Prostaglandin B1 (CHEM035483)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:48:24 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035483
Identification
Common NameProstaglandin B1
ClassSmall Molecule
DescriptionA member of the class of prostaglandins B that is prosta-8(12),13-dien-1-oic acid carrying oxo and hydroxy substituents at positions 9 and 15 respectively (the 13E,15S-stereoisomer).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PGB1ChEBI
(13E,15S)-15-Hydroxy-9-oxoprosta-8(12),13-dien-1-OateHMDB
(13E,15S)-15-Hydroxy-9-oxoprosta-8(12),13-dien-1-Oic acidHMDB
9-oxo-15S-Hydroxy-8(12),13E-prostadienoateHMDB
9-oxo-15S-Hydroxy-8(12),13E-prostadienoic acidHMDB
Prostaglandin-b1HMDB
Prostaglandin b1MeSH
Chemical FormulaC20H32O4
Average Molecular Mass336.466 g/mol
Monoisotopic Mass336.230 g/mol
CAS Registry Number13345-51-2
IUPAC Name7-{2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}heptanoic acid
Traditional Nameprostaglandin-B1
SMILESCCCCC[C@H](O)\C=C\C1=C(CCCCCCC(O)=O)C(=O)CC1
InChI IdentifierInChI=1S/C20H32O4/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/h12,14,17,21H,2-11,13,15H2,1H3,(H,23,24)/b14-12+/t17-/m0/s1
InChI KeyYBHMPNRDOVPQIN-VSOYFRJCSA-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
  • Fatty alcohol
  • Hydroxy fatty acid
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.99ALOGPS
logP4.55ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity97.49 m³·mol⁻¹ChemAxon
Polarizability40.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05n0-5192000000-a7e9f36e25137b9fabccSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-010c-9126300000-342d7eee52879bb192e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0029000000-0690d2f3dfb5d1ee9afeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l6u-4495000000-96548847dc77e5ecb0ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06du-9230000000-bdbc4c091593478de78bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-af954838d61275b1a6b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-2059000000-e381e90f103a41486292Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-c082f378971a61d35c10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0129000000-2d428b3ff47d60ebed59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uy0-6797000000-9e0090cf284a26438dc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-9400000000-79d7c252855e7c736ea6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-877d392a3ea777176963Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ri-1297000000-51af315e563050950d6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05tn-5930000000-05a9fe2c2833996f0a2aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002982
FooDB IDFDB023088
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID408
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444076
ChEBI ID27624
PubChem Compound ID5280388
Kegg Compound IDC00959
YMDB IDNot Available
ECMDB IDM2MDB005507
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hishinuma T, Nakamura H, Itoh K, Ohyama Y, Ishibashi M, Mizugaki M: Microdetermination of the prostaglandin B1 in human plasma by gas chromatography/selected ion monitoring using [18O]prostaglandin B1 as an internal standard. Prostaglandins. 1995 Apr;49(4):239-46.
2. Fry MR, Ghosh SS, East JM, Franson RC: Role of human sperm phospholipase A2 in fertilization: effects of a novel inhibitor of phospholipase A2 activity on membrane perturbations and oocyte penetration. Biol Reprod. 1992 Nov;47(5):751-9.
3. Franson R, Raghupathi R, Fry M, Saal J, Vishwanath B, Ghosh SS, Rosenthal MD: Inhibition of human phospholipases A2 by cis-unsaturated fatty acids and oligomers of prostaglandin B1. Adv Exp Med Biol. 1990;279:219-30.
4. Franson RC, Rosenthal MD: Oligomers of prostaglandin B1 inhibit in vitro phospholipase A2 activity. Biochim Biophys Acta. 1989 Dec 18;1006(3):272-7.
5. Himori N, Burkman AM: Prostaglandin B1 can modify the pressor responses to sympathetic nerve stimulation. Res Commun Chem Pathol Pharmacol. 1983 Sep;41(3):397-405.