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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:27 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0003034
Secondary Accession Numbers
  • HMDB03034
Metabolite Identification
Common NameProstaglandin D3
DescriptionProstaglandin D3 (PGD3) is a prostanoid that has been identified as an inhibitor of human platelet aggregation and as a modulator of autonomic nerve transmission. 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: 16986207 , 6252026 , 6952267 , 4019112 , 6945633 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?1582752261
Synonyms
ValueSource
(5Z)-7-[(1R,2R,5S)-5-Hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-3-oxocyclopentyl]hept-5-enoic acidChEBI
(5Z,13E,15S,17Z)-9alpha,15-Dihydroxy-11-oxoprosta-5,13,17-trien-1-Oic acidChEBI
9S,15S-Dihydroxy-11-oxo-5Z,13E,17Z-prostatrienoic acidChEBI
(5Z)-7-[(1R,2R,5S)-5-Hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-3-oxocyclopentyl]hept-5-enoateGenerator
(5Z,13E,15S,17Z)-9a,15-Dihydroxy-11-oxoprosta-5,13,17-trien-1-OateGenerator
(5Z,13E,15S,17Z)-9a,15-Dihydroxy-11-oxoprosta-5,13,17-trien-1-Oic acidGenerator
(5Z,13E,15S,17Z)-9alpha,15-Dihydroxy-11-oxoprosta-5,13,17-trien-1-OateGenerator
(5Z,13E,15S,17Z)-9Α,15-dihydroxy-11-oxoprosta-5,13,17-trien-1-OateGenerator
(5Z,13E,15S,17Z)-9Α,15-dihydroxy-11-oxoprosta-5,13,17-trien-1-Oic acidGenerator
9S,15S-Dihydroxy-11-oxo-5Z,13E,17Z-prostatrienoateGenerator
PGD3HMDB
Prostaglandin D3MeSH
Chemical FormulaC20H30O5
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
IUPAC Name(5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
Traditional Nameprostaglandin D3
CAS Registry Number71902-47-1
SMILES
CC\C=C/C[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O
InChI Identifier
InChI=1S/C20H30O5/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/h3-4,6-7,12-13,15-18,21-22H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,18-/m0/s1
InChI KeyANOICLBSJIMQTA-WXGBOJPQSA-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
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility0.085 g/LALOGPS
logP2.88ALOGPS
logP2.86ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity100.55 m³·mol⁻¹ChemAxon
Polarizability39.67 ųChemAxon
Number of Rings1ChemAxon
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]+187.50231661259
DarkChem[M-H]-183.43131661259
DeepCCS[M+H]+194.11430932474
DeepCCS[M-H]-191.71830932474
DeepCCS[M-2H]-224.65430932474
DeepCCS[M+Na]+200.02630932474
AllCCS[M+H]+191.732859911
AllCCS[M+H-H2O]+189.032859911
AllCCS[M+NH4]+194.332859911
AllCCS[M+Na]+195.032859911
AllCCS[M-H]-189.932859911
AllCCS[M+Na-2H]-191.332859911
AllCCS[M+HCOO]-192.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prostaglandin D3CC\C=C/C[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O4478.1Standard polar33892256
Prostaglandin D3CC\C=C/C[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O2671.7Standard non polar33892256
Prostaglandin D3CC\C=C/C[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O2904.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin D3,1TMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2904.2Semi standard non polar33892256
Prostaglandin D3,1TMS,isomer #2CC/C=C\C[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2804.1Semi standard non polar33892256
Prostaglandin D3,1TMS,isomer #3CC/C=C\C[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O2811.3Semi standard non polar33892256
Prostaglandin D3,1TMS,isomer #4CC/C=C\C[C@H](O)/C=C/C1=C(O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O2879.5Semi standard non polar33892256
Prostaglandin D3,1TMS,isomer #5CC/C=C\C[C@H](O)/C=C/[C@H]1C(O[Si](C)(C)C)=C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O2759.9Semi standard non polar33892256
Prostaglandin D3,2TMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@H]1C(=O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2772.7Semi standard non polar33892256
Prostaglandin D3,2TMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2812.2Semi standard non polar33892256
Prostaglandin D3,2TMS,isomer #3CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2955.0Semi standard non polar33892256
Prostaglandin D3,2TMS,isomer #4CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C)=C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2796.4Semi standard non polar33892256
Prostaglandin D3,2TMS,isomer #5CC/C=C\C[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2756.2Semi standard non polar33892256
Prostaglandin D3,2TMS,isomer #6CC/C=C\C[C@H](O)/C=C/C1=C(O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2861.4Semi standard non polar33892256
Prostaglandin D3,2TMS,isomer #7CC/C=C\C[C@H](O)/C=C/[C@H]1C(O[Si](C)(C)C)=C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2744.9Semi standard non polar33892256
Prostaglandin D3,2TMS,isomer #8CC/C=C\C[C@H](O)/C=C/C1=C(O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O2847.7Semi standard non polar33892256
Prostaglandin D3,2TMS,isomer #9CC/C=C\C[C@H](O)/C=C/[C@H]1C(O[Si](C)(C)C)=C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O2778.0Semi standard non polar33892256
Prostaglandin D3,3TMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@H]1C(=O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2741.3Semi standard non polar33892256
Prostaglandin D3,3TMS,isomer #2CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2867.1Semi standard non polar33892256
Prostaglandin D3,3TMS,isomer #3CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C)=C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2789.1Semi standard non polar33892256
Prostaglandin D3,3TMS,isomer #4CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2894.8Semi standard non polar33892256
Prostaglandin D3,3TMS,isomer #5CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C)=C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2767.8Semi standard non polar33892256
Prostaglandin D3,3TMS,isomer #6CC/C=C\C[C@H](O)/C=C/C1=C(O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2813.8Semi standard non polar33892256
Prostaglandin D3,3TMS,isomer #7CC/C=C\C[C@H](O)/C=C/[C@H]1C(O[Si](C)(C)C)=C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2749.1Semi standard non polar33892256
Prostaglandin D3,4TMS,isomer #1CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2836.6Semi standard non polar33892256
Prostaglandin D3,4TMS,isomer #1CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2811.6Standard non polar33892256
Prostaglandin D3,4TMS,isomer #1CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2896.3Standard polar33892256
Prostaglandin D3,4TMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C)=C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2796.3Semi standard non polar33892256
Prostaglandin D3,4TMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C)=C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2670.2Standard non polar33892256
Prostaglandin D3,4TMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C)=C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2904.3Standard polar33892256
Prostaglandin D3,1TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3134.0Semi standard non polar33892256
Prostaglandin D3,1TBDMS,isomer #2CC/C=C\C[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3055.0Semi standard non polar33892256
Prostaglandin D3,1TBDMS,isomer #3CC/C=C\C[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O3015.0Semi standard non polar33892256
Prostaglandin D3,1TBDMS,isomer #4CC/C=C\C[C@H](O)/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O3108.0Semi standard non polar33892256
Prostaglandin D3,1TBDMS,isomer #5CC/C=C\C[C@H](O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O3011.0Semi standard non polar33892256
Prostaglandin D3,2TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@H]1C(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3246.2Semi standard non polar33892256
Prostaglandin D3,2TBDMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3296.4Semi standard non polar33892256
Prostaglandin D3,2TBDMS,isomer #3CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3376.6Semi standard non polar33892256
Prostaglandin D3,2TBDMS,isomer #4CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3276.8Semi standard non polar33892256
Prostaglandin D3,2TBDMS,isomer #5CC/C=C\C[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3224.1Semi standard non polar33892256
Prostaglandin D3,2TBDMS,isomer #6CC/C=C\C[C@H](O)/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3321.5Semi standard non polar33892256
Prostaglandin D3,2TBDMS,isomer #7CC/C=C\C[C@H](O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3241.4Semi standard non polar33892256
Prostaglandin D3,2TBDMS,isomer #8CC/C=C\C[C@H](O)/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O3280.5Semi standard non polar33892256
Prostaglandin D3,2TBDMS,isomer #9CC/C=C\C[C@H](O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O3241.6Semi standard non polar33892256
Prostaglandin D3,3TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/[C@H]1C(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3458.7Semi standard non polar33892256
Prostaglandin D3,3TBDMS,isomer #2CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3506.4Semi standard non polar33892256
Prostaglandin D3,3TBDMS,isomer #3CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3502.8Semi standard non polar33892256
Prostaglandin D3,3TBDMS,isomer #4CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3563.4Semi standard non polar33892256
Prostaglandin D3,3TBDMS,isomer #5CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3503.1Semi standard non polar33892256
Prostaglandin D3,3TBDMS,isomer #6CC/C=C\C[C@H](O)/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3496.2Semi standard non polar33892256
Prostaglandin D3,3TBDMS,isomer #7CC/C=C\C[C@H](O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3473.1Semi standard non polar33892256
Prostaglandin D3,4TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3667.8Semi standard non polar33892256
Prostaglandin D3,4TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3438.2Standard non polar33892256
Prostaglandin D3,4TBDMS,isomer #1CC/C=C\C[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3150.6Standard polar33892256
Prostaglandin D3,4TBDMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3689.0Semi standard non polar33892256
Prostaglandin D3,4TBDMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3214.6Standard non polar33892256
Prostaglandin D3,4TBDMS,isomer #2CC/C=C\C[C@@H](/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3155.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin D3 GC-MS (Non-derivatized) - 70eV, Positivesplash10-05po-8395000000-44ba79a27b1cb029e0652017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin D3 GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-3620690000-cee4d57fecd9b15010652017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin D3 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 D3 10V, Positive-QTOFsplash10-00lr-0019000000-556c5941c1bd947aa13d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 20V, Positive-QTOFsplash10-0159-3096000000-7308f804ecfd913b19842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 40V, Positive-QTOFsplash10-014r-9310000000-135a6bbfabaf1b739b8a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 10V, Negative-QTOFsplash10-000t-0009000000-50f3213aa3eff0d0faf72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 20V, Negative-QTOFsplash10-001j-2149000000-89d63bd18af619a97e662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 40V, Negative-QTOFsplash10-0a4i-9531000000-1f37f093b3d2f8ec45af2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 10V, Negative-QTOFsplash10-000t-0009000000-669e3ea846c980353beb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 20V, Negative-QTOFsplash10-06rt-0059000000-3be047d22831afb5d0f02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 40V, Negative-QTOFsplash10-052p-9441000000-6a5fd85e6df4f33930ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 10V, Positive-QTOFsplash10-014i-0019000000-928cd476df97ec2d1eb42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 20V, Positive-QTOFsplash10-014i-4194000000-7014986c36784cd7e0242021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin D3 40V, Positive-QTOFsplash10-05mo-9310000000-3fcdcc5aa45a25f6dab02021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000123 +/- 0.000015 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023097
KNApSAcK IDNot Available
Chemspider ID4445434
KEGG Compound IDC13802
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2560
PubChem Compound5282260
PDB IDNot Available
ChEBI ID34939
Food Biomarker OntologyNot Available
VMH IDHC02210
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tsikas D, Schwedhelm E, Suchy MT, Niemann J, Gutzki FM, Erpenbeck VJ, Hohlfeld JM, Surdacki A, Frolich JC: Divergence in urinary 8-iso-PGF(2alpha) (iPF(2alpha)-III, 15-F(2t)-IsoP) levels from gas chromatography-tandem mass spectrometry quantification after thin-layer chromatography and immunoaffinity column chromatography reveals heterogeneity of 8-iso-PGF(2alpha). Possible methodological, mechanistic and clinical implications. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Sep 5;794(2):237-55. [PubMed:12954376 ]
  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. [PubMed:16986207 ]
  3. Hemker DP, Aiken JW: Effects of prostaglandin D3 on nerve transmission in nictitating membrane of cats. Eur J Pharmacol. 1980 Oct 3;67(1):155-8. [PubMed:6252026 ]
  4. Hemker DP, Aiken JW: Effects of prostaglandins on autonomic function in vivo, with special emphasis on PGD2 and PGD3. Prog Lipid Res. 1981;20:511-4. [PubMed:6952267 ]
  5. Kulkarni PS, Srinivasan BD: Prostaglandins E3 and D3 lower intraocular pressure. Invest Ophthalmol Vis Sci. 1985 Aug;26(8):1178-82. [PubMed:4019112 ]
  6. Wendling MG, DuCharme DW: Cardiovascular effects of prostaglandin D3 and D2 in anesthetized dogs. Prostaglandins. 1981 Aug;22(2):235-43. [PubMed:6945633 ]