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Record Information
Version1.0
Creation Date2016-09-30 22:45:27 UTC
Update Date2020-05-20 23:10:00 UTC
BMDB IDBMDB0001403
Secondary Accession Numbers
  • BMDB01403
Metabolite Identification
Common NameProstaglandin D2
DescriptionProstaglandin D2, also known as prostaglandin D2 or Prostaglandin d2, 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 D2 is considered to be an eicosanoid lipid molecule. Prostaglandin D2 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Prostaglandin D2 exists in all living organisms, ranging from bacteria to humans. Prostaglandin D2 participates in a number of enzymatic reactions, within cattle. In particular, Prostaglandin D2 can be converted into prostaglandin D2 through its interaction with the enzyme prostaglandin D2 receptor. In addition, Prostaglandin D2 can be converted into prostaglandin D2; which is mediated by the enzyme prostaglandin D2 receptor. In cattle, prostaglandin D2 is involved in the metabolic pathway called the intracellular signalling through prostaglandin D2 receptor and prostaglandin D2 pathway.
Structure
Thumb
Synonyms
ValueSource
(5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoateChEBI
(5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoateChEBI
11-Dehydroprostaglandin F2-alphaChEBI
PGD2ChEBI
(5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoateGenerator
(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E,15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoateGenerator
(5Z,13E,15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoic acidGenerator
11-Dehydroprostaglandin F2-aGenerator
11-Dehydroprostaglandin F2-αGenerator
(5Z,13E)-(15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dienoateHMDB
(5Z,13E)-(15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidHMDB
(5Z,13E)-(15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoateHMDB
(5Z,13E)-(15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidHMDB
(5Z,13E,15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoateHMDB
(5Z,13E,15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acidHMDB
(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dien-1-OateHMDB
(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dien-1-Oic acidHMDB
(5Z,9-alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-OateHMDB
(5Z,9-alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oic acidHMDB
(5Z,9alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-OateHMDB
(5Z,9alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oic acidHMDB
11-Dehydroprostaglandin F2alphaHMDB
9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoateHMDB
9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoic acidHMDB
F2alpha, 11-DehydroprostaglandinHMDB
11 Dehydroprostaglandin F2alphaHMDB
11 Dehydroprostaglandin F2 alphaHMDB
D2, ProstaglandinHMDB
F2 alpha, 11-DehydroprostaglandinHMDB
alpha, 11-Dehydroprostaglandin F2HMDB
11-Dehydroprostaglandin F2 alphaHMDB
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid
Traditional Nameprostaglandin D2
CAS Registry Number41598-07-6
SMILES
[H][C@](O)(CCCCC)\C=C\[C@@]1([H])C(=O)C[C@]([H])(O)[C@]1([H])C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O5/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/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
InChI KeyBHMBVRSPMRCCGG-OUTUXVNYSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point56 - 57 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.12ALOGPS
logP3.23ChemAxon
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 Count12ChemAxon
Refractivity99.44 m³·mol⁻¹ChemAxon
Polarizability40.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-005i-4920000000-0865a8f516450183b07cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0040-4920000000-7b37e8b3ecc2583f0fdcView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005i-4920000000-0865a8f516450183b07cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0040-4920000000-7b37e8b3ecc2583f0fdcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004u-8295000000-f73b3416dd6c7bbb428bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0umi-9301550000-0fbea1d102dfc38f0246View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 20V, Negativesplash10-00yr-0494000000-005f78cb3131ac258d23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 25V, Negativesplash10-00dr-0592000000-3541be2f7c29b70b97a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 30V, Negativesplash10-00dr-0691000000-a08a3850e6fbf73fe539View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 35V, Negativesplash10-00dr-0690000000-395bf1624fb183650268View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 40V, Negativesplash10-0079-0980000000-a0d1eacded9a909d2d07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 45V, Negativesplash10-000i-0960000000-982ce65a71003d3086b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 50V, Negativesplash10-0079-0930000000-15446e0930a7e4e23effView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 55V, Negativesplash10-00di-0920000000-5f7db7776dd0364029d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 60V, Negativesplash10-00dj-0900000000-16cfbecd58e5a59ab631View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00yr-0494000000-65af63dd6c30ad10793dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0592000000-3541be2f7c29b70b97a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0691000000-a08a3850e6fbf73fe539View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0690000000-fef454d771f83be8e0b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0079-0980000000-a0d1eacded9a909d2d07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-000i-0960000000-982ce65a71003d3086b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0079-0930000000-15446e0930a7e4e23effView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0920000000-5f7db7776dd0364029d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dj-0900000000-88efef42e905aa15039fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00y0-0493000000-654476042b0ee0709cedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-c056c1df1ae03ef020cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2196000000-38a7e3f085222b728c06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06du-9310000000-70af19409d627a582c45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-81ee6b3c0a320262466fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kar-2159000000-9a9fde23b29db29913b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9520000000-d51eb51b9db8ff82e0d6View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Brain
  • Epidermis
  • Leukocyte
  • Liver
  • Neuron
  • Platelet
  • Smooth Muscle
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LeukocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Smooth MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001403
DrugBank IDDB02056
Phenol Explorer Compound IDNot Available
FooDB IDFDB022602
KNApSAcK IDNot Available
Chemspider ID395250
KEGG Compound IDC00696
BioCyc IDNot Available
BiGG ID35725
Wikipedia LinkProstaglandin_D2
METLIN ID6221
PubChem Compound448457
PDB IDNot Available
ChEBI ID15555
References
Synthesis ReferenceOgawa, Yuji; Nunomoto, Makoto; Shibasaki, Masakatsu. A novel synthesis of prostaglandin D2. Journal of Organic Chemistry (1986), 51(9), 1625-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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 G-protein coupled receptor protein signalin
Specific function:
Receptor for prostaglandin D2 (PGD2). The activity of this receptor is mainly mediated by G(s) proteins that stimulate adenylate cyclase, resulting in an elevation of intracellular cAMP. A mobilization of calcium is also observed, but without formation of inositol 1,4,5-trisphosphate (By similarity).
Gene Name:
PTGDR
Uniprot ID:
A5D7K8
Molecular weight:
40372.0