NP-MRD: Showing NP-Card for prostaglandin-H2 (NP0092281)

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Record Information

Version

2.0

Created at

2022-05-11 19:02:19 UTC

Updated at

2022-05-11 19:02:19 UTC

NP-MRD ID

NP0092281

Secondary Accession Numbers

None

Natural Product Identification

Common Name

prostaglandin-H2

Description

Prostaglandin H2, also known as PGH2 or endoperoxide H2, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, prostaglandin H2 is considered to be an eicosanoid lipid molecule. Prostaglandin H2 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Prostaglandin H2 exists in all living organisms, ranging from bacteria to humans. The conversion from Arachidonic acid to Prostaglandin H2 is a two step process. Within humans, prostaglandin H2 participates in a number of enzymatic reactions. In particular, prostaglandin H2 can be converted into prostaglandin I2; which is mediated by the enzyme prostacyclin synthase. In addition, prostaglandin H2 can be converted into prostaglandin D2; which is catalyzed by the enzyme prostaglandin-H2 D-isomerase. It is acted upon by:Prostacyclin synthase to create prostacyclinThromboxane-A synthase to create thromboxane A2 and 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) (see 12-Hydroxyheptadecatrienoic acid)Prostaglandin D2 synthase to create prostaglandin D2Prostaglandin E synthase to create prostaglandin E2It rearranges non-enzymatically to:A mixture of 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) and 12-(S)-hydroxy-5Z,8Z,10E-heptadecatrienoic acid (see 12-Hydroxyheptadecatrienoic acid)Use of prostaglandin H2:Regulating the constriction and dilation of blood vesselsstimulating platelet aggregationbinds to Thromboxane receptor on platelets' cell membranes to trigger platelet migration and adhesion to other platelets. In humans, prostaglandin H2 is involved in mefenamic acid action pathway. It is synthesized from arachidonic acid in a reaction catalyzed by a cyclooxygenase enzyme. Outside of the human body, Prostaglandin H2 has been detected, but not quantified in, several different foods, such as eggplants, arrowroots, mung beans, beans, and horseradish tree. This could make prostaglandin H2 a potential biomarker for the consumption of these foods. Prostaglandin H2 is a type of prostaglandin and a precursor for many other biologically significant molecules. Other peroxidases like Hydroquinone have been observed to reduce PGG2 to PGH2. PGH2 is unstable at room temperature, with a half life of 90-100 seconds, so it is often converted into a different prostaglandin. First, COX-1 catalyzes the addition of two free oxygens to form the 1,2-Dioxane bridge and a peroxide functional group to form Prostaglandin G2. prostaglandin-H2 is found in Mus musculus. prostaglandin-H2 was first documented in 1983 (PMID: 6310815). Second, COX-2 reduces the peroxide functional group to a Secondary alcohol, forming Prostaglandin H2 (PMID: 16627914) (PMID: 16134166) (PMID: 2517034) (PMID: 2449295).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
    7.5764   -2.0761   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3680   -1.5630   -1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2562   -1.1822   -0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -0.6868   -1.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -0.2781   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1617    0.8262    0.3742 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0832    0.4693    1.3164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9464    1.4676    0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7214    0.9766    0.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5017    1.6097    1.4148 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2471    2.9289    2.0771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2585    3.8307    0.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803    3.4246    0.4701 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2920    3.6214    1.6991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    3.3486    2.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5061    1.9292    0.2975 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8532    1.2739    0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042   -0.1814    0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4487   -1.0292   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174   -0.6618   -1.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7508   -1.0132   -1.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1645   -2.4180   -1.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8804   -3.1171    0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4904   -2.5696    1.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0520   -4.4983    0.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3347   -2.5744    0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1958   -2.7299   -1.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2736   -1.2329   -0.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950   -2.3411   -2.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6491   -0.6875   -2.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7368   -0.4401    0.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0256   -2.0974    0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -1.4585   -2.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5137    0.1751   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5899   -1.1852    0.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -0.0787   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512    1.6447   -0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6959   -0.2691    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587    2.4073    1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819    0.0388    0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    0.9330    2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6025    3.0290    2.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1814    4.8912    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4194    3.4734    0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1048    3.9407   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0668    1.6433   -0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5757    1.6784   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1782    1.7165    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1728   -0.6175    1.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665   -2.0869    0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017   -1.0844   -2.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    0.4479   -1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3254   -0.4075   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1996   -0.6446   -2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2977   -2.4318   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8482   -3.0256   -1.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2351   -5.0582   -0.6178 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
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 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 25  1  0
 23 24  2  0
 16 10  1  0
 15 11  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  1
 11 42  1  1
 12 43  1  0
 12 44  1  0
 13 45  1  6
 16 46  1  6
 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

  Mrv1652305171817272D          

 25 26  0  0  0  0            999 V2000
10011.108510013.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.823710013.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.647810013.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.361710013.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.075810013.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.789810013.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.503810013.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.217810013.8190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.503810012.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.108510012.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.823710012.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.536810012.1701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10013.251210012.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.965310012.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.679310012.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.393310012.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.107310012.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.536810011.3456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.953610012.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.680810013.8203    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10008.965410013.4073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.965410012.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.680810012.1683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10010.396210012.5812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10010.396210013.4073    0.0000 C   0  0  1  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  6  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
 20 25  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 21 22  1  0  0  0  0
 24 10  1  1  0  0  0
 25  1  1  6  0  0  0
 20 19  1  1  0  0  0
 23 19  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0092281

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

> <INCHI_KEY>
YIBNHAJFJUQSRA-YNNPMVKQSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.904322068518134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
3.956927585999999

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.680578207201535

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355294049144599

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6260430885771613

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
98.0419

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prostaglandin H2

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0    8687.4038692.462   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8688.7388691.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8690.2768691.691   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8691.6088692.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8692.9418691.691   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8694.2748692.462   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8695.6078691.691   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8696.9408692.462   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8695.6078690.154   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8687.4038689.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8688.7388690.154   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8690.0698689.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8691.4028690.154   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8692.7358689.384   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8694.0688690.154   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8695.4018689.384   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8696.7348690.154   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8690.0698687.845   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8685.2478690.923   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8684.7388692.465   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8683.4028691.694   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8683.4028690.152   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    8684.7388689.381   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8686.0738690.152   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8686.0738691.694   0.000  0.00  0.00           C+0
CONECT    1    2   25                                                       
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   24                                                       
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   20   23                                                       
CONECT   20   25   21   19                                                  
CONECT   21   20   22                                                       
CONECT   22   23   21                                                       
CONECT   23   24   22   19                                                  
CONECT   24   23   25   10                                                  
CONECT   25   20   24    1                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
(5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate	ChEBI
(5Z,13E,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate	ChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid	ChEBI
9,11-Epoxymethano-PGH2	ChEBI
PGH2	ChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoate	Kegg
(5Z,13E)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E,15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoate	Generator
(5Z,13E,15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E,15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoate	Generator
(5Z,13E,15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acid	Generator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid	Generator
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid	Generator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoate	Generator
(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoic acid	Generator
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoic acid	Generator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate	Generator
(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoic acid	Generator
(15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoate	HMDB
(15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoic acid	HMDB
(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoate	HMDB
(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoic acid	HMDB
(5Z,13E)-(15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	HMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	HMDB
(5Z,13E,15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate	HMDB
(5Z,13E,15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid	HMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dien-1-Oate	HMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dien-1-Oic acid	HMDB
15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoate	HMDB
15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoic acid	HMDB
9S,11R-Epidioxy-15S-hydroxy-5Z,13E-prostadienoate	HMDB
9S,11R-Epidioxy-15S-hydroxy-5Z,13E-prostadienoic acid	HMDB
Endoperoxide H2	HMDB
Prostaglandin R2	HMDB
Prostaglandin-H2	HMDB
PGH(2)	HMDB

Chemical Formula

C₂₀H₃₂O₅

Average Mass

352.4651 Da

Monoisotopic Mass

352.22497 Da

IUPAC Name

(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid

Traditional Name

prostaglandin H2

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

InChI Key

YIBNHAJFJUQSRA-YNNPMVKQSA-N

Experimental Spectra

Not Available

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	¹³C NMR Spectrum (1D, 50 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, 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	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, 800 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
1D NMR	¹H NMR Spectrum (1D, 900 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
Lagopus muta	FooDB	FooDB
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
Heterocyclic fatty acid
Hydroxy fatty acid
Ortho-dioxane
Fatty acid
Unsaturated fatty acid
Ortho-dioxolane
Dialkyl peroxide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

prostaglandins H (CHEBI:15554 )
oxylipin (CHEBI:15554 )
Prostaglandins (C00427 )
Prostaglandins (LMFA03010010 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.27	ALOGPS
logP	3.96	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	98.04 m³·mol⁻¹	ChemAxon
Polarizability	39.9 Å³	ChemAxon
Number of Rings	2	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

HMDB0001381

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031134

KNApSAcK ID

Not Available

Chemspider ID

392800

KEGG Compound ID

C00427

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15554

Good Scents ID

Not Available

References

General References

Onguru O, Casey MB, Kajita S, Nakamura N, Lloyd RV: Cyclooxygenase-2 and thromboxane synthase in non-endocrine and endocrine tumors: a review. Endocr Pathol. 2005 Winter;16(4):253-77. doi: 10.1385/ep:16:4:253. [PubMed:16627914 ]
Rybicki JP, Le Breton GC: Prostaglandin H2 directly lowers human platelet cAMP levels. Thromb Res. 1983 Jun 1;30(5):407-14. doi: 10.1016/0049-3848(83)90174-3. [PubMed:6310815 ]
Ulrich CM, Carlson CS, Sibert J, Poole EM, Yu JH, Wang LH, Sparks R, Potter JD, Bigler J: Thromboxane synthase (TBXAS1) polymorphisms in African-American and Caucasian populations: evidence for selective pressure. Hum Mutat. 2005 Oct;26(4):394-5. doi: 10.1002/humu.9371. [PubMed:16134166 ]
Hornberger W, Patscheke H: Transient concentrations and agonist potency of PGH2 in platelet activation by endogenous arachidonate. Eicosanoids. 1989;2(4):241-8. [PubMed:2517034 ]
Johnson GJ, Dunlop PC, Leis LA, From AH: Dihydropyridine agonist Bay K 8644 inhibits platelet activation by competitive antagonism of thromboxane A2-prostaglandin H2 receptor. Circ Res. 1988 Mar;62(3):494-505. doi: 10.1161/01.res.62.3.494. [PubMed:2449295 ]

Showing NP-Card for prostaglandin-H2 (NP0092281)

MOL for NP0092281 (prostaglandin-H2)

3D MOL for NP0092281 (prostaglandin-H2)

3D SDF for NP0092281 (prostaglandin-H2)

3D-SDF for NP0092281 (prostaglandin-H2)

PDB for NP0092281 (prostaglandin-H2)

3D PDB for NP0092281 (prostaglandin-H2)

SMILES for NP0092281 (prostaglandin-H2)

INCHI for NP0092281 (prostaglandin-H2)

Structure for NP0092281 (prostaglandin-H2)

3D Structure for NP0092281 (prostaglandin-H2)