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Human Metabolome Database Version 2.5

 

Showing metabocard for 8-Isoprostaglandin F2a (HMDB05083)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-10-25 12:03:23
Update Date 2010-12-17 09:56:54
Accession Number HMDB05083
Secondary Accession Numbers Not Available
Common Name 8-Isoprostaglandin F2a
Description 8-Isoprostaglandin F2a is an isoprostane and a potent renal vasoconstrictor. Isoprostanes are prostaglandin-like compounds that are produced in vivo in humans by a noncyclooxygenase mechanism involving free radical-catalyzed peroxidation of arachidonic acid. The formation of these prostanoids proceeds through bicyclic endoperoxide intermediates that are then reduced to form ring isoprostanes. Of considerable interest is that, in contradistinction to cyclooxygenase-derived prostaglandins, isoprostanes have been shown to be initially formed in situ, esterified to phospholipids, and subsequently released preformed, presumably by phospholipases. The fact that prostanoids are produced in vivo by a noncyclooxygenase mechanism is of considerable interest from a biochemical perspective. However, this may also be associated with biological ramifications since it has been shown that these compounds are capable of exerting potent biological activity. (PMID: 7825845, 17012140) 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. 8-epi-PGF2alpha
  2. 8-iso-PGF2alpha
  3. 8-Epi PGF-2alpha
  4. 8-Epiprostaglandin F2alpha
  5. 8-Isoprostaglandin F2alpha
  6. 8-Epi-prostaglandin F2alpha
  7. 9,11,15-Trihydroxy-prosta-5,13-dien-1-oic acid
  8. 9S,11R,15S-trihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12R]
  9. (5Z,13E,15S)-9alpha,11alpha,15-trihydroxy-8beta-prosta-5,13-dien-1-oic acid
  10. 9,11,15-trihydroxy Prosta-5,13-dien-1-oic acid
  11. 9,11,15-Trihydroxy-prosta-5,13-dien-1-oate
  12. 9S,11R,15S-trihydroxy-5Z,13E-prostadienoate
  13. (5Z,13E,15S)-9alpha,11alpha,15-trihydroxy-8beta-prosta-5,13-dien-1-oate
  14. 9,11,15-trihydroxy Prosta-5,13-dien-1-oate
  15. 9S,11R,15S-trihydroxy-5Z,13E-prostadienoic acid
  16. 8-iso-PGF2a
Chemical IUPAC Name (Z)-7-[(1S,2S,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopenty
Chemical Formula C20H34O5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Prostanoids
Sub Class
  • Isoprostanes
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 354.481
Monoisotopic Molecular Weight 354.240631
Isomeric SMILES CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@H]1CC=C/CCCC(O)=O
Canonical SMILES CCCCCC(O)C=CC1C(O)CC(O)C1CC=CCCCC(O)=O
KEGG Compound ID C13809 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB05083 Link Image
Metagene Link HMDB05083 Link Image
METLIN ID Not Available
PubChem Compound 5282263 Link Image
PubChem Substance 14718377 Link Image
ChEBI ID 34505 Link Image
CAS Registry Number 27415-26-5
InChI Identifier InChI=1/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,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 0.117 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity 2.183 Source: PhysProp
Predicted LogP/Hydrophobicity 3.2 [Predicted by PubChem via XLOGP]; 3.11 [Predicted by ALOGPS] 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
  • Urine
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 0.00057 +/- 0.000057 uM
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • Sanchez-Moreno C, Cano MP, de Ancos B, Plaza L, Olmedilla B, Granado F, Martin A: Mediterranean vegetable soup consumption increases plasma vitamin C and decreases F2-isoprostanes, prostaglandin E2 and monocyte chemotactic protein-1 in healthy humans. J Nutr Biochem. 2006 Mar;17(3):183-9. Epub 2005 Aug 15. [PubMed Link Image]
Biofluid Blood
Value 0.00038 +/- 0.000048 uM
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Sanchez-Moreno C, Cano MP, de Ancos B, Plaza L, Olmedilla B, Granado F, Martin A: Mediterranean vegetable soup consumption increases plasma vitamin C and decreases F2-isoprostanes, prostaglandin E2 and monocyte chemotactic protein-1 in healthy humans. J Nutr Biochem. 2006 Mar;17(3):183-9. Epub 2005 Aug 15. [PubMed Link Image]
Biofluid Blood
Value 0.000957 +/- 0.00102 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Blood
Value 0.000079 +/- 0.0000096 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Basu S: Radioimmunoassay of 8-iso-prostaglandin F2alpha: an index for oxidative injury via free radical catalysed lipid peroxidation. Prostaglandins Leukot Essent Fatty Acids. 1998 Apr;58(4):319-25. [PubMed Link Image]
Biofluid Blood
Value 0.000151 +/- 1.8E-5 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. Epub 2010 Jul 29. [PubMed Link Image]
Biofluid Urine
Value 0.00018 +/- 0.000059 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
Biofluid Urine
Value 0.00019 +/- 0.0001 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
Biofluid Urine
Value 0.00027 +/- 0.00011 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Helmersson J, Basu S: F(2)-isoprostane and prostaglandin F(2 alpha)metabolite excretion rate and day to day variation in healthy humans. Prostaglandins Leukot Essent Fatty Acids. 2001 Aug;65(2):99-102. [PubMed Link Image]
Biofluid Urine
Value 0.00022 +/- 0.000019 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Basu S: Radioimmunoassay of 8-iso-prostaglandin F2alpha: an index for oxidative injury via free radical catalysed lipid peroxidation. Prostaglandins Leukot Essent Fatty Acids. 1998 Apr;58(4):319-25. [PubMed Link Image]
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways Not Available
General References Not Available