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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-25 11:03:23 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005083

Secondary Accession Numbers

HMDB05083

Metabolite Identification

Common Name

8-Isoprostaglandin F2a

Description

8-Isoprostaglandin F2a is an isoprostane and a potent renal vasoconstrictor. Isoprostanes are prostaglandin-like compounds that are produced in vivo in humans by a noncyclooxygenase mechanism involving free radical-catalyzed peroxidation of arachidonic acid. The formation of these prostanoids proceeds through bicyclic endoperoxide intermediates that are then reduced to form ring isoprostanes. Of considerable interest is that, in contradistinction to cyclooxygenase-derived prostaglandins, isoprostanes have been shown to be initially formed in situ, esterified to phospholipids, and subsequently released preformed, presumably by phospholipases. The fact that prostanoids are produced in vivo by a noncyclooxygenase mechanism is of considerable interest from a biochemical perspective. However, this may also be associated with biological ramifications since it has been shown that these compounds are capable of exerting potent biological activity. (PMID: 7825845 , 17012140 ). 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. 8-iso-prostaglandin F2A is a biomarker for the consumption of offal meat.

Structure

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

HMDB0005083
     RDKit          3D
8-Isoprostaglandin F2a
 59 59  0  0  0  0  0  0  0  0999 V2000
    5.1496    4.1843    0.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9995    2.9511    0.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1310    1.6796    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2612    1.7384   -0.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4135    0.5331   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4478    0.2367    0.3485 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0036    0.0231    1.5989 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7472   -1.0457   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4251   -1.1960    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2122   -2.4468   -0.2175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2411   -2.4012   -1.2752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3178   -1.3796   -1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1685   -1.4323    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2926   -0.4300    0.8627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6314    0.8744    0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917    1.9831    0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5323    1.7715   -0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5509    2.8481   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3747    2.8965   -1.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6431    3.8394    0.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886   -3.8251   -1.2471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9729   -4.6217   -2.0491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885   -4.2330    0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8723   -3.1838    0.9133 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1485   -3.7762    1.6697 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5427    4.9383    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0742    4.7223   -0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046    3.9416    1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6972    3.0030   -0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6043    2.8608    1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5443    1.6975    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8247    0.8336    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6987    2.6970   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9795    1.7409   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1177   -0.3502   -0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310    0.5208   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6751    1.0475    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2516    0.0835    2.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650   -1.8126   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488   -0.3483    0.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899   -3.1511   -0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -2.2991   -2.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639   -0.3661   -1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -1.5966   -2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577   -2.3374    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9691   -0.5698    1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    1.0223    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9495    1.0527   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1955    2.9730    0.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3515    1.9358    1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9488    0.7667   -0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8579    1.9099   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3447    4.7869    0.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8051   -3.8850   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183   -4.5300   -3.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -5.2174    0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640   -4.4291    0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935   -2.5434    1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -4.6860    1.9517 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  2  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  1  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  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  6
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  6
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  1
 25 59  1  0
M  END


  Mrv0541 02231220212D          

 25 25  0  0  1  0            999 V2000
   17.7438  -12.8746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0934  -11.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6412   -8.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7075   -8.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2659   -9.8929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9738  -11.4226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.6412  -10.9376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2287  -12.2072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.3087  -11.4226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.0537  -12.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1891  -11.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6412  -10.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5761  -11.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3557   -9.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3557   -8.8751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7914  -11.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0702   -8.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0702   -7.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6199  -10.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7847   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8352  -10.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7847   -6.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6637   -9.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4992   -5.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8791   -9.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  9  2  1  6  0  0  0
 15  3  1  1  0  0  0
  4 25  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  1  0  0  0
  7  9  1  0  0  0  0
  7 12  1  1  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 16  2  0  0  0  0
 14 15  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 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005083

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,18-,19+/m0/s1

> <INCHI_KEY>
PXGPLTODNUVGFL-NAPLMKITSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.70638545754415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.6110544173333317

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.513964334215405

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355294048784039

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263153076120291

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
100.47070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-isoprostane

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005083
     RDKit          3D
8-Isoprostaglandin F2a
 59 59  0  0  0  0  0  0  0  0999 V2000
    5.1496    4.1843    0.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9995    2.9511    0.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1310    1.6796    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2612    1.7384   -0.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4135    0.5331   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4478    0.2367    0.3485 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0036    0.0231    1.5989 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7472   -1.0457   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4251   -1.1960    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2122   -2.4468   -0.2175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2411   -2.4012   -1.2752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3178   -1.3796   -1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1685   -1.4323    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2926   -0.4300    0.8627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6314    0.8744    0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917    1.9831    0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5323    1.7715   -0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5509    2.8481   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3747    2.8965   -1.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6431    3.8394    0.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886   -3.8251   -1.2471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9729   -4.6217   -2.0491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885   -4.2330    0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8723   -3.1838    0.9133 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1485   -3.7762    1.6697 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5427    4.9383    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0742    4.7223   -0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046    3.9416    1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6972    3.0030   -0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6043    2.8608    1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5443    1.6975    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8247    0.8336    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6987    2.6970   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9795    1.7409   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1177   -0.3502   -0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310    0.5208   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6751    1.0475    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2516    0.0835    2.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650   -1.8126   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488   -0.3483    0.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899   -3.1511   -0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -2.2991   -2.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639   -0.3661   -1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -1.5966   -2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577   -2.3374    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9691   -0.5698    1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    1.0223    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9495    1.0527   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1955    2.9730    0.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3515    1.9358    1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9488    0.7667   -0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8579    1.9099   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3447    4.7869    0.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8051   -3.8850   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183   -4.5300   -3.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -5.2174    0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640   -4.4291    0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935   -2.5434    1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -4.6860    1.9517 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  2  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  1  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  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  6
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  6
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  1
 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      33.122 -24.033   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.508 -20.846   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.797 -15.797   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      25.587 -15.930   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      24.763 -18.467   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      33.551 -21.322   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.797 -20.417   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.027 -22.787   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      36.043 -21.322   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.567 -22.787   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.086 -20.846   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.797 -18.877   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.942 -21.877   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.131 -18.107   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.131 -16.567   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.477 -21.401   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.464 -15.797   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.464 -14.257   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.157 -19.894   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.798 -13.487   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.692 -19.419   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      38.798 -11.947   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.372 -17.912   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      40.132 -11.177   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.908 -17.436   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4   25                                                            
CONECT    5   25                                                            
CONECT    6    7    8   11                                                  
CONECT    7    6    9   12                                                  
CONECT    8    1    6   10                                                  
CONECT    9    2    7   10                                                  
CONECT   10    8    9                                                       
CONECT   11    6   13                                                       
CONECT   12    7   14                                                       
CONECT   13   11   16                                                       
CONECT   14   12   15                                                       
CONECT   15    3   14   17                                                  
CONECT   16   13   19                                                       
CONECT   17   15   18                                                       
CONECT   18   17   20                                                       
CONECT   19   16   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22                                                            
CONECT   25    4    5   23                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0005083
HETATM    1  C1  UNL     1       5.150   4.184   0.803  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.999   2.951   0.724  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.131   1.680   0.637  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.261   1.738  -0.592  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.413   0.533  -0.742  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.448   0.237   0.349  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.004   0.023   1.599  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.747  -1.046  -0.037  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.425  -1.196   0.168  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.212  -2.447  -0.218  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.241  -2.401  -1.275  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.318  -1.380  -1.168  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.168  -1.432   0.010  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.293  -0.430   0.863  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.631   0.874   0.797  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.692   1.983   0.711  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.532   1.771  -0.542  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.551   2.848  -0.612  1.00  0.00           C  
HETATM   19  O2  UNL     1      -6.375   2.896  -1.562  1.00  0.00           O  
HETATM   20  O3  UNL     1      -5.643   3.839   0.353  1.00  0.00           O  
HETATM   21  C18 UNL     1      -1.789  -3.825  -1.247  1.00  0.00           C  
HETATM   22  O4  UNL     1      -0.973  -4.622  -2.049  1.00  0.00           O  
HETATM   23  C19 UNL     1      -1.688  -4.233   0.190  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.872  -3.184   0.913  1.00  0.00           C  
HETATM   25  O5  UNL     1       0.149  -3.776   1.670  1.00  0.00           O  
HETATM   26  H1  UNL     1       5.543   4.938   1.527  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.074   4.722  -0.170  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.105   3.942   1.113  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.697   3.003  -0.130  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.604   2.861   1.640  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.544   1.698   1.586  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.825   0.834   0.559  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.699   2.697  -0.660  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.980   1.741  -1.463  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.118  -0.350  -0.806  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.831   0.521  -1.700  1.00  0.00           H  
HETATM   37  H12 UNL     1       1.675   1.047   0.472  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.252   0.083   2.256  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.365  -1.813  -0.477  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.049  -0.348   0.614  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.590  -3.151  -0.595  1.00  0.00           H  
HETATM   42  H17 UNL     1      -0.723  -2.299  -2.279  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.964  -0.366  -1.375  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.014  -1.597  -2.053  1.00  0.00           H  
HETATM   45  H20 UNL     1      -3.758  -2.337   0.241  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.969  -0.570   1.734  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.126   1.022   1.791  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.950   1.053  -0.033  1.00  0.00           H  
HETATM   49  H24 UNL     1      -3.195   2.973   0.646  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.351   1.936   1.593  1.00  0.00           H  
HETATM   51  H26 UNL     1      -4.949   0.767  -0.599  1.00  0.00           H  
HETATM   52  H27 UNL     1      -3.858   1.910  -1.425  1.00  0.00           H  
HETATM   53  H28 UNL     1      -5.345   4.787   0.227  1.00  0.00           H  
HETATM   54  H29 UNL     1      -2.805  -3.885  -1.667  1.00  0.00           H  
HETATM   55  H30 UNL     1      -1.218  -4.530  -3.007  1.00  0.00           H  
HETATM   56  H31 UNL     1      -1.137  -5.217   0.242  1.00  0.00           H  
HETATM   57  H32 UNL     1      -2.664  -4.429   0.673  1.00  0.00           H  
HETATM   58  H33 UNL     1      -1.493  -2.543   1.554  1.00  0.00           H  
HETATM   59  H34 UNL     1      -0.081  -4.686   1.952  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   14   45
CONECT   14   15   46
CONECT   15   16   47   48
CONECT   16   17   49   50
CONECT   17   18   51   52
CONECT   18   19   19   20
CONECT   20   53
CONECT   21   22   23   54
CONECT   22   55
CONECT   23   24   56   57
CONECT   24   25   58
CONECT   25   59
END

HMDB0005083
     RDKit          3D
8-Isoprostaglandin F2a
 59 59  0  0  0  0  0  0  0  0999 V2000
    5.1496    4.1843    0.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9995    2.9511    0.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1310    1.6796    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2612    1.7384   -0.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4135    0.5331   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4478    0.2367    0.3485 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0036    0.0231    1.5989 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7472   -1.0457   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4251   -1.1960    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2122   -2.4468   -0.2175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2411   -2.4012   -1.2752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3178   -1.3796   -1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1685   -1.4323    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2926   -0.4300    0.8627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6314    0.8744    0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917    1.9831    0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5323    1.7715   -0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5509    2.8481   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3747    2.8965   -1.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6431    3.8394    0.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886   -3.8251   -1.2471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9729   -4.6217   -2.0491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885   -4.2330    0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8723   -3.1838    0.9133 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1485   -3.7762    1.6697 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5427    4.9383    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0742    4.7223   -0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046    3.9416    1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6972    3.0030   -0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6043    2.8608    1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5443    1.6975    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8247    0.8336    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6987    2.6970   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9795    1.7409   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1177   -0.3502   -0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310    0.5208   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6751    1.0475    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2516    0.0835    2.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650   -1.8126   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488   -0.3483    0.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899   -3.1511   -0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -2.2991   -2.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639   -0.3661   -1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -1.5966   -2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577   -2.3374    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9691   -0.5698    1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    1.0223    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9495    1.0527   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1955    2.9730    0.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3515    1.9358    1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9488    0.7667   -0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8579    1.9099   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3447    4.7869    0.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8051   -3.8850   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183   -4.5300   -3.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -5.2174    0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640   -4.4291    0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935   -2.5434    1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -4.6860    1.9517 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  2  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  1  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  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  6
 12 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  6
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  1
 25 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Epi-PGF2alpha	ChEBI
8-Epiprostaglandin F2alpha	ChEBI
8-Iso-PGF2a	ChEBI
8-Iso-PGF2alpha	ChEBI
8-Iso-PGF2alpha-III	ChEBI
8-IsoP	ChEBI
8-Isoprostaglandin F2alpha	ChEBI
8-Isoprostane	ChEBI
9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acid	ChEBI
8-Epi-prostaglandin F2alpha	Kegg
8-Epi-PGF2a	Generator
8-Epi-PGF2α	Generator
8-Epiprostaglandin F2a	Generator
8-Epiprostaglandin F2α	Generator
8-Iso-PGF2α	Generator
8-Iso-PGF2a-III	Generator
8-Iso-PGF2α-III	Generator
8-Isoprostaglandin F2α	Generator
9,11,15-Trihydroxy-prosta-5,13-dien-1-Oate	Generator
8-Epi-prostaglandin F2a	Generator
8-Epi-prostaglandin F2α	Generator
(5Z,13E,15S)-9alpha,11alpha,15-Trihydroxy-8beta-prosta-5,13-dien-1-Oate	HMDB
(5Z,13E,15S)-9alpha,11alpha,15-Trihydroxy-8beta-prosta-5,13-dien-1-Oic acid	HMDB
8-Epi PGF-2alpha	HMDB
9,11,15-Trihydroxy prosta-5,13-dien-1-Oate	HMDB
9,11,15-Trihydroxy prosta-5,13-dien-1-Oic acid	HMDB
9S,11R,15S-Trihydroxy-5Z,13E-prostadienoate	HMDB
9S,11R,15S-Trihydroxy-5Z,13E-prostadienoic acid	HMDB
9S,11R,15S-Trihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12R]	HMDB
15-F(2t)-IsoP	HMDB
15-F(2t)-Isoprostane	HMDB
8-F(2t)-Isoprostane	HMDB
8-Epi-PGF2 alpha	HMDB
8-Iso-PGF(2alpha)	HMDB
Isoprostaglandin F2alpha type-III	HMDB
15-F2t-IsoP	HMDB
15-F2t-Isoprostane	HMDB
8-Isoprostaglandin F2a	Generator

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

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

Traditional Name

8-isoprostane

CAS Registry Number

27415-26-5

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,18-,19+/m0/s1

InChI Key

PXGPLTODNUVGFL-NAPLMKITSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Hydroxy fatty acid
Cyclopentanol
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostanoid (CHEBI:34505 )
Isoprostanes (C13809 )
Isoprostanes (LMFA03110001 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16169205)

Excreta

Biofluid or Excreta

Urine (PMID: 16469980)

Cellular substructure

Extracellular (HMDB: HMDB0005083)
Membrane (HMDB: HMDB0005083)

Source

Exogenous

Exogenous (HMDB: HMDB0005083)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0005083)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.183	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	197.255	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001873

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.11	ALOGPS
logP	2.61	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	100.47 m³·mol⁻¹	ChemAxon
Polarizability	41.71 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]+	187.121	31661259
DarkChem	[M-H]-	190.843	31661259
DeepCCS	[M+H]+	199.729	30932474
DeepCCS	[M-H]-	197.333	30932474
DeepCCS	[M-2H]-	230.918	30932474
DeepCCS	[M+Na]+	205.666	30932474
AllCCS	[M+H]+	194.3	32859911
AllCCS	[M+H-H2O]+	191.7	32859911
AllCCS	[M+NH4]+	196.7	32859911
AllCCS	[M+Na]+	197.3	32859911
AllCCS	[M-H]-	191.8	32859911
AllCCS	[M+Na-2H]-	193.1	32859911
AllCCS	[M+HCOO]-	194.8	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.	5.99 minutes	32390414
Predicted by Siyang on May 30, 2022	12.6993 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.76 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	65.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2585.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	196.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	206.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	552.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	452.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	161.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1144.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	494.6 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	1368.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	335.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	372.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	368.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	167.6 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	11.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Isoprostaglandin F2a	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O	4461.2	Standard polar	33892256
8-Isoprostaglandin F2a	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O	2708.1	Standard non polar	33892256
8-Isoprostaglandin F2a	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O	2924.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Isoprostaglandin F2a,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O)O[Si](C)(C)C	2883.7	Semi standard non polar	33892256
8-Isoprostaglandin F2a,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O[Si](C)(C)C	2784.6	Semi standard non polar	33892256
8-Isoprostaglandin F2a,1TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C)C[C@H]1O	2765.8	Semi standard non polar	33892256
8-Isoprostaglandin F2a,1TMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O)C[C@H]1O	2816.1	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O)C[C@H]1O)O[Si](C)(C)C	2827.9	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C	2746.0	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TMS,isomer #3	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2755.7	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O)C[C@H]1O[Si](C)(C)C	2762.8	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TMS,isomer #5	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C	2750.7	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TMS,isomer #6	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O	2742.2	Semi standard non polar	33892256
8-Isoprostaglandin F2a,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C	2730.6	Semi standard non polar	33892256
8-Isoprostaglandin F2a,3TMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2744.9	Semi standard non polar	33892256
8-Isoprostaglandin F2a,3TMS,isomer #3	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2718.1	Semi standard non polar	33892256
8-Isoprostaglandin F2a,3TMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C	2713.7	Semi standard non polar	33892256
8-Isoprostaglandin F2a,4TMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2746.0	Semi standard non polar	33892256
8-Isoprostaglandin F2a,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3139.4	Semi standard non polar	33892256
8-Isoprostaglandin F2a,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C	2997.0	Semi standard non polar	33892256
8-Isoprostaglandin F2a,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O	2980.6	Semi standard non polar	33892256
8-Isoprostaglandin F2a,1TBDMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C[C@H]1O	3080.5	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3363.9	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3232.7	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TBDMS,isomer #3	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3245.1	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TBDMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C	3243.4	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TBDMS,isomer #5	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C	3197.2	Semi standard non polar	33892256
8-Isoprostaglandin F2a,2TBDMS,isomer #6	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O	3227.3	Semi standard non polar	33892256
8-Isoprostaglandin F2a,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3479.2	Semi standard non polar	33892256
8-Isoprostaglandin F2a,3TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3490.6	Semi standard non polar	33892256
8-Isoprostaglandin F2a,3TBDMS,isomer #3	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O)[C@@H](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	3429.7	Semi standard non polar	33892256
8-Isoprostaglandin F2a,3TBDMS,isomer #4	CCCCC[C@H](O)/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C	3432.6	Semi standard non polar	33892256
8-Isoprostaglandin F2a,4TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@@H]1[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@@H](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	3625.0	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-Isoprostaglandin F2a GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-6489000000-bf681ff653e664e9cde0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Isoprostaglandin F2a GC-MS (4 TMS) - 70eV, Positive	splash10-004i-9100177000-79583ccaf34002541a28	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Isoprostaglandin F2a GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Isoprostaglandin F2a 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 F2a 10V, Positive-QTOF	splash10-014r-0019000000-2c9767841fa4893c60b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 20V, Positive-QTOF	splash10-01bi-2297000000-8aa402b01c233708c42e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 40V, Positive-QTOF	splash10-0103-9170000000-b6c0e28782ad3916af75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 10V, Negative-QTOF	splash10-0udi-0019000000-43645725f77edc02f608	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 20V, Negative-QTOF	splash10-0f7c-1049000000-d2fc6ca599de8bc5b9a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 40V, Negative-QTOF	splash10-0a4i-9611000000-80d02fb42a0a241d8e2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 10V, Positive-QTOF	splash10-014r-0019000000-ece58dc4c35634d7fe3f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 20V, Positive-QTOF	splash10-014i-9255000000-c6aef7e365cba872a558	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 40V, Positive-QTOF	splash10-05mo-9300000000-552900f74505f7605b0b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 10V, Negative-QTOF	splash10-0udi-0009000000-4f29fd22c6b0dfe3ac77	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 20V, Negative-QTOF	splash10-0udr-0098000000-06ede09931efe0fba78e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Isoprostaglandin F2a 40V, Negative-QTOF	splash10-00el-9182000000-f1a4c9aba7f705d2868d	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00057 +/- 0.000057 uM	Adult (>18 years old)	Male	Normal	16169205	details
Blood	Detected and Quantified	0.00038 +/- 0.000048 uM	Adult (>18 years old)	Female	Normal	16169205	details
Blood	Detected and Quantified	0.000957 +/- 0.00102 uM	Adult (>18 years old)	Both	Normal	18953024	details
Blood	Detected and Quantified	0.000079 +/- 0.0000096 uM	Adult (>18 years old)	Both	Normal	9654406	details
Blood	Detected and Quantified	0.000151 +/- 0.000018 uM	Adult (>18 years old)	Both	Normal	20671299	details
Urine	Detected and Quantified	0.00018 +/- 0.000059 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	16469980	details
Urine	Detected and Quantified	0.00019 +/- 0.0001 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	16469980	details
Urine	Detected and Quantified	0.00027 +/- 0.00011 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	11545626	details
Urine	Detected and Quantified	0.00022 +/- 0.000019 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9654406	details
Urine	Detected and Quantified	0.000003 +/- 0 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	24817352	details
Urine	Detected and Quantified	0.000003 +/- 0.000003 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	24817352	details

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

FDB023622

KNApSAcK ID

Not Available

Chemspider ID

4445435

KEGG Compound ID

C13809

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282263

PDB ID

Not Available

ChEBI ID

34505

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

Roberts LJ 2nd, Morrow JD: Isoprostanes. Novel markers of endogenous lipid peroxidation and potential mediators of oxidant injury. Ann N Y Acad Sci. 1994 Nov 15;744:237-42. [PubMed:7825845 ]
Berg K, Haaverstad R, Astudillo R, Bjorngaard M, Skarra S, Wiseth R, Basu S, Jynge P: Oxidative stress during coronary artery bypass operations: importance of surgical trauma and drug treatment. Scand Cardiovasc J. 2006 Oct;40(5):291-7. [PubMed:17012140 ]

Showing metabocard for 8-Isoprostaglandin F2a (HMDB0005083)

MOL for HMDB0005083 (8-Isoprostaglandin F2a)

3D MOL for HMDB0005083 (8-Isoprostaglandin F2a)

3D SDF for HMDB0005083 (8-Isoprostaglandin F2a)

3D-SDF for HMDB0005083 (8-Isoprostaglandin F2a)

PDB for HMDB0005083 (8-Isoprostaglandin F2a)

3D PDB for HMDB0005083 (8-Isoprostaglandin F2a)

SMILES for HMDB0005083 (8-Isoprostaglandin F2a)

INCHI for HMDB0005083 (8-Isoprostaglandin F2a)

Structure for HMDB0005083 (8-Isoprostaglandin F2a)

3D Structure for HMDB0005083 (8-Isoprostaglandin F2a)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra