NP-MRD: Showing NP-Card for Prostaglandin E2 (NP0000938)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:40:12 UTC

NP-MRD ID

NP0000938

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Prostaglandin E2

Description

The naturally occurring prostaglandin E2 (PGE2) is known in medicine as dinoprostone, and it is the most common and most biologically active of the mammalian prostaglandins. It has important effects during labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 is also the prostaglandin that ultimately induces fever. PGE2 has been shown to increase vasodilation and cAMP production, enhance the effects of bradykinin and histamine, and induce uterine contractions and platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus, decreasing T-cell proliferation and lymphocyte migration, and activating the secretion of IL-1α and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation, and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC). PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype (PMID: 16978535 ). 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 and are 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

HMDB0001220
     RDKit          3D
Prostaglandin E2
 57 57  0  0  0  0  0  0  0  0999 V2000
    6.3710    1.9964   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0791    0.9317   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5598    0.4489    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915   -0.3107    1.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -0.1015    0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3974   -0.1652   -0.4032 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7484    0.6573   -1.3962 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585   -0.1427   -0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406   -0.6941   -1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3457   -0.7477   -1.3034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6767   -2.2405   -1.0665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0072   -2.5157   -1.2724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916   -2.3193    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0675   -1.1154    0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685   -1.0110    2.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.0827   -0.1213 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4193    0.3819   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720    1.0108    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0453    0.6631    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8694   -0.4833    0.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2761    0.0767    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1571    1.1288   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5000    1.6838   -0.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6125    2.5678   -1.5976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6512    1.2777   -0.0513 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0832    1.6783   -2.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5299    2.4795   -0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0502    2.8927   -1.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3125    0.0432   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1431    1.3345   -0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4525   -0.1576    1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6487    1.3710    1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -0.5148    2.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6605   -1.4278    0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3672   -0.8640    1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138    0.8657    1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5559   -1.2493   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6816    0.2503   -2.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055    0.3234    0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365   -1.1405   -2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648   -0.4122   -2.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0060   -2.8810   -1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2948   -3.1540   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721   -3.2585    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7040   -2.1838    0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4627    0.8091    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775   -0.4300   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2400    1.2074   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4275    1.8849    1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3622    1.2238    2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9942   -1.2152    1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5478   -0.9454    0.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8859   -0.7795    0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6913    0.5622    1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7638    0.5758   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4647    1.9212   -0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7432    0.2956    0.2300 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  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  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  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  6
 12 43  1  0
 13 44  1  0
 13 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


  Mrv1652305271900272D          

 25 25  0  0  0  0            999 V2000
10017.073510020.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.789810020.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.614610020.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.328810020.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.043010020.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.756810020.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.470710020.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.186510020.2947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10021.470710021.5325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10018.442810019.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.156810018.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.871810019.3790    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10020.585710018.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.299510019.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.013210018.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.727010019.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.442810018.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.871810020.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.608510019.2214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10017.935110017.5188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10017.056910019.4612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10016.388210018.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.643610018.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.470210018.1891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10017.725610018.9752    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 19  2  0  0  0  0
 24 20  1  6  0  0  0
 25 10  1  1  0  0  0
 21  1  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000938

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1

> <INCHI_KEY>
XEYBRNLFEZDVAW-ARSRFYASSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.99510239897604

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
3.2252701369999994

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.678908140463108

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.303359525644919

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263175986188916

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
99.43509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dinoprostone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001220
     RDKit          3D
Prostaglandin E2
 57 57  0  0  0  0  0  0  0  0999 V2000
    6.3710    1.9964   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0791    0.9317   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5598    0.4489    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915   -0.3107    1.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -0.1015    0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3974   -0.1652   -0.4032 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7484    0.6573   -1.3962 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585   -0.1427   -0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406   -0.6941   -1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3457   -0.7477   -1.3034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6767   -2.2405   -1.0665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0072   -2.5157   -1.2724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916   -2.3193    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0675   -1.1154    0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685   -1.0110    2.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.0827   -0.1213 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4193    0.3819   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720    1.0108    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0453    0.6631    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8694   -0.4833    0.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2761    0.0767    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1571    1.1288   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5000    1.6838   -0.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6125    2.5678   -1.5976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6512    1.2777   -0.0513 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0832    1.6783   -2.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5299    2.4795   -0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0502    2.8927   -1.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3125    0.0432   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1431    1.3345   -0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4525   -0.1576    1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6487    1.3710    1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -0.5148    2.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6605   -1.4278    0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3672   -0.8640    1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138    0.8657    1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5559   -1.2493   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6816    0.2503   -2.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055    0.3234    0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365   -1.1405   -2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648   -0.4122   -2.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0060   -2.8810   -1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2948   -3.1540   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721   -3.2585    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7040   -2.1838    0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4627    0.8091    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775   -0.4300   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2400    1.2074   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4275    1.8849    1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3622    1.2238    2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9942   -1.2152    1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5478   -0.9454    0.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8859   -0.7795    0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6913    0.5622    1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7638    0.5758   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4647    1.9212   -0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7432    0.2956    0.2300 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  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  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  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  6
 12 43  1  0
 13 44  1  0
 13 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    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8698.5378704.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8699.8748705.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8701.4148705.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8702.7478704.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8704.0808705.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8705.4138704.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8706.7458705.320   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8708.0818704.550   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8706.7458706.861   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8701.0938702.841   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8702.4268702.069   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8703.7618702.841   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8705.0938702.069   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8706.4268702.841   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8707.7588702.069   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8709.0908702.841   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8710.4278702.069   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8703.7618704.381   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    8695.8038702.547   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8700.1468699.368   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8698.5068702.994   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8697.2588702.087   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8697.7358700.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8699.2788700.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8699.7548702.087   0.000  0.00  0.00           C+0
CONECT    1    2   21                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   11   25                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   12                                                            
CONECT   19   22                                                            
CONECT   20   24                                                            
CONECT   21   22   25    1                                                  
CONECT   22   21   23   19                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   20                                                  
CONECT   25   21   24   10                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0001220
HETATM    1  C1  UNL     1       6.371   1.996  -1.168  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.079   0.932  -0.417  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.560   0.449   0.848  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.392  -0.311   1.158  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.984  -0.102   0.931  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.397  -0.165  -0.403  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.748   0.657  -1.396  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.858  -0.143  -0.304  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.141  -0.694  -1.263  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.346  -0.748  -1.303  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.677  -2.241  -1.067  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.007  -2.516  -1.272  1.00  0.00           O  
HETATM   13  C11 UNL     1      -0.392  -2.319   0.418  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.068  -1.115   0.942  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.568  -1.011   2.034  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.008  -0.083  -0.121  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.419   0.382  -0.496  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.972   1.011   0.715  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.045   0.663   1.388  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.869  -0.483   0.964  1.00  0.00           C  
HETATM   21  C18 UNL     1      -6.276   0.077   0.684  1.00  0.00           C  
HETATM   22  C19 UNL     1      -6.157   1.129  -0.423  1.00  0.00           C  
HETATM   23  C20 UNL     1      -7.500   1.684  -0.712  1.00  0.00           C  
HETATM   24  O4  UNL     1      -7.612   2.568  -1.598  1.00  0.00           O  
HETATM   25  O5  UNL     1      -8.651   1.278  -0.051  1.00  0.00           O  
HETATM   26  H1  UNL     1       6.083   1.678  -2.193  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.530   2.479  -0.599  1.00  0.00           H  
HETATM   28  H3  UNL     1       7.050   2.893  -1.375  1.00  0.00           H  
HETATM   29  H4  UNL     1       7.313   0.043  -1.095  1.00  0.00           H  
HETATM   30  H5  UNL     1       8.143   1.334  -0.249  1.00  0.00           H  
HETATM   31  H6  UNL     1       7.453  -0.158   1.331  1.00  0.00           H  
HETATM   32  H7  UNL     1       6.649   1.371   1.584  1.00  0.00           H  
HETATM   33  H8  UNL     1       5.479  -0.515   2.327  1.00  0.00           H  
HETATM   34  H9  UNL     1       5.661  -1.428   0.854  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.367  -0.864   1.565  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.614   0.866   1.451  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.556  -1.249  -0.763  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.682   0.250  -2.283  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.405   0.323   0.556  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.736  -1.141  -2.083  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.765  -0.412  -2.267  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.006  -2.881  -1.661  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.295  -3.154  -0.569  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.772  -3.258   0.866  1.00  0.00           H  
HETATM   45  H20 UNL     1       0.704  -2.184   0.621  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.463   0.809   0.179  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.978  -0.430  -0.932  1.00  0.00           H  
HETATM   48  H23 UNL     1      -2.240   1.207  -1.232  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.428   1.885   1.120  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.362   1.224   2.297  1.00  0.00           H  
HETATM   51  H26 UNL     1      -4.994  -1.215   1.805  1.00  0.00           H  
HETATM   52  H27 UNL     1      -4.548  -0.945   0.043  1.00  0.00           H  
HETATM   53  H28 UNL     1      -6.886  -0.780   0.346  1.00  0.00           H  
HETATM   54  H29 UNL     1      -6.691   0.562   1.587  1.00  0.00           H  
HETATM   55  H30 UNL     1      -5.764   0.576  -1.324  1.00  0.00           H  
HETATM   56  H31 UNL     1      -5.465   1.921  -0.099  1.00  0.00           H  
HETATM   57  H32 UNL     1      -8.743   0.296   0.230  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   13   42
CONECT   12   43
CONECT   13   14   44   45
CONECT   14   15   15   16
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

HMDB0001220
     RDKit          3D
Prostaglandin E2
 57 57  0  0  0  0  0  0  0  0999 V2000
    6.3710    1.9964   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0791    0.9317   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5598    0.4489    0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915   -0.3107    1.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -0.1015    0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3974   -0.1652   -0.4032 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7484    0.6573   -1.3962 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585   -0.1427   -0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406   -0.6941   -1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3457   -0.7477   -1.3034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6767   -2.2405   -1.0665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0072   -2.5157   -1.2724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916   -2.3193    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0675   -1.1154    0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685   -1.0110    2.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.0827   -0.1213 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4193    0.3819   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720    1.0108    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0453    0.6631    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8694   -0.4833    0.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2761    0.0767    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1571    1.1288   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5000    1.6838   -0.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6125    2.5678   -1.5976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6512    1.2777   -0.0513 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0832    1.6783   -2.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5299    2.4795   -0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0502    2.8927   -1.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3125    0.0432   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1431    1.3345   -0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4525   -0.1576    1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6487    1.3710    1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -0.5148    2.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6605   -1.4278    0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3672   -0.8640    1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138    0.8657    1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5559   -1.2493   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6816    0.2503   -2.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055    0.3234    0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365   -1.1405   -2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648   -0.4122   -2.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0060   -2.8810   -1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2948   -3.1540   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721   -3.2585    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7040   -2.1838    0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4627    0.8091    0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775   -0.4300   -0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2400    1.2074   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4275    1.8849    1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3622    1.2238    2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9942   -1.2152    1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5478   -0.9454    0.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8859   -0.7795    0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6913    0.5622    1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7638    0.5758   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4647    1.9212   -0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7432    0.2956    0.2300 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  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  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  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  6
 12 43  1  0
 13 44  1  0
 13 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
(15S)-Prostaglandin e2	ChEBI
(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid	ChEBI
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate	ChEBI
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate	ChEBI
(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid	ChEBI
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid	ChEBI
Cervidil	ChEBI
Cerviprime	ChEBI
Cerviprost	ChEBI
Dinoproston	ChEBI
Dinoprostona	ChEBI
Dinoprostone	ChEBI
Dinoprostonum	ChEBI
Enzaprost e	ChEBI
Glandin-e2	ChEBI
Minprositin e2	ChEBI
Minprostin e2	ChEBI
PGE2	ChEBI
Prepidil	ChEBI
Propess	ChEBI
Prostarmon e	ChEBI
Prostenone	ChEBI
Prostin	ChEBI
Prostin e2	ChEBI
U 12062	ChEBI
U-12,062	ChEBI
U-12062	ChEBI
(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oate	Generator
(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid	Generator
(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oate	Generator
(5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oate	Generator
(5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid	Generator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate	Generator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid	Generator
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid	Generator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoate	Generator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acid	Generator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoic acid	Generator
(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoate	Generator
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoate	Generator
(-)-Prostaglandin e2	HMDB
(5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoate	HMDB
(5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoic acid	HMDB
5-trans-PGE2	HMDB
Glandin	HMDB
L-Prostaglandin e2	HMDB
Prostaglandin e	HMDB
Prostaglandin e2alpha	HMDB
e2, Prostaglandin	HMDB
Prepidil gel	HMDB
alpha, Prostaglandin e2	HMDB
e2 alpha, Prostaglandin	HMDB
e2alpha, Prostaglandin	HMDB
alpha, PGE2	HMDB
Prostenon	HMDB
Gel, prepidil	HMDB
PGE2 alpha	HMDB
PGE2alpha	HMDB
Prostaglandin e2 alpha	HMDB

Chemical Formula

C₂₀H₃₂O₅

Average Mass

352.4651 Da

Monoisotopic Mass

352.22497 Da

IUPAC Name

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

Traditional Name

dinoprostone

CAS Registry Number

363-24-6

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1

InChI Key

XEYBRNLFEZDVAW-ARSRFYASSA-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	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, 126 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	¹H NMR Spectrum (1D, 700 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, 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
Cervus nippon	LOTUS Database	35616633
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
Populus balsamifera	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633

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 E (CHEBI:15551 )
Prostaglandins (C00584 )
Prostaglandins (LMFA03010003 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	67 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.82	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	3.31	ALOGPS
logP	3.23	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.3	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	41 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

HMDB0001220

DrugBank ID

DB00917

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022498

KNApSAcK ID

Not Available

Chemspider ID

4444059

KEGG Compound ID

C00584

BioCyc ID

5Z13E-15S-1115-DIHYDROXY-9-OXOPROS

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15551

Good Scents ID

Not Available

References

General References

Catanzarite VA: Prophylactic intramyometrial carboprost tromethamine does not substantially reduce blood loss relative to intramyometrial oxytocin at routine cesarean section. Am J Perinatol. 1990 Jan;7(1):39-42. [PubMed:2403792 ]
Ilzecka J: Prostaglandin E2 is increased in amyotrophic lateral sclerosis patients. Acta Neurol Scand. 2003 Aug;108(2):125-9. [PubMed:12859290 ]
Waschbisch A, Fiebich BL, Akundi RS, Schmitz ML, Hoozemans JJ, Candelario-Jalil E, Virtainen N, Veerhuis R, Slawik H, Yrjanheikki J, Hull M: Interleukin-1 beta-induced expression of the prostaglandin E-receptor subtype EP3 in U373 astrocytoma cells depends on protein kinase C and nuclear factor-kappaB. J Neurochem. 2006 Feb;96(3):680-93. Epub 2006 Jan 9. [PubMed:16405508 ]
Seo JY, Kim EK, Lee SH, Park KC, Kim KH, Eun HC, Chung JH: Enhanced expression of cylooxygenase-2 by UV in aged human skin in vivo. Mech Ageing Dev. 2003 Aug-Sep;124(8-9):903-10. [PubMed:14499495 ]
Amato F, Rizzuto G, Nicoletti A, Senatore M, Roberti R: [Isolated peripheral arterial ischaemia and medullary neurostimulation: case report]. G Ital Nefrol. 2003 Mar-Apr;20(2):200-4. [PubMed:12746806 ]
Laitinen K, Arvola T, Moilanen E, Lampi AM, Ruuska T, Isolauri E: Characterization of breast milk received by infants with gross blood in stools. Biol Neonate. 2005;87(1):66-72. Epub 2004 Nov 9. [PubMed:15542928 ]
Yamada M, Ogata M, Kawai M, Mashima Y, Nishida T: Substance P in human tears. Cornea. 2003 Oct;22(7 Suppl):S48-54. [PubMed:14703707 ]
Choi SH, Langenbach R, Bosetti F: Cyclooxygenase-1 and -2 enzymes differentially regulate the brain upstream NF-kappa B pathway and downstream enzymes involved in prostaglandin biosynthesis. J Neurochem. 2006 Aug;98(3):801-11. Epub 2006 Jun 19. [PubMed:16787416 ]
Schmitz T, Dallot E, Leroy MJ, Breuiller-Fouche M, Ferre F, Cabrol D: EP(4) receptors mediate prostaglandin E(2)-stimulated glycosaminoglycan synthesis in human cervical fibroblasts in culture. Mol Hum Reprod. 2001 Apr;7(4):397-402. [PubMed:11279302 ]
Christidis N, Kopp S, Ernberg M: The effect on mechanical pain threshold over human muscles by oral administration of granisetron and diclofenac-sodium. Pain. 2005 Feb;113(3):265-70. [PubMed:15661432 ]
Konopka T, Rutkowska M, Hirnle L, Kopec W, Karolewska E: The secretion of prostaglandin E2 and interleukin 1-beta in women with periodontal diseases and preterm low-birth-weight. Bull Group Int Rech Sci Stomatol Odontol. 2003 Jan-Apr;45(1):18-28. [PubMed:14535055 ]
Iizuka H, Ohkawara A, Ishibashi Y: Human skin epidermal adenylate cyclase systems: defective beta-adrenergic responsiveness in the involved epidermis of Darier's disease. Curr Probl Dermatol. 1983;11:45-58. [PubMed:6317292 ]
Greaves MW: Does ultraviolet-evoked prostaglandin formation protect skin from actinic cancer? Lancet. 1978 Jan 28;1(8057):189. [PubMed:74611 ]
Harizi H, Gualde N: Pivotal role of PGE2 and IL-10 in the cross-regulation of dendritic cell-derived inflammatory mediators. Cell Mol Immunol. 2006 Aug;3(4):271-7. [PubMed:16978535 ]

Showing NP-Card for Prostaglandin E2 (NP0000938)

MOL for NP0000938 (Prostaglandin E2)

3D MOL for NP0000938 (Prostaglandin E2)

3D SDF for NP0000938 (Prostaglandin E2)

3D-SDF for NP0000938 (Prostaglandin E2)

PDB for NP0000938 (Prostaglandin E2)

3D PDB for NP0000938 (Prostaglandin E2)

SMILES for NP0000938 (Prostaglandin E2)

INCHI for NP0000938 (Prostaglandin E2)

Structure for NP0000938 (Prostaglandin E2)

3D Structure for NP0000938 (Prostaglandin E2)