-65-3
Structure
Thumb
Synonyms
SynonymSource
(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoateHMDB
(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acidHMDB
(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoateHMDB
(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acidHMDB
(-)-Prostaglandin e1HMDB
(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoateHMDB
(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acidHMDB
(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoateHMDB
(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoic acidHMDB
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoateHMDB
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acidHMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-OateHMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acidHMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid (acd/name 4.0)HMDB
3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoateHMDB
3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acidHMDB
AlprostadilHMDB
Alprostadil prostoglandin e1HMDB
Alprostadil(usan)HMDB
BefarHMDB
CaverjectHMDB
EDEXHMDB
L-Prostaglandin e1HMDB
MUSEHMDB
PGE1HMDB
PrinkHMDB
Prostin VRHMDB
Abbott brand OF alprostadilMeSH
Allphar brand OF alprostadilMeSH
Astra brand OF alprostadilMeSH
AstraZeneca brand OF alprostadilMeSH
Hoyer brand OF alprostadilMeSH
Janssen brand OF alprostadilMeSH
lipo PGE1MeSH
lipo-PGE1MeSH
MinprogMeSH
PGE1alphaMeSH
Paladin brand OF alprostadilMeSH
Pharmacia brand 1 OF alprostadilMeSH
Pharmacia brand 2 OF alprostadilMeSH
Prostaglandin e1alphaMeSH
ProstavasinMeSH
Prostine VRMeSH
Schwarz brand OF alprostadilMeSH
Schwarz pharma brand OF alprostadilMeSH
SugiranMeSH
VasaprostanMeSH
ViridalMeSH
Vivus brand OF alprostadilMeSH
(-)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoatehmdb
(-)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoic acidhmdb
(-)-Prostaglandin E1hmdb
(+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoatehmdb
(+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoic acidhmdb
(11a,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-OateGenerator
(11a,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acidGenerator
(11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-OateGenerator
(11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acidChEBI
(11α,13e,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-OateGenerator
(11α,13e,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oic acidGenerator
(13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoatehmdb
(13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoic acidhmdb
(13E)-(15S)-11,15-dihydroxy-9-oxoprost-13-enoatehmdb
(13E)-(15S)-11,15-dihydroxy-9-oxoprost-13-enoic acidhmdb
(13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoateGenerator
(13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acidGenerator
(13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoatehmdb
(13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoic acidhmdb
(13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoateGenerator
(13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoic acidGenerator
11,15-Dihydroxy-9-oxoprost-13-en-1-oatehmdb
11,15-Dihydroxy-9-oxoprost-13-en-1-oic acidhmdb
11,15-dihydroxy-9-oxoprost-13-en-1-oic acid (ACD/Name 4.0)hmdb
11a,15a-Dihydroxy-9-oxo-13-trans-prostenoateGenerator
11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acidGenerator
11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoateGenerator
11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acidChEBI
11α,15α-dihydroxy-9-oxo-13-trans-prostenoateGenerator
11α,15α-dihydroxy-9-oxo-13-trans-prostenoic acidGenerator
Alprostadil Prostoglandin E1hmdb
AlprostadilumChEBI
Befar (TN)hmdb
l-Prostaglandin E1hmdb
PGE-1ChEBI
Prink (TN)hmdb
prostaglandin E1hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.079 g/LALOGPS
logP3.04ALOGPS
logP3.59ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity98.32 m³·mol⁻¹ChemAxon
Polarizability42.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H34O5
IUPAC name7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
InChI IdentifierInChI=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 KeyGMVPRGQOIOIIMI-DODZYUBVSA-N
Isomeric SMILESCCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
Classification
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins 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 FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSProstaglandin E1, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03du-8496000000-7d3b810081e27f50d55eSpectrum
Predicted GC-MSProstaglandin E1, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4l-9201660000-7be6126c29341044cbc0Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-8df8823c74db989620bfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0673-4297000000-470e93d0689f9efe2bf4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06du-9120000000-617b73c4fa8e71daf174Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-67bf705be88aef628788Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k9l-2159000000-ea5fde7ba374a4b745acSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9420000000-64831d7733e0f1578bc7Spectrum
NMRNot Available
ChemSpider ID4444306
ChEMBL IDCHEMBL495
KEGG Compound IDC04741
Pubchem Compound ID5280723
Pubchem Substance IDNot Available
ChEBI ID15544
Phenol-Explorer IDNot Available
DrugBank IDDB00770
HMDB IDHMDB01442
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID44455
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAlprostadil
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Carbonyl reductase [NADPH] 1CBR1P16152
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference