General Information of MET (ID: META00093)
Name 6-Keto-prostaglandin F1a
Synonyms   Click to Show/Hide Synonyms of This Metabolite
6 Keto PGF1 alpha; 6 Ketoprostaglandin F1 alpha; 6 Oxoprostaglandin F1 alpha; 6 oxo PGF1 alpha; 6-Keto-PGF1 alpha; 6-Keto-PGF1a; 6-Keto-PGF1alpha; 6-Keto-prostaglandin F1alpha; 6-Ketoprostaglandin F1 alpha; 6-Ketoprostaglandin F1alpha; 6-Oxoprostaglandin F1 alpha; 6-Oxoprostaglandin F1alpha; 6-oxo-9S,11R,15S-Trihydroxy-13E-prostenoate; 6-oxo-9S,11R,15S-Trihydroxy-13E-prostenoic acid; 6-oxo-PGF1 alpha; 6-oxo-PGF1alpha; F1 alpha, 6-Ketoprostaglandin; F1 alpha, 6-Oxoprostaglandin; alpha, 6-Keto-PGF1; alpha, 6-Ketoprostaglandin F1; alpha, 6-Oxoprostaglandin F1; alpha, 6-oxo-PGF1
Source Endogenous;Drug Metabolite;Fatty acyls;Food
Structure Type   Eicosanoids  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Eicosanoids
PubChem CID
5280888
HMDB ID
HMDB0002886
Formula
C20H34O6
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C05961
ChEBI ID
28158
FooDB ID
FDB023077
ChemSpider ID
4444411
METLIN ID
6782
Physicochemical Properties Molecular Weight 370.5 Topological Polar Surface Area 115
XlogP 1.4 Complexity 461
Heavy Atom Count 26 Rotatable Bond Count 13
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Function
6-keto-Prostaglandin F1a is the physiologically active and stable metabolite of prostacyclin. (A prostaglandin found in nearly all mammalian tissue that is a powerful vasodilator and inhibits platelet aggregation; it is biosynthesized enzymatically from prostaglandin endoperoxides in human vascular tissue; the sodium salt has been also used to treat primary pulmonary hypertension (Hypertension, Pulmonary). A delayed and prolonged increase in 6-keto-PGF1 alpha is reported in animals with septic shock, i.e., those with fecal peritonitis or cecal ligation. 6-keto-Prostaglandin F1a plasma levels has been found increased in patients with epidemic hemorrhagic fever, in patients with acute obstructive suppurative cholangitis, in patients with gynecologic cancer and has significant correlation with the level of high density lipoprotein cholesterol in plasma. 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.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      Voltage-gated ion channel (VIC)
            Cation channel sperm-associated 1 (CatSper1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation 6-Keto-prostaglandin F1a addition (6 hours)
                      Induced Change CATSPER1 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that 6-keto-prostaglandin F1a addition causes the increase of CATSPER1 protein activity compared with control group.
            Cation channel sperm-associated 2 (CatSper2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation 6-Keto-prostaglandin F1a addition (6 hours)
                      Induced Change CATSPER2 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that 6-keto-prostaglandin F1a addition causes the increase of CATSPER2 protein activity compared with control group.
            Cation channel sperm-associated 3 (CatSper3) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation 6-Keto-prostaglandin F1a addition (6 hours)
                      Induced Change CATSPER3 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that 6-keto-prostaglandin F1a addition causes the increase of CATSPER3 protein activity compared with control group.
            Cation channel sperm-associated 4 (CATSPER4) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation 6-Keto-prostaglandin F1a addition (6 hours)
                      Induced Change CATSPER4 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that 6-keto-prostaglandin F1a addition causes the increase of CATSPER4 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change 6-Keto-prostaglandin F1a concentration: decrease (FC = 0.21 / 0.21)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of 6-keto-prostaglandin F1a levels compared with control group.
References
1 Progesterone activates the principal Ca2+ channel of human sperm. Nature. 2011 Mar 17;471(7338):387-91.
2 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.

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