You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-10-25 15:06:25 UTC
Update Date2016-02-11 01:07:05 UTC
HMDB IDHMDB05102
Secondary Accession NumbersNone
Metabolite Identification
Common NameProstaglandin D1
DescriptionProstaglandin D1 is a prostanoid that elicits contractile and relaxant on isolated human pial arteries with small potency. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 6091419 , 16986207 )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
Synonyms
ValueSource
5-Hydroxy-2-(3-hydroxy-1-octenyl)-3-oxocyclopentaneheptanoic acidChEBI
PGD1ChEBI
5-Hydroxy-2-(3-hydroxy-1-octenyl)-3-oxocyclopentaneheptanoateGenerator
(13E,15S)-9alpha,15-Dihydroxy-11-oxoprost-13-en-1-OateHMDB
(13E,15S)-9alpha,15-Dihydroxy-11-oxoprost-13-en-1-Oic acidHMDB
11-dehydro-Prostaglandin F1aHMDB
2-Hydroxy-5-(3S-hydroxy-1-octenyl)-3-oxocyclopentaneheptanoateHMDB
2-Hydroxy-5-(3S-hydroxy-1-octenyl)-3-oxocyclopentaneheptanoic acidHMDB
5-Hydroxy-2-(3-hydroxy-1-octenyl)-3-oxo-cyclopentaneheptanoateHMDB
5-Hydroxy-2-(3-hydroxy-1-octenyl)-3-oxo-cyclopentaneheptanoic acidHMDB
9a,15-Dihydroxy-11-ketoprost-13-enoateHMDB
9a,15-Dihydroxy-11-ketoprost-13-enoic acidHMDB
9S,15S-Dihydroxy-11-oxo-13E-prostaenoateHMDB
9S,15S-Dihydroxy-11-oxo-13E-prostaenoic acidHMDB
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]heptanoic acid
Traditional Nameprostaglandin D1
CAS Registry Number17968-82-0
SMILES
CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](CCCCCCC(O)=O)[C@@H](O)CC1=O
InChI Identifier
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-18,21-22H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,18-/m0/s1
InChI KeyInChIKey=CIMMACURCPXICP-PNQRDDRVSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydroxy fatty acid
  • Fatty alcohol
  • Carbocyclic fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.172Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.075 mg/mLALOGPS
logP3.12ALOGPS
logP3.59ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.45ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity98.32 m3·mol-1ChemAxon
Polarizability42.16 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1E-5 +/- 1E-6 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023631
KNApSAcK IDNot Available
Chemspider ID4444438
KEGG Compound IDC06438
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05102
Metagene LinkHMDB05102
METLIN IDNot Available
PubChem Compound5280936
PDB IDNot Available
ChEBI ID27696
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Uski TK, Andersson KE, Brandt L, Ljunggren B: Characterization of the prostanoid receptors and of the contractile effects of prostaglandin F2 alpha in human pial arteries. Acta Physiol Scand. 1984 Aug;121(4):369-78. [6091419 ]
  2. Masoodi M, Nicolaou A: Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(20):3023-9. [16986207 ]
  3. Lipid Maps (LMFA03010049) [Link]