Human Metabolome Database Version 3.5

Showing metabocard for PGH3 (HMDB13040)

Record Information
Version 3.5
Creation Date 2009-07-24 18:12:08 -0600
Update Date 2013-02-08 17:29:42 -0700
Secondary Accession Numbers None
Metabolite Identification
Common Name PGH3
Description Prostaglandin H3 (PGH3)can be enzymatically converted by platelets into thromboxane A3. Both PGH2 and thromboxane A2 aggregate human platelet-rich plasma. In contrast, PGH3 and thromboxane A3 do not. PGH3 and thromboxane A3 increase platelet cyclic AMP in platelet-rich plasma and thereby: (i) inhibit. aggregation by other agonists, (ii) block the ADP-induced release reaction, and (iii) suppress platelet phospholipase-A2 activity or events leading to its activation. PGI3 (A'7-prostacyclin; synthesized from PGH3 by blood vessel enzyme) and PGI2(prostacyclin) exert similar effects. Both compounds are potent coronary relaxants that also inhibit aggregation in human platelet-rich plasma and increase platelet adenylate cyclase activity. 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 signaling pathways.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
  1. Prostaglandin H(,3)
Chemical Formula C20H30O5
Average Molecular Weight 350.4492
Monoisotopic Molecular Weight 350.20932407
IUPAC Name (5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3R,5Z)-3-hydroxyocta-1,5-dien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
Traditional IUPAC Name (5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3R,5Z)-3-hydroxyocta-1,5-dien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
CAS Registry Number 42935-17-1
SMILES CC\C=C/C[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/C20H30O5/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/h3-4,6-7,12-13,15-19,21H,2,5,8-11,14H2,1H3,(H,22,23)/b6-3-,7-4-,13-12+/t15-,16-,17-,18+,19-/m1/s1
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Prostaglandins and related compounds
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Heterocyclic Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
  • Allyl Alcohol
  • Carboxylic Acid Salt
  • Fatty Alcohol
  • Ortho Dioxane
  • Ortho Dioxolane
  • Secondary Alcohol
Direct Parent Prostaglandins and related compounds
Status Expected and Not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.041 g/L ALOGPS
LogP 4.22 ALOGPS
LogP 3.6 ChemAxon
LogS -3.93 ALOGPS
pKa (strongest acidic) 4.36 ChemAxon
pKa (strongest basic) -1.7 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 75.99 A2 ChemAxon
Rotatable Bond Count 11 ChemAxon
Refractivity 99.16 ChemAxon
Polarizability 38.97 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029265
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C00427 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB13040 Link_out
Metagene Link HMDB13040 Link_out
METLIN ID Not Available
PubChem Compound 53481592 Link_out
PDB ID Not Available
ChEBI ID 15554 Link_out
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available