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Human Metabolome Database Version 3.5

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Showing metabocard for Prostaglandin A1 (HMDB02656)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:01 -0600
Update Date 2013-02-08 17:12:02 -0700
HMDB ID HMDB02656
Secondary Accession Numbers None
Metabolite Identification
Common Name Prostaglandin A1
Description Prostaglandin 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 Link_out, 11104898 Link_out)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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (13E,15S)-15-hydroxy-9-oxo-Prosta-10,13-dien-1-oate
  2. (13E,15S)-15-hydroxy-9-oxo-Prosta-10,13-dien-1-oic acid
  3. 15-Hydroxy-9-oxoprosta-10,13-dienoate
  4. 15-Hydroxy-9-oxoprosta-10,13-dienoic acid
  5. 15a-Hydroxy-9-ketoprosta-10,13-dienoate
  6. 15a-Hydroxy-9-ketoprosta-10,13-dienoic acid
  7. 15a-Hydroxy-9-oxo-10,13E-prostadienoate
  8. 15a-Hydroxy-9-oxo-10,13E-prostadienoic acid
  9. 2-(3-Hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoate
  10. 2-(3-Hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoic acid
  11. 2-(3-Hydroxy-1-octenyl)-5-oxo-3-Cyclopentene-1-heptanoate
  12. 2-(3-Hydroxy-1-octenyl)-5-oxo-3-Cyclopentene-1-heptanoic acid
  13. PGA1
  14. Prostaglandin A1
  15. Prostaglandin E1-217
Chemical Formula C20H32O4
Average Molecular Weight 336.4657
Monoisotopic Molecular Weight 336.230059512
IUPAC Name 7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoic acid
Traditional IUPAC Name prostaglandin A1
CAS Registry Number 14152-28-4
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 Key BGKHCLZFGPIKKU-LDDQNKHRSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Prostaglandins and related compounds
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Carbocyclic Fatty Acids
  • Keto Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Ketone
  • Secondary Alcohol
Direct Parent Prostaglandins and related compounds
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • RNA component
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.015 g/L ALOGPS
LogP 4.21 ALOGPS
LogP 4.74 ChemAxon
LogS -4.35 ALOGPS
pKa (strongest acidic) 4.45 ChemAxon
pKa (strongest basic) -1.6 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 97.97 ChemAxon
Polarizability 40.11 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Platelet
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.000074 +/- 0.000048 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023040
KNApSAcK ID Not Available
Chemspider ID 4445196 Link_out
KEGG Compound ID C04685 Link_out
BioCyc ID CPD-1911 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02656 Link_out
Metagene Link HMDB02656 Link_out
METLIN ID 407 Link_out
PubChem Compound 5281912 Link_out
PDB ID Not Available
ChEBI ID 15545 Link_out
References
Synthesis Reference Pike, 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out