NP-MRD: Showing NP-Card for Prostaglandin D2 (NP0000634)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-06-29 00:47:03 UTC

NP-MRD ID

NP0000634

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Prostaglandin D2

Description

Prostaglandin D2 (or PGD2) is a prostaglandin that is actively produced in various organs such as the brain, spleen, thymus, bone marrow, uterus, ovary, oviduct, testis, prostate and epididymis, and is involved in many physiological events. PGD2 binds to the prostaglandin D2 receptor (PTGDR) which is a G-protein-coupled receptor. Its activity is mainly mediated by G-S proteins that stimulate adenylate cyclase resulting in an elevation of intracellular cAMP and Ca2+. PGD2 promotes sleep; regulates body temperature, olfactory function, hormone release, and nociception in the central nervous system; prevents platelet aggregation; and induces vasodilation and bronchoconstriction. PGD2 is also released from mast cells as an allergic and inflammatory mediator. Prostaglandin H2 is an unstable intermediate formed from PGG2 by the action of cyclooxygenase (COX) in the arachidonate cascade. In mammalian systems, it is efficiently converted into more stable arachidonate metabolites, such as PGD2, PGE2, PGF2a by the action of three groups of enzymes, PGD synthases (PGDS), PGE synthases and PGF synthases, respectively. PGDS catalyzes the isomerization of PGH2 to PGD2. Two types of PGD2 synthase are known. Lipocalin-type PGD synthase is present in cerebrospinal fluid, seminal plasma and may play an important role in male reproduction. Another PGD synthase, hematopoietic PGD synthase is present in the spleen, fallopian tube, endometrial gland cells, extravillous trophoblasts and villous trophoblasts, and perhaps plays an important role in female reproduction. Recent studies demonstrate that PGD2 is probably involved in multiple aspects of inflammation through its dual receptor systems, DP and CRTH2. (PMID: 12148545 )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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

PG2
  Mrv1652305271900272D          

 29 29  0  0  0  0            999 V2000
   -3.5770   -0.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7923   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208    0.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8362    0.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2231    0.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385    0.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670    1.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5177    1.5143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7726    2.2989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5976    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525    1.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    1.0293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1851    0.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4706   -0.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4706   -1.0332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1851   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -1.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -1.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0430   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1901   -0.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2877    2.9663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6372    1.2593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2438   -1.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1048    1.9272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1959    2.2075    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    0.7642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -0.7412    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  8 26  1  6  0  0  0
  9 10  1  0  0  0  0
  9 23  1  1  0  0  0
  9 27  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 24  2  0  0  0  0
 12 13  1  6  0  0  0
 12 28  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  1  0  0  0
 15 29  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END

HMDB0001403
     RDKit          3D
Prostaglandin D2
 57 57  0  0  0  0  0  0  0  0999 V2000
    8.2171    1.8590    0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9489    1.0768    0.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8837   -0.0486   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6471   -0.9026    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3843   -0.1206   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1898   -1.0192    0.1523 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2307   -2.0519   -0.8096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9246   -0.2425    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -0.6940    0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4845    0.0110    0.5074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3664    1.0738   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1342    2.2353   -0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    0.4448   -1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509   -0.9973   -1.5375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5090   -1.7171   -2.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089   -0.9037   -0.1984 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8299   -0.1319   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8519   -0.9689   -0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577   -1.3636   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3094   -1.0300    1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6455   -0.2600    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4708    0.9937    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7082    1.7780    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7693    1.4175    0.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7117    2.9515   -0.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9798    1.1871    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0399    2.7495    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6487    2.2445    1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0243    0.7168    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1061    1.7988    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8910    0.4105   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8045   -0.6539    0.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6633   -1.6938   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157   -1.3907    1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875    0.3147   -1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882    0.7056    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -1.5138    1.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487   -1.6825   -1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.6955   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574   -1.6330    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661    0.4005    1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    0.9581   -2.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346    0.5310   -2.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1541   -1.4514   -1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8872   -2.1893   -3.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164   -1.8596    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675    0.1786    0.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6677    0.7892   -0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980   -1.2879   -1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6459   -1.9961   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -0.3733    1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487   -1.9380    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3852   -0.9635    0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9840    0.0252    2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7155    1.6143    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1574    0.6706   -0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5516    3.2467   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 13 42  1  0
 13 43  1  0
 14 44  1  1
 15 45  1  0
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END

PG2
  Mrv1652305271900272D          

 29 29  0  0  0  0            999 V2000
   -3.5770   -0.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7923   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208    0.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8362    0.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2231    0.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385    0.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670    1.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5177    1.5143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7726    2.2989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5976    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525    1.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    1.0293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1851    0.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4706   -0.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4706   -1.0332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1851   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -1.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -1.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0430   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1901   -0.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2877    2.9663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6372    1.2593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2438   -1.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1048    1.9272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1959    2.2075    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    0.7642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -0.7412    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  8 26  1  6  0  0  0
  9 10  1  0  0  0  0
  9 23  1  1  0  0  0
  9 27  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 24  2  0  0  0  0
 12 13  1  6  0  0  0
 12 28  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  1  0  0  0
 15 29  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000634

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
BHMBVRSPMRCCGG-OUTUXVNYSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.78026836323468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
3.2252701369999994

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.982935976351872

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.404553499966841

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5973979110025343

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
99.43509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prostaglandin D2

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001403
     RDKit          3D
Prostaglandin D2
 57 57  0  0  0  0  0  0  0  0999 V2000
    8.2171    1.8590    0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9489    1.0768    0.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8837   -0.0486   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6471   -0.9026    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3843   -0.1206   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1898   -1.0192    0.1523 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2307   -2.0519   -0.8096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9246   -0.2425    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -0.6940    0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4845    0.0110    0.5074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3664    1.0738   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1342    2.2353   -0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    0.4448   -1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509   -0.9973   -1.5375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5090   -1.7171   -2.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089   -0.9037   -0.1984 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8299   -0.1319   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8519   -0.9689   -0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577   -1.3636   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3094   -1.0300    1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6455   -0.2600    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4708    0.9937    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7082    1.7780    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7693    1.4175    0.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7117    2.9515   -0.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9798    1.1871    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0399    2.7495    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6487    2.2445    1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0243    0.7168    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1061    1.7988    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8910    0.4105   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8045   -0.6539    0.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6633   -1.6938   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157   -1.3907    1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875    0.3147   -1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882    0.7056    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -1.5138    1.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487   -1.6825   -1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.6955   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574   -1.6330    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661    0.4005    1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    0.9581   -2.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346    0.5310   -2.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1541   -1.4514   -1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8872   -2.1893   -3.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164   -1.8596    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675    0.1786    0.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6677    0.7892   -0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980   -1.2879   -1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6459   -1.9961   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -0.3733    1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487   -1.9380    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3852   -0.9635    0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9840    0.0252    2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7155    1.6143    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1574    0.6706   -0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5516    3.2467   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 13 42  1  0
 13 43  1  0
 14 44  1  1
 15 45  1  0
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PG2                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -6.677  -1.059   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.212  -0.583   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.892   0.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.428   1.399   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.283   0.368   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.819   0.844   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.498   2.351   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.966   2.827   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.442   4.291   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.982   4.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.458   2.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.212   1.921   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.212   0.381   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.878  -0.389   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.878  -1.929   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.212  -2.699   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.546  -1.929   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.879  -2.699   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.213  -1.929   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.547  -2.699   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.997  -2.566   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -7.822  -0.029   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.537   5.537   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.923   2.351   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.455  -2.699   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       0.196   3.597   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.366   4.121   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.241   1.427   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.822  -1.384   0.000  0.00  0.00           H+0
CONECT    1    2   21   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12   26                                             
CONECT    9    8   10   23   27                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12    8   11   13   28                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25   29                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25   15                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28   12                                                            
CONECT   29   15                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

COMPND    HMDB0001403
HETATM    1  C1  UNL     1       8.217   1.859   0.668  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.949   1.077   0.939  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.884  -0.049  -0.050  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.647  -0.903   0.130  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.384  -0.121  -0.037  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.190  -1.019   0.152  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.231  -2.052  -0.810  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.925  -0.242   0.031  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.802  -0.694   0.582  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.485   0.011   0.507  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.366   1.074  -0.559  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.134   2.235  -0.286  1.00  0.00           O  
HETATM   13  C11 UNL     1      -0.577   0.445  -1.893  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.851  -0.997  -1.537  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.509  -1.717  -2.491  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.509  -0.904  -0.198  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.830  -0.132  -0.218  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.852  -0.969  -0.879  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.958  -1.364  -0.274  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.309  -1.030   1.104  1.00  0.00           C  
HETATM   21  C18 UNL     1      -6.645  -0.260   1.043  1.00  0.00           C  
HETATM   22  C19 UNL     1      -6.471   0.994   0.213  1.00  0.00           C  
HETATM   23  C20 UNL     1      -7.708   1.778   0.112  1.00  0.00           C  
HETATM   24  O4  UNL     1      -8.769   1.417   0.665  1.00  0.00           O  
HETATM   25  O5  UNL     1      -7.712   2.951  -0.613  1.00  0.00           O  
HETATM   26  H1  UNL     1       8.980   1.187   0.242  1.00  0.00           H  
HETATM   27  H2  UNL     1       8.040   2.750   0.048  1.00  0.00           H  
HETATM   28  H3  UNL     1       8.649   2.244   1.635  1.00  0.00           H  
HETATM   29  H4  UNL     1       7.024   0.717   1.990  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.106   1.799   0.805  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.891   0.410  -1.067  1.00  0.00           H  
HETATM   32  H7  UNL     1       7.805  -0.654   0.058  1.00  0.00           H  
HETATM   33  H8  UNL     1       5.663  -1.694  -0.647  1.00  0.00           H  
HETATM   34  H9  UNL     1       5.716  -1.391   1.130  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.387   0.315  -1.056  1.00  0.00           H  
HETATM   36  H11 UNL     1       4.288   0.706   0.695  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.208  -1.514   1.128  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.149  -1.683  -1.729  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.920   0.695  -0.511  1.00  0.00           H  
HETATM   40  H15 UNL     1       0.857  -1.633   1.111  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.866   0.400   1.447  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.384   0.958  -2.410  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.335   0.531  -2.530  1.00  0.00           H  
HETATM   44  H19 UNL     1       0.154  -1.451  -1.355  1.00  0.00           H  
HETATM   45  H20 UNL     1      -0.887  -2.189  -3.105  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.616  -1.860   0.332  1.00  0.00           H  
HETATM   47  H22 UNL     1      -3.067   0.179   0.785  1.00  0.00           H  
HETATM   48  H23 UNL     1      -2.668   0.789  -0.845  1.00  0.00           H  
HETATM   49  H24 UNL     1      -3.698  -1.288  -1.945  1.00  0.00           H  
HETATM   50  H25 UNL     1      -5.646  -1.996  -0.898  1.00  0.00           H  
HETATM   51  H26 UNL     1      -4.639  -0.373   1.659  1.00  0.00           H  
HETATM   52  H27 UNL     1      -5.449  -1.938   1.748  1.00  0.00           H  
HETATM   53  H28 UNL     1      -7.385  -0.964   0.609  1.00  0.00           H  
HETATM   54  H29 UNL     1      -6.984   0.025   2.056  1.00  0.00           H  
HETATM   55  H30 UNL     1      -5.715   1.614   0.724  1.00  0.00           H  
HETATM   56  H31 UNL     1      -6.157   0.671  -0.802  1.00  0.00           H  
HETATM   57  H32 UNL     1      -8.552   3.247  -1.077  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9    9   39
CONECT    9   10   40
CONECT   10   11   16   41
CONECT   11   12   12   13
CONECT   13   14   42   43
CONECT   14   15   16   44
CONECT   15   45
CONECT   16   17   46
CONECT   17   18   47   48
CONECT   18   19   19   49
CONECT   19   20   50
CONECT   20   21   51   52
CONECT   21   22   53   54
CONECT   22   23   55   56
CONECT   23   24   24   25
CONECT   25   57
END

HMDB0001403
     RDKit          3D
Prostaglandin D2
 57 57  0  0  0  0  0  0  0  0999 V2000
    8.2171    1.8590    0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9489    1.0768    0.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8837   -0.0486   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6471   -0.9026    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3843   -0.1206   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1898   -1.0192    0.1523 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2307   -2.0519   -0.8096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9246   -0.2425    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -0.6940    0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4845    0.0110    0.5074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3664    1.0738   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1342    2.2353   -0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    0.4448   -1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509   -0.9973   -1.5375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5090   -1.7171   -2.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089   -0.9037   -0.1984 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8299   -0.1319   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8519   -0.9689   -0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577   -1.3636   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3094   -1.0300    1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6455   -0.2600    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4708    0.9937    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7082    1.7780    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7693    1.4175    0.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7117    2.9515   -0.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9798    1.1871    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0399    2.7495    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6487    2.2445    1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0243    0.7168    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1061    1.7988    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8910    0.4105   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8045   -0.6539    0.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6633   -1.6938   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157   -1.3907    1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875    0.3147   -1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882    0.7056    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -1.5138    1.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487   -1.6825   -1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.6955   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574   -1.6330    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661    0.4005    1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    0.9581   -2.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346    0.5310   -2.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1541   -1.4514   -1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8872   -2.1893   -3.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164   -1.8596    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675    0.1786    0.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6677    0.7892   -0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980   -1.2879   -1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6459   -1.9961   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -0.3733    1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487   -1.9380    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3852   -0.9635    0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9840    0.0252    2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7155    1.6143    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1574    0.6706   -0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5516    3.2467   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 13 42  1  0
 13 43  1  0
 14 44  1  1
 15 45  1  0
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate	ChEBI
(5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate	ChEBI
11-Dehydroprostaglandin F2-alpha	ChEBI
PGD2	ChEBI
(5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoic acid	Generator
(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoate	Generator
(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid	Generator
(5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid	Generator
(5Z,13E,15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoate	Generator
(5Z,13E,15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoic acid	Generator
11-Dehydroprostaglandin F2-a	Generator
11-Dehydroprostaglandin F2-α	Generator
(5Z,13E)-(15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid	HMDB
(5Z,13E)-(15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid	HMDB
(5Z,13E,15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate	HMDB
(5Z,13E,15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid	HMDB
(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dien-1-Oate	HMDB
(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dien-1-Oic acid	HMDB
(5Z,9-alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oate	HMDB
(5Z,9-alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oic acid	HMDB
(5Z,9alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oate	HMDB
(5Z,9alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oic acid	HMDB
11-Dehydroprostaglandin F2alpha	HMDB
9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoate	HMDB
9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoic acid	HMDB
F2alpha, 11-Dehydroprostaglandin	HMDB
11 Dehydroprostaglandin F2alpha	HMDB
11 Dehydroprostaglandin F2 alpha	HMDB
D2, Prostaglandin	HMDB
F2 alpha, 11-Dehydroprostaglandin	HMDB
alpha, 11-Dehydroprostaglandin F2	HMDB
11-Dehydroprostaglandin F2 alpha	HMDB

Chemical Formula

C₂₀H₃₂O₅

Average Mass

352.4651 Da

Monoisotopic Mass

352.22497 Da

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 Name

prostaglandin D2

CAS Registry Number

41598-07-6

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 Key

BHMBVRSPMRCCGG-OUTUXVNYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Gersemia fruticosa	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Larix sibirica	LOTUS Database	35616633
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins 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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins D (CHEBI:15555 )
Prostaglandins (C00696 )
Prostaglandins (LMFA03010004 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	56 - 57 °C	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	0.086 g/L	ALOGPS
logP	3.12	ALOGPS
logP	3.23	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	99.44 m³·mol⁻¹	ChemAxon
Polarizability	40.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001403

DrugBank ID

DB02056

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022602

KNApSAcK ID

Not Available

Chemspider ID

395250

KEGG Compound ID

C00696

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15555

Good Scents ID

Not Available

References

General References

O'Sullivan S, Dahlen B, Dahlen SE, Kumlin M: Increased urinary excretion of the prostaglandin D2 metabolite 9 alpha, 11 beta-prostaglandin F2 after aspirin challenge supports mast cell activation in aspirin-induced airway obstruction. J Allergy Clin Immunol. 1996 Aug;98(2):421-32. [PubMed:8757220 ]
Parsons WG 3rd, Roberts LJ 2nd: Transformation of prostaglandin D2 to isomeric prostaglandin F2 compounds by human eosinophils: a potential mast cell-eosinophil interaction. Adv Prostaglandin Thromboxane Leukot Res. 1989;19:499-502. [PubMed:2526527 ]
Parsons WG 3rd, Roberts LJ 2nd: Transformation of prostaglandin D2 to isomeric prostaglandin F2 compounds by human eosinophils. A potential mast cell-eosinophil interaction. J Immunol. 1988 Oct 1;141(7):2413-9. [PubMed:3139758 ]
Cooper B: Diminished platelet adenylate cyclase activation by prostaglandin D2 in acute thrombosis. Blood. 1979 Sep;54(3):684-93. [PubMed:380688 ]
Bushfield M, McNicol A, MacIntyre DE: Inhibition of platelet-activating-factor-induced human platelet activation by prostaglandin D2. Differential sensitivity of platelet transduction processes and functional responses to inhibition by cyclic AMP. Biochem J. 1985 Nov 15;232(1):267-71. [PubMed:3002327 ]
Awad JA, Morrow JD, Roberts LJ 2nd: Detection of the major urinary metabolite of prostaglandin D2 in the circulation: demonstration of elevated levels in patients with disorders of systemic mast cell activation. J Allergy Clin Immunol. 1994 May;93(5):817-24. [PubMed:8182221 ]
Wolfe LS, Rostworowski K, Pellerin L, Sherwin A: Metabolism of prostaglandin D2 by human cerebral cortex into 9 alpha, 11 beta-prostaglandin F2 by an active NADPH-dependent 11-ketoreductase. J Neurochem. 1989 Jul;53(1):64-70. [PubMed:2723663 ]
Cutler LS, Christian CP, Feinstein MB: Cytochemical localization of adenylate cyclase in the dense tubule system of human blood platelets stimulated by forskolin, prostacyclin and prostaglandin D2. Biochim Biophys Acta. 1985 Jun 30;845(3):403-10. [PubMed:3890960 ]
Murray JJ, Tonnel AB, Brash AR, Roberts LJ 2nd, Gosset P, Workman R, Capron A, Oates JA: Release of prostaglandin D2 into human airways during acute antigen challenge. N Engl J Med. 1986 Sep 25;315(13):800-4. [PubMed:3462506 ]
Liston TE, Roberts LJ 2nd: Transformation of prostaglandin D2 to 9 alpha, 11 beta-(15S)-trihydroxyprosta-(5Z,13E)-dien-1-oic acid (9 alpha, 11 beta-prostaglandin F2): a unique biologically active prostaglandin produced enzymatically in vivo in humans. Proc Natl Acad Sci U S A. 1985 Sep;82(18):6030-4. [PubMed:3862115 ]
Haberl C, Hultner L, Flugel A, Falk M, Geuenich S, Wilmanns W, Denzlinger C: Release of prostaglandin D2 by murine mast cells: importance of metabolite formation for antiproliferative activity. Mediators Inflamm. 1998;7(2):79-84. [PubMed:9836493 ]
Bate C, Kempster S, Williams A: Prostaglandin D2 mediates neuronal damage by amyloid-beta or prions which activates microglial cells. Neuropharmacology. 2006 Feb;50(2):229-37. Epub 2005 Nov 11. [PubMed:16289250 ]
Nishizawa EE, Miller WL, Gorman RR, Bundy GL, Svensson J, Hamberg M: Prostaglandin d2 as a potential antithrombotic agent. Prostaglandins. 1975 Jan;9(1):109-21. [PubMed:806102 ]
Fuller RW, Dixon CM, Dollery CT, Barnes PJ: Prostaglandin D2 potentiates airway responsiveness to histamine and methacholine. Am Rev Respir Dis. 1986 Feb;133(2):252-4. [PubMed:3511806 ]
Lewis RA, Soter NA, Diamond PT, Austen KF, Oates JA, Roberts LJ 2nd: Prostaglandin D2 generation after activation of rat and human mast cells with anti-IgE. J Immunol. 1982 Oct;129(4):1627-31. [PubMed:6809826 ]
Gresele P, Deckmyn H, Huybrechts E, Vermylen J: Serum albumin enhances the impairment of platelet aggregation with thromboxane synthase inhibition by increasing the formation of prostaglandin D2. Biochem Pharmacol. 1984 Jul 1;33(13):2083-8. [PubMed:6430299 ]
VanderEnde DS, Morrow JD: Release of markedly increased quantities of prostaglandin D2 from the skin in vivo in humans after the application of cinnamic aldehyde. J Am Acad Dermatol. 2001 Jul;45(1):62-7. [PubMed:11423836 ]
Downard CD, Roberts LJ 2nd, Morrow JD: Topical benzoic acid induces the increased biosynthesis of prostaglandin D2 in human skin in vivo. Clin Pharmacol Ther. 1995 Apr;57(4):441-5. [PubMed:7712673 ]
Morrow JD, Minton TA, Awad JA, Roberts LJ: Release of markedly increased quantities of prostaglandin D2 from the skin in vivo in humans following the application of sorbic acid. Arch Dermatol. 1994 Nov;130(11):1408-12. [PubMed:7979442 ]
Morrow JD, Awad JA, Oates JA, Roberts LJ 2nd: Identification of skin as a major site of prostaglandin D2 release following oral administration of niacin in humans. J Invest Dermatol. 1992 May;98(5):812-5. [PubMed:1373750 ]
Saito S, Tsuda H, Michimata T: Prostaglandin D2 and reproduction. Am J Reprod Immunol. 2002 May;47(5):295-302. [PubMed:12148545 ]

Showing NP-Card for Prostaglandin D2 (NP0000634)

MOL for NP0000634 (Prostaglandin D2)

3D MOL for NP0000634 (Prostaglandin D2)

3D SDF for NP0000634 (Prostaglandin D2)

3D-SDF for NP0000634 (Prostaglandin D2)

PDB for NP0000634 (Prostaglandin D2)

3D PDB for NP0000634 (Prostaglandin D2)

SMILES for NP0000634 (Prostaglandin D2)

INCHI for NP0000634 (Prostaglandin D2)

Structure for NP0000634 (Prostaglandin D2)

3D Structure for NP0000634 (Prostaglandin D2)