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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:10 UTC
HMDB IDHMDB0001483
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 signalling pathways.
Structure
Data?1582752204
Synonyms
ValueSource
5-Heptenoic acid, 7-[3,5-dihydroxy-2(3-hydroxy-1-octenyl)cyclopentyl]-, stereoisomerChEBI
9beta,11alpha-PGF2aChEBI
9beta,11alpha-PGF2alphaChEBI
PGF2bChEBI
PGF2betaChEBI
Prostaglandin F2-betaChEBI
5-Heptenoate, 7-[3,5-dihydroxy-2(3-hydroxy-1-octenyl)cyclopentyl]-, stereoisomerGenerator
9b,11a-PGF2aGenerator
9Β,11α-PGF2aGenerator
9Β,11α-PGF2αGenerator
PGF2ΒGenerator
Prostaglandin F2-bGenerator
Prostaglandin F2-βGenerator
(5Z,13E)-9,11,15-Trihydroxy-prosta-5,13-dien-1-OateHMDB
(5Z,13E)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acidHMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoateHMDB
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-heptenoateHMDB
7-[3a,5b-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acidHMDB
9b,11a-PGF2HMDB
Prostaglandin F2betaHMDB
Prostaglandin F2beta, (5Z,8beta,9beta,11alpha,12alpha,13E,15S)-isomerHMDB
Prostaglandin F2beta, (5Z,9beta,11beta,13E,15S)-isomerHMDB
Prostaglandin F2beta, (5Z,9beta,11beta,13E,15R)-isomerHMDB
Prostaglandin F2bChEBI
Prostaglandin F2βGenerator
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
SMILES
CCCCC[C@H](O)\C=C\[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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18+,19+/m0/s1
InChI KeyPXGPLTODNUVGFL-JZFBHDEDSA-N
Chemical Taxonomy
Description 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
  • 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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.39BODOR,H & HUANG,M (1992)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.11ALOGPS
logP2.61ChemAxon
logS-3.5ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.10431661259
DarkChem[M-H]-191.031661259
AllCCS[M+H]+194.25232859911
AllCCS[M-H]-191.7832859911
DeepCCS[M+H]+202.4430932474
DeepCCS[M-H]-200.04430932474
DeepCCS[M-2H]-233.31730932474
DeepCCS[M+Na]+208.35330932474
AllCCS[M+H]+194.332859911
AllCCS[M+H-H2O]+191.632859911
AllCCS[M+NH4]+196.732859911
AllCCS[M+Na]+197.432859911
AllCCS[M-H]-191.832859911
AllCCS[M+Na-2H]-193.132859911
AllCCS[M+HCOO]-194.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prostaglandin F2bCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C\C=C/CCCC(O)=O4461.2Standard polar33892256
Prostaglandin F2bCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C\C=C/CCCC(O)=O2708.1Standard non polar33892256
Prostaglandin F2bCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C\C=C/CCCC(O)=O2924.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin F2b,1TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2883.7Semi standard non polar33892256
Prostaglandin F2b,1TMS,isomer #2CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O2784.6Semi standard non polar33892256
Prostaglandin F2b,1TMS,isomer #3CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O2765.8Semi standard non polar33892256
Prostaglandin F2b,1TMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2816.1Semi standard non polar33892256
Prostaglandin F2b,2TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2755.7Semi standard non polar33892256
Prostaglandin F2b,2TMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2746.0Semi standard non polar33892256
Prostaglandin F2b,2TMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2827.9Semi standard non polar33892256
Prostaglandin F2b,2TMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O2750.7Semi standard non polar33892256
Prostaglandin F2b,2TMS,isomer #5CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2762.8Semi standard non polar33892256
Prostaglandin F2b,2TMS,isomer #6CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2742.2Semi standard non polar33892256
Prostaglandin F2b,3TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2718.1Semi standard non polar33892256
Prostaglandin F2b,3TMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2744.9Semi standard non polar33892256
Prostaglandin F2b,3TMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2730.6Semi standard non polar33892256
Prostaglandin F2b,3TMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2713.7Semi standard non polar33892256
Prostaglandin F2b,4TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2746.0Semi standard non polar33892256
Prostaglandin F2b,1TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3139.4Semi standard non polar33892256
Prostaglandin F2b,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O2997.0Semi standard non polar33892256
Prostaglandin F2b,1TBDMS,isomer #3CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O2980.6Semi standard non polar33892256
Prostaglandin F2b,1TBDMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3080.5Semi standard non polar33892256
Prostaglandin F2b,2TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3245.1Semi standard non polar33892256
Prostaglandin F2b,2TBDMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3232.7Semi standard non polar33892256
Prostaglandin F2b,2TBDMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3363.9Semi standard non polar33892256
Prostaglandin F2b,2TBDMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O3197.2Semi standard non polar33892256
Prostaglandin F2b,2TBDMS,isomer #5CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3243.4Semi standard non polar33892256
Prostaglandin F2b,2TBDMS,isomer #6CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3227.3Semi standard non polar33892256
Prostaglandin F2b,3TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3429.7Semi standard non polar33892256
Prostaglandin F2b,3TBDMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3490.6Semi standard non polar33892256
Prostaglandin F2b,3TBDMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3479.2Semi standard non polar33892256
Prostaglandin F2b,3TBDMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3432.6Semi standard non polar33892256
Prostaglandin F2b,4TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3625.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin F2b GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-6489000000-bf681ff653e664e9cde02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin F2b GC-MS (4 TMS) - 70eV, Positivesplash10-004i-9300188000-0fc1fbcf7464fb00c07e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin F2b GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 10V, Positive-QTOFsplash10-014r-0019000000-3c46ffbee46021b809012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 20V, Positive-QTOFsplash10-01bi-2297000000-9fe530991fdc645e26f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 40V, Positive-QTOFsplash10-0103-9170000000-0fa33343bc482bd6f5a52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 10V, Negative-QTOFsplash10-0udr-0009000000-a337fc1b13431013f06a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 20V, Negative-QTOFsplash10-000i-1039000000-40b895b35529c4a817632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 40V, Negative-QTOFsplash10-0a4i-9631000000-8dc66a223446641955e62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 10V, Negative-QTOFsplash10-0udi-0009000000-4f29fd22c6b0dfe3ac772021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 20V, Negative-QTOFsplash10-0udr-0098000000-06ede09931efe0fba78e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 40V, Negative-QTOFsplash10-00el-9182000000-f1a4c9aba7f705d2868d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 10V, Positive-QTOFsplash10-014r-0019000000-ece58dc4c35634d7fe3f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 20V, Positive-QTOFsplash10-014i-9255000000-c6aef7e365cba872a5582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin F2b 40V, Positive-QTOFsplash10-05mo-9300000000-552900f74505f7605b0b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
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
FooDB IDFDB022647
KNApSAcK IDNot Available
Chemspider ID4444144
KEGG Compound IDC02314
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280506
PDB IDNot Available
ChEBI ID28922
Food Biomarker OntologyNot Available
VMH IDHC02216
MarkerDB IDNot Available
Good Scents IDNot Available
References
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 ]