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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 23:19:54 UTC

Update Date

2021-09-14 15:15:56 UTC

HMDB ID

HMDB0004659

Secondary Accession Numbers

HMDB04659

Metabolite Identification

Common Name

8-Isoprostane

Description

8-isoprostane concentrations are elevated in asthma and increase with the clinical severity and during acute asthma episodes. Isoprostane is formed in the airways of asthmatic patients from peroxidation of poly-unsaturated fatty acids in cell membranes, the effect of reactive oxygen species resulting of the NADPH oxidase of eosinophils, neutrophils and alveolar macrophages, which produces superoxide anion which undergoes dismutation to H2O2. (PMID 16354413 ). 8-isoprostane is also elevated in Bronchopulmonary dysplasia, which remains an important cause of morbidity and mortality in extremely premature newborn infants receiving intensive care and is the most common contributing factor to severe respiratory morbidity and mortality in early childhood. (PMID 14980283 ). 8-Isoprostaglandin F(2a) is a marker of oxidative stress in the aqueous humour of patients with exfoliation syndrome (XFS) (PubMed ID 12598453).

Structure

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

HMDB0004659
     RDKit          3D
8-Isoprostane
 60 60  0  0  0  0  0  0  0  0999 V2000
   -8.9737   -0.2031   -0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5494    0.0995   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6516   -1.0757   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2280   -0.8285    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6322    0.3600   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2217    0.5941   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3211   -0.5476   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171   -0.4606    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504    0.6072   -0.5473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4606    2.0135   -0.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8479    2.7098    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    1.6237    0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3864    0.4639   -0.0857 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7161   -0.8459    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1583   -0.9361    0.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1226   -0.7509   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5253   -0.8643    0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5790   -0.6930   -0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9277   -0.8205    0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0100    0.2773    1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5923   -0.4316    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9387   -1.0741   -1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3614    0.6878   -1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1567    0.9696   -0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5589    0.3362    0.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0124   -1.9656    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6517   -1.3867   -1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2743   -0.7110    1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6576   -1.7582   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6501    0.1919   -1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2000    1.2809   -0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3091    0.9076    0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8469    1.4557   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597   -1.4314    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -0.9038   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4435   -1.4419   -0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -0.4166    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    0.4583   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366    2.5304   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1113    2.1608    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141    3.6056    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478    2.9742   -0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    1.4237    1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5617    1.8344    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827    0.6984   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -1.6245   -0.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912   -1.0089    1.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3649   -0.1524    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122   -1.9673    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9759   -1.4792   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529    0.2548   -0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6077   -1.8955    0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6834   -0.0912    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4555   -1.3917   -1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380    0.3531   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7693   -0.7822   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9018   -1.7824    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0602    0.5810    1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5402   -0.0554    2.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4211    1.1608    0.7261 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
  7  8  1  0
  8  9  1  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  1  0
 19 20  1  0
 13  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  6
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  6
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 20 60  1  0
M  END

  Mrv0541 02231219572D          

 22 22  0  0  1  0            999 V2000
    8.6528   -5.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1378   -5.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1377   -6.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9224   -5.4375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9224   -6.2625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6427   -5.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3512   -5.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0715   -5.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7800   -5.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5003   -5.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2088   -5.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9292   -5.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6368   -6.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3514   -6.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0658   -6.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7803   -6.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4948   -6.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2092   -6.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9237   -6.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6382   -6.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281   -7.0615    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281   -4.6704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 14 13  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 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
  5 21  1  6  0  0  0
  4 22  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0004659

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CCCCCCC)CCC[C@]1([H])CCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C20H40/c1-3-5-7-9-11-13-16-20-18-14-17-19(20)15-12-10-8-6-4-2/h19-20H,3-18H2,1-2H3/t19-,20+/m1/s1

> <INCHI_KEY>
UKVVPDHLUHAJNZ-UXHICEINSA-N

> <FORMULA>
C20H40

> <MOLECULAR_WEIGHT>
280.5316

> <EXACT_MASS>
280.31300128

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
40.04806458602158

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S)-1-heptyl-2-octylcyclopentane

> <ALOGPS_LOGP>
9.29

> <JCHEM_LOGP>
8.576274162666666

> <ALOGPS_LOGS>
-7.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
91.9152

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.76e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8β-prostane

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004659
     RDKit          3D
8-Isoprostane
 60 60  0  0  0  0  0  0  0  0999 V2000
   -8.9737   -0.2031   -0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5494    0.0995   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6516   -1.0757   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2280   -0.8285    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6322    0.3600   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2217    0.5941   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3211   -0.5476   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171   -0.4606    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504    0.6072   -0.5473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4606    2.0135   -0.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8479    2.7098    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    1.6237    0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3864    0.4639   -0.0857 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7161   -0.8459    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1583   -0.9361    0.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1226   -0.7509   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5253   -0.8643    0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5790   -0.6930   -0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9277   -0.8205    0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0100    0.2773    1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5923   -0.4316    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9387   -1.0741   -1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3614    0.6878   -1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1567    0.9696   -0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5589    0.3362    0.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0124   -1.9656    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6517   -1.3867   -1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2743   -0.7110    1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6576   -1.7582   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6501    0.1919   -1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2000    1.2809   -0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3091    0.9076    0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8469    1.4557   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597   -1.4314    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -0.9038   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4435   -1.4419   -0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -0.4166    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    0.4583   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366    2.5304   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1113    2.1608    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141    3.6056    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478    2.9742   -0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    1.4237    1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5617    1.8344    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827    0.6984   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -1.6245   -0.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912   -1.0089    1.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3649   -0.1524    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122   -1.9673    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9759   -1.4792   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529    0.2548   -0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6077   -1.8955    0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6834   -0.0912    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4555   -1.3917   -1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380    0.3531   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7693   -0.7822   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9018   -1.7824    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0602    0.5810    1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5402   -0.0554    2.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4211    1.1608    0.7261 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
  7  8  1  0
  8  9  1  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  1  0
 19 20  1  0
 13  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  6
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  6
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 20 60  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      16.152 -10.920   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.057  -9.674   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.057 -12.166   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.522 -10.150   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.522 -11.690   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.866  -9.399   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.189 -10.188   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.533  -9.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.856 -10.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.201  -9.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.523 -10.265   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.868  -9.515   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.855 -12.460   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.189 -11.690   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.523 -12.460   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.857 -11.690   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.190 -12.460   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.524 -11.690   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.858 -12.460   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.191 -11.690   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      18.532 -13.181   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      18.532  -8.718   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    5    6   22                                             
CONECT    5    3    4   13   21                                             
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    5                                                            
CONECT   22    4                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0004659
HETATM    1  C1  UNL     1      -8.974  -0.203  -0.676  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.549   0.100  -0.192  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.652  -1.076  -0.464  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.228  -0.829   0.006  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.632   0.360  -0.695  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.222   0.594  -0.197  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.321  -0.548  -0.442  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.917  -0.461   0.003  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.050   0.607  -0.547  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.461   2.014  -0.294  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.848   2.710   0.106  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.521   1.624   0.915  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.386   0.464  -0.086  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.716  -0.846   0.531  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.158  -0.936   0.983  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.123  -0.751  -0.166  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.525  -0.864   0.425  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.579  -0.693  -0.647  1.00  0.00           C  
HETATM   19  C19 UNL     1       7.928  -0.820   0.030  1.00  0.00           C  
HETATM   20  C20 UNL     1       8.010   0.277   1.080  1.00  0.00           C  
HETATM   21  H1  UNL     1      -9.592  -0.432   0.217  1.00  0.00           H  
HETATM   22  H2  UNL     1      -8.939  -1.074  -1.329  1.00  0.00           H  
HETATM   23  H3  UNL     1      -9.361   0.688  -1.178  1.00  0.00           H  
HETATM   24  H4  UNL     1      -7.157   0.970  -0.781  1.00  0.00           H  
HETATM   25  H5  UNL     1      -7.559   0.336   0.889  1.00  0.00           H  
HETATM   26  H6  UNL     1      -7.012  -1.966   0.125  1.00  0.00           H  
HETATM   27  H7  UNL     1      -6.652  -1.387  -1.515  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.274  -0.711   1.099  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.658  -1.758  -0.208  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.650   0.192  -1.790  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.200   1.281  -0.428  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.309   0.908   0.852  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.847   1.456  -0.823  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.760  -1.431   0.128  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.377  -0.904  -1.506  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.444  -1.442  -0.326  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.912  -0.417   1.123  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.043   0.458  -1.672  1.00  0.00           H  
HETATM   39  H19 UNL     1      -0.837   2.530  -1.207  1.00  0.00           H  
HETATM   40  H20 UNL     1      -1.111   2.161   0.600  1.00  0.00           H  
HETATM   41  H21 UNL     1       0.614   3.606   0.739  1.00  0.00           H  
HETATM   42  H22 UNL     1       1.448   2.974  -0.775  1.00  0.00           H  
HETATM   43  H23 UNL     1       0.875   1.424   1.790  1.00  0.00           H  
HETATM   44  H24 UNL     1       2.562   1.834   1.154  1.00  0.00           H  
HETATM   45  H25 UNL     1       2.083   0.698  -0.927  1.00  0.00           H  
HETATM   46  H26 UNL     1       1.549  -1.624  -0.266  1.00  0.00           H  
HETATM   47  H27 UNL     1       1.091  -1.009   1.431  1.00  0.00           H  
HETATM   48  H28 UNL     1       3.365  -0.152   1.720  1.00  0.00           H  
HETATM   49  H29 UNL     1       3.312  -1.967   1.366  1.00  0.00           H  
HETATM   50  H30 UNL     1       3.976  -1.479  -0.971  1.00  0.00           H  
HETATM   51  H31 UNL     1       4.053   0.255  -0.612  1.00  0.00           H  
HETATM   52  H32 UNL     1       5.608  -1.895   0.826  1.00  0.00           H  
HETATM   53  H33 UNL     1       5.683  -0.091   1.178  1.00  0.00           H  
HETATM   54  H34 UNL     1       6.455  -1.392  -1.483  1.00  0.00           H  
HETATM   55  H35 UNL     1       6.538   0.353  -1.050  1.00  0.00           H  
HETATM   56  H36 UNL     1       8.769  -0.782  -0.683  1.00  0.00           H  
HETATM   57  H37 UNL     1       7.902  -1.782   0.610  1.00  0.00           H  
HETATM   58  H38 UNL     1       9.060   0.581   1.260  1.00  0.00           H  
HETATM   59  H39 UNL     1       7.540  -0.055   2.023  1.00  0.00           H  
HETATM   60  H40 UNL     1       7.421   1.161   0.726  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT    9   10   13   38
CONECT   10   11   39   40
CONECT   11   12   41   42
CONECT   12   13   43   44
CONECT   13   14   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   54   55
CONECT   19   20   56   57
CONECT   20   58   59   60
END

HMDB0004659
     RDKit          3D
8-Isoprostane
 60 60  0  0  0  0  0  0  0  0999 V2000
   -8.9737   -0.2031   -0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5494    0.0995   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6516   -1.0757   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2280   -0.8285    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6322    0.3600   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2217    0.5941   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3211   -0.5476   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171   -0.4606    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504    0.6072   -0.5473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4606    2.0135   -0.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8479    2.7098    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    1.6237    0.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3864    0.4639   -0.0857 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7161   -0.8459    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1583   -0.9361    0.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1226   -0.7509   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5253   -0.8643    0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5790   -0.6930   -0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9277   -0.8205    0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0100    0.2773    1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5923   -0.4316    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9387   -1.0741   -1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3614    0.6878   -1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1567    0.9696   -0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5589    0.3362    0.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0124   -1.9656    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6517   -1.3867   -1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2743   -0.7110    1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6576   -1.7582   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6501    0.1919   -1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2000    1.2809   -0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3091    0.9076    0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8469    1.4557   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597   -1.4314    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -0.9038   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4435   -1.4419   -0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -0.4166    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    0.4583   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366    2.5304   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1113    2.1608    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141    3.6056    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478    2.9742   -0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    1.4237    1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5617    1.8344    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827    0.6984   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -1.6245   -0.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912   -1.0089    1.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3649   -0.1524    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122   -1.9673    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9759   -1.4792   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529    0.2548   -0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6077   -1.8955    0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6834   -0.0912    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4555   -1.3917   -1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380    0.3531   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7693   -0.7822   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9018   -1.7824    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0602    0.5810    1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5402   -0.0554    2.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4211    1.1608    0.7261 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
  7  8  1  0
  8  9  1  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  1  0
 19 20  1  0
 13  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  6
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  6
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 20 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1R,2S)-1-Heptyl-2-octylcyclopentane	ChEBI
(8beta)-Prostane	ChEBI
(8b)-Prostane	Generator
(8Β)-prostane	Generator
8-beta-Prostane	HMDB
15-F(2t)-Isoprostane	MeSH, HMDB
8-iso-PGF(2alpha)	MeSH, HMDB
15-F(2t)-IsoP	MeSH, HMDB
8-Epi-PGF2alpha	MeSH, HMDB
8-Epi-prostaglandin F2alpha	MeSH, HMDB
8-iso-PGF2alpha	MeSH, HMDB
Isoprostaglandin F2alpha type-III	MeSH, HMDB
8-Isoprostaglandin F2alpha	MeSH, HMDB
8-Epiprostaglandin F2alpha	MeSH, HMDB
8-F(2t)-Isoprostane	MeSH, HMDB
8-Epi-PGF2 alpha	MeSH, HMDB
15-F2t-IsoP	MeSH, HMDB
15-F2t-Isoprostane	MeSH, HMDB

Chemical Formula

C₂₀H₄₀

Average Molecular Weight

280.5316

Monoisotopic Molecular Weight

280.31300128

IUPAC Name

(1R,2S)-1-heptyl-2-octylcyclopentane

Traditional Name

8β-prostane

CAS Registry Number

155976-51-5

SMILES

[H][C@@]1(CCCCCCC)CCC[C@]1([H])CCCCCCCC

InChI Identifier

InChI=1S/C20H40/c1-3-5-7-9-11-13-16-20-18-14-17-19(20)15-12-10-8-6-4-2/h19-20H,3-18H2,1-2H3/t19-,20+/m1/s1

InChI Key

UKVVPDHLUHAJNZ-UXHICEINSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloalkanes. These are saturated monocyclic hydrocarbons (with or without side chains).

Kingdom

Organic compounds

Super Class

Hydrocarbons

Class

Saturated hydrocarbons

Sub Class

Cycloalkanes

Direct Parent

Cycloalkanes

Alternative Parents

Not Available

Substituents

Cycloalkane
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

1-heptyl-2-octylcyclopentane (CHEBI:33023 )

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	7.8e-06 g/L	ALOGPS
logP	9.29	ALOGPS
logP	8.58	ChemAxon
logS	-7.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	91.92 m³·mol⁻¹	ChemAxon
Polarizability	40.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	170.61	31661259
DarkChem	[M-H]-	171.296	31661259
DeepCCS	[M+H]+	175.519	30932474
DeepCCS	[M-H]-	173.119	30932474
DeepCCS	[M-2H]-	206.505	30932474
DeepCCS	[M+Na]+	181.491	30932474
AllCCS	[M+H]+	184.7	32859911
AllCCS	[M+H-H2O]+	181.8	32859911
AllCCS	[M+NH4]+	187.4	32859911
AllCCS	[M+Na]+	188.2	32859911
AllCCS	[M-H]-	184.7	32859911
AllCCS	[M+Na-2H]-	186.2	32859911
AllCCS	[M+HCOO]-	187.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Isoprostane	[H][C@@]1(CCCCCCC)CCC[C@]1([H])CCCCCCCC	2043.2	Standard polar	33892256
8-Isoprostane	[H][C@@]1(CCCCCCC)CCC[C@]1([H])CCCCCCCC	1984.8	Standard non polar	33892256
8-Isoprostane	[H][C@@]1(CCCCCCC)CCC[C@]1([H])CCCCCCCC	1926.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Isoprostane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0q3a-5690000000-8578513810f15e2b1675	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Isoprostane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Isoprostane 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-Isoprostane 10V, Positive-QTOF	splash10-001i-0290000000-a20b197c3e7f1d74f249	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 20V, Positive-QTOF	splash10-001j-4890000000-eb1a2356a35d532ad8e6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 40V, Positive-QTOF	splash10-059g-9570000000-b243e014ae11d5220934	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 10V, Negative-QTOF	splash10-004i-0090000000-ea56d8a3a2a3da747c77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 20V, Negative-QTOF	splash10-004i-0090000000-b99d9f57d25c668e68d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 40V, Negative-QTOF	splash10-03g1-2590000000-7060fdcd4f3536c40ac1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 10V, Positive-QTOF	splash10-001i-2090000000-1aa04390e1979d610a49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 20V, Positive-QTOF	splash10-0560-9560000000-24c9aaae80f6353f7332	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 40V, Positive-QTOF	splash10-0a4l-9510000000-2a35251ab7150a2a305d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 10V, Negative-QTOF	splash10-004i-0090000000-bc21dbf6b7d615cdf298	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 20V, Negative-QTOF	splash10-004i-0090000000-bc21dbf6b7d615cdf298	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostane 40V, Negative-QTOF	splash10-004i-0090000000-8d49c6985a616961b999	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Adipose Tissue
Epidermis
Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00011 +/- 0.00004 uM	Adult (>18 years old)	Male	Normal	18203893	details
Blood	Detected and Quantified	0.00053 +/- 0.000043 uM	Adult (>18 years old)	Male	Normal	12840179	details
Blood	Detected and Quantified	0.00047 +/- 0.000014 uM	Adult (>18 years old)	Female	Normal	12840179	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00003 +/- 0.00002 uM	Adult (>18 years old)	Not Specified	Normal	11978879	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000021 (0.0000071-0.000035) uM	Adult (>18 years old)	Not Specified	Normal	11978879	details
Urine	Detected and Quantified	0.00007 - 0.0005 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	11339277	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0003 +/- 0.0001 uM	Children (1-13 years old)	Not Specified	Brain injury	11978879	details

Associated Disorders and Diseases

Disease References

Traumatic brain injury
Bayir H, Kagan VE, Tyurina YY, Tyurin V, Ruppel RA, Adelson PD, Graham SH, Janesko K, Clark RS, Kochanek PM: Assessment of antioxidant reserves and oxidative stress in cerebrospinal fluid after severe traumatic brain injury in infants and children. Pediatr Res. 2002 May;51(5):571-8. [PubMed:11978879 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023392

KNApSAcK ID

Not Available

Chemspider ID

97008

KEGG Compound ID

C13809

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoprostane

METLIN ID

7067

PubChem Compound

107873

PDB ID

Not Available

ChEBI ID

33023

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

Bayir H, Kagan VE, Tyurina YY, Tyurin V, Ruppel RA, Adelson PD, Graham SH, Janesko K, Clark RS, Kochanek PM: Assessment of antioxidant reserves and oxidative stress in cerebrospinal fluid after severe traumatic brain injury in infants and children. Pediatr Res. 2002 May;51(5):571-8. [PubMed:11978879 ]
Beisswenger PJ, Drummond KS, Nelson RG, Howell SK, Szwergold BS, Mauer M: Susceptibility to diabetic nephropathy is related to dicarbonyl and oxidative stress. Diabetes. 2005 Nov;54(11):3274-81. [PubMed:16249455 ]
Raal FJ, Pilcher GJ, Waisberg R, Buthelezi EP, Veller MG, Joffe BI: Low-density lipoprotein cholesterol bulk is the pivotal determinant of atherosclerosis in familial hypercholesterolemia. Am J Cardiol. 1999 May 1;83(9):1330-3. [PubMed:10235090 ]
Ryan-Borchers TA, Park JS, Chew BP, McGuire MK, Fournier LR, Beerman KA: Soy isoflavones modulate immune function in healthy postmenopausal women. Am J Clin Nutr. 2006 May;83(5):1118-25. [PubMed:16685055 ]
Luo X, Sedlackova L, Belcastro R, Cabacungan J, Lye SJ, Tanswell AK: Effect of the 21-aminosteroid U74389G on oxygen-induced free radical production, lipid peroxidation, and inhibition of lung growth in neonatal rats. Pediatr Res. 1999 Aug;46(2):215-23. [PubMed:10447118 ]
Roberts CK, Won D, Pruthi S, Kurtovic S, Sindhu RK, Vaziri ND, Barnard RJ: Effect of a short-term diet and exercise intervention on oxidative stress, inflammation, MMP-9, and monocyte chemotactic activity in men with metabolic syndrome factors. J Appl Physiol (1985). 2006 May;100(5):1657-65. Epub 2005 Dec 15. [PubMed:16357066 ]
Volpe A, Biasi D, Caramaschi P, Mantovani W, Bambara LM, Canestrini S, Ferrari M, Poli G, Degan M, Carletto A, Pieropan S, Minuz P: Levels of F2-isoprostanes in systemic sclerosis: correlation with clinical features. Rheumatology (Oxford). 2006 Mar;45(3):314-20. Epub 2005 Oct 11. [PubMed:16219641 ]
Simpson JL, Wood LG, Gibson PG: Inflammatory mediators in exhaled breath, induced sputum and saliva. Clin Exp Allergy. 2005 Sep;35(9):1180-5. [PubMed:16164445 ]
Belli R, Amerio P, Brunetti L, Orlando G, Toto P, Proietto G, Vacca M, Tulli A: Elevated 8-isoprostane levels in basal cell carcinoma and in UVA irradiated skin. Int J Immunopathol Pharmacol. 2005 Jul-Sep;18(3):497-502. [PubMed:16164830 ]
Kranzhofer R, Ruef J: Aspirin resistance in coronary artery disease is correlated to elevated markers for oxidative stress but not to the expression of cyclooxygenase (COX) 1/2, a novel COX-1 polymorphism or the PlA(1/2) polymorphism. Platelets. 2006 May;17(3):163-9. [PubMed:16702043 ]
Khaw KS, Wang CC, Ngan Kee WD, Pang CP, Rogers MS: Effects of high inspired oxygen fraction during elective caesarean section under spinal anaesthesia on maternal and fetal oxygenation and lipid peroxidation. Br J Anaesth. 2002 Jan;88(1):18-23. [PubMed:11883375 ]
Schneider LA, Bloch W, Kopp K, Hainzl A, Rettberg P, Wlaschek M, Horneck G, Scharffetter-Kochanek K: 8-Isoprostane is a dose-related biomarker for photo-oxidative ultraviolet (UV) B damage in vivo: a pilot study with personal UV dosimetry. Br J Dermatol. 2006 Jun;154(6):1147-54. [PubMed:16704647 ]
Kuhn M, Wolber R, Kolbe L, Schnorr O, Sies H: Solar-simulated radiation induces secretion of IL-6 and production of isoprostanes in human skin in vivo. Arch Dermatol Res. 2006 Apr;297(10):477-9. Epub 2006 Feb 21. [PubMed:16491351 ]
McKinney ET, Shouri R, Hunt RS, Ahokas RA, Sibai BM: Plasma, urinary, and salivary 8-epi-prostaglandin f2alpha levels in normotensive and preeclamptic pregnancies. Am J Obstet Gynecol. 2000 Oct;183(4):874-7. [PubMed:11035329 ]
Carpagnano GE, Kharitonov SA, Resta O, Foschino-Barbaro MP, Gramiccioni E, Barnes PJ: 8-Isoprostane, a marker of oxidative stress, is increased in exhaled breath condensate of patients with obstructive sleep apnea after night and is reduced by continuous positive airway pressure therapy. Chest. 2003 Oct;124(4):1386-92. [PubMed:14555570 ]
Karowicz-Bilinska A, Kowalska-Koprek U, Suzin J, Sieroszewski P: [Analysis of 8-isoprostane concentration as a marker of oxidative stress in pregnant women diagnosed with IUGR]. Ginekol Pol. 2003 Oct;74(10):1137-42. [PubMed:14669408 ]
Lappas M, Permezel M, Rice GE: Release of proinflammatory cytokines and 8-isoprostane from placenta, adipose tissue, and skeletal muscle from normal pregnant women and women with gestational diabetes mellitus. J Clin Endocrinol Metab. 2004 Nov;89(11):5627-33. [PubMed:15531521 ]
Ohashi N, Yoshikawa M: Rapid and sensitive quantification of 8-isoprostaglandin F2alpha in human plasma and urine by liquid chromatography-electrospray ionization mass spectrometry. J Chromatogr B Biomed Sci Appl. 2000 Sep 1;746(1):17-24. [PubMed:11048736 ]
Ide T, Tsutsui H, Ohashi N, Hayashidani S, Suematsu N, Tsuchihashi M, Tamai H, Takeshita A: Greater oxidative stress in healthy young men compared with premenopausal women. Arterioscler Thromb Vasc Biol. 2002 Mar 1;22(3):438-42. [PubMed:11884287 ]
Misso NL, Thompson PJ: Oxidative stress and antioxidant deficiencies in asthma: potential modification by diet. Redox Rep. 2005;10(5):247-55. [PubMed:16354413 ]
Jankov RP, Keith Tanswell A: Growth factors, postnatal lung growth and bronchopulmonary dysplasia. Paediatr Respir Rev. 2004;5 Suppl A:S265-75. [PubMed:14980283 ]

Showing metabocard for 8-Isoprostane (HMDB0004659)

MOL for HMDB0004659 (8-Isoprostane)

3D MOL for HMDB0004659 (8-Isoprostane)

3D SDF for HMDB0004659 (8-Isoprostane)

3D-SDF for HMDB0004659 (8-Isoprostane)

PDB for HMDB0004659 (8-Isoprostane)

3D PDB for HMDB0004659 (8-Isoprostane)

SMILES for HMDB0004659 (8-Isoprostane)

INCHI for HMDB0004659 (8-Isoprostane)

Structure for HMDB0004659 (8-Isoprostane)

3D Structure for HMDB0004659 (8-Isoprostane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra