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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:43 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002236

Secondary Accession Numbers

HMDB02236

Metabolite Identification

Common Name

8-iso-PGA1

Description

8-iso-PGA1 is an isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia reperfusion injury. For this reason, they are frequently used as markers of oxidative stress; however, many are now finding that these molecules are not inert, but in fact evoke powerful biological responses in an increasing array of cell types. In many cases, these biological effects can account in part for the various features and manifestations of those clinical conditions. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states. (PMID: 14504139 )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

HMDB0002236
     RDKit          3D
8-iso-PGA1
 56 56  0  0  0  0  0  0  0  0999 V2000
    6.3121    0.9842   -1.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9867    0.6151   -0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8776   -0.4237   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4999   -0.8458    0.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.2828    1.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    0.9357    1.2816 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4223    1.9836    2.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950   -0.0308    1.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2873   -0.8946    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663   -1.8605    0.4581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7127   -1.7881    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9388   -2.1059    1.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9288   -2.4083   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7020   -3.1710   -0.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7999   -1.5935   -0.7211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1061   -0.1498   -0.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    0.4568   -1.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3624   -0.0077   -1.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2777    0.1160   -0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4426    1.5720   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4116    1.4920    0.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6836    0.8962    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2154    1.4943   -0.5535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2497   -0.2436    0.9979 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1127    0.3522   -2.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677    0.9443   -2.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6040    2.0730   -1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715    0.1796    0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350    1.4922    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0233   -0.0692   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2975   -1.2941   -0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558   -1.6690    0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4275   -1.2404    1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8077    1.0065    1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407   -0.1384    2.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8729    1.2829    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418    2.5215    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -0.0409    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -0.9208   -0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5074   -2.9151    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5205   -1.5253    2.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534   -2.1612    1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3754   -1.9556   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1325    0.4352   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5410    0.0511    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889    0.4499   -2.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    1.5705   -1.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3531   -1.0125   -2.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184    0.6449   -2.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0126   -0.4386    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3155   -0.1536   -1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8563    2.2031   -0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4816    1.8840    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6575    2.5013    1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0069    0.8387    1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7668   -0.2017    1.8586 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  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 12 42  1  0
 15 43  1  6
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END


  Mrv0541 02231219262D          

 24 24  0  0  1  0            999 V2000
   18.3598  -10.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2574   -5.8515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9990   -9.9998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4405   -8.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5899   -8.8115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2574   -8.3265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8053   -8.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1922   -9.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8449   -9.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9247   -8.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4075   -8.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2574   -7.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6699   -9.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7944   -9.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9717   -7.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9717   -6.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.0099   -9.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6863   -5.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6863   -5.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4008   -4.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3968   -9.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4008   -3.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1152   -3.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6121   -9.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
 16  2  1  1  0  0  0
  3 24  1  0  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  1  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  1  0  0  0
  7  8  1  0  0  0  0
  8 11  1  0  0  0  0
  9 13  1  0  0  0  0
 10 13  2  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  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
M  END
> <DATABASE_ID>
HMDB0002236

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18-/m0/s1

> <INCHI_KEY>
BGKHCLZFGPIKKU-DRSVPBQLSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.81320961212484

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
4.737872620333333

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.74675363107826

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.45154130592671

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5972323838202795

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
97.9733

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-iso-PGA1

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002236
     RDKit          3D
8-iso-PGA1
 56 56  0  0  0  0  0  0  0  0999 V2000
    6.3121    0.9842   -1.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9867    0.6151   -0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8776   -0.4237   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4999   -0.8458    0.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.2828    1.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    0.9357    1.2816 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4223    1.9836    2.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950   -0.0308    1.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2873   -0.8946    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663   -1.8605    0.4581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7127   -1.7881    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9388   -2.1059    1.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9288   -2.4083   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7020   -3.1710   -0.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7999   -1.5935   -0.7211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1061   -0.1498   -0.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    0.4568   -1.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3624   -0.0077   -1.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2777    0.1160   -0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4426    1.5720   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4116    1.4920    0.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6836    0.8962    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2154    1.4943   -0.5535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2497   -0.2436    0.9979 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1127    0.3522   -2.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677    0.9443   -2.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6040    2.0730   -1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715    0.1796    0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350    1.4922    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0233   -0.0692   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2975   -1.2941   -0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558   -1.6690    0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4275   -1.2404    1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8077    1.0065    1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407   -0.1384    2.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8729    1.2829    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418    2.5215    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -0.0409    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -0.9208   -0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5074   -2.9151    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5205   -1.5253    2.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534   -2.1612    1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3754   -1.9556   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1325    0.4352   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5410    0.0511    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889    0.4499   -2.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    1.5705   -1.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3531   -1.0125   -2.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184    0.6449   -2.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0126   -0.4386    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3155   -0.1536   -1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8563    2.2031   -0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4816    1.8840    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6575    2.5013    1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0069    0.8387    1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7668   -0.2017    1.8586 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  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 12 42  1  0
 15 43  1  6
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  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      34.272 -19.158   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.947 -10.923   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      24.265 -18.666   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      25.089 -16.129   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      34.701 -16.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.947 -15.543   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.237 -15.972   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.092 -17.003   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.177 -17.913   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.193 -16.448   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.627 -16.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.947 -14.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.717 -17.913   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.483 -17.557   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.281 -13.233   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.281 -11.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.018 -17.081   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.614 -10.923   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.614  -9.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.948  -8.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.874 -18.112   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      39.948  -7.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      41.282  -6.303   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.409 -17.636   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   16                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    6    7    9                                                  
CONECT    6    5   10   12                                                  
CONECT    7    5    8                                                       
CONECT    8    7   11                                                       
CONECT    9    1    5   13                                                  
CONECT   10    6   13                                                       
CONECT   11    8   14                                                       
CONECT   12    6   15                                                       
CONECT   13    9   10                                                       
CONECT   14   11   17                                                       
CONECT   15   12   16                                                       
CONECT   16    2   15   18                                                  
CONECT   17   14   21                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   22                                                       
CONECT   21   17   24                                                       
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24    3    4   21                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0002236
HETATM    1  C1  UNL     1       6.312   0.984  -1.809  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.987   0.615  -0.385  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.878  -0.424  -0.439  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.500  -0.846   0.956  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.998   0.283   1.793  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.748   0.936   1.282  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.422   1.984   2.162  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.595  -0.031   1.363  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.287  -0.895   0.422  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.166  -1.861   0.458  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.713  -1.788   1.601  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.939  -2.106   1.229  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.929  -2.408  -0.217  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.702  -3.171  -0.815  1.00  0.00           O  
HETATM   15  C13 UNL     1      -0.800  -1.593  -0.721  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.106  -0.150  -0.659  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.976   0.457  -1.672  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.362  -0.008  -1.837  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.278   0.116  -0.676  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.443   1.572  -0.210  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.412   1.492   0.983  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.684   0.896   0.444  1.00  0.00           C  
HETATM   23  O3  UNL     1      -7.215   1.494  -0.553  1.00  0.00           O  
HETATM   24  O4  UNL     1      -7.250  -0.244   0.998  1.00  0.00           O  
HETATM   25  H1  UNL     1       7.113   0.352  -2.251  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.368   0.944  -2.396  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.604   2.073  -1.799  1.00  0.00           H  
HETATM   28  H4  UNL     1       6.871   0.180   0.143  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.635   1.492   0.203  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.023  -0.069  -1.026  1.00  0.00           H  
HETATM   31  H7  UNL     1       5.298  -1.294  -0.995  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.756  -1.669   0.858  1.00  0.00           H  
HETATM   33  H9  UNL     1       5.428  -1.240   1.451  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.808   1.006   1.998  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.741  -0.138   2.806  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.873   1.283   0.264  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.242   2.521   2.351  1.00  0.00           H  
HETATM   38  H14 UNL     1       0.954  -0.041   2.245  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.896  -0.921  -0.474  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.507  -2.915   0.338  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.520  -1.525   2.657  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.853  -2.161   1.821  1.00  0.00           H  
HETATM   43  H19 UNL     1      -0.375  -1.956  -1.660  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.133   0.435  -0.629  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.541   0.051   0.369  1.00  0.00           H  
HETATM   46  H22 UNL     1      -1.489   0.450  -2.697  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.021   1.570  -1.438  1.00  0.00           H  
HETATM   48  H24 UNL     1      -3.353  -1.013  -2.302  1.00  0.00           H  
HETATM   49  H25 UNL     1      -3.818   0.645  -2.656  1.00  0.00           H  
HETATM   50  H26 UNL     1      -4.013  -0.439   0.225  1.00  0.00           H  
HETATM   51  H27 UNL     1      -5.316  -0.154  -1.043  1.00  0.00           H  
HETATM   52  H28 UNL     1      -4.856   2.203  -0.994  1.00  0.00           H  
HETATM   53  H29 UNL     1      -3.482   1.884   0.190  1.00  0.00           H  
HETATM   54  H30 UNL     1      -5.657   2.501   1.352  1.00  0.00           H  
HETATM   55  H31 UNL     1      -5.007   0.839   1.771  1.00  0.00           H  
HETATM   56  H32 UNL     1      -7.767  -0.202   1.859  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    8   36
CONECT    7   37
CONECT    8    9    9   38
CONECT    9   10   39
CONECT   10   11   15   40
CONECT   11   12   12   41
CONECT   12   13   42
CONECT   13   14   14   15
CONECT   15   16   43
CONECT   16   17   44   45
CONECT   17   18   46   47
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   23   23   24
CONECT   24   56
END

HMDB0002236
     RDKit          3D
8-iso-PGA1
 56 56  0  0  0  0  0  0  0  0999 V2000
    6.3121    0.9842   -1.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9867    0.6151   -0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8776   -0.4237   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4999   -0.8458    0.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.2828    1.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    0.9357    1.2816 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4223    1.9836    2.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950   -0.0308    1.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2873   -0.8946    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663   -1.8605    0.4581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7127   -1.7881    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9388   -2.1059    1.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9288   -2.4083   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7020   -3.1710   -0.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7999   -1.5935   -0.7211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1061   -0.1498   -0.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758    0.4568   -1.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3624   -0.0077   -1.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2777    0.1160   -0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4426    1.5720   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4116    1.4920    0.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6836    0.8962    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2154    1.4943   -0.5535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2497   -0.2436    0.9979 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1127    0.3522   -2.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677    0.9443   -2.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6040    2.0730   -1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715    0.1796    0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350    1.4922    0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0233   -0.0692   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2975   -1.2941   -0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558   -1.6690    0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4275   -1.2404    1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8077    1.0065    1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407   -0.1384    2.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8729    1.2829    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418    2.5215    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -0.0409    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -0.9208   -0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5074   -2.9151    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5205   -1.5253    2.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534   -2.1612    1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3754   -1.9556   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1325    0.4352   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5410    0.0511    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889    0.4499   -2.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    1.5705   -1.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3531   -1.0125   -2.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184    0.6449   -2.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0126   -0.4386    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3155   -0.1536   -1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8563    2.2031   -0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4816    1.8840    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6575    2.5013    1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0069    0.8387    1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7668   -0.2017    1.8586 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  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 12 42  1  0
 15 43  1  6
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(8S,12S)-15S-Hydroxy-9-oxoprosta-10Z,13E-dien-1-Oate	HMDB
(8S,12S)-15S-Hydroxy-9-oxoprosta-10Z,13E-dien-1-Oic acid	HMDB
8-Isoprostaglandin a1 (8-iso pga1)	HMDB
9-oxo-15S-Hydroxy-10Z,13E-prostadienoate	HMDB
9-oxo-15S-Hydroxy-10Z,13E-prostadienoic acid	HMDB
9-oxo-15S-Hydroxy-10Z,13E-prostadienoic acid-cyclo[8S,12S]	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

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

Traditional Name

8-iso-PGA1

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18-/m0/s1

InChI Key

BGKHCLZFGPIKKU-DRSVPBQLSA-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
Ketone
Cyclic ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Isoprostanes (LMFA03110008 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002236)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002236)

Source

Endogenous

Endogenous (HMDB: HMDB0002236)

Animal

Animal (HMDB: HMDB0002236)

Exogenous

Food

Food (HMDB: HMDB0002236)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0002236)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002236)

Modulator

Immunomodulator (HMDB: HMDB0002236)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002236)

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	0.015 g/L	ALOGPS
logP	4.21	ALOGPS
logP	4.74	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	97.97 m³·mol⁻¹	ChemAxon
Polarizability	39.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	192.041	30932474
DeepCCS	[M-H]-	189.682	30932474
DeepCCS	[M-2H]-	223.783	30932474
DeepCCS	[M+Na]+	199.01	30932474
AllCCS	[M+H]+	189.2	32859911
AllCCS	[M+H-H2O]+	186.4	32859911
AllCCS	[M+NH4]+	191.7	32859911
AllCCS	[M+Na]+	192.5	32859911
AllCCS	[M-H]-	189.1	32859911
AllCCS	[M+Na-2H]-	190.4	32859911
AllCCS	[M+HCOO]-	191.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.2 minutes	32390414
Predicted by Siyang on May 30, 2022	16.0771 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.9 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	40.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2797.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	433.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	701.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	540.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	117.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1590.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	524.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1550.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	486.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	291.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	313.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-iso-PGA1	CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@H]1CCCCCCC(O)=O	4357.3	Standard polar	33892256
8-iso-PGA1	CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@H]1CCCCCCC(O)=O	2548.3	Standard non polar	33892256
8-iso-PGA1	CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@H]1CCCCCCC(O)=O	2743.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-iso-PGA1,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@H]1CCCCCCC(=O)O)O[Si](C)(C)C	2801.9	Semi standard non polar	33892256
8-iso-PGA1,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1C=CC(=O)[C@H]1CCCCCCC(=O)O[Si](C)(C)C	2711.2	Semi standard non polar	33892256
8-iso-PGA1,1TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O	2866.4	Semi standard non polar	33892256
8-iso-PGA1,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@H]1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2788.2	Semi standard non polar	33892256
8-iso-PGA1,2TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O)O[Si](C)(C)C	2927.0	Semi standard non polar	33892256
8-iso-PGA1,2TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C	2841.4	Semi standard non polar	33892256
8-iso-PGA1,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2941.2	Semi standard non polar	33892256
8-iso-PGA1,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2755.6	Standard non polar	33892256
8-iso-PGA1,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3073.2	Standard polar	33892256
8-iso-PGA1,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@H]1CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3050.1	Semi standard non polar	33892256
8-iso-PGA1,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1C=CC(=O)[C@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2975.2	Semi standard non polar	33892256
8-iso-PGA1,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O	3108.0	Semi standard non polar	33892256
8-iso-PGA1,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@H]1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3316.6	Semi standard non polar	33892256
8-iso-PGA1,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3395.4	Semi standard non polar	33892256
8-iso-PGA1,2TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3315.4	Semi standard non polar	33892256
8-iso-PGA1,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3642.2	Semi standard non polar	33892256
8-iso-PGA1,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3227.2	Standard non polar	33892256
8-iso-PGA1,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3267.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-PGA1 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0673-4092000000-6874868660d1be2cc397	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-PGA1 GC-MS (2 TMS) - 70eV, Positive	splash10-0006-9103300000-0b8807822e2ae6a44c8e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-PGA1 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 10V, Positive-QTOF	splash10-0gb9-0029000000-ef612f000f40cf5fb612	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 20V, Positive-QTOF	splash10-0l6u-3194000000-1d504119f0ddf6f99cfc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 40V, Positive-QTOF	splash10-05tv-9120000000-04e28ba462f08d52e16b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 10V, Negative-QTOF	splash10-000i-0019000000-af954838d61275b1a6b2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 20V, Negative-QTOF	splash10-014r-2159000000-3d6b28690c12cfabfbb1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 40V, Negative-QTOF	splash10-0a4i-9540000000-0657404cf2ca8a295d26	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 10V, Positive-QTOF	splash10-0uxr-0019000000-943865bd4f76ac81c5b5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 20V, Positive-QTOF	splash10-0uxr-8978000000-1b9129ec137ac84e784f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 40V, Positive-QTOF	splash10-05qc-9500000000-74f6b19254976131ff01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 10V, Negative-QTOF	splash10-014r-0029000000-eee5cd4fa1c96d9b3408	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 20V, Negative-QTOF	splash10-00kr-0597000000-eae1be9c15781533cefc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGA1 40V, Negative-QTOF	splash10-05oa-5940000000-1dadced25493924491cc	2021-09-22	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

FDB022923

KNApSAcK ID

Not Available

Chemspider ID

4975993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6473771

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Tazzeo T, Miller J, Janssen LJ: Vasoconstrictor responses, and underlying mechanisms, to isoprostanes in human and porcine bronchial arterial smooth muscle. Br J Pharmacol. 2003 Oct;140(4):759-63. Epub 2003 Sep 22. [PubMed:14504139 ]
Lipid Maps (LMFA03110008) [Link]

Showing metabocard for 8-iso-PGA1 (HMDB0002236)

MOL for HMDB0002236 (8-iso-PGA1)

3D MOL for HMDB0002236 (8-iso-PGA1)

3D SDF for HMDB0002236 (8-iso-PGA1)

3D-SDF for HMDB0002236 (8-iso-PGA1)

PDB for HMDB0002236 (8-iso-PGA1)

3D PDB for HMDB0002236 (8-iso-PGA1)

SMILES for HMDB0002236 (8-iso-PGA1)

INCHI for HMDB0002236 (8-iso-PGA1)

Structure for HMDB0002236 (8-iso-PGA1)

3D Structure for HMDB0002236 (8-iso-PGA1)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra