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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-14 00:27:57 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004686

Secondary Accession Numbers

HMDB04686

Metabolite Identification

Common Name

8-Isoprostaglandin E1

Description

8-Isoprostaglandin E1 is an isoprostane. The isoprostanes embody a vast family of novel prostaglandin-like lipids that are produced by nonenzymatic peroxidation of arachidonic acid (AA) in response to free radicals and reactive oxygen species. Although free AA is required for the formation of prostaglandins by cyclooxygenases, the isoprostanes can be generated nonenzymatically from esterified AA in membrane phospholipids before being released by a phospholipase(s). Another dissimilarity is that isoprostanes feature side chains that are almost exclusively orientated cis relative to the cyclopentane ring and are therefore distinct from the prostaglandins, which always have side chains in the trans configuration. Nevertheless, isoprostanes are isomeric with prostaglandins and have been given the prefix D-, E-, and F{alpha}- to denote the prostane ring shared with PGD2, PGE2, and PGF2{alpha} respectively. An additional level of complexity is that peroxidation of AA can occur at one of any of four carbon atoms producing regioisomers, the so-called 5-, 12-, 8-, and 15-series isoprostanes, each consisting of eight racemic diastereomers. Thus, a total of 64 isomers can be generated for each of the D-, E-, and F{alpha}-ring isoprostanes. (PMID: 15528403 )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

HMDB0004686
     RDKit          3D
8-Isoprostaglandin E1
 59 59  0  0  0  0  0  0  0  0999 V2000
   -6.5086    0.8480    1.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4360    0.7662   -0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5667    1.7719   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1561    1.9042   -0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1801    0.8169   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4077   -0.3886    0.2969 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3932   -0.0288    1.6703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782   -1.3856    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2629   -1.2289   -0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -2.2107   -0.8019 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1941   -1.5083   -0.7248 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3300   -0.7066    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7307   -0.0694    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845    0.7616    1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3476    1.3862    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4007    0.3327    1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8093    0.8846    1.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0620    1.7270    0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1957    2.3012    0.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833    1.9526   -0.6830 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -0.6484   -1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2845    0.5113   -2.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -1.6020   -2.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1433   -2.6797   -2.2363 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4494   -3.9236   -2.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1337   -0.1166    1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8971    1.6761    1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5349    0.9713    1.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3606   -0.2650   -0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5129    1.0523   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1224    2.7724   -0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6884    1.5966   -1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0930    2.3475    0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402    2.7819   -0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1427    0.5773   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1157    1.1809   -0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3632   -0.8595    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308   -0.8184    2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -2.2856    0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -0.3458   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298   -3.0400   -0.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943   -2.2253   -0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2972   -1.3324    1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283    0.1496    0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4460   -0.9185    0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8422    0.5611   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703    0.1701    2.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    1.6207    1.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3467    2.0235    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5122    2.1119    2.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2685   -0.2405    0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3336   -0.3318    2.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0165    1.4163    2.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4845   -0.0047    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045    1.2127   -1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -1.1242   -3.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674   -2.0452   -3.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1936   -2.6820   -2.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.9368   -1.8606 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
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 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  1
 11 42  1  6
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 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
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 16 52  1  0
 17 53  1  0
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 20 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  6
 25 59  1  0
M  END


  Mrv0541 02231219582D          

 25 25  0  0  1  0            999 V2000
   23.4852  -19.5224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1356  -21.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0331  -16.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7746  -20.9658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2162  -19.6067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3656  -19.7774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.0331  -19.2925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.7005  -19.7774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.4456  -20.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5810  -19.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6206  -20.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9679  -20.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0331  -18.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1832  -19.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7475  -18.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5701  -20.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7475  -17.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.4620  -16.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7855  -20.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4620  -15.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1724  -20.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1766  -15.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1766  -14.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3877  -20.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8910  -14.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  2 11  2  0  0  0  0
 17  3  1  1  0  0  0
  4 24  1  0  0  0  0
  5 24  2  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  1  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  1  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004686

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1CCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16-,17+,19+/m0/s1

> <INCHI_KEY>
GMVPRGQOIOIIMI-JCPCGATGSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.51397882505392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
3.5871917936666664

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.680474481265463

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.353232088584439

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263175145935014

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
98.31849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iso-PGE1

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004686
     RDKit          3D
8-Isoprostaglandin E1
 59 59  0  0  0  0  0  0  0  0999 V2000
   -6.5086    0.8480    1.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4360    0.7662   -0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5667    1.7719   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1561    1.9042   -0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1801    0.8169   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4077   -0.3886    0.2969 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3932   -0.0288    1.6703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782   -1.3856    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2629   -1.2289   -0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -2.2107   -0.8019 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1941   -1.5083   -0.7248 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3300   -0.7066    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7307   -0.0694    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845    0.7616    1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3476    1.3862    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4007    0.3327    1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8093    0.8846    1.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0620    1.7270    0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1957    2.3012    0.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833    1.9526   -0.6830 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -0.6484   -1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2845    0.5113   -2.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -1.6020   -2.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1433   -2.6797   -2.2363 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4494   -3.9236   -2.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1337   -0.1166    1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8971    1.6761    1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5349    0.9713    1.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3606   -0.2650   -0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5129    1.0523   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1224    2.7724   -0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6884    1.5966   -1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0930    2.3475    0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402    2.7819   -0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1427    0.5773   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1157    1.1809   -0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3632   -0.8595    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308   -0.8184    2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -2.2856    0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -0.3458   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298   -3.0400   -0.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943   -2.2253   -0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2972   -1.3324    1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283    0.1496    0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4460   -0.9185    0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8422    0.5611   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703    0.1701    2.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    1.6207    1.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3467    2.0235    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5122    2.1119    2.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2685   -0.2405    0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3336   -0.3318    2.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0165    1.4163    2.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4845   -0.0047    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045    1.2127   -1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -1.1242   -3.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674   -2.0452   -3.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1936   -2.6820   -2.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.9368   -1.8606 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
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 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  1
 11 42  1  6
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 20 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  6
 25 59  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  O   UNK     0      43.839 -36.442   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      39.453 -39.628   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      41.128 -31.392   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      29.446 -39.136   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.270 -36.599   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      39.882 -36.918   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.128 -36.013   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      42.374 -36.918   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      41.898 -38.382   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.418 -36.442   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      40.358 -38.382   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.273 -37.472   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.128 -34.472   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.809 -36.997   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      42.462 -33.702   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.664 -38.027   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      42.462 -32.162   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      43.796 -31.392   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.200 -37.551   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      43.796 -29.852   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.055 -38.582   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      45.130 -29.082   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.130 -27.542   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.590 -38.106   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      46.463 -26.772   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   11                                                            
CONECT    3   17                                                            
CONECT    4   24                                                            
CONECT    5   24                                                            
CONECT    6    7   10   11                                                  
CONECT    7    6    8   13                                                  
CONECT    8    1    7    9                                                  
CONECT    9    8   11                                                       
CONECT   10    6   12                                                       
CONECT   11    2    6    9                                                  
CONECT   12   10   14                                                       
CONECT   13    7   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   19                                                       
CONECT   17    3   15   18                                                  
CONECT   18   17   20                                                       
CONECT   19   16   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   24                                                       
CONECT   22   20   23                                                       
CONECT   23   22   25                                                       
CONECT   24    4    5   21                                                  
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0004686
HETATM    1  C1  UNL     1      -6.509   0.848   1.447  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.436   0.766  -0.052  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.567   1.772  -0.696  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.156   1.904  -0.345  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.180   0.817  -0.517  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.408  -0.389   0.297  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.393  -0.029   1.670  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.278  -1.386   0.157  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.263  -1.229  -0.669  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.155  -2.211  -0.802  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.194  -1.508  -0.725  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.330  -0.707   0.539  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.731  -0.069   0.491  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.985   0.762   1.697  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.348   1.386   1.620  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.401   0.333   1.556  1.00  0.00           C  
HETATM   17  C16 UNL     1       6.809   0.885   1.510  1.00  0.00           C  
HETATM   18  C17 UNL     1       7.062   1.727   0.337  1.00  0.00           C  
HETATM   19  O2  UNL     1       8.196   2.301   0.254  1.00  0.00           O  
HETATM   20  O3  UNL     1       6.183   1.953  -0.683  1.00  0.00           O  
HETATM   21  C18 UNL     1       1.082  -0.648  -1.933  1.00  0.00           C  
HETATM   22  O4  UNL     1       1.284   0.511  -2.115  1.00  0.00           O  
HETATM   23  C19 UNL     1       0.619  -1.602  -2.999  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.143  -2.680  -2.236  1.00  0.00           C  
HETATM   25  O5  UNL     1       0.449  -3.924  -2.389  1.00  0.00           O  
HETATM   26  H1  UNL     1      -6.134  -0.117   1.899  1.00  0.00           H  
HETATM   27  H2  UNL     1      -5.897   1.676   1.860  1.00  0.00           H  
HETATM   28  H3  UNL     1      -7.535   0.971   1.835  1.00  0.00           H  
HETATM   29  H4  UNL     1      -6.361  -0.265  -0.419  1.00  0.00           H  
HETATM   30  H5  UNL     1      -7.513   1.052  -0.395  1.00  0.00           H  
HETATM   31  H6  UNL     1      -6.122   2.772  -0.583  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.688   1.597  -1.826  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.093   2.348   0.716  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.740   2.782  -0.972  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.143   0.577  -1.631  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.116   1.181  -0.298  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.363  -0.859   0.100  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.531  -0.818   2.231  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.284  -2.286   0.760  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.219  -0.346  -1.289  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.230  -3.040  -0.080  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.994  -2.225  -0.891  1.00  0.00           H  
HETATM   43  H18 UNL     1       1.297  -1.332   1.449  1.00  0.00           H  
HETATM   44  H19 UNL     1       0.628   0.150   0.557  1.00  0.00           H  
HETATM   45  H20 UNL     1       3.446  -0.919   0.397  1.00  0.00           H  
HETATM   46  H21 UNL     1       2.842   0.561  -0.408  1.00  0.00           H  
HETATM   47  H22 UNL     1       2.870   0.170   2.653  1.00  0.00           H  
HETATM   48  H23 UNL     1       2.252   1.621   1.739  1.00  0.00           H  
HETATM   49  H24 UNL     1       4.347   2.024   0.693  1.00  0.00           H  
HETATM   50  H25 UNL     1       4.512   2.112   2.450  1.00  0.00           H  
HETATM   51  H26 UNL     1       5.269  -0.240   0.594  1.00  0.00           H  
HETATM   52  H27 UNL     1       5.334  -0.332   2.437  1.00  0.00           H  
HETATM   53  H28 UNL     1       7.016   1.416   2.480  1.00  0.00           H  
HETATM   54  H29 UNL     1       7.484  -0.005   1.452  1.00  0.00           H  
HETATM   55  H30 UNL     1       5.805   1.213  -1.234  1.00  0.00           H  
HETATM   56  H31 UNL     1       0.039  -1.124  -3.783  1.00  0.00           H  
HETATM   57  H32 UNL     1       1.567  -2.045  -3.422  1.00  0.00           H  
HETATM   58  H33 UNL     1      -1.194  -2.682  -2.624  1.00  0.00           H  
HETATM   59  H34 UNL     1       1.275  -3.937  -1.861  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   24   41
CONECT   11   12   21   42
CONECT   12   13   43   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   49   50
CONECT   16   17   51   52
CONECT   17   18   53   54
CONECT   18   19   19   20
CONECT   20   55
CONECT   21   22   22   23
CONECT   23   24   56   57
CONECT   24   25   58
CONECT   25   59
END

HMDB0004686
     RDKit          3D
8-Isoprostaglandin E1
 59 59  0  0  0  0  0  0  0  0999 V2000
   -6.5086    0.8480    1.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4360    0.7662   -0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5667    1.7719   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1561    1.9042   -0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1801    0.8169   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4077   -0.3886    0.2969 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3932   -0.0288    1.6703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782   -1.3856    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2629   -1.2289   -0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -2.2107   -0.8019 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1941   -1.5083   -0.7248 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3300   -0.7066    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7307   -0.0694    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845    0.7616    1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3476    1.3862    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4007    0.3327    1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8093    0.8846    1.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0620    1.7270    0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1957    2.3012    0.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833    1.9526   -0.6830 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -0.6484   -1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2845    0.5113   -2.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -1.6020   -2.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1433   -2.6797   -2.2363 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4494   -3.9236   -2.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1337   -0.1166    1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8971    1.6761    1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5349    0.9713    1.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3606   -0.2650   -0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5129    1.0523   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1224    2.7724   -0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6884    1.5966   -1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0930    2.3475    0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402    2.7819   -0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1427    0.5773   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1157    1.1809   -0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3632   -0.8595    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308   -0.8184    2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -2.2856    0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -0.3458   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298   -3.0400   -0.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943   -2.2253   -0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2972   -1.3324    1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283    0.1496    0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4460   -0.9185    0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8422    0.5611   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703    0.1701    2.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    1.6207    1.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3467    2.0235    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5122    2.1119    2.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2685   -0.2405    0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3336   -0.3318    2.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0165    1.4163    2.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4845   -0.0047    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045    1.2127   -1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -1.1242   -3.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674   -2.0452   -3.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1936   -2.6820   -2.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.9368   -1.8606 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
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 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  1
 11 42  1  6
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 20 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  6
 25 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11a,15-(S)-Dihydroxy-9-oxo-13-trans-8-isoprostenoate	HMDB
11a,15-(S)-Dihydroxy-9-oxo-13-trans-8-isoprostenoic acid	HMDB
8-iso-PGE1	HMDB
Isoprostaglandin e1	HMDB, MeSH
Ovinonic acid	HMDB
iso-PGE1	MeSH, HMDB
Isoprostaglandin e1, (8beta,11alpha,12alpha,13E,15S)-isomer	MeSH, HMDB
Isoprostaglandin e1, (8beta,11beta,12alpha,13E,15R)-isomer	MeSH, HMDB
Isoprostaglandin e1, (8beta,11beta,12alpha,13E,15S)-isomer	MeSH, HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

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

Traditional Name

iso-PGE1

CAS Registry Number

21003-46-3

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1CCCCCCC(O)=O

InChI Identifier

InChI=1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16-,17+,19+/m0/s1

InChI Key

GMVPRGQOIOIIMI-JCPCGATGSA-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
Fatty alcohol
Hydroxy fatty acid
Cyclopentanol
Cyclic alcohol
Cyclic ketone
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Isoprostanes (LMFA03110002 )

Ontology

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	0.079 g/L	ALOGPS
logP	3.04	ALOGPS
logP	3.59	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.35	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	13	ChemAxon
Refractivity	98.32 m³·mol⁻¹	ChemAxon
Polarizability	41.51 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
DarkChem	[M+H]+	186.82	31661259
DarkChem	[M-H]-	188.638	31661259
DeepCCS	[M+H]+	200.401	30932474
DeepCCS	[M-H]-	197.956	30932474
DeepCCS	[M-2H]-	232.334	30932474
DeepCCS	[M+Na]+	207.562	30932474
AllCCS	[M+H]+	194.1	32859911
AllCCS	[M+H-H2O]+	191.5	32859911
AllCCS	[M+NH4]+	196.6	32859911
AllCCS	[M+Na]+	197.2	32859911
AllCCS	[M-H]-	192.3	32859911
AllCCS	[M+Na-2H]-	193.6	32859911
AllCCS	[M+HCOO]-	195.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Isoprostaglandin E1	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1CCCCCCC(O)=O	4341.1	Standard polar	33892256
8-Isoprostaglandin E1	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1CCCCCCC(O)=O	2723.6	Standard non polar	33892256
8-Isoprostaglandin E1	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1CCCCCCC(O)=O	2845.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Isoprostaglandin E1,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](CCCCCCC(=O)O)C(=O)C[C@H]1O)O[Si](C)(C)C	2820.8	Semi standard non polar	33892256
8-Isoprostaglandin E1,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](CCCCCCC(=O)O)C(=O)C[C@H]1O[Si](C)(C)C	2745.3	Semi standard non polar	33892256
8-Isoprostaglandin E1,1TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](CCCCCCC(=O)O[Si](C)(C)C)C(=O)C[C@H]1O	2785.3	Semi standard non polar	33892256
8-Isoprostaglandin E1,1TMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1C(CCCCCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O	2835.5	Semi standard non polar	33892256
8-Isoprostaglandin E1,1TMS,isomer #5	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@H]1CCCCCCC(=O)O	2729.3	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](CCCCCCC(=O)O[Si](C)(C)C)C(=O)C[C@H]1O)O[Si](C)(C)C	2811.4	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1[C@H](CCCCCCC(=O)O)C(=O)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2748.5	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TMS,isomer #3	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C	2870.3	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TMS,isomer #4	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@H]1CCCCCCC(=O)O)O[Si](C)(C)C	2754.3	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TMS,isomer #5	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](CCCCCCC(=O)O[Si](C)(C)C)C(=O)C[C@H]1O[Si](C)(C)C	2732.4	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TMS,isomer #6	CCCCC[C@H](O)/C=C/[C@@H]1C(CCCCCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C	2824.5	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TMS,isomer #7	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1CCCCCCC(=O)O	2769.5	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TMS,isomer #8	CCCCC[C@H](O)/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O	2824.3	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TMS,isomer #9	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C	2746.1	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](CCCCCCC(=O)O[Si](C)(C)C)C(=O)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2737.7	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C	2848.8	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TMS,isomer #3	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2766.0	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TMS,isomer #4	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2808.2	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TMS,isomer #5	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1CCCCCCC(=O)O)O[Si](C)(C)C	2790.2	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TMS,isomer #6	CCCCC[C@H](O)/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C	2795.7	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TMS,isomer #7	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C	2785.2	Semi standard non polar	33892256
8-Isoprostaglandin E1,4TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2819.7	Semi standard non polar	33892256
8-Isoprostaglandin E1,4TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2893.6	Standard non polar	33892256
8-Isoprostaglandin E1,4TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2916.2	Standard polar	33892256
8-Isoprostaglandin E1,4TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2815.5	Semi standard non polar	33892256
8-Isoprostaglandin E1,4TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2731.3	Standard non polar	33892256
8-Isoprostaglandin E1,4TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3001.4	Standard polar	33892256
8-Isoprostaglandin E1,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](CCCCCCC(=O)O)C(=O)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3076.9	Semi standard non polar	33892256
8-Isoprostaglandin E1,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](CCCCCCC(=O)O)C(=O)C[C@H]1O[Si](C)(C)C(C)(C)C	2957.6	Semi standard non polar	33892256
8-Isoprostaglandin E1,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)C[C@H]1O	3049.9	Semi standard non polar	33892256
8-Isoprostaglandin E1,1TBDMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1C(CCCCCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O	3067.4	Semi standard non polar	33892256
8-Isoprostaglandin E1,1TBDMS,isomer #5	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCCCCCC(=O)O	2964.6	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3328.6	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1[C@H](CCCCCCC(=O)O)C(=O)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3212.0	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TBDMS,isomer #3	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3317.9	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TBDMS,isomer #4	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3216.0	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TBDMS,isomer #5	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)C[C@H]1O[Si](C)(C)C(C)(C)C	3192.3	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TBDMS,isomer #6	CCCCC[C@H](O)/C=C/[C@@H]1C(CCCCCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C	3251.4	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TBDMS,isomer #7	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCCCCCC(=O)O	3216.8	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TBDMS,isomer #8	CCCCC[C@H](O)/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O	3288.2	Semi standard non polar	33892256
8-Isoprostaglandin E1,2TBDMS,isomer #9	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3216.9	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3470.1	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3559.5	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TBDMS,isomer #3	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3486.2	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TBDMS,isomer #4	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3487.4	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TBDMS,isomer #5	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3477.4	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TBDMS,isomer #6	CCCCC[C@H](O)/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C	3464.7	Semi standard non polar	33892256
8-Isoprostaglandin E1,3TBDMS,isomer #7	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3469.8	Semi standard non polar	33892256
8-Isoprostaglandin E1,4TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3683.6	Semi standard non polar	33892256
8-Isoprostaglandin E1,4TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3480.9	Standard non polar	33892256
8-Isoprostaglandin E1,4TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3243.3	Standard polar	33892256
8-Isoprostaglandin E1,4TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3692.6	Semi standard non polar	33892256
8-Isoprostaglandin E1,4TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3213.4	Standard non polar	33892256
8-Isoprostaglandin E1,4TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3276.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Isoprostaglandin E1 GC-MS (Non-derivatized) - 70eV, Positive	splash10-03du-8496000000-7d3b810081e27f50d55e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Isoprostaglandin E1 GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-5111690000-a4b76b0035fa00f6c191	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Isoprostaglandin E1 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-Isoprostaglandin E1 10V, Positive-QTOF	splash10-00kr-0019000000-f5b5a1445394c1875ab5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 20V, Positive-QTOF	splash10-014u-3298000000-914d4dd2398f2330aadc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 40V, Positive-QTOF	splash10-00kr-9210000000-cae0b0e2e44b318ffc15	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 10V, Negative-QTOF	splash10-0udr-0009000000-2ae4bda00bf8a87d2cc8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 20V, Negative-QTOF	splash10-0f79-2149000000-253cbdfcc6971a59bcbe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 40V, Negative-QTOF	splash10-0a4i-9430000000-d886399479c4a7f3bafd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 10V, Negative-QTOF	splash10-0fri-0009000000-923c8a53409a3df92c03	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 20V, Negative-QTOF	splash10-000i-0069000000-1771266ae55287330e24	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 40V, Negative-QTOF	splash10-001v-9481000000-4f3fb6bba04c2db22a67	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 10V, Positive-QTOF	splash10-014i-0009000000-48b67d3860a0408d6017	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 20V, Positive-QTOF	splash10-014i-7369000000-67c0756e11758bfc63bd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin E1 40V, Positive-QTOF	splash10-05mo-9600000000-b116946f56f764ec762e	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

FDB023405

KNApSAcK ID

Not Available

Chemspider ID

4446333

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283212

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

Clarke DL, Belvisi MG, Hardaker E, Newton R, Giembycz MA: E-ring 8-isoprostanes are agonists at EP2- and EP4-prostanoid receptors on human airway smooth muscle cells and regulate the release of colony-stimulating factors by activating cAMP-dependent protein kinase. Mol Pharmacol. 2005 Feb;67(2):383-93. Epub 2004 Nov 4. [PubMed:15528403 ]

Showing metabocard for 8-Isoprostaglandin E1 (HMDB0004686)

MOL for HMDB0004686 (8-Isoprostaglandin E1)

3D MOL for HMDB0004686 (8-Isoprostaglandin E1)

3D SDF for HMDB0004686 (8-Isoprostaglandin E1)

3D-SDF for HMDB0004686 (8-Isoprostaglandin E1)

PDB for HMDB0004686 (8-Isoprostaglandin E1)

3D PDB for HMDB0004686 (8-Isoprostaglandin E1)

SMILES for HMDB0004686 (8-Isoprostaglandin E1)

INCHI for HMDB0004686 (8-Isoprostaglandin E1)

Structure for HMDB0004686 (8-Isoprostaglandin E1)

3D Structure for HMDB0004686 (8-Isoprostaglandin E1)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra