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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:08 UTC
Update Date2018-05-19 21:52:25 UTC
HMDB IDHMDB0002752
Secondary Accession Numbers
  • HMDB0062524
  • HMDB02752
  • HMDB62524
Metabolite Identification
Common NameProstaglandin A2
DescriptionProduced by the seminal vesicles, prostaglandins are a group of lipid compounds that are derived enzymatically from fatty acids. Technically hormones, the prostanoid class of fatty acid derivatives is a subclass of 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. Prostaglandin A is a cyclopentenone and is an endogenous metabolite derived from arachidonic acid. It exhibits potent cellular anti-proliferative activity in vivo and in vitro. Excess PGA2 causes an accumulation in both S and G2/M, and a marked decrease in G1. There is also an increase in DNA content preceeding the G0/G1 peak (indicative of apoptotic body formation) mediated by changes in expression levels of Bax and Bcl-2.
Structure
Thumb
Synonyms
ValueSource
(15S)-PGA2ChEBI
(15S)-Prostaglandin a2ChEBI
5,6-cis-PGA2ChEBI
MedullinChEBI
7-[2-(3-hydroxy-1-octenyl)-5-oxo-3-cyclopenten-1-yl]-5-Heptenoic acidCAS
(5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5,10,13-trien-1-oic acidCAS
(+)-Prostaglandin A2CAS
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoateCAS
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoic acidCAS
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoateCAS
15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoic acidCAS
15(S)-Prostaglandin A2CAS
15α-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylateCAS
15α-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylic acidCAS
15α-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoateCAS
15α-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoic acidCAS
NSC 165561CAS
PGA2CAS
Prostaglandin A2CAS
Chemical FormulaC20H30O4
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
IUPAC Name(5Z)-7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid
Traditional Nameprostaglandin A2
CAS Registry Number13345-50-1
SMILES
CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O4/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/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-12+/t16-,17-,18+/m0/s1
InChI KeyMYHXHCUNDDAEOZ-FOSBLDSVSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • 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 Solubility0.021 g/LALOGPS
logP4.08ALOGPS
logP4.38ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.09 m³·mol⁻¹ChemAxon
Polarizability38.66 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0059-4920000000-710b83c9a85f25a1d16cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0059-4910000000-db2352d8228dc4eb9a18View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02bo-6293000000-822f7d0eecbf0f64639bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0209-9313300000-440ddaf4dbe3670c7d28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0169000000-4a6959ca7f335a56a955View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ds-3192000000-3ab10f6f0529d4cee7b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l0j-9120000000-0ee0572914cf0adba33bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-17f7af2365a9dd00dcd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-2159000000-c7485c819c912f1819ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9430000000-9a1157c44c3655697519View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0000448 +/- 0.000496 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0010 +/- 0.0002 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.000167 +/- 0.000401 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.0019 +/- 0.0004 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0027 +/- 0.0008 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0000747 +/- 0.000254 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0008 +/- 0.0002 uMAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05953
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280880
PDB IDNot Available
ChEBI ID27820
References
Synthesis ReferenceGrieco, Paul A.; Abood, Norman. Facile retro Diels-Alder reaction of a pentamethyltricyclo[5.2.1.02,6]decenone derivative: synthesis of (+)-15(S)-prostaglandin A2. Journal of the Chemical Society, Chemical Communications (1990), (5), 410-12.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.