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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:48 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002341

Secondary Accession Numbers

HMDB02341

Metabolite Identification

Common Name

8-iso-15-keto-PGE2

Description

8-iso-15-keto-PGE2 is an isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia reperfusion injury. For this reason, they are frequently used as markers of oxidative stress; however, many are now finding that these molecules are not inert, but in fact evoke powerful biological responses in an increasing array of cell types. In many cases, these biological effects can account in part for the various features and manifestations of those clinical conditions. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states (PMID: 14504139 ). Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in 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 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate 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-1alpha 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), and 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, 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

HMDB0002341
     RDKit          3D
8-iso-15-keto-PGE2
 55 55  0  0  0  0  0  0  0  0999 V2000
    5.0107    3.1969    2.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2615    2.8987    0.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276    2.0687    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9786    0.7667    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8749   -0.1031    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9827   -0.5102   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9586   -0.1357   -1.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698   -1.3394   -1.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981   -1.7731   -1.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684   -2.6093   -1.7590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2359   -3.9799   -1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148   -3.9545    0.2468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5952   -4.4203   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -3.2104   -2.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495   -3.2120   -2.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549   -2.0147   -1.8039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9053   -1.5127   -0.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2471   -0.9655   -0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311    0.2781   -0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5495    1.2337    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9425    1.7689    1.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2790    2.4545    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6708    3.0049    2.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7451    3.6215    2.8448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080    2.8134    3.7416 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7064    3.9536    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456    2.2392    2.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849    3.5600    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2317    2.3788    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3050    3.8442    0.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2558    2.0224   -1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1950    2.6750    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9348    0.2008    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180    1.0197    1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9055    0.4220    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448   -0.9970    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -1.6234   -2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8161   -1.4797   -0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -2.7840   -2.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887   -4.6237   -1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835   -4.5629    0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1633   -4.9313   -0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -5.1748   -2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5594   -1.2156   -2.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388   -2.4422    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633   -0.9326    0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0307   -1.6287   -0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5626    0.6652   -0.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    2.1449   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901    0.9835    0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943    2.4961    1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0631    0.9329    2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1064    1.7433    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701    3.2767    0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7177    3.4727    4.4979 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  2  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
  8 37  1  0
  9 38  1  0
 10 39  1  6
 11 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  6
 17 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 25 55  1  0
M  END


  Mrv0541 02231219292D          

 25 25  0  0  1  0            999 V2000
   16.4312  -15.1639    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0986  -14.6790    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7660  -15.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5112  -15.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6862  -15.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2011  -16.6160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5507  -14.9089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6466  -14.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0986  -13.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8132  -13.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8132  -12.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5276  -12.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0986  -12.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5276  -11.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2420  -10.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2420  -10.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9565   -9.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0335  -15.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2488  -15.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0773  -14.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2927  -14.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1211  -13.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3366  -13.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7235  -13.6343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1651  -12.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  5  1  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  1  8  1  1  0  0  0
  2  9  1  1  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18  8  1  0  0  0  0
 19 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  2  0  0  0  0
 25 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002341

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(=O)\C=C\[C@H]1C(O)CC(=O)[C@H]1C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17+,19?/m0/s1

> <INCHI_KEY>
YRTJDWROBKPZNV-LSAJIUQUSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.4492

> <EXACT_MASS>
350.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.98810330259776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
3.636608624999999

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.678218203398721

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.303359015207499

> <JCHEM_PKA_STRONGEST_BASIC>
-2.93524020776586

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
98.53769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-iso-15-keto-PGE2

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002341
     RDKit          3D
8-iso-15-keto-PGE2
 55 55  0  0  0  0  0  0  0  0999 V2000
    5.0107    3.1969    2.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2615    2.8987    0.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276    2.0687    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9786    0.7667    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8749   -0.1031    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9827   -0.5102   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9586   -0.1357   -1.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698   -1.3394   -1.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981   -1.7731   -1.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684   -2.6093   -1.7590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2359   -3.9799   -1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148   -3.9545    0.2468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5952   -4.4203   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -3.2104   -2.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495   -3.2120   -2.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549   -2.0147   -1.8039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9053   -1.5127   -0.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2471   -0.9655   -0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311    0.2781   -0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5495    1.2337    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9425    1.7689    1.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2790    2.4545    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6708    3.0049    2.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7451    3.6215    2.8448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080    2.8134    3.7416 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7064    3.9536    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456    2.2392    2.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849    3.5600    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2317    2.3788    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3050    3.8442    0.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2558    2.0224   -1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1950    2.6750    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9348    0.2008    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180    1.0197    1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9055    0.4220    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448   -0.9970    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -1.6234   -2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8161   -1.4797   -0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -2.7840   -2.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887   -4.6237   -1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835   -4.5629    0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1633   -4.9313   -0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -5.1748   -2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5594   -1.2156   -2.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388   -2.4422    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633   -0.9326    0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0307   -1.6287   -0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5626    0.6652   -0.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    2.1449   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901    0.9835    0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943    2.4961    1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0631    0.9329    2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1064    1.7433    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701    3.2767    0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7177    3.4727    4.4979 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  2  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
  8 37  1  0
  9 38  1  0
 10 39  1  6
 11 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  6
 17 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 25 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      30.672 -28.306   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.917 -27.401   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.163 -28.306   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.688 -29.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.148 -29.771   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      30.242 -31.017   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      34.628 -27.830   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      29.207 -27.830   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.917 -25.861   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.251 -25.091   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.251 -23.551   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.585 -22.781   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      31.917 -22.781   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      34.585 -21.241   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.918 -20.471   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      35.918 -18.931   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.252 -18.161   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.063 -28.861   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.598 -28.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.278 -26.878   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.813 -26.402   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.493 -24.896   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.028 -24.420   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.884 -25.451   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      22.708 -22.914   0.000  0.00  0.00           O+0
CONECT    1    2    5    8                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    3                                                            
CONECT    8    1   18                                                       
CONECT    9    2   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    8   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0002341
HETATM    1  C1  UNL     1       5.011   3.197   2.085  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.262   2.899   0.618  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.128   2.069   0.065  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.979   0.767   0.778  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.875  -0.103   0.281  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.983  -0.510  -1.128  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.959  -0.136  -1.808  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.970  -1.339  -1.731  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.898  -1.773  -1.049  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.068  -2.609  -1.759  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.236  -3.980  -1.137  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.115  -3.955   0.247  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.595  -4.420  -1.593  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.284  -3.210  -2.116  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.349  -3.212  -2.701  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.455  -2.015  -1.804  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.905  -1.513  -0.446  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.247  -0.966  -0.614  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.531   0.278  -0.361  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.549   1.234   0.107  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.942   1.769   1.457  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.279   2.455   1.337  1.00  0.00           C  
HETATM   23  C20 UNL     1      -4.671   3.005   2.679  1.00  0.00           C  
HETATM   24  O4  UNL     1      -5.745   3.622   2.845  1.00  0.00           O  
HETATM   25  O5  UNL     1      -3.808   2.813   3.742  1.00  0.00           O  
HETATM   26  H1  UNL     1       5.706   3.954   2.476  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.146   2.239   2.648  1.00  0.00           H  
HETATM   28  H3  UNL     1       3.985   3.560   2.236  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.232   2.379   0.492  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.305   3.844   0.031  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.256   2.022  -1.015  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.195   2.675   0.243  1.00  0.00           H  
HETATM   33  H8  UNL     1       4.935   0.201   0.859  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.718   1.020   1.847  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.906   0.422   0.497  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.845  -0.997   0.971  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.075  -1.623  -2.770  1.00  0.00           H  
HETATM   38  H13 UNL     1       0.816  -1.480  -0.026  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.232  -2.784  -2.812  1.00  0.00           H  
HETATM   40  H15 UNL     1       0.589  -4.624  -1.522  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.783  -4.563   0.696  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.163  -4.931  -0.794  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.428  -5.175  -2.414  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.559  -1.216  -2.550  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.039  -2.442   0.207  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.163  -0.933   0.075  1.00  0.00           H  
HETATM   47  H22 UNL     1      -4.031  -1.629  -0.963  1.00  0.00           H  
HETATM   48  H23 UNL     1      -4.563   0.665  -0.506  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.650   2.145  -0.587  1.00  0.00           H  
HETATM   50  H25 UNL     1      -1.490   0.984   0.027  1.00  0.00           H  
HETATM   51  H26 UNL     1      -2.194   2.496   1.805  1.00  0.00           H  
HETATM   52  H27 UNL     1      -3.063   0.933   2.207  1.00  0.00           H  
HETATM   53  H28 UNL     1      -5.106   1.743   1.075  1.00  0.00           H  
HETATM   54  H29 UNL     1      -4.270   3.277   0.601  1.00  0.00           H  
HETATM   55  H30 UNL     1      -3.718   3.473   4.498  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    7    8
CONECT    8    9    9   37
CONECT    9   10   38
CONECT   10   11   16   39
CONECT   11   12   13   40
CONECT   12   41
CONECT   13   14   42   43
CONECT   14   15   15   16
CONECT   16   17   44
CONECT   17   18   45   46
CONECT   18   19   19   47
CONECT   19   20   48
CONECT   20   21   49   50
CONECT   21   22   51   52
CONECT   22   23   53   54
CONECT   23   24   24   25
CONECT   25   55
END

HMDB0002341
     RDKit          3D
8-iso-15-keto-PGE2
 55 55  0  0  0  0  0  0  0  0999 V2000
    5.0107    3.1969    2.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2615    2.8987    0.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276    2.0687    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9786    0.7667    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8749   -0.1031    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9827   -0.5102   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9586   -0.1357   -1.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698   -1.3394   -1.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981   -1.7731   -1.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684   -2.6093   -1.7590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2359   -3.9799   -1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148   -3.9545    0.2468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5952   -4.4203   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -3.2104   -2.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495   -3.2120   -2.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549   -2.0147   -1.8039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9053   -1.5127   -0.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2471   -0.9655   -0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311    0.2781   -0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5495    1.2337    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9425    1.7689    1.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2790    2.4545    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6708    3.0049    2.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7451    3.6215    2.8448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080    2.8134    3.7416 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7064    3.9536    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456    2.2392    2.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849    3.5600    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2317    2.3788    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3050    3.8442    0.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2558    2.0224   -1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1950    2.6750    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9348    0.2008    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180    1.0197    1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9055    0.4220    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448   -0.9970    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -1.6234   -2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8161   -1.4797   -0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -2.7840   -2.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887   -4.6237   -1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835   -4.5629    0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1633   -4.9313   -0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -5.1748   -2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5594   -1.2156   -2.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388   -2.4422    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633   -0.9326    0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0307   -1.6287   -0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5626    0.6652   -0.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    2.1449   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901    0.9835    0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943    2.4961    1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0631    0.9329    2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1064    1.7433    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701    3.2767    0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7177    3.4727    4.4979 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  2  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
  8 37  1  0
  9 38  1  0
 10 39  1  6
 11 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  6
 17 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 25 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8b,11a,13E)-11-Hydroxy-9,15-dioxo-prosta-5,13-dien-1-Oate	HMDB
(5Z,8b,11a,13E)-11-Hydroxy-9,15-dioxo-prosta-5,13-dien-1-Oic acid	HMDB
8-Iso-15-keto-prostaglandine e2	HMDB
(5Z)-7-[(1S,2R)-3-Hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoate	HMDB

Chemical Formula

C₂₀H₃₀O₅

Average Molecular Weight

350.4492

Monoisotopic Molecular Weight

350.20932407

IUPAC Name

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

Traditional Name

8-iso-15-keto-PGE2

CAS Registry Number

914804-63-0

SMILES

CCCCCC(=O)\C=C\[C@H]1C(O)CC(=O)[C@H]1C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17+,19?/m0/s1

InChI Key

YRTJDWROBKPZNV-LSAJIUQUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

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
Unsaturated fatty acid
Fatty acid
Alpha,beta-unsaturated ketone
Cyclic alcohol
Acryloyl-group
Enone
Secondary alcohol
Cyclic ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0002341)
Membrane (HMDB: HMDB0002341)

Source

Exogenous

Exogenous (HMDB: HMDB0002341)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002341)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	3.27	ALOGPS
logP	3.64	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	98.54 m³·mol⁻¹	ChemAxon
Polarizability	39.99 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	201.581	30932474
DeepCCS	[M-H]-	198.669	30932474
DeepCCS	[M-2H]-	233.514	30932474
DeepCCS	[M+Na]+	208.742	30932474
AllCCS	[M+H]+	191.0	32859911
AllCCS	[M+H-H2O]+	188.3	32859911
AllCCS	[M+NH4]+	193.5	32859911
AllCCS	[M+Na]+	194.2	32859911
AllCCS	[M-H]-	190.6	32859911
AllCCS	[M+Na-2H]-	191.9	32859911
AllCCS	[M+HCOO]-	193.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.21 minutes	32390414
Predicted by Siyang on May 30, 2022	14.226 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2741.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	236.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	186.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	604.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	517.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	122.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1333.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	522.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1453.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	364.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	414.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	314.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	214.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-iso-15-keto-PGE2	CCCCCC(=O)\C=C\[C@H]1C(O)CC(=O)[C@H]1C\C=C/CCCC(O)=O	4453.4	Standard polar	33892256
8-iso-15-keto-PGE2	CCCCCC(=O)\C=C\[C@H]1C(O)CC(=O)[C@H]1C\C=C/CCCC(O)=O	2649.1	Standard non polar	33892256
8-iso-15-keto-PGE2	CCCCCC(=O)\C=C\[C@H]1C(O)CC(=O)[C@H]1C\C=C/CCCC(O)=O	2844.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-iso-15-keto-PGE2,1TMS,isomer #1	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O	2774.4	Semi standard non polar	33892256
8-iso-15-keto-PGE2,1TMS,isomer #2	CCCCCC(=O)/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2829.7	Semi standard non polar	33892256
8-iso-15-keto-PGE2,1TMS,isomer #3	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O	2853.8	Semi standard non polar	33892256
8-iso-15-keto-PGE2,1TMS,isomer #4	CCCCC=C(/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	3110.9	Semi standard non polar	33892256
8-iso-15-keto-PGE2,1TMS,isomer #5	CCCCCC(=O)/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O	2761.1	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TMS,isomer #1	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2704.6	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TMS,isomer #2	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C	2836.5	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TMS,isomer #3	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	3000.9	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TMS,isomer #4	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O	2755.4	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TMS,isomer #5	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O	2826.3	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TMS,isomer #6	CCCCC=C(/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3022.5	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TMS,isomer #7	CCCCCC(=O)/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2728.3	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TMS,isomer #8	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O)O[Si](C)(C)C	3090.5	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TMS,isomer #9	CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	3015.5	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #1	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C	2782.9	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #1	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C	2853.0	Standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #1	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C	2998.3	Standard polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2964.9	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2887.2	Standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3079.9	Standard polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #3	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2749.4	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #3	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2792.7	Standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #3	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	3062.3	Standard polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #4	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C	3054.9	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #4	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C	2844.5	Standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #4	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C	3320.9	Standard polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #5	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	3008.4	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #5	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2771.7	Standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #5	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	3339.4	Standard polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #6	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O)O[Si](C)(C)C	3043.4	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #6	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O)O[Si](C)(C)C	2882.3	Standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #6	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O)O[Si](C)(C)C	3381.7	Standard polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #7	CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2971.6	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #7	CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2818.2	Standard non polar	33892256
8-iso-15-keto-PGE2,3TMS,isomer #7	CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3462.7	Standard polar	33892256
8-iso-15-keto-PGE2,4TMS,isomer #1	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C	3012.2	Semi standard non polar	33892256
8-iso-15-keto-PGE2,4TMS,isomer #1	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C	2905.9	Standard non polar	33892256
8-iso-15-keto-PGE2,4TMS,isomer #1	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C	3016.4	Standard polar	33892256
8-iso-15-keto-PGE2,4TMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2984.1	Semi standard non polar	33892256
8-iso-15-keto-PGE2,4TMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2793.3	Standard non polar	33892256
8-iso-15-keto-PGE2,4TMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3070.5	Standard polar	33892256
8-iso-15-keto-PGE2,1TBDMS,isomer #1	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O	2997.2	Semi standard non polar	33892256
8-iso-15-keto-PGE2,1TBDMS,isomer #2	CCCCCC(=O)/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3089.1	Semi standard non polar	33892256
8-iso-15-keto-PGE2,1TBDMS,isomer #3	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O	3112.1	Semi standard non polar	33892256
8-iso-15-keto-PGE2,1TBDMS,isomer #4	CCCCC=C(/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3353.5	Semi standard non polar	33892256
8-iso-15-keto-PGE2,1TBDMS,isomer #5	CCCCCC(=O)/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O	3003.8	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #1	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3201.9	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #2	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C	3286.0	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #3	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3460.1	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #4	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O	3247.6	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #5	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O	3337.9	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #6	CCCCC=C(/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3518.8	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #7	CCCCCC(=O)/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3241.2	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #8	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O)O[Si](C)(C)C(C)(C)C	3569.7	Semi standard non polar	33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #9	CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3490.9	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #1	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C	3483.2	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #1	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C	3391.4	Standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #1	CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C	3189.6	Standard polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3664.7	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3434.1	Standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3253.6	Standard polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #3	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3454.4	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #3	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3257.0	Standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #3	CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3226.2	Standard polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #4	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3723.9	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #4	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3348.2	Standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #4	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3463.7	Standard polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #5	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3703.3	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #5	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3169.1	Standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #5	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3491.4	Standard polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #6	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O)O[Si](C)(C)C(C)(C)C	3761.8	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #6	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O)O[Si](C)(C)C(C)(C)C	3410.8	Standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #6	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O)O[Si](C)(C)C(C)(C)C	3502.5	Standard polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #7	CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3692.7	Semi standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #7	CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3240.7	Standard non polar	33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #7	CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3581.2	Standard polar	33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #1	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3896.0	Semi standard non polar	33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #1	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3543.8	Standard non polar	33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #1	CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3256.4	Standard polar	33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3881.9	Semi standard non polar	33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3315.9	Standard non polar	33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #2	CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3288.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-15-keto-PGE2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-052u-4493000000-0d0c2247610da9ad51de	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-15-keto-PGE2 GC-MS (2 TMS) - 70eV, Positive	splash10-002b-7318900000-e3deca635536990d3ff8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-15-keto-PGE2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-15-keto-PGE2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 10V, Positive-QTOF	splash10-00lr-0029000000-9303b63bd2ebcbb5c384	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 20V, Positive-QTOF	splash10-067i-2195000000-4191e15aa7f06f807e38	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 40V, Positive-QTOF	splash10-000i-9210000000-7c06db5bb5cf1359caab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 10V, Negative-QTOF	splash10-0002-0019000000-3ef3528ac5a012ba1cf7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 20V, Negative-QTOF	splash10-001j-3079000000-e1ebbca36295283f32e1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 40V, Negative-QTOF	splash10-0a4i-9452000000-aa26e5f3571b762113f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 10V, Negative-QTOF	splash10-001j-0019000000-319ec8417f062af25ae2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 20V, Negative-QTOF	splash10-008i-0094000000-ecf8159ba7722550f80a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 40V, Negative-QTOF	splash10-053u-9270000000-4f5b9ab71a4cd04afdc9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 10V, Positive-QTOF	splash10-0159-0019000000-e747c20277d6c7786fa3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 20V, Positive-QTOF	splash10-014i-6369000000-c74c0a7bb044927841f9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 40V, Positive-QTOF	splash10-00kf-9200000000-e6002eb037e36f06c242	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022970

KNApSAcK ID

Not Available

Chemspider ID

35013045

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477750

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Tazzeo T, Miller J, Janssen LJ: Vasoconstrictor responses, and underlying mechanisms, to isoprostanes in human and porcine bronchial arterial smooth muscle. Br J Pharmacol. 2003 Oct;140(4):759-63. Epub 2003 Sep 22. [PubMed:14504139 ]
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 metabocard for 8-iso-15-keto-PGE2 (HMDB0002341)

MOL for HMDB0002341 (8-iso-15-keto-PGE2)

3D MOL for HMDB0002341 (8-iso-15-keto-PGE2)

3D SDF for HMDB0002341 (8-iso-15-keto-PGE2)

3D-SDF for HMDB0002341 (8-iso-15-keto-PGE2)

PDB for HMDB0002341 (8-iso-15-keto-PGE2)

3D PDB for HMDB0002341 (8-iso-15-keto-PGE2)

SMILES for HMDB0002341 (8-iso-15-keto-PGE2)

INCHI for HMDB0002341 (8-iso-15-keto-PGE2)

Structure for HMDB0002341 (8-iso-15-keto-PGE2)

3D Structure for HMDB0002341 (8-iso-15-keto-PGE2)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra