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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

HMDB0002132

Secondary Accession Numbers

HMDB02132

Metabolite Identification

Common Name

8-iso-PGF3a

Description

8-iso-PGF3alpha is an isoprostane with an antiaggregatory action in human blood. Isoprostanes (IsoPs) are formed in vivo from the free radical-catalyzed peroxidation of arachidonate independent of cyclooxygenase (COX). Although the structures of these compounds are very similar to COX-derived prostaglandins (PGs), an important distinction between IsoPs and PGs is that IsoP bicycloendoperoxide intermediates contain side chains that are predominantly (>90%) oriented cis in relation to the prostane ring because the generation of these intermediates is favored kinetically. In contrast to other types of prostanoids, E2/D2-IsoPs are beta-hydroxyketone-containing compounds that can undergo reversible keto-enol tautomerization under both acidic and basic conditions, allowing rearrangement of the side chains that are initially cis to the more stable trans-configuration. (PMID: 12746435 ).

Structure

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

HMDB0002132
     RDKit          3D
8-iso-PGF3a
 57 57  0  0  0  0  0  0  0  0999 V2000
    7.2260   -1.1588    1.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1786   -0.2224    2.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5345    0.5590    1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2424    0.5069    0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2593   -0.3099    1.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6260   -1.2385    0.6461 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6570   -1.9938    0.1181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -0.4037   -0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635    0.3868   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2620    1.2485   -1.1390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0933    0.7644   -1.5744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2413    0.8653   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    0.1994    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434   -0.7280    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1940   -1.2118    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5259   -0.9194    0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5586    0.5865    0.9191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7979    1.0223    1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9407    2.2456    1.8191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7699    0.1432    2.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135   -0.6132   -2.0808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7465   -1.2699   -2.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3673   -0.1685   -3.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.1049   -2.5358 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4624    2.1937   -3.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7996   -2.1683    1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1498   -1.1718    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5038   -0.7179    0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -0.7264    2.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930    0.5255    2.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    1.1988    0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8963    1.1494    0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6525   -0.9715    2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4116    0.2930    2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -1.8887    1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -2.7860   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838   -0.4544   -1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454    0.3870    0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277    2.2985   -0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    1.3669   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    1.9917   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1589    0.7252   -1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    0.4766    1.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966   -1.1963    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371   -2.3280    0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3111   -0.7828   -0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5741   -1.4659    1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3558   -1.2403    0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5422    1.0527   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6462    0.9045    1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7771   -0.3166    2.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2590   -1.1939   -1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4662   -0.6830   -3.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2383    0.0604   -4.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0734   -0.9534   -3.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    1.1780   -2.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4993    1.9946   -4.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  1
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  1
 11 40  1  6
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 20 51  1  0
 21 52  1  1
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  1
 25 57  1  0
M  END


  Mrv0541 02231219222D          

 25 25  0  0  1  0            999 V2000
   17.3513   -9.0892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7007   -7.3823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2485   -4.6775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3151   -4.7486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8736   -6.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5812   -7.6374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2485   -7.1524    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8361   -8.4218    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9161   -7.6374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.6611   -8.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7965   -7.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2485   -6.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1835   -7.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9631   -5.9150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9631   -5.0900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.3990   -7.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2275   -6.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6775   -4.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4428   -6.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6775   -3.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2713   -5.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3919   -3.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4867   -5.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1065   -3.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8209   -3.4400    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 23  1  0  0  0  0
  5 23  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 18  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002132

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C[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/C20H32O5/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/h3-4,6-7,12-13,15-19,21-23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16-,17+,18-,19+/m0/s1

> <INCHI_KEY>
SAKGBZWJAIABSY-PJCXKLBTSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.351395910432814

> <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,5Z)-3-hydroxyocta-1,5-dien-1-yl]cyclopentyl]hept-5-enoic acid

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
2.2491327606666656

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.513964223287505

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355294009909431

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6652743603062334

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
101.5873

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-iso-PGF3α

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002132
     RDKit          3D
8-iso-PGF3a
 57 57  0  0  0  0  0  0  0  0999 V2000
    7.2260   -1.1588    1.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1786   -0.2224    2.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5345    0.5590    1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2424    0.5069    0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2593   -0.3099    1.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6260   -1.2385    0.6461 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6570   -1.9938    0.1181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -0.4037   -0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635    0.3868   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2620    1.2485   -1.1390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0933    0.7644   -1.5744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2413    0.8653   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    0.1994    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434   -0.7280    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1940   -1.2118    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5259   -0.9194    0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5586    0.5865    0.9191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7979    1.0223    1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9407    2.2456    1.8191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7699    0.1432    2.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135   -0.6132   -2.0808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7465   -1.2699   -2.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3673   -0.1685   -3.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.1049   -2.5358 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4624    2.1937   -3.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7996   -2.1683    1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1498   -1.1718    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5038   -0.7179    0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -0.7264    2.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930    0.5255    2.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    1.1988    0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8963    1.1494    0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6525   -0.9715    2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4116    0.2930    2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -1.8887    1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -2.7860   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838   -0.4544   -1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454    0.3870    0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277    2.2985   -0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    1.3669   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    1.9917   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1589    0.7252   -1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    0.4766    1.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966   -1.1963    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371   -2.3280    0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3111   -0.7828   -0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5741   -1.4659    1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3558   -1.2403    0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5422    1.0527   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6462    0.9045    1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7771   -0.3166    2.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2590   -1.1939   -1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4662   -0.6830   -3.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2383    0.0604   -4.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0734   -0.9534   -3.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    1.1780   -2.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4993    1.9946   -4.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  1
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  1
 11 40  1  6
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 20 51  1  0
 21 52  1  1
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  1
 25 57  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      32.389 -16.967   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      36.775 -13.780   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.064  -8.731   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      24.855  -8.864   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      24.031 -11.401   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      32.818 -14.256   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.064 -13.351   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.294 -15.721   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.310 -14.256   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.834 -15.721   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.354 -13.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.064 -11.811   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.209 -14.811   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.398 -11.041   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.398  -9.501   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.745 -14.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.425 -12.829   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.731  -8.731   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.960 -12.353   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.731  -7.191   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.640 -10.846   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      38.065  -6.421   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.175 -10.371   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      39.399  -7.191   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      40.732  -6.421   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4   23                                                            
CONECT    5   23                                                            
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   18                                                  
CONECT   16   13   17                                                       
CONECT   17   16   19                                                       
CONECT   18   15   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23    4    5   21                                                  
CONECT   24   22   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0002132
HETATM    1  C1  UNL     1       7.226  -1.159   1.647  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.179  -0.222   2.268  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.535   0.559   1.207  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.242   0.507   0.970  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.259  -0.310   1.696  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.626  -1.238   0.646  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.657  -1.994   0.118  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.995  -0.404  -0.437  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.964   0.387  -0.171  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.262   1.248  -1.139  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.093   0.764  -1.574  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.241   0.865  -0.689  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.262   0.199   0.593  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.143  -0.728   0.890  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.194  -1.212   0.013  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.526  -0.919   0.733  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.559   0.586   0.919  1.00  0.00           C  
HETATM   18  C17 UNL     1      -6.798   1.022   1.608  1.00  0.00           C  
HETATM   19  O2  UNL     1      -6.941   2.246   1.819  1.00  0.00           O  
HETATM   20  O3  UNL     1      -7.770   0.143   2.010  1.00  0.00           O  
HETATM   21  C18 UNL     1      -0.714  -0.613  -2.081  1.00  0.00           C  
HETATM   22  O4  UNL     1      -1.746  -1.270  -2.701  1.00  0.00           O  
HETATM   23  C19 UNL     1       0.367  -0.168  -3.090  1.00  0.00           C  
HETATM   24  C20 UNL     1       0.948   1.105  -2.536  1.00  0.00           C  
HETATM   25  O5  UNL     1       0.462   2.194  -3.284  1.00  0.00           O  
HETATM   26  H1  UNL     1       6.800  -2.168   1.477  1.00  0.00           H  
HETATM   27  H2  UNL     1       8.150  -1.172   2.261  1.00  0.00           H  
HETATM   28  H3  UNL     1       7.504  -0.718   0.669  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.534  -0.726   2.978  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.793   0.525   2.863  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.187   1.199   0.610  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.896   1.149   0.141  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.652  -0.972   2.466  1.00  0.00           H  
HETATM   34  H9  UNL     1       2.412   0.293   2.083  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.884  -1.889   1.109  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.352  -2.786  -0.393  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.384  -0.454  -1.416  1.00  0.00           H  
HETATM   38  H13 UNL     1       0.645   0.387   0.861  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.228   2.299  -0.845  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.297   1.367  -2.537  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.345   1.992  -0.434  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.159   0.725  -1.319  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.541   0.477   1.369  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.097  -1.196   1.901  1.00  0.00           H  
HETATM   45  H20 UNL     1      -4.137  -2.328   0.009  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.311  -0.783  -0.968  1.00  0.00           H  
HETATM   47  H22 UNL     1      -5.574  -1.466   1.674  1.00  0.00           H  
HETATM   48  H23 UNL     1      -6.356  -1.240   0.077  1.00  0.00           H  
HETATM   49  H24 UNL     1      -5.542   1.053  -0.088  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.646   0.905   1.460  1.00  0.00           H  
HETATM   51  H26 UNL     1      -7.777  -0.317   2.924  1.00  0.00           H  
HETATM   52  H27 UNL     1      -0.259  -1.194  -1.253  1.00  0.00           H  
HETATM   53  H28 UNL     1      -2.466  -0.683  -3.026  1.00  0.00           H  
HETATM   54  H29 UNL     1      -0.238   0.060  -4.016  1.00  0.00           H  
HETATM   55  H30 UNL     1       1.073  -0.953  -3.331  1.00  0.00           H  
HETATM   56  H31 UNL     1       2.017   1.178  -2.485  1.00  0.00           H  
HETATM   57  H32 UNL     1       0.499   1.995  -4.258  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    4   31
CONECT    4    5   32
CONECT    5    6   33   34
CONECT    6    7    8   35
CONECT    7   36
CONECT    8    9    9   37
CONECT    9   10   38
CONECT   10   11   24   39
CONECT   11   12   21   40
CONECT   12   13   41   42
CONECT   13   14   14   43
CONECT   14   15   44
CONECT   15   16   45   46
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   19   20
CONECT   20   51
CONECT   21   22   23   52
CONECT   22   53
CONECT   23   24   54   55
CONECT   24   25   56
CONECT   25   57
END

HMDB0002132
     RDKit          3D
8-iso-PGF3a
 57 57  0  0  0  0  0  0  0  0999 V2000
    7.2260   -1.1588    1.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1786   -0.2224    2.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5345    0.5590    1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2424    0.5069    0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2593   -0.3099    1.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6260   -1.2385    0.6461 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6570   -1.9938    0.1181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -0.4037   -0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635    0.3868   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2620    1.2485   -1.1390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0933    0.7644   -1.5744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2413    0.8653   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    0.1994    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434   -0.7280    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1940   -1.2118    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5259   -0.9194    0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5586    0.5865    0.9191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7979    1.0223    1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9407    2.2456    1.8191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7699    0.1432    2.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135   -0.6132   -2.0808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7465   -1.2699   -2.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3673   -0.1685   -3.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.1049   -2.5358 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4624    2.1937   -3.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7996   -2.1683    1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1498   -1.1718    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5038   -0.7179    0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -0.7264    2.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930    0.5255    2.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    1.1988    0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8963    1.1494    0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6525   -0.9715    2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4116    0.2930    2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -1.8887    1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -2.7860   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838   -0.4544   -1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454    0.3870    0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277    2.2985   -0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    1.3669   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    1.9917   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1589    0.7252   -1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    0.4766    1.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966   -1.1963    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371   -2.3280    0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3111   -0.7828   -0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5741   -1.4659    1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3558   -1.2403    0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5422    1.0527   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6462    0.9045    1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7771   -0.3166    2.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2590   -1.1939   -1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4662   -0.6830   -3.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2383    0.0604   -4.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0734   -0.9534   -3.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    1.1780   -2.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4993    1.9946   -4.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  1
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  1
 11 40  1  6
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 20 51  1  0
 21 52  1  1
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  1
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8b,9a,11a,13E,15S,17Z)-9,11,15-Trihydroxy-prosta-5,13,17-trien-1-Oate	HMDB
(5Z,8b,9a,11a,13E,15S,17Z)-9,11,15-Trihydroxy-prosta-5,13,17-trien-1-Oic acid	HMDB
7-[3a,5a-Dihydroxy-2-(3-hydroxy-1,5-octadienyl)cyclopentyl]-5-heptenoate	HMDB
7-[3a,5a-Dihydroxy-2-(3-hydroxy-1,5-octadienyl)cyclopentyl]-5-heptenoic acid	HMDB
8-Iso-PGF3alpha	HMDB
9S,11R,15S-Trihydroxy-5Z,13E,17Z-prostatrienoate	HMDB
9S,11R,15S-Trihydroxy-5Z,13E,17Z-prostatrienoic acid	HMDB
9S,11R,15S-Trihydroxy-5Z,13E,17Z-prostatrienoic acid-cyclo[8S,12R]	HMDB
8-Iso-PGF3α	HMDB
8-Iso-PGF3a	Generator

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

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

Traditional Name

8-iso-PGF3α

CAS Registry Number

7045-31-0

SMILES

CC\C=C/C[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/C20H32O5/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/h3-4,6-7,12-13,15-19,21-23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16-,17+,18-,19+/m0/s1

InChI Key

SAKGBZWJAIABSY-PJCXKLBTSA-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 (LMFA03110007 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0002132)
Membrane (HMDB: HMDB0002132)

Source

Exogenous

Exogenous (HMDB: HMDB0002132)

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: HMDB0002132)

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.7	ALOGPS
logP	2.25	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-1.7	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	11	ChemAxon
Refractivity	101.59 m³·mol⁻¹	ChemAxon
Polarizability	40.35 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]+	189.228	31661259
DarkChem	[M-H]-	183.649	31661259
DeepCCS	[M+H]+	198.587	30932474
DeepCCS	[M-H]-	196.191	30932474
DeepCCS	[M-2H]-	229.608	30932474
DeepCCS	[M+Na]+	204.499	30932474
AllCCS	[M+H]+	193.1	32859911
AllCCS	[M+H-H2O]+	190.4	32859911
AllCCS	[M+NH4]+	195.6	32859911
AllCCS	[M+Na]+	196.3	32859911
AllCCS	[M-H]-	190.4	32859911
AllCCS	[M+Na-2H]-	191.8	32859911
AllCCS	[M+HCOO]-	193.5	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.	4.78 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8065 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.75 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	70.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2538.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	203.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	156.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	159.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	507.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	406.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	153.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1112.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	484.2 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	1246.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	334.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	403.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	188.2 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-iso-PGF3a	CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O	4597.6	Standard polar	33892256
8-iso-PGF3a	CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O	2704.3	Standard non polar	33892256
8-iso-PGF3a	CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O	2970.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-iso-PGF3a,1TMS,isomer #1	CC/C=C\C[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	2931.6	Semi standard non polar	33892256
8-iso-PGF3a,1TMS,isomer #2	CC/C=C\C[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	2826.6	Semi standard non polar	33892256
8-iso-PGF3a,1TMS,isomer #3	CC/C=C\C[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	2807.9	Semi standard non polar	33892256
8-iso-PGF3a,1TMS,isomer #4	CC/C=C\C[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	2827.7	Semi standard non polar	33892256
8-iso-PGF3a,2TMS,isomer #1	CC/C=C\C[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	2844.7	Semi standard non polar	33892256
8-iso-PGF3a,2TMS,isomer #2	CC/C=C\C[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	2783.8	Semi standard non polar	33892256
8-iso-PGF3a,2TMS,isomer #3	CC/C=C\C[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	2798.6	Semi standard non polar	33892256
8-iso-PGF3a,2TMS,isomer #4	CC/C=C\C[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	2772.3	Semi standard non polar	33892256
8-iso-PGF3a,2TMS,isomer #5	CC/C=C\C[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	2777.9	Semi standard non polar	33892256
8-iso-PGF3a,2TMS,isomer #6	CC/C=C\C[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	2753.0	Semi standard non polar	33892256
8-iso-PGF3a,3TMS,isomer #1	CC/C=C\C[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	2741.9	Semi standard non polar	33892256
8-iso-PGF3a,3TMS,isomer #2	CC/C=C\C[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	2760.9	Semi standard non polar	33892256
8-iso-PGF3a,3TMS,isomer #3	CC/C=C\C[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	2736.7	Semi standard non polar	33892256
8-iso-PGF3a,3TMS,isomer #4	CC/C=C\C[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	2739.7	Semi standard non polar	33892256
8-iso-PGF3a,4TMS,isomer #1	CC/C=C\C[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	2750.1	Semi standard non polar	33892256
8-iso-PGF3a,1TBDMS,isomer #1	CC/C=C\C[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	3179.6	Semi standard non polar	33892256
8-iso-PGF3a,1TBDMS,isomer #2	CC/C=C\C[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	3046.5	Semi standard non polar	33892256
8-iso-PGF3a,1TBDMS,isomer #3	CC/C=C\C[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	3026.2	Semi standard non polar	33892256
8-iso-PGF3a,1TBDMS,isomer #4	CC/C=C\C[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	3097.2	Semi standard non polar	33892256
8-iso-PGF3a,2TBDMS,isomer #1	CC/C=C\C[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	3367.5	Semi standard non polar	33892256
8-iso-PGF3a,2TBDMS,isomer #2	CC/C=C\C[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	3255.7	Semi standard non polar	33892256
8-iso-PGF3a,2TBDMS,isomer #3	CC/C=C\C[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	3264.5	Semi standard non polar	33892256
8-iso-PGF3a,2TBDMS,isomer #4	CC/C=C\C[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	3258.1	Semi standard non polar	33892256
8-iso-PGF3a,2TBDMS,isomer #5	CC/C=C\C[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	3228.5	Semi standard non polar	33892256
8-iso-PGF3a,2TBDMS,isomer #6	CC/C=C\C[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	3240.2	Semi standard non polar	33892256
8-iso-PGF3a,3TBDMS,isomer #1	CC/C=C\C[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	3474.3	Semi standard non polar	33892256
8-iso-PGF3a,3TBDMS,isomer #2	CC/C=C\C[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	3487.0	Semi standard non polar	33892256
8-iso-PGF3a,3TBDMS,isomer #3	CC/C=C\C[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	3440.9	Semi standard non polar	33892256
8-iso-PGF3a,3TBDMS,isomer #4	CC/C=C\C[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	3454.8	Semi standard non polar	33892256
8-iso-PGF3a,4TBDMS,isomer #1	CC/C=C\C[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	3625.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-PGF3a GC-MS (Non-derivatized) - 70eV, Positive	splash10-0690-5569000000-b6d9924bb1e1598b9d72	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-PGF3a GC-MS (4 TMS) - 70eV, Positive	splash10-004i-6100298000-cefdc46b7ca2307e3bfd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-PGF3a GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 10V, Positive-QTOF	splash10-014r-0019000000-f98b94189569251d37a2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 20V, Positive-QTOF	splash10-014r-3197000000-85761caed143126a0974	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 40V, Positive-QTOF	splash10-01bi-9170000000-9c3f2455a6d592ea0a4a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 10V, Negative-QTOF	splash10-0ue9-0009000000-3b5070d3e2790d2cb20f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 20V, Negative-QTOF	splash10-001i-1039000000-d00dd3f608a0e190f458	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 40V, Negative-QTOF	splash10-0a4i-9631000000-10bc983babf036749841	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 10V, Negative-QTOF	splash10-0uxr-0009000000-33af08865c9568c21f7a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 20V, Negative-QTOF	splash10-0fs9-0097000000-18f214d33dfa137da432	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 40V, Negative-QTOF	splash10-007y-9162000000-31a96bbf479dad16df6e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 10V, Positive-QTOF	splash10-014r-0019000000-40e30046291432c91b56	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 20V, Positive-QTOF	splash10-014i-9276000000-4e19df362ec1af060bb2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-PGF3a 40V, Positive-QTOF	splash10-014l-9300000000-ba6ae7b1d6d0d6589c1f	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022859

KNApSAcK ID

Not Available

Chemspider ID

4446338

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283217

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

Beal, Philip F., III; Fonken, Gunther S.; Pike, John E. Microbiological conversions of unsaturated fatty acids. (1965), 34 pp. BE 659984 19650819 CAN 64:87998 AN 1966:87998

Material Safety Data Sheet (MSDS)

Not Available

General References

Gao L, Zackert WE, Hasford JJ, Danekis ME, Milne GL, Remmert C, Reese J, Yin H, Tai HH, Dey SK, Porter NA, Morrow JD: Formation of prostaglandins E2 and D2 via the isoprostane pathway: a mechanism for the generation of bioactive prostaglandins independent of cyclooxygenase. J Biol Chem. 2003 Aug 1;278(31):28479-89. Epub 2003 May 13. [PubMed:12746435 ]

Showing metabocard for 8-iso-PGF3a (HMDB0002132)

MOL for HMDB0002132 (8-iso-PGF3a)

3D MOL for HMDB0002132 (8-iso-PGF3a)

3D SDF for HMDB0002132 (8-iso-PGF3a)

3D-SDF for HMDB0002132 (8-iso-PGF3a)

PDB for HMDB0002132 (8-iso-PGF3a)

3D PDB for HMDB0002132 (8-iso-PGF3a)

SMILES for HMDB0002132 (8-iso-PGF3a)

INCHI for HMDB0002132 (8-iso-PGF3a)

Structure for HMDB0002132 (8-iso-PGF3a)

3D Structure for HMDB0002132 (8-iso-PGF3a)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra