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Record Information
Version1.0
Creation Date2016-09-30 22:45:05 UTC
Update Date2020-05-21 16:28:39 UTC
BMDB IDBMDB0001381
Secondary Accession Numbers
  • BMDB01381
Metabolite Identification
Common NameProstaglandin H2
DescriptionProstaglandin H2, also known as PGH2 or endoperoxide H2, 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. Thus, prostaglandin H2 is considered to be an eicosanoid lipid molecule. Prostaglandin H2 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
(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
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
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
Traditional Nameprostaglandin H2
CAS Registry Number42935-17-1
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=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
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
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05d3-5192000000-448e0e493622387c9600View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gr-9221300000-2098865f850184449832View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-f1f4732bb2fcf1ecdd31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-4298000000-8f02063e16efefaecab3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tu-9300000000-e3cb6f0175b4d6d56475View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-661131f879ff507a5adfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kai-1049000000-c49ffddba6a8b323d42fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9332000000-145fc48bf43661f2584fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001381
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031134
KNApSAcK IDNot Available
Chemspider ID392800
KEGG Compound IDC00427
BioCyc IDNot Available
BiGG ID34952
Wikipedia LinkProstaglandin H2
METLIN ID3495
PubChem Compound445049
PDB IDNot Available
ChEBI ID15554
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:
PTGIS
Uniprot ID:
Q29626
Molecular weight:
56629.0
Reactions
Prostaglandin H2 → Prostaglandin I2details
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
TBXAS1
Uniprot ID:
Q2KIG5
Molecular weight:
60539.0
Reactions
Prostaglandin H2 → Thromboxane A2details
General function:
Involved in prostaglandin-D synthase activity
Specific function:
Catalyzes the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation. Involved in a variety of CNS functions, such as sedation, NREM sleep and PGE2-induced allodynia, and may have an anti-apoptotic role in oligodendrocytes. Binds small non-substrate lipophilic molecules, including biliverdin, bilirubin, retinal, retinoic acid and thyroid hormone, and may act as a scavenger for harmful hydrophobic molecules and as a secretory retinoid and thyroid hormone transporter. Possibly involved in development and maintenance of the blood-brain, blood-retina, blood-aqueous humor and blood-testis barrier. It is likely to play important roles in both maturation and maintenance of the central nervous system and male reproductive system (By similarity).
Gene Name:
PTGDS
Uniprot ID:
O02853
Molecular weight:
21229.0
Reactions
Prostaglandin H2 → Prostaglandin D2details
General function:
Involved in prostaglandin-E synthase activity
Specific function:
Isomerase that catalyzes the conversion of PGH2 into the more stable prostaglandin E2 (PGE2).
Gene Name:
PTGES2
Uniprot ID:
Q66LN0
Molecular weight:
41738.0
General function:
Not Available
Specific function:
Catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2).
Gene Name:
PTGES
Uniprot ID:
Q95L14
Molecular weight:
17298.0
Reactions
Prostaglandin H2 → Prostaglandin E2details
General function:
Not Available
Specific function:
Catalyzes the reduction of prostaglandin-ethanolamide H(2) (prostamide H(2)) to prostamide F(2alpha) with NADPH as proton donor. Also able to reduce prostaglandin H(2) to prostaglandin F(2alpha) (By similarity).
Gene Name:
PRXL2B
Uniprot ID:
Q58CY6
Molecular weight:
21497.0
Reactions
Prostaglandin H2 → Prostaglandin F2adetails