Prostaglandin A1 (CHEM035459)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:47:01 UTC
Update Date2026-04-03 00:39:03 UTC
Accession NumberCHEM035459
Identification
Common NameProstaglandin A1
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(13E)-(15S)-15-Hydroxy-9-oxoprosta-10,13-dienoateChEBI
PGA1ChEBI
(13E)-(15S)-15-Hydroxy-9-oxoprosta-10,13-dienoic acidGenerator
(13E,15S)-15-Hydroxy-9-oxo-prosta-10,13-dien-1-OateHMDB
(13E,15S)-15-Hydroxy-9-oxo-prosta-10,13-dien-1-Oic acidHMDB
15-Hydroxy-9-oxoprosta-10,13-dienoateHMDB
15-Hydroxy-9-oxoprosta-10,13-dienoic acidHMDB
15a-Hydroxy-9-ketoprosta-10,13-dienoateHMDB
15a-Hydroxy-9-ketoprosta-10,13-dienoic acidHMDB
15a-Hydroxy-9-oxo-10,13E-prostadienoateHMDB
15a-Hydroxy-9-oxo-10,13E-prostadienoic acidHMDB
2-(3-Hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoateHMDB
2-(3-Hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoic acidHMDB
2-(3-Hydroxy-1-octenyl)-5-oxo-3-cyclopentene-1-heptanoateHMDB
2-(3-Hydroxy-1-octenyl)-5-oxo-3-cyclopentene-1-heptanoic acidHMDB
Prostaglandin e1-217HMDB
Prostaglandin a1, (13E,15R)-(+-)-isomerMeSH, HMDB
Prostaglandin a1, (13E,15R)-isomerMeSH, HMDB
Prostaglandin a1, (13E,15S)-(+-)-isomerMeSH, HMDB
Prostaglandin a1, (8beta,12alpha,13E,15S)-isomerMeSH, HMDB
Prostaglandin a1MeSH
Chemical FormulaC20H32O4
Average Molecular Mass336.466 g/mol
Monoisotopic Mass336.230 g/mol
CAS Registry Number14152-28-4
IUPAC Name7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoic acid
Traditional Nameprostaglandin A1
SMILESCCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=O
InChI IdentifierInChI=1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1
InChI KeyBGKHCLZFGPIKKU-LDDQNKHRSA-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
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • 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
Water Solubility0.015 g/LALOGPS
logP4.21ALOGPS
logP4.74ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.45ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity97.97 m³·mol⁻¹ChemAxon
Polarizability40.11 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, Positivesplash10-0673-4092000000-6874868660d1be2cc397Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-9103300000-0b8807822e2ae6a44c8eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0029000000-ef612f000f40cf5fb612Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l6u-3194000000-1d504119f0ddf6f99cfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tv-9120000000-04e28ba462f08d52e16bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-af954838d61275b1a6b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-2159000000-3d6b28690c12cfabfbb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9540000000-0657404cf2ca8a295d26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0019000000-943865bd4f76ac81c5b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-8978000000-1b9129ec137ac84e784fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05qc-9500000000-74f6b19254976131ff01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0029000000-eee5cd4fa1c96d9b3408Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0597000000-eae1be9c15781533cefcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05oa-5940000000-1dadced25493924491ccSpectrum
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 IDHMDB0002656
FooDB IDFDB023040
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID407
PDB IDNot Available
Wikipedia LinkProstaglandin-A1 Delta-isomerase
Chemspider ID4445196
ChEBI ID15545
PubChem Compound ID5281912
Kegg Compound IDC04685
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Pike, John E.; Lincoln, F. H.; Schneider, William Paul. Prostanoic acid chemistry. Journal of Organic Chemistry (1969), 34(11), 3552-7.
2. Sasaki H, Fukushima M: Prostaglandins in the treatment of cancer. Anticancer Drugs. 1994 Apr;5(2):131-8.
3. Gueriguian FL: Prostaglandin-macromolecule interactions. I. Noncovalent binding of prostaglandins A1, E1, F2alpha, and E2 by human and bovine serum albumins. J Pharmacol Exp Ther. 1976 May;197(2):391-401.
4. Montgomery RG, Patel NC, Lee JG: A comparison of the diuretic effects of prostaglandin A1, sodium ethacrynate, and placebo. Int J Clin Pharmacol Biopharm. 1975 Jul;12(1-2):102-8.
5. Aitokallio-Tallberg A, Viinikka L, Ylikorkala O: Urinary 6-keto-prostaglandin F1a in patients with gynaecological tumours. Cancer Lett. 1987 Feb;34(2):201-6.
6. Zhu Y, Gu ZL, Liang ZQ, Zhang HL, Qin ZH: Prostaglandin A1 inhibits increases in intracellular calcium concentration, TXA(2) production and platelet activation. Acta Pharmacol Sin. 2006 May;27(5):549-54.
7. Santoro MG: Heat shock proteins and virus replication: hsp70s as mediators of the antiviral effects of prostaglandins. Experientia. 1994 Nov 30;50(11-12):1039-47.
8. Fukushima S, Kishimoto S, Takeuchi Y, Fukushima M: Preparation and evaluation of o/w type emulsions containing antitumor prostaglandin. Adv Drug Deliv Rev. 2000 Dec 6;45(1):65-75.