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We are currently updating the database - data may be missing for the next 10 minutes. We apologize for any inconvenience.

Human Metabolome Database Version 2.5

Showing metabocard for Prostaglandin A2 (HMDB02752)

Version	2.5
Creation Date	2006-05-22 16:12:08
Update Date	2009-05-15 16:01:56
Accession Number	HMDB02752
Secondary Accession Numbers	Not Available
Common Name	Prostaglandin A2
Description	Produced by the seminal vessicals: Prostaglandins are a group of lipid compounds that are derived enzymatically from fattyacids. Technically a hormone, the prostanoid class of fatty acid derivatives is a subclass of eicosanoids. Prostaglandin A is cyclopentenone and endogenous metabolite derived from arachidonic acid. 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. As well there is an increase in DNA content preceeding the G0/G1 peak (indicative of apoptic body formation) mediated by changes in expression levels of Bax and Bcl-2. 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.
Synonyms	(+)-Prostaglandin A2 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoate 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoic acid 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoate 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoic acid 15(S)-Prostaglandin A2 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylate 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylic acid 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoate 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoic acid Prostaglandin A2
Chemical IUPAC Name	(5Z,13E,15S)15-hydroxy-9-oxo-prosta-5,10,13-trien-1-oic acid
Chemical Formula	C20H30O4
Chemical Structure
Chemical Taxonomy	Kingdom Organic Super Class Organic acids Class Prostanoids Sub Class Prostaglandins Family Mammalian Metabolite Species ketone secondary alcohol carboxylic acid alkene Biofunction — Application — Source Endogenous
Average Molecular Weight	334.450
Monoisotopic Molecular Weight	334.214417
Isomeric SMILES	CCCCC[C@H](O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O
Canonical SMILES	CCCCCC(O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O
KEGG Compound ID	C05953
BioCyc ID	Not Available
BiGG ID	Not Available
Wikipedia Link	Not Available
NuGOwiki Link	HMDB02752
Metagene Link	HMDB02752
METLIN ID	3465
PubChem Compound	4953
PubChem Substance	439750
ChEBI ID	Not Available
CAS Registry Number	13345-50-1
InChI Identifier	InChI=1/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
Synthesis Reference	Grieco, 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.
Melting Point (Experimental)	Not Available
Experimental Water Solubility	Not Available Source: PhysProp
Predicted Water Solubility	0.020599999 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge	-1
State	Solid
Experimental LogP/Hydrophobicity	Not Available Source: PhysProp
Predicted LogP/Hydrophobicity	4.08 [Predicted by ALOGPS]; 3.8 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)	Show PDF/HTML
MOL File	Show
SDF File	Show
PDB File	Show
2D Structure
3D Structure
Experimental PDB ID	Not Available
Experimental 1H NMR Spectrum	Not Available
Experimental 13C NMR Spectrum	Not Available
Experimental 13C HSQC Spectrum	Not Available
Predicted 1H NMR Spectrum	Show Image Show Peaklist
Predicted 13C NMR Spectrum	Show Image Show Peaklist
Mass Spectrum	Not Available
Simplified TOCSY Spectrum	Not Available
BMRB Spectrum	Not Available
Cellular Location	Membrane (Predicted from LogP)
Biofluid Location	Blood
Tissue Location	Not Available
Concentrations (Normal)	Biofluid Blood Value 0.0000448 +/- 0.000496 uM Age Adult:>18 yrs old Sex Both Patient information Normal Comments Random sodium intake References Frolich JC, Sweetman BJ, Carr K, Hollifield JW, Oates JA: Assessment of the levels of pga2 in human plasma by gas chromatography-mass spectrometry. Prostaglandins. 1975 Jul;10(1):185-95. [PubMed ] Biofluid Blood Value 0.0010 +/- 0.0002 uM Age Adult:>18 yrs old Sex Male Patient information Normal Comments Normal sodium diet References Speckart P, Golub M, Zia P, Zipser R, Horton R: The effect of angiotensin II and indomethacin on immunoreactive prostaglandin "A" levels in man. Prostaglandins. 1976 Mar;11(3):481-8. [PubMed ] Biofluid Blood Value 0.0000747 +/- 0.000254 uM Age Adult:>18 yrs old Sex Both Patient information Normal Comments After sodium depletion References Frolich JC, Sweetman BJ, Carr K, Hollifield JW, Oates JA: Assessment of the levels of pga2 in human plasma by gas chromatography-mass spectrometry. Prostaglandins. 1975 Jul;10(1):185-95. [PubMed ] Biofluid Blood Value 0.0008 +/- 0.0002 uM Age Adult:>18 yrs old Sex Male Patient information Normal Comments Low sodium diet References Speckart P, Golub M, Zia P, Zipser R, Horton R: The effect of angiotensin II and indomethacin on immunoreactive prostaglandin "A" levels in man. Prostaglandins. 1976 Mar;11(3):481-8. [PubMed ] Biofluid Blood Value 0.000167 +/- 0.000401 uM Age Adult:>18 yrs old Sex N/A Patient information Normal Comments Random sodium intake References Frolich JC, Sweetman BJ, Carr K, Hollifield JW, Oates JA: Assessment of the levels of pga2 in human plasma by gas chromatography-mass spectrometry. Prostaglandins. 1975 Jul;10(1):185-95. [PubMed ] Biofluid Blood Value 0.0019 +/- 0.0004 uM Age Adult:>18 yrs old Sex Male Patient information Normal Comments Normal sodium diet with pressor infusions of angiotensin II References Speckart P, Golub M, Zia P, Zipser R, Horton R: The effect of angiotensin II and indomethacin on immunoreactive prostaglandin "A" levels in man. Prostaglandins. 1976 Mar;11(3):481-8. [PubMed ] Biofluid Blood Value 0.0027 +/- 0.0008 uM Age Adult:>18 yrs old Sex Male Patient information Normal Comments Low sodium diet with pressor infusions of angiotensin II References Speckart P, Golub M, Zia P, Zipser R, Horton R: The effect of angiotensin II and indomethacin on immunoreactive prostaglandin "A" levels in man. Prostaglandins. 1976 Mar;11(3):481-8. [PubMed ]
Concentrations (Abnormal)	Not Available
Associated Disorders	Not Available
OMIM ID	Not Available
Pathways	Name SMPDB Link KEGG Link Arachidonic Acid Metabolism SMP00075 map00590
General References	Not Available

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