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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:37 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002115

Secondary Accession Numbers

HMDB02115

Metabolite Identification

Common Name

8-isoprostaglandin PGF2b

Description

8-isoprostaglandin PGF2beta 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

HMDB0002115
     RDKit          3D
8-isoprostaglandin PGF2b
 59 59  0  0  0  0  0  0  0  0999 V2000
   -6.3411    2.0455   -1.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1201    0.8194   -0.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8084    1.2150    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5839    0.0248    1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4546   -0.8698    1.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1121   -0.2141    1.0423 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0131    0.8560    0.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0212   -1.1639    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9681   -0.8218   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512   -1.7896   -0.3387 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4358   -1.5835    0.1641 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3221   -0.6372   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8894    0.7445   -0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703    1.7399   -0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226    1.5524    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9922    2.2764   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2720    2.0571    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4194    2.7376    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3035    3.4173   -1.0089 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6758    2.6523    0.6143 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9794   -3.0117   -0.2130 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3457   -3.0506   -0.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -3.1300   -1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3138   -2.1324   -1.7853 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8137   -2.7549   -2.3183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902    1.9514   -2.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402    2.9859   -1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3805    2.1117   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0554    0.2149   -0.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2993    0.1822   -1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9985    1.9475    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7373    1.7505    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4991    0.3311    2.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5369   -0.5790    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232   -1.3380    0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4144   -1.7092    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9002    0.1061    2.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9482    0.5495   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -2.1794    1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721    0.1828   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -2.8291    0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5041   -1.4484    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4249   -0.9879   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3568   -0.8072   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756    0.9596   -1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082    2.7936   -0.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740    0.5713    0.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6863    2.1649    1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392    1.9471   -1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8141    3.3706   -0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4776    0.9490    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1753    2.4244    1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1494    1.7756    0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4747   -3.6814    0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -2.6171    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0222   -4.1466   -1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2516   -2.9521   -2.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532   -1.2826   -2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049   -3.6905   -2.0145 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  1
 11 42  1  1
 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  1
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  6
 25 59  1  0
M  END


  Mrv0541 02231219222D          

 25 25  0  0  1  0            999 V2000
   17.7088  -10.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0584   -8.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6062   -5.8380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6727   -5.9091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2310   -7.2682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9388   -8.7978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.6062   -8.3129    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1938   -9.5824    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.2737   -8.7978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.0188   -9.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1542   -8.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6062   -7.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5412   -9.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3207   -7.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3207   -6.2504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7565   -8.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0352   -5.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0352   -5.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5850   -8.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7497   -4.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8003   -7.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7497   -3.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6288   -6.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4641   -3.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8443   -6.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  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>
HMDB0002115

> <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-HMALSPAFSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.07769855728773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1S,2R,3R,5R)-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-iso-PGF2β

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002115
     RDKit          3D
8-isoprostaglandin PGF2b
 59 59  0  0  0  0  0  0  0  0999 V2000
   -6.3411    2.0455   -1.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1201    0.8194   -0.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8084    1.2150    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5839    0.0248    1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4546   -0.8698    1.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1121   -0.2141    1.0423 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0131    0.8560    0.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0212   -1.1639    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9681   -0.8218   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512   -1.7896   -0.3387 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4358   -1.5835    0.1641 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3221   -0.6372   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8894    0.7445   -0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703    1.7399   -0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226    1.5524    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9922    2.2764   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2720    2.0571    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4194    2.7376    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3035    3.4173   -1.0089 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6758    2.6523    0.6143 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9794   -3.0117   -0.2130 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3457   -3.0506   -0.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -3.1300   -1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3138   -2.1324   -1.7853 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8137   -2.7549   -2.3183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902    1.9514   -2.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402    2.9859   -1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3805    2.1117   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0554    0.2149   -0.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2993    0.1822   -1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9985    1.9475    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7373    1.7505    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4991    0.3311    2.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5369   -0.5790    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232   -1.3380    0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4144   -1.7092    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9002    0.1061    2.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9482    0.5495   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -2.1794    1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721    0.1828   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -2.8291    0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5041   -1.4484    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4249   -0.9879   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3568   -0.8072   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756    0.9596   -1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082    2.7936   -0.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740    0.5713    0.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6863    2.1649    1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392    1.9471   -1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8141    3.3706   -0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4776    0.9490    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1753    2.4244    1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1494    1.7756    0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4747   -3.6814    0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -2.6171    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0222   -4.1466   -1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2516   -2.9521   -2.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532   -1.2826   -2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049   -3.6905   -2.0145 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  1
 11 42  1  1
 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  1
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  6
 25 59  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      33.057 -19.133   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.442 -15.947   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.732 -10.898   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      25.522 -11.030   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      24.698 -13.567   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      33.486 -16.423   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.732 -15.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.962 -17.887   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.978 -16.423   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.502 -17.887   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.021 -15.947   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.732 -13.977   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.877 -16.977   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.065 -13.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.065 -11.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.412 -16.501   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.399 -10.898   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.399  -9.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.092 -14.995   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.733  -8.587   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.627 -14.519   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      38.733  -7.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.307 -13.013   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      40.066  -6.277   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.843 -12.537   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    HMDB0002115
HETATM    1  C1  UNL     1      -6.341   2.046  -1.666  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.120   0.819  -0.813  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.808   1.215   0.626  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.584   0.025   1.497  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.455  -0.870   1.078  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.112  -0.214   1.042  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.013   0.856   0.173  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.021  -1.164   0.707  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.968  -0.822  -0.053  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.051  -1.790  -0.339  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.436  -1.584   0.164  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.322  -0.637  -0.572  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.889   0.745  -0.677  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.570   1.740  -0.167  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.823   1.552   0.555  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.992   2.276  -0.117  1.00  0.00           C  
HETATM   17  C16 UNL     1       6.272   2.057   0.661  1.00  0.00           C  
HETATM   18  C17 UNL     1       7.419   2.738   0.047  1.00  0.00           C  
HETATM   19  O2  UNL     1       7.303   3.417  -1.009  1.00  0.00           O  
HETATM   20  O3  UNL     1       8.676   2.652   0.614  1.00  0.00           O  
HETATM   21  C18 UNL     1       1.979  -3.012  -0.213  1.00  0.00           C  
HETATM   22  O4  UNL     1       3.346  -3.051  -0.116  1.00  0.00           O  
HETATM   23  C19 UNL     1       1.455  -3.130  -1.633  1.00  0.00           C  
HETATM   24  C20 UNL     1       0.314  -2.132  -1.785  1.00  0.00           C  
HETATM   25  O5  UNL     1      -0.814  -2.755  -2.318  1.00  0.00           O  
HETATM   26  H1  UNL     1      -5.690   1.951  -2.575  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.140   2.986  -1.123  1.00  0.00           H  
HETATM   28  H3  UNL     1      -7.381   2.112  -2.053  1.00  0.00           H  
HETATM   29  H4  UNL     1      -7.055   0.215  -0.831  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.299   0.182  -1.205  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.998   1.947   0.588  1.00  0.00           H  
HETATM   32  H7  UNL     1      -6.737   1.751   0.995  1.00  0.00           H  
HETATM   33  H8  UNL     1      -5.499   0.331   2.571  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.537  -0.579   1.463  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.723  -1.338   0.088  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.414  -1.709   1.821  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.900   0.106   2.107  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.948   0.549  -0.750  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.048  -2.179   1.075  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.972   0.183  -0.407  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.242  -2.829   0.103  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.504  -1.448   1.247  1.00  0.00           H  
HETATM   43  H18 UNL     1       2.425  -0.988  -1.672  1.00  0.00           H  
HETATM   44  H19 UNL     1       3.357  -0.807  -0.204  1.00  0.00           H  
HETATM   45  H20 UNL     1       0.976   0.960  -1.223  1.00  0.00           H  
HETATM   46  H21 UNL     1       2.208   2.794  -0.268  1.00  0.00           H  
HETATM   47  H22 UNL     1       4.074   0.571   0.926  1.00  0.00           H  
HETATM   48  H23 UNL     1       3.686   2.165   1.518  1.00  0.00           H  
HETATM   49  H24 UNL     1       5.139   1.947  -1.161  1.00  0.00           H  
HETATM   50  H25 UNL     1       4.814   3.371  -0.142  1.00  0.00           H  
HETATM   51  H26 UNL     1       6.478   0.949   0.660  1.00  0.00           H  
HETATM   52  H27 UNL     1       6.175   2.424   1.702  1.00  0.00           H  
HETATM   53  H28 UNL     1       9.149   1.776   0.795  1.00  0.00           H  
HETATM   54  H29 UNL     1       1.475  -3.681   0.504  1.00  0.00           H  
HETATM   55  H30 UNL     1       3.590  -2.617   0.757  1.00  0.00           H  
HETATM   56  H31 UNL     1       1.022  -4.147  -1.732  1.00  0.00           H  
HETATM   57  H32 UNL     1       2.252  -2.952  -2.381  1.00  0.00           H  
HETATM   58  H33 UNL     1       0.553  -1.283  -2.419  1.00  0.00           H  
HETATM   59  H34 UNL     1      -0.905  -3.690  -2.014  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

HMDB0002115
     RDKit          3D
8-isoprostaglandin PGF2b
 59 59  0  0  0  0  0  0  0  0999 V2000
   -6.3411    2.0455   -1.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1201    0.8194   -0.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8084    1.2150    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5839    0.0248    1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4546   -0.8698    1.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1121   -0.2141    1.0423 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0131    0.8560    0.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0212   -1.1639    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9681   -0.8218   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512   -1.7896   -0.3387 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4358   -1.5835    0.1641 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3221   -0.6372   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8894    0.7445   -0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703    1.7399   -0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226    1.5524    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9922    2.2764   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2720    2.0571    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4194    2.7376    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3035    3.4173   -1.0089 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6758    2.6523    0.6143 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9794   -3.0117   -0.2130 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3457   -3.0506   -0.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -3.1300   -1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3138   -2.1324   -1.7853 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8137   -2.7549   -2.3183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902    1.9514   -2.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402    2.9859   -1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3805    2.1117   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0554    0.2149   -0.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2993    0.1822   -1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9985    1.9475    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7373    1.7505    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4991    0.3311    2.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5369   -0.5790    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232   -1.3380    0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4144   -1.7092    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9002    0.1061    2.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9482    0.5495   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475   -2.1794    1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721    0.1828   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -2.8291    0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5041   -1.4484    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4249   -0.9879   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3568   -0.8072   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756    0.9596   -1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082    2.7936   -0.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740    0.5713    0.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6863    2.1649    1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392    1.9471   -1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8141    3.3706   -0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4776    0.9490    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1753    2.4244    1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1494    1.7756    0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4747   -3.6814    0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -2.6171    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0222   -4.1466   -1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2516   -2.9521   -2.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532   -1.2826   -2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049   -3.6905   -2.0145 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  1
 11 42  1  1
 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  1
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  6
 25 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Iso-PGF2b	HMDB
8-Iso-PGF2beta	HMDB
8-Isoprostaglandin PGF2beta	HMDB
9R,11R,15S-Trihydroxy-5Z,13E-prostadienoate	HMDB
9R,11R,15S-Trihydroxy-5Z,13E-prostadienoic acid	HMDB
9R,11R,15S-Trihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12R]	HMDB
8-Iso-PGF(2beta)	HMDB
8-Iso-PGF2β	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

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

Traditional Name

8-iso-PGF2β

CAS Registry Number

177020-26-7

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-HMALSPAFSA-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

Isoprostanes (LMFA03110006 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 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	41.08 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]+	188.683	31661259
DarkChem	[M-H]-	191.673	31661259
DeepCCS	[M+H]+	199.41	30932474
DeepCCS	[M-H]-	197.015	30932474
DeepCCS	[M-2H]-	230.32	30932474
DeepCCS	[M+Na]+	205.323	30932474
AllCCS	[M+H]+	194.3	32859911
AllCCS	[M+H-H2O]+	191.6	32859911
AllCCS	[M+NH4]+	196.7	32859911
AllCCS	[M+Na]+	197.4	32859911
AllCCS	[M-H]-	191.8	32859911
AllCCS	[M+Na-2H]-	193.1	32859911
AllCCS	[M+HCOO]-	194.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-isoprostaglandin PGF2b	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 PGF2b	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 PGF2b	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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b,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 PGF2b 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 PGF2b 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 PGF2b 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 PGF2b 10V, Positive-QTOF	splash10-014r-0019000000-3c46ffbee46021b80901	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 20V, Positive-QTOF	splash10-01bi-2297000000-9fe530991fdc645e26f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 40V, Positive-QTOF	splash10-0103-9170000000-0fa33343bc482bd6f5a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 10V, Negative-QTOF	splash10-0udr-0009000000-a337fc1b13431013f06a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 20V, Negative-QTOF	splash10-000i-1039000000-40b895b35529c4a81763	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 40V, Negative-QTOF	splash10-0a4i-9631000000-8dc66a223446641955e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 10V, Negative-QTOF	splash10-0udi-0009000000-4f29fd22c6b0dfe3ac77	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 20V, Negative-QTOF	splash10-0udr-0098000000-06ede09931efe0fba78e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 40V, Negative-QTOF	splash10-00el-9182000000-f1a4c9aba7f705d2868d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 10V, Positive-QTOF	splash10-014r-0019000000-ece58dc4c35634d7fe3f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 20V, Positive-QTOF	splash10-014i-9255000000-c6aef7e365cba872a558	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-isoprostaglandin PGF2b 40V, Positive-QTOF	splash10-05mo-9300000000-552900f74505f7605b0b	2021-09-24	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

FDB022851

KNApSAcK ID

Not Available

Chemspider ID

4446337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283216

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 ]

Showing metabocard for 8-isoprostaglandin PGF2b (HMDB0002115)

MOL for HMDB0002115 (8-isoprostaglandin PGF2b)

3D MOL for HMDB0002115 (8-isoprostaglandin PGF2b)

3D SDF for HMDB0002115 (8-isoprostaglandin PGF2b)

3D-SDF for HMDB0002115 (8-isoprostaglandin PGF2b)

PDB for HMDB0002115 (8-isoprostaglandin PGF2b)

3D PDB for HMDB0002115 (8-isoprostaglandin PGF2b)

SMILES for HMDB0002115 (8-isoprostaglandin PGF2b)

INCHI for HMDB0002115 (8-isoprostaglandin PGF2b)

Structure for HMDB0002115 (8-isoprostaglandin PGF2b)

3D Structure for HMDB0002115 (8-isoprostaglandin PGF2b)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra