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Human Metabolome Database Version 2.5

 

Showing metabocard for 6-Keto-prostaglandin F1a (HMDB02886)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-22 16:12:17
Update Date 2010-06-02 16:21:06
Accession Number HMDB02886
Secondary Accession Numbers Not Available
Common Name 6-Keto-prostaglandin F1a
Description 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. (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.
Synonyms
  1. 6-Keto-PGF1a
  2. 6-Keto-PGF1alpha
  3. 6-Keto-prostaglandin F1a
  4. 6-Keto-prostaglandin F1alpha
  5. 6-Ketoprostaglandin F1 alpha
  6. 6-Ketoprostaglandin F1alpha
  7. 6-oxo-9S,11R,15S-trihydroxy-13E-prostenoic acid
  8. 6-Oxo-PGF1a
  9. 6-Oxo-PGF1alpha
  10. 6-oxo-prostaglandin F1alpha
  11. 6-Oxoprostaglandin F1a
  12. 6-Oxoprostaglandin F1alpha
  13. 6-oxo-9S,11R,15S-trihydroxy-13E-prostenoate
Chemical IUPAC Name 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]-6-oxoheptanoic acid
Chemical Formula C20H34O6
Chemical Structure 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 370.480
Monoisotopic Molecular Weight 370.235535
Isomeric SMILES CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=O
Canonical SMILES CCCCCC(O)C=CC1C(O)CC(O)C1CC(=O)CCCCC(O)=O
KEGG Compound ID C05961 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02886 Link Image
Metagene Link HMDB02886 Link Image
METLIN ID 6782 Link Image
PubChem Compound 5280888 Link Image
PubChem Substance 8139929 Link Image
ChEBI ID 28158 Link Image
CAS Registry Number 58962-34-8
InChI Identifier InChI=1/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
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.45900002 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 1.75 [Predicted by ALOGPS]; 1.6 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
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 Not Available
Biofluid Location
  • Blood
  • Cerebrospinal Fluid
  • Urine
Tissue Location
Tissue References
Adipose Tissue —
Placenta —
Platelet —
Concentrations (Normal)
Biofluid Blood
Value 0.000081 (0.0-0.00016) uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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. [PubMed Link Image]
Biofluid Blood
Value 0.000575 +/- 0.000337 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Oxygenated lipids were quantified by Theresa L. Pedersen and John W. Newman at the USDA’s Western Human Nutrition Research Center, Davis, CA, and Lipomics Technologies, Inc.
References
  • Psychogios N, Hau DD, Peng J, Guo AC, Mandal R, Bouatra S, Sinelnikov I, Krishnamurthy R, Eisner R, Gautam B, Young N, Xia J, Knox C, Dong E, Huang P, Hollander Z, Pedersen TL, Smith SR, Bamforth F, Greiner R, McManus B, Newman JW, Goodfriend T, Wishart DS: The human serum metabolome. PLoS One. 2011 Feb 16;6(2):e16957. [PubMed Link Image]
  • Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [PubMed Link Image]
Biofluid CSF
Value 0.00199 +/- 0.00012 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Measured via MS/MS techniques from 4 pooled CSF samples provided by TNO/NuGO – The Netherlands
References
  • John W. Newman, USDA ARS Western Human Nutrition Research Center, Davis CA (personal communication - March 2, 2009)
Biofluid CSF
Value 8.913e-05 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal (control)
Comments Not Available
References
  • Romero SD, Chyatte D, Byer DE, Romero JC, Yaksh TL: Measurement of prostaglandins in the cerebrospinal fluid in cat, dog, and man. J Neurochem. 1984 Dec;43(6):1642-9. [PubMed Link Image]
Biofluid CSF
Value 9.264e-05 +/- 1.134e-05 uM
Age N/A
Sex N/A
Patient information Normal
Comments Not Available
References
  • Nishisho T, Tonai T, Tamura Y, Ikata T: Experimental and clinical studies of eicosanoids in cerebrospinal fluid after spinal cord injury. Neurosurgery. 1996 Nov;39(5):950-6; discussion 956-7. [PubMed Link Image]
Biofluid Urine
Value 0.00000026 (0.00000021-0.00000032) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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. [PubMed Link Image]
Biofluid Urine
Value 0.0023 +/- 0.00039 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Farker K, Schweer H, Vollandt R, Nassr N, Nagel U, Seyberth HW, Hoffmann A, Oettel M: Measurements of urinary prostaglandins in young ovulatory women during the menstrual cycle and in postmenopausal women. Prostaglandins. 1997 Sep;54(3):655-64. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Blood
Value 0.00074 +/- 0.00017 uM
Age Adult:>18 yrs old
Sex Both
Condition Cardiopulmonary resuscitation
Comments Resuscitated patients group
References
  • 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. [PubMed Link Image]
Biofluid Blood
Value 0.00099 +/- 0.00027 uM
Age Adult:>18 yrs old
Sex Both
Condition Cardiopulmonary resuscitation
Comments Discharged patients group
References
  • 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. [PubMed Link Image]
Biofluid CSF
Value 0.00153 (0.000675-0.00314) uM
Age Children:1-13 yrs old
Sex N/A
Comments Not Available
References
  • Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed Link Image]
Biofluid CSF
Value 0.000335 uM
Age Children:1-13 yrs old
Sex N/A
Comments Not Available
References
  • Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed Link Image]
Biofluid CSF
Value 9.994e-05 uM
Age Children:1-13 yrs old
Sex N/A
Comments Not Available
References
  • Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed Link Image]
Biofluid CSF
Value 0.000173 +/- 0.000227 uM
Age Children:1-13 yrs old
Sex N/A
Comments Not Available
References
  • Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed Link Image]
Biofluid CSF
Value 0.00115 (0.000891-0.00140) uM
Age Children:1-13 yrs old
Sex N/A
Comments Not Available
References
  • Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed Link Image]
Biofluid CSF
Value 0.00309 (0.000313-0.00548) uM
Age Children:1-13 yrs old
Sex N/A
Comments Not Available
References
  • Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed Link Image]
Biofluid CSF
Value 0.000579 +/- 5.391e-05 uM
Age N/A
Sex N/A
Comments Not Available
References
  • Rodriguez y Baena R, Gaetani P, Paoletti P: A study on cisternal CSF levels of arachidonic acid metabolites after aneurysmal subarachnoid hemorrhage. J Neurol Sci. 1988 Apr;84(2-3):329-35. [PubMed Link Image]
Biofluid CSF
Value 0.000828 +/- 0.000240 uM
Age N/A
Sex N/A
Comments Not Available
References
  • Rodriguez y Baena R, Gaetani P, Paoletti P: A study on cisternal CSF levels of arachidonic acid metabolites after aneurysmal subarachnoid hemorrhage. J Neurol Sci. 1988 Apr;84(2-3):329-35. [PubMed Link Image]
Biofluid CSF
Value 0.000452 +/- 0.000108 uM
Age Adult:>18 yrs old
Sex N/A
Comments Not Available
References
  • Nishisho T, Tonai T, Tamura Y, Ikata T: Experimental and clinical studies of eicosanoids in cerebrospinal fluid after spinal cord injury. Neurosurgery. 1996 Nov;39(5):950-6; discussion 956-7. [PubMed Link Image]
Biofluid Urine
Value 0.00000035 (0.00000033-0.00000037) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Rheumatoid arthritis
Comments Not Available
References
  • 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. [PubMed Link Image]
Biofluid Urine
Value 0.0026 +/- 0.00048 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Condition Normal
Comments Not Available
References
  • Farker K, Schweer H, Vollandt R, Nassr N, Nagel U, Seyberth HW, Hoffmann A, Oettel M: Measurements of urinary prostaglandins in young ovulatory women during the menstrual cycle and in postmenopausal women. Prostaglandins. 1997 Sep;54(3):655-64. [PubMed Link Image]
Associated Disorders
Condition References
Cardiopulmonary resuscitation
  • 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. [PubMed Link Image]
Normal
  • Farker K, Schweer H, Vollandt R, Nassr N, Nagel U, Seyberth HW, Hoffmann A, Oettel M: Measurements of urinary prostaglandins in young ovulatory women during the menstrual cycle and in postmenopausal women. Prostaglandins. 1997 Sep;54(3):655-64. [PubMed Link Image]
Rheumatoid arthritis
  • 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. [PubMed Link Image]
OMIM ID
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 Link Image map00590 Link Image
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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]