Alprostadil (CHEM016555)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:36:55 UTC
Update Date2016-11-09 01:15:25 UTC
Accession NumberCHEM016555
Identification
Common NameAlprostadil
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acidChEBI
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoateChEBI
11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acidChEBI
AlprostadilChEBI
AlprostadilumChEBI
BefarChEBI
CaverjectChEBI
EdexChEBI
MuseChEBI
PGE-1ChEBI
PGE1ChEBI
Prostin VRChEBI
Prostin VR pediatricKegg
(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
(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)-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-enoic acidGenerator
(13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoateGenerator
(13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acidGenerator
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
11Α,15α-dihydroxy-9-oxo-13-trans-prostenoateGenerator
11Α,15α-dihydroxy-9-oxo-13-trans-prostenoic acidGenerator
Abbott brand OF alprostadilMeSH, HMDB
MinprogMeSH, HMDB
Paladin brand OF alprostadilMeSH, HMDB
Prostaglandin e1alphaMeSH, HMDB
Schwarz pharma brand OF alprostadilMeSH, HMDB
Astra brand OF alprostadilMeSH, HMDB
Hoyer brand OF alprostadilMeSH, HMDB
SugiranMeSH, HMDB
Allphar brand OF alprostadilMeSH, HMDB
AstraZeneca brand OF alprostadilMeSH, HMDB
lipo PGE1MeSH, HMDB
ViridalMeSH, HMDB
lipo-PGE1MeSH, HMDB
VasaprostanMeSH, HMDB
Janssen brand OF alprostadilMeSH, HMDB
PGE1alphaMeSH, HMDB
Pharmacia brand 1 OF alprostadilMeSH, HMDB
ProstavasinMeSH, HMDB
Prostine VRMeSH, HMDB
Pharmacia brand 2 OF alprostadilMeSH, HMDB
Prostaglandin e1MeSH, KEGG
Schwarz brand OF alprostadilMeSH, HMDB
Vivus brand OF alprostadilMeSH, HMDB
PrinkKEGG, HMDB
VitarosKEGG, HMDB
Caverject impulseChEMBL, HMDB
U-10136prostinChEMBL, HMDB
U-10136alprostadilChEMBL, HMDB
(+)-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
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
Alprostadil prostoglandin e1HMDB
Alprostadil(usan)HMDB
L-Prostaglandin e1HMDB
Chemical FormulaC20H34O5
Average Molecular Mass354.487 g/mol
Monoisotopic Mass354.241 g/mol
CAS Registry Number745-65-3
IUPAC Name7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
Traditional Namealprostadil
SMILES[H]\C(=C(\[H])[C@@]1([H])[C@]([H])(O)CC(=O)[C@]1([H])CCCCCCC(O)=O)[C@@]([H])(O)CCCCC
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)/b13-12+/t15-,16+,17+,19+/m0/s1
InChI KeyGMVPRGQOIOIIMI-DWKJAMRDSA-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.
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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP3.59ChemAxon
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
Polarizability42.13 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00ri-0196000000-76a244edad65f2d63bd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-8df8823c74db989620bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0673-4297000000-470e93d0689f9efe2bf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06du-9120000000-617b73c4fa8e71daf174Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-67bf705be88aef628788Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k9l-2159000000-ea5fde7ba374a4b745acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9420000000-64831d7733e0f1578bc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fri-0009000000-923c8a53409a3df92c03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0069000000-1771266ae55287330e24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001v-9481000000-4f3fb6bba04c2db22a67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-48b67d3860a0408d6017Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-7369000000-67c0756e11758bfc63bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9600000000-b116946f56f764ec762eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001442
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkProstaglandin_E1
Chemspider ID4444306
ChEBI ID15544
PubChem Compound ID5280723
Kegg Compound IDC04741
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15295081
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18176061
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=7732902