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Record Information
Version3.6
Creation Date2006-05-22 15:12:17 UTC
Update Date2016-02-11 01:05:51 UTC
HMDB IDHMDB02886
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-Keto-prostaglandin F1a
Description6-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. (PMID 1976492 , 2298410 , 2379443 , 2111556 )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
Synonyms
ValueSource
6-keto-PGF1aChEBI
6-keto-PGF1alphaChEBI
6-keto-Prostaglandin F1aChEBI
6-keto-Prostaglandin F1alphaChEBI
6-Ketoprostaglandin F1alphaChEBI
6-oxo-PGF1alphaChEBI
6-Oxoprostaglandin F1alphaChEBI
6-oxo-Prostaglandin F1aGenerator
6-oxo-Prostaglandin F1αGenerator
6-keto-PGF1αGenerator
6-keto-Prostaglandin F1αGenerator
6-Ketoprostaglandin F1aGenerator
6-Ketoprostaglandin F1αGenerator
6-oxo-PGF1aGenerator
6-oxo-PGF1αGenerator
6-Oxoprostaglandin F1aGenerator
6-Oxoprostaglandin F1αGenerator
6-Ketoprostaglandin F1 alphaHMDB
6-oxo-9S,11R,15S-Trihydroxy-13E-prostenoateHMDB
6-oxo-9S,11R,15S-Trihydroxy-13E-prostenoic acidHMDB
Chemical FormulaC20H34O6
Average Molecular Weight370.4804
Monoisotopic Molecular Weight370.23553882
IUPAC Name7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoic acid
Traditional Name6 keto PGF1 α
CAS Registry Number58962-34-8
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=O
InChI Identifier
InChI=1S/C20H34O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-19,21,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+,19-/m0/s1
InChI KeyInChIKey=KFGOFTHODYBSGM-ZUNNJUQCSA-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
  • Keto fatty acid
  • Hydroxy fatty acid
  • Fatty alcohol
  • Carbocyclic fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility0.46 mg/mLALOGPS
logP1.75ALOGPS
logP1.79ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity100 m3·mol-1ChemAxon
Polarizability42.03 Å3ChemAxon
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; 4 TMS)splash10-0fj0-4920000000-106328b50f1f2f297ec4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Kidney
  • Liver
  • Placenta
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000575 +/- 0.000337 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000359 +/- 0.000023 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000081 (0.0-0.00016) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0000607 +/- 0.000028 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified8.913e-05 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00199 +/- 0.00012 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
Cerebrospinal Fluid (CSF)Detected and Quantified9.264e-05 +/- 1.134e-05 uMNot SpecifiedNot SpecifiedNormal details
UrineDetected and Quantified0.0023 +/- 0.00039 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0026 +/- 0.00048 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified2.6E-7 (2.1E-7 - 32E-7) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00099 +/- 0.00027 uMAdult (>18 years old)Both
Cardiopulmonary resuscitation
details
BloodDetected and Quantified0.00074 +/- 0.00017 uMAdult (>18 years old)Both
Cardiopulmonary resuscitation
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000452 +/- 0.000108 uMAdult (>18 years old)Not SpecifiedSpinal cord injuries (acute stage) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00153 (0.000675-0.00314) uMChildren (1-13 years old)Not Specifiedclosed head injury details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000335 uMChildren (1-13 years old)Not Specifiedclosed head injury details
Cerebrospinal Fluid (CSF)Detected and Quantified9.994e-05 uMChildren (1-13 years old)Not Specifiedgunshot wound details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000173 +/- 0.000227 uMChildren (1-13 years old)Not Specifiedhydrocephalus details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00115 (0.000891-0.00140) uMChildren (1-13 years old)Not SpecifiedHypoxia/Ischemia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00309 (0.000313-0.00548) uMChildren (1-13 years old)Not Specifiedmeningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000579 +/- 5.391e-05 uMNot SpecifiedNot Specifiedsubarachnoid hemorrhage with cerebral vasospasm details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000828 +/- 0.000240 uMNot SpecifiedNot Specifiedsubarachnoid hemorrhage without cerebral vasospasm details
UrineDetected and Quantified0.00000035 (0.00000033-0.00000037) umol/mmol creatinineAdult (>18 years old)BothRheumatoid arthritis details
Associated Disorders and Diseases
Disease References
Cardiopulmonary resuscitation
  1. Strohmenger HU, Lindner KH, Keller A, Lindner IM, Bothner U, Georgieff M: Concentrations of prolactin and prostaglandins during and after cardiopulmonary resuscitation. Crit Care Med. 1995 Aug;23(8):1347-55. [7634804 ]
Rheumatoid arthritis
  1. Laitinen O, Seppala E, Nissila M, Vapaatalo H: Plasma levels and urinary excretion of prostaglandins in patients with rheumatoid arthritis. Clin Rheumatol. 1983 Dec;2(4):401-6. [6589104 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00557
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023077
KNApSAcK IDNot Available
Chemspider ID4444411
KEGG Compound IDC05961
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02886
Metagene LinkHMDB02886
METLIN ID6782
PubChem Compound5280888
PDB IDNot Available
ChEBI ID28158
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. de la Cruz JP, Guerrero A, Gonzalez-Correa JA, Marquez E, Nacle I, Sanchez de la Cuesta F: Effects of two preparations of 75-mg extended-release aspirin on platelet aggregation, prostanoids and nitric oxide production in humans. Eur J Clin Pharmacol. 2002 Jan;57(11):775-80. [11871383 ]
  2. Laitinen O, Seppala E, Nissila M, Vapaatalo H: Plasma levels and urinary excretion of prostaglandins in patients with rheumatoid arthritis. Clin Rheumatol. 1983 Dec;2(4):401-6. [6589104 ]
  3. Jawerbaum A, Rosello Catafau J, Gonzalez ET, Novaro V, Gomez G, Gelpi E, Gimeno MA: Eicosanoid production by placental and amnion tissues from control and non-insulin-dependent diabetic rats. Influence of oxytocin in the incubating medium. Prostaglandins Leukot Essent Fatty Acids. 1997 Jun;56(6):425-9. [9223652 ]
  4. Cerletti C, Dell'Elba G, Manarini S, Pecce R, Di Castelnuovo A, Scorpiglione N, Feliziani V, de Gaetano G: Pharmacokinetic and pharmacodynamic differences between two low dosages of aspirin may affect therapeutic outcomes. Clin Pharmacokinet. 2003;42(12):1059-70. [12959636 ]
  5. Katori M, Majima M, Harada Y: Possible background mechanisms of the effectiveness of cyclooxygenase-2 inhibitors in the treatment of rheumatoid arthritis. Inflamm Res. 1998 Oct;47 Suppl 2:S107-11. [9831332 ]
  6. Fain JN, Ballou LR, Bahouth SW: Obesity is induced in mice heterozygous for cyclooxygenase-2. Prostaglandins Other Lipid Mediat. 2001 Jul;65(4):199-209. [11444591 ]
  7. Rogov VA, Shilov EM, Kozlovskaia NL, Gordovskaia NB, Sidorova IS, Krylova MIu, Artem'eva VB: [Endothelium and platelets in pregnant women with chronic glomerulonephritis and therapeutic efficacy of acetylsalicylic acid and dipiridamol] Ter Arkh. 2004;76(12):58-64. [15724929 ]
  8. Wubert J, Reder E, Kaser A, Weber PC, Lorenz RL: Simultaneous solid phase extraction, derivatization, and gas chromatographic mass spectrometric quantification of thromboxane and prostacyclin metabolites, prostaglandins, and isoprostanes in urine. Anal Chem. 1997 Jun 1;69(11):2143-6. [9183177 ]
  9. Miao XY: [Plasma level and effects of thromboxane A2 and 6-keto-PGF1 alpha in patients with acute obstructive suppurative cholangitis] Zhonghua Wai Ke Za Zhi. 1990 Apr;28(4):228-30, 253-4. [2379443 ]
  10. Terada K, Hayashi G, Hokama Y: C-reactive protein and 6-keto prostaglandin F 1-alpha in patients with gynecologic cancer. Gynecol Oncol. 1990 Feb;36(2):212-4. [2298410 ]
  11. Symons JD: Longitudinal and cross-sectional studies of the relationship between 6-keto PGF1 alpha and high density lipoproteins. Prostaglandins Leukot Essent Fatty Acids. 1990 Feb;39(2):159-65. [2111556 ]
  12. Wang GQ, Zou ZZ, Yu DP: [A study of the role of plasma thromboxane B2 and 6-keto-prostaglandin F1 alpha in epidemic hemorrhagic fever] Zhonghua Nei Ke Za Zhi. 1990 Mar;29(3):138-40, 188. [1976492 ]