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Showing Compound prostaglandin-H2 (FDB031134)

Record Information
Version1.0
Creation date2015-05-07 21:06:19 UTC
Update date2019-11-26 03:22:09 UTC
Primary IDFDB031134
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameprostaglandin-H2
DescriptionProstaglandin h2, also known as pgh2 or 9s,11r-epidioxy-15s-hydroxy-5z,13e-prostadienoate, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds 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. Thus, prostaglandin h2 is considered to be an eicosanoid lipid molecule. Prostaglandin h2 is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Prostaglandin h2 can be found in a number of food items such as gooseberry, evergreen huckleberry, quince, and capers, which makes prostaglandin h2 a potential biomarker for the consumption of these food products. Prostaglandin h2 can be found primarily in human platelet tissue. In humans, prostaglandin h2 is involved in several metabolic pathways, some of which include magnesium salicylate action pathway, ketorolac action pathway, trisalicylate-choline action pathway, and salicylate-sodium action pathway. Prostaglandin h2 is also involved in a couple of metabolic disorders, which include leukotriene C4 synthesis deficiency and tiaprofenic acid action pathway. Prostaglandin h2 is acted upon by: Prostacyclin synthase to create prostacyclin Thromboxane-A synthase to create thromboxane A2 and 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) (see 12-Hydroxyheptadecatrienoic acid) Prostaglandin D2 synthase to create prostaglandin D2 Prostaglandin E synthase to create prostaglandin E2 Prostaglandin h2 rearranges non-enzymatically to: A mixture of 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) and 12-(S)-hydroxy-5Z,8Z,10E-heptadecatrienoic acid (see 12-Hydroxyheptadecatrienoic acid) Use of Prostaglandin H2: regulating the constriction and dilation of blood vessels stimulating platelet aggregation Effects of Aspirin on Prostaglandin H2: Aspirin has been hypothesized to block the conversion of arachidonic acid to Prostaglandin .
CAS Number42935-17-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoateChEBI
(5Z,13E,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoateChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acidChEBI
9,11-Epoxymethano-PGH2ChEBI
PGH2ChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoateKegg
(5Z,13E)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoateGenerator
(5Z,13E,15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoateGenerator
(5Z,13E,15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acidGenerator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-OateGenerator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acidGenerator
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-OateGenerator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-OateGenerator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acidGenerator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoateGenerator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoic acidGenerator
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoic acidGenerator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoateGenerator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoic acidGenerator
(15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoateHMDB
(15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoic acidHMDB
(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoateHMDB
(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoic acidHMDB
(5Z,13E)-(15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dienoateHMDB
(5Z,13E)-(15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dienoic acidHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoateHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acidHMDB
(5Z,13E,15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoateHMDB
(5Z,13E,15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acidHMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dien-1-OateHMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dien-1-Oic acidHMDB
15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoateHMDB
15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoic acidHMDB
9S,11R-Epidioxy-15S-hydroxy-5Z,13E-prostadienoateHMDB
9S,11R-Epidioxy-15S-hydroxy-5Z,13E-prostadienoic acidHMDB
Endoperoxide H2HMDB
Prostaglandin R2HMDB
Prostaglandin-H2HMDB
PGH(2)HMDB
Predicted Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP4.27ALOGPS
logP3.96ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity98.04 m³·mol⁻¹ChemAxon
Polarizability39.9 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O5
IUPAC name(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
InChI IdentifierInChI=1S/C20H32O5/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/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
InChI KeyYIBNHAJFJUQSRA-YNNPMVKQSA-N
Isomeric SMILESCCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
Classification
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
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Ortho-dioxane
  • Fatty acid
  • Unsaturated fatty acid
  • 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
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSprostaglandin-H2, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05d3-5192000000-448e0e493622387c9600Spectrum
Predicted GC-MSprostaglandin-H2, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00gr-9221300000-2098865f850184449832Spectrum
Predicted GC-MSprostaglandin-H2, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSprostaglandin-H2, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-f1f4732bb2fcf1ecdd312017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-4298000000-8f02063e16efefaecab32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tu-9300000000-e3cb6f0175b4d6d564752017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-661131f879ff507a5adf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kai-1049000000-c49ffddba6a8b323d42f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9332000000-145fc48bf43661f2584f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-416c95b6b6ca7d458ed62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4298000000-1e1b7f327aae394c65092021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00r6-9600000000-0dcbe56cd4069bcb23502021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-c3076b041f51673c7c5b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0019000000-1908f881874f924ccebd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3094000000-05963bfb2b050a03f37c2021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference