You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:01 UTC
Update Date2020-02-26 21:24:13 UTC
HMDB IDHMDB0002656
Secondary Accession Numbers
  • HMDB02656
Metabolite Identification
Common NameProstaglandin A1
DescriptionProstaglandin A1 (PGA1, a prostaglandin characterized by a cyclopentenone structure) has a fundamental structure common to punaglandin and clavulone, the antitumor eicosanoids discovered in marine organisms such as corals. It is well established that PGA1, which exert potent antiviral activity in several DNA and RNA virus models, induce heat shock protein (hsp)70 syntheses through cycloheximide sensitive activation of heat shock transcription factor. Antitumor prostaglandins are actively incorporated through cell membrane and control gene expression. P53 (protein 53, is a transcription factor that regulates the cell cycle and functions as a tumor suppressor) independent expression of p21 (also known as cyclin-dependent kinase inhibitor 1A or CDKN1A, is a human gene on chromosome 6 (location 6p21.2), that encodes a cyclin-dependent kinase) and gadd 45 (growth arrest and DNA-damage-inducible, alpha 45, a major breast cancer (BRCA1) target is the DNA damage-responsive gene GADD45) activation of peroxisome proliferative activated receptor gamma (PPARgamma) are involved in antitumor mechanism of these prostaglandins. At the low concentration, these prostaglandins exhibit physiological or pathological activity such as osteoblast calcification, promotion of colon cancer cell proliferation. One of the mechanisms of anti-cancer activity of prostaglandins, has been believed to be that these prostaglandins might have p53 like effect in cells lacking p53. (PMID: 7988663 , 11104898 )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 signalling pathways.
Structure
Data?1582752253
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)-(+-)-isomerHMDB
Prostaglandin a1, (13E,15R)-isomerHMDB
Prostaglandin a1, (13E,15S)-(+-)-isomerHMDB
Prostaglandin a1, (8beta,12alpha,13E,15S)-isomerHMDB
Prostaglandin a1MeSH
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoic acid
Traditional Nameprostaglandin A1
CAS Registry Number14152-28-4
SMILES
CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=O
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000074 +/- 0.000048 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023040
KNApSAcK IDNot Available
Chemspider ID4445196
KEGG Compound IDC04685
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProstaglandin-A1 Delta-isomerase
METLIN ID407
PubChem Compound5281912
PDB IDNot Available
ChEBI ID15545
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferencePike, John E.; Lincoln, F. H.; Schneider, William Paul. Prostanoic acid chemistry. Journal of Organic Chemistry (1969), 34(11), 3552-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sasaki H, Fukushima M: Prostaglandins in the treatment of cancer. Anticancer Drugs. 1994 Apr;5(2):131-8. [PubMed:8049495 ]
  2. 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. [PubMed:944773 ]
  3. 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. [PubMed:1165130 ]
  4. 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. [PubMed:3545443 ]
  5. 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. [PubMed:16626509 ]
  6. 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. [PubMed:7988663 ]
  7. 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. [PubMed:11104898 ]