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Human Metabolome Database Version 3.5

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Showing metabocard for 8-iso-13,14-dihydro-15-keto-PGF2a (HMDB06562)

Record Information
Version 3.5
Creation Date 2007-05-23 10:06:47 -0600
Update Date 2013-02-08 17:15:00 -0700
HMDB ID HMDB06562
Secondary Accession Numbers None
Metabolite Identification
Common Name 8-iso-13,14-dihydro-15-keto-PGF2a
Description 8-iso-13,14-dihydro-15-keto-PGF2a is an isoprostane. Isoprostanes are a family of prostaglandin (PG) isomers generated by free radical-catalysed peroxidation and then rearrangement of arachidonic acid. In addition, isoprostanes can be produced by cyclo-oxygenase (COX) dependent pathways. Several cell types have been shown to release increased levels of the F2 isoprostane, 8-iso PGF2alpha, when stimulated with inflammatory mediators or subjected to oxidative stress in vitro. Furthermore, 8-iso PGF2alpha levels are elevated in rats in vivo when prooxidant conditions are induced experimentally. Similarly, elevated isoprostane production has been demonstrated in clinical conditions characterized by oxidant stress including diabetes, alcoholism, paraquat poisoning, myocardial reperfusion, critical illness, pre-eclampsia and smoking. Consequently, the measurement of 8-iso PGF2alpha in plasma and urine has been proposed as a relevant and convenient method to monitor oxidant stress in man. (PMID: 11309241 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (5Z,8b,9a,11a)-9,11-dihydroxy-15-oxo-Prost-5-en-1-oate
  2. (5Z,8b,9a,11a)-9,11-dihydroxy-15-oxo-Prost-5-en-1-oic acid
  3. 9S,11R-Dihydroxy-15-oxo-5Z-prostaenoate
  4. 9S,11R-Dihydroxy-15-oxo-5Z-prostaenoic acid
  5. 9S,11R-Dihydroxy-15-oxo-5Z-prostaenoic acid-cyclo[8S,12R]
Chemical Formula C20H34O5
Average Molecular Weight 354.481
Monoisotopic Molecular Weight 354.240624198
IUPAC Name (5Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
Traditional IUPAC Name (5Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
CAS Registry Number 191919-02-5
SMILES CCCCCC(=O)CC[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O
InChI Identifier InChI=1S/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/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17+,18-,19+/m0/s1
InChI Key VKTIONYPMSCHQI-JPRPWBOBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Prostaglandins and related compounds
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Carbocyclic Fatty Acids
  • Keto Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Carboxylic Acid
  • Cyclic Alcohol
  • Ketone
  • Secondary Alcohol
Direct Parent Prostaglandins and related compounds
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.11 g/L ALOGPS
LogP 3.12 ALOGPS
LogP 3.02 ChemAxon
LogS -3.52 ALOGPS
pKa (strongest acidic) 4.31 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 94.83 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 98.48 ChemAxon
Polarizability 41.28 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023973
KNApSAcK ID Not Available
Chemspider ID 4446335 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06562 Link_out
Metagene Link HMDB06562 Link_out
METLIN ID Not Available
PubChem Compound 5283214 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available