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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:12:09 UTC
Update Date2022-03-07 02:51:28 UTC
HMDB IDHMDB0013041
Secondary Accession Numbers
  • HMDB13041
Metabolite Identification
Common NameProstaglandin H1
DescriptionProstaglandin H1 (PGH1) is the precursor to all 1-series thromboxanes, and is a suicide inhibitor of platelet thromboxane synthase, possessing a Ki of 28 mM.2 PGH1 also acts on the aryl hydrocarbon receptor (AhR) by stimulating AhR transformation and DNA binding in vitro. It also induces AhR-dependent reporter gene expression in mouse hepatoma cells in culture.3. 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
9alpha,11alpha-Epidioxy-15(S)-hydroxy-13-trans-prostenoateHMDB
9alpha,11alpha-Epidioxy-15(S)-hydroxy-13-trans-prostenoic acidHMDB
PGH(,1)HMDB
7-[(1S,4R,5S,6S)-6-[(1E,3S)-3-Hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoateGenerator
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name7-[(1S,4R,5S,6S)-6-[(1E,3S)-3-hydroxyoct-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-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid
CAS Registry NumberNot Available
SMILES
CCCCC[C@H](O)\C=C\[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h12-13,15-19,21H,2-11,14H2,1H3,(H,22,23)/b13-12+/t15-,16-,17-,18+,19-/m0/s1
InChI KeyNTAYABHEVAQSJS-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
  • Fatty alcohol
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Ortho-dioxane
  • Ortho-dioxolane
  • Dialkyl peroxide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility0.017 g/LALOGPS
logP4.37ALOGPS
logP4.32ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.41ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity96.93 m³·mol⁻¹ChemAxon
Polarizability41.56 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]+188.4531661259
DarkChem[M-H]-188.75331661259
DeepCCS[M+H]+197.44130932474
DeepCCS[M-H]-195.04430932474
DeepCCS[M-2H]-228.7830932474
DeepCCS[M+Na]+203.38430932474
AllCCS[M+H]+194.332859911
AllCCS[M+H-H2O]+191.732859911
AllCCS[M+NH4]+196.732859911
AllCCS[M+Na]+197.432859911
AllCCS[M-H]-193.832859911
AllCCS[M+Na-2H]-195.032859911
AllCCS[M+HCOO]-196.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prostaglandin H1CCCCC[C@H](O)\C=C\[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(O)=O4088.6Standard polar33892256
Prostaglandin H1CCCCC[C@H](O)\C=C\[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(O)=O2636.5Standard non polar33892256
Prostaglandin H1CCCCC[C@H](O)\C=C\[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(O)=O2673.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin H1,1TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(=O)O)O[Si](C)(C)C2676.2Semi standard non polar33892256
Prostaglandin H1,1TMS,isomer #2CCCCC[C@H](O)/C=C/[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(=O)O[Si](C)(C)C2649.0Semi standard non polar33892256
Prostaglandin H1,2TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2740.0Semi standard non polar33892256
Prostaglandin H1,1TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2880.9Semi standard non polar33892256
Prostaglandin H1,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C2882.6Semi standard non polar33892256
Prostaglandin H1,2TBDMS,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)O[Si](C)(C)C(C)(C)C3169.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin H1 GC-MS (Non-derivatized) - 70eV, Positivesplash10-01wu-4192000000-bc99d7562ca1dd0e54a92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin H1 GC-MS (2 TMS) - 70eV, Positivesplash10-00gr-9242300000-88d88d034143c85f0ad02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin H1 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 H1 10V, Positive-QTOFsplash10-000i-0019000000-2c081e879b4aa402d2982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 20V, Positive-QTOFsplash10-05n0-5579000000-590ab4244e220b0caa9f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 40V, Positive-QTOFsplash10-05to-9300000000-f6e1bf96abe81b6952fc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 10V, Negative-QTOFsplash10-0udi-0009000000-142292a24df2444e493e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 20V, Negative-QTOFsplash10-0f79-1029000000-18da725097025f2b15f82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 40V, Negative-QTOFsplash10-0a4i-9242000000-15942f2140f731ead6d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 10V, Positive-QTOFsplash10-014r-0009000000-9366db7527d16336dec22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 20V, Positive-QTOFsplash10-014l-5379000000-eeaefff600dc9037681a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 40V, Positive-QTOFsplash10-05mo-9500000000-5251e610b43b3ef3ae452021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 10V, Negative-QTOFsplash10-0udi-0009000000-c17a630eaa2ea7e31c4e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 20V, Negative-QTOFsplash10-00di-0009000000-17100385a9b3f576ce832021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin H1 40V, Negative-QTOFsplash10-0f83-2095000000-077e73dd859c29e303ec2021-09-24Wishart 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 IDFDB029266
KNApSAcK IDNot Available
Chemspider ID30776687
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound50921242
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.