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Record Information
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:39:30 UTC
Secondary Accession Numbers
  • HMDB01483
Metabolite Identification
Common NameProstaglandin F2b
DescriptionProstaglandin F2b is a naturally occurring isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia-reperfusion injury. For this reason, they are frequently used as markers of oxidative stress; however, many are now finding that these molecules are not inert, but in fact evoke powerful biological responses in an increasing array of cell types. In many cases, these biological effects can account in part for the various features and manifestations of those clinical conditions. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states. Lipid-peroxidation forms primary- or secondary-end products like conjugated dienes, lipid hydroperoxides, gaseous alkanes, and prostaglandin F2-like products. They are created as major products by free-radical catalyzed peroxidation of esterified arachidonic acid (AA) in membrane phospholipids. They are also minor products of the activity of platelet cyclooxygenase-1 (COX-1) in response to stimuli such as collagen, thrombin, or arachidonate. The levels of Prostaglandin F2b and F2-isoprostanes in CSF and urine are elevated in Alzheimer's disease (AD) patients when compared to that of age-matched controls. (PMID: 15275956 , 14504139 )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.
5-Heptenoic acid, 7-[3,5-dihydroxy-2(3-hydroxy-1-octenyl)cyclopentyl]-, stereoisomerChEBI
Prostaglandin F2-betaChEBI
5-Heptenoate, 7-[3,5-dihydroxy-2(3-hydroxy-1-octenyl)cyclopentyl]-, stereoisomerGenerator
Prostaglandin F2-bGenerator
Prostaglandin F2-βGenerator
(5Z,13E)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acidHMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acidHMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid stereoisomerHMDB
7-[3a,5b-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acidHMDB
Prostaglandin F2betaHMDB
Prostaglandin F2beta, (5Z,8beta,9beta,11alpha,12alpha,13E,15S)-isomerMeSH
Prostaglandin F2beta, (5Z,9beta,11beta,13E,15S)-isomerMeSH
Prostaglandin F2beta, (5Z,9beta,11beta,13E,15R)-isomerMeSH
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name(5Z)-7-[(1R,2R,3R,5R)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Namepgf(sub 2-β)
CAS Registry Number4510-16-1
InChI Identifier
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
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.39BODOR,H & HUANG,M (1992)
Predicted Properties
Water Solubility0.12 g/LALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.47 m³·mol⁻¹ChemAxon
Polarizability40.86 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-6489000000-bf681ff653e664e9cde0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-9300188000-0fc1fbcf7464fb00c07eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-3c46ffbee46021b80901View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bi-2297000000-9fe530991fdc645e26f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0103-9170000000-0fa33343bc482bd6f5a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-0009000000-a337fc1b13431013f06aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1039000000-40b895b35529c4a81763View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9631000000-8dc66a223446641955e6View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022647
KNApSAcK IDNot Available
Chemspider ID4444144
KEGG Compound IDC02314
BioCyc IDCPD-8348
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280506
PDB IDNot Available
ChEBI ID28922
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tazzeo T, Miller J, Janssen LJ: Vasoconstrictor responses, and underlying mechanisms, to isoprostanes in human and porcine bronchial arterial smooth muscle. Br J Pharmacol. 2003 Oct;140(4):759-63. Epub 2003 Sep 22. [PubMed:14504139 ]
  2. Kim KM, Jung BH, Paeng KJ, Kim I, Chung BC: Increased urinary F(2)-isoprostanes levels in the patients with Alzheimer's disease. Brain Res Bull. 2004 Jul 30;64(1):47-51. [PubMed:15275956 ]