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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 14:58:41 UTC
Update Date2022-03-07 02:49:20 UTC
HMDB IDHMDB0004236
Secondary Accession Numbers
  • HMDB04236
Metabolite Identification
Common NameProstaglandin B2
DescriptionProstaglandin B2 (PGB2) is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207 ). 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?1582752303
Synonyms
ValueSource
PGB2HMDB
Chemical FormulaC20H30O4
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
IUPAC Name(5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid
Traditional Name(5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid
CAS Registry Number13367-85-6
SMILES
CCCCC[C@@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1
InChI Identifier
InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/b7-4-,14-12+/t17-/m1/s1
InChI KeyPRFXRIUZNKLRHM-RYPCXPIFSA-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
  • Fatty acid
  • Unsaturated fatty acid
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.154Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP4.07ALOGPS
logP4.18ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity98.61 m³·mol⁻¹ChemAxon
Polarizability39.64 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
DeepCCS[M+H]+195.05130932474
DeepCCS[M-H]-192.25930932474
DeepCCS[M-2H]-226.98630932474
DeepCCS[M+Na]+202.21330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prostaglandin B2CCCCC[C@@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC14368.5Standard polar33892256
Prostaglandin B2CCCCC[C@@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC12717.1Standard non polar33892256
Prostaglandin B2CCCCC[C@@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC12864.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin B2,1TMS,isomer #1CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O)C(=O)CC1)O[Si](C)(C)C2887.3Semi standard non polar33892256
Prostaglandin B2,1TMS,isomer #2CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(=O)CC12819.0Semi standard non polar33892256
Prostaglandin B2,1TMS,isomer #3CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C)=CC12862.8Semi standard non polar33892256
Prostaglandin B2,2TMS,isomer #1CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(=O)CC1)O[Si](C)(C)C2855.1Semi standard non polar33892256
Prostaglandin B2,2TMS,isomer #2CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C2900.6Semi standard non polar33892256
Prostaglandin B2,2TMS,isomer #3CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC12838.8Semi standard non polar33892256
Prostaglandin B2,3TMS,isomer #1CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C2859.7Semi standard non polar33892256
Prostaglandin B2,3TMS,isomer #1CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C2758.5Standard non polar33892256
Prostaglandin B2,3TMS,isomer #1CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C3005.4Standard polar33892256
Prostaglandin B2,1TBDMS,isomer #1CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O)C(=O)CC1)O[Si](C)(C)C(C)(C)C3115.1Semi standard non polar33892256
Prostaglandin B2,1TBDMS,isomer #2CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CC13056.1Semi standard non polar33892256
Prostaglandin B2,1TBDMS,isomer #3CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC13096.0Semi standard non polar33892256
Prostaglandin B2,2TBDMS,isomer #1CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CC1)O[Si](C)(C)C(C)(C)C3353.0Semi standard non polar33892256
Prostaglandin B2,2TBDMS,isomer #2CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C3356.5Semi standard non polar33892256
Prostaglandin B2,2TBDMS,isomer #3CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC13322.3Semi standard non polar33892256
Prostaglandin B2,3TBDMS,isomer #1CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C3567.2Semi standard non polar33892256
Prostaglandin B2,3TBDMS,isomer #1CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C3164.7Standard non polar33892256
Prostaglandin B2,3TBDMS,isomer #1CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C3183.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin B2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lm-6391000000-3b069d42dd8ba363e1c32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin B2 GC-MS (2 TMS) - 70eV, Positivesplash10-020c-9107400000-3e378b304e81c97672752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin B2 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 B2 10V, Positive-QTOFsplash10-014j-0169000000-ab7e151e7512a92175702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 20V, Positive-QTOFsplash10-02ga-3951000000-6eb2a7a228914281a6f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 40V, Positive-QTOFsplash10-0f76-9220000000-0ee4fdc9b2a755b944e02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 10V, Negative-QTOFsplash10-001i-0019000000-dbe0b0e74e1f3b041bda2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 20V, Negative-QTOFsplash10-0159-2159000000-e67ebc50c5d1f2b7f75f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 40V, Negative-QTOFsplash10-0a4l-9140000000-dc05680aa61a1ac559032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 10V, Negative-QTOFsplash10-0159-0029000000-9e6efa43b3e01f68d9d32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 20V, Negative-QTOFsplash10-00lr-1397000000-82f85934c72172d6f0bd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 40V, Negative-QTOFsplash10-05mo-7931000000-b9dc32b05b5d304a8c152021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 10V, Positive-QTOFsplash10-00kb-0095000000-ec2f02e0ccce84d132402021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 20V, Positive-QTOFsplash10-00kb-4291000000-c675b9e2faa54ccca0982021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin B2 40V, Positive-QTOFsplash10-00nf-9510000000-f147c78bdfdeae923ab02021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000373 +/- 0.000212 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000519 +/- 0.000096 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.0007 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000002992 uMNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000004488 uMNot SpecifiedNot Specifiedischaemic stroke details
Associated Disorders and Diseases
Disease References
Cerebral infarction
  1. Fagan SC, Castellani D, Gengo FM: Prostanoid concentrations in human CSF following acute ischaemic brain infarction. Clin Exp Pharmacol Physiol. 1986 Aug;13(8):629-32. [PubMed:3791712 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023342
KNApSAcK IDNot Available
Chemspider ID4450370
KEGG Compound IDC05954
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5288144
PDB IDE2P
ChEBI ID28099
Food Biomarker OntologyNot Available
VMH IDHC02205
MarkerDB IDMDB00013451
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Masoodi M, Nicolaou A: Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(20):3023-9. [PubMed:16986207 ]