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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:12:07 UTC
Update Date2022-03-07 02:51:28 UTC
HMDB IDHMDB0013039
Secondary Accession Numbers
  • HMDB13039
Metabolite Identification
Common NameProstaglandin G1
DescriptionProstaglandin G1 belongs to the family of Prostaglandins. 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?1582753086
Synonyms
ValueSource
(9S)-Hydroperoxy-(5Z,7E,11Z,14Z)-eicosatetraenoateHMDB
(9S)-Hydroperoxy-(5Z,7E,11Z,14Z)-eicosatetraenoic acidHMDB
9alpha, 11alpha-Epidioxy-15(S)-hydroperoxy-13-trans-prostenoateHMDB
9alpha, 11alpha-Epidioxy-15(S)-hydroperoxy-13-trans-prostenoic acidHMDB
9S-HPETEHMDB
PGG(,1)HMDB
7-[(1S,4R,5S,6S)-6-[(1E,3S)-3-Hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoateGenerator
Chemical FormulaC20H34O6
Average Molecular Weight370.4804
Monoisotopic Molecular Weight370.23553882
IUPAC Name7-[(1S,4R,5S,6S)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid
Traditional Name7-[(1S,4R,5S,6S)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid
CAS Registry NumberNot Available
SMILES
CCCCC[C@H](OO)\C=C\[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H34O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h12-13,15-19,23H,2-11,14H2,1H3,(H,21,22)/b13-12+/t15-,16-,17-,18+,19-/m0/s1
InChI KeyQXCRWNZYEVOQMB-NDWDMBLISA-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
  • Hydroperoxy fatty acid
  • Heterocyclic fatty acid
  • Ortho-dioxane
  • Allylic hydroperoxide
  • Ortho-dioxolane
  • Dialkyl peroxide
  • Hydroperoxide
  • Alkyl hydroperoxide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Peroxol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.32ALOGPS
logP4.77ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.41ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity98.28 m³·mol⁻¹ChemAxon
Polarizability42.05 ųChemAxon
Number of Rings2ChemAxon
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]+192.26431661259
DarkChem[M-H]-191.48831661259
DeepCCS[M+H]+197.62130932474
DeepCCS[M-H]-195.22330932474
DeepCCS[M-2H]-228.72430932474
DeepCCS[M+Na]+203.38830932474
AllCCS[M+H]+196.832859911
AllCCS[M+H-H2O]+194.332859911
AllCCS[M+NH4]+199.232859911
AllCCS[M+Na]+199.832859911
AllCCS[M-H]-196.132859911
AllCCS[M+Na-2H]-197.532859911
AllCCS[M+HCOO]-199.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prostaglandin G1CCCCC[C@H](OO)\C=C\[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(O)=O4080.5Standard polar33892256
Prostaglandin G1CCCCC[C@H](OO)\C=C\[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(O)=O2618.1Standard non polar33892256
Prostaglandin G1CCCCC[C@H](OO)\C=C\[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(O)=O2748.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin G1,1TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(=O)O[Si](C)(C)C)OO2738.7Semi standard non polar33892256
Prostaglandin G1,1TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OO2968.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin G1 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-5392000000-a39269272a3d12bcc9cd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin G1 GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9362200000-117f1f131cbd3e5cd5f52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin G1 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 G1 10V, Positive-QTOFsplash10-0udi-0119000000-79bbd81864eb098a29ce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 20V, Positive-QTOFsplash10-0kbr-5739000000-b74e6cc9639a4ea6413d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 40V, Positive-QTOFsplash10-0q2c-9300000000-90bf6e099fd6cfe0688a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 10V, Negative-QTOFsplash10-014i-0009000000-c4b9e12c053ab977e3472017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 20V, Negative-QTOFsplash10-0uxr-2139000000-c08770bafb1f5459721e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 40V, Negative-QTOFsplash10-0a4i-9253000000-7403bbe778c714c686f72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 10V, Negative-QTOFsplash10-014i-0009000000-3240dd782ece915daf522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 20V, Negative-QTOFsplash10-00kr-0009000000-f4307540344396711f172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 40V, Negative-QTOFsplash10-066r-4097000000-c718deaa24b708c9fb7a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 10V, Positive-QTOFsplash10-0gi9-0009000000-aa97018f038f38eec3ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 20V, Positive-QTOFsplash10-0fy9-3169000000-80c4ca9833ca37b7a7272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin G1 40V, Positive-QTOFsplash10-059x-9410000000-3dec3a5ec880fc7a5a112021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB029264
KNApSAcK IDNot Available
Chemspider ID30776685
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481591
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.