Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-25 09:43:39 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005077

Secondary Accession Numbers

HMDB05077

Metabolite Identification

Common Name

8-iso-15-keto-PGF2a

Description

8-iso-15-keto-PGF2alpha is an isoprostane. Isoprostanes are produced during peroxidation of membrane lipids by free radicals and reactive oxygen species, and are currently used as markers of many disease states and experimental conditions in which oxidative stress is a prominent feature. A small number of reports have described the ability of some isoprostanes to evoke important biological effects in smooth muscle and other cell types. There is a long (and growing) list of disease states and pathophysiological conditions which are associated with marked elevation in the levels of iso- prostanes. For example, measured levels of the plasma, urine, bronchoalveolar lavage fluid, and/or tissues of smokers, patients with asthma chronic obstructive pulmonary disease, interstitial lung disease, cystic fibrosis, or acute chest syndrome, during exposure to allergen, ozone or hyperoxia; and during ventilated ischemia. Likewise, cardiovascular conditions such as renal, myocardial, ischemia-reperfusion injury, atherosclerosis, and pre-eclampsia are also indicated by a marked elevation of plasma/urinary levels of isoprostanes. (PMID: 10930353 ).

Structure

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

HMDB0005077
     RDKit          3D
8-iso-15-keto-PGF2a
 57 57  0  0  0  0  0  0  0  0999 V2000
    6.4787    2.5384   -1.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8282    1.5029   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2036    0.1647   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6909    0.2059   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2302   -1.2156   -0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7595   -1.3481   -0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -1.4404   -2.0351 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577   -1.3722    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6491   -1.5022    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622   -1.5401    1.4021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2727   -0.3814    1.3733 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8296   -0.1057    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -1.2820   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145   -1.2139   -0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6992   -0.0523   -0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2661    0.2963   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1582    1.5101   -1.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2499    1.2061   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1467    1.2970    0.3304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4864    0.7887   -1.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    0.7054    1.9824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1393    1.8646    2.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0224   -0.0044    3.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -1.4039    2.7582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3703   -2.2730    3.6530 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4155    2.8749   -1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7311    2.1764   -2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0267    3.4153   -0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6116    1.8501    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9420    1.3159   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6255   -0.1823   -1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4794   -0.5383    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2786    0.9362   -1.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790    0.5240    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -1.8648   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7244   -1.6227   -1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -1.2811    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2139   -1.5926   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -2.4605    1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -0.5941    2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9364    0.0768   -0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657    0.8362    0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0392   -2.2368   -0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2888   -2.1442   -1.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6275   -0.3978   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3001    0.8672   -0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4678    0.4667   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9478   -0.5373   -2.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5695    1.8814   -2.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5264    2.2856   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8396   -0.1456   -1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4952    0.8980    1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900    2.5424    1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197    0.5118    3.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8206    0.0083    4.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.6051    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -3.2088    3.3042 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  2  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
  8 37  1  0
  9 38  1  0
 10 39  1  1
 11 40  1  1
 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  6
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  6
 25 57  1  0
M  END


  Mrv0541 02231220202D          

 25 25  0  0  1  0            999 V2000
   16.9900  -12.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3395  -11.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8874   -8.3961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9538   -8.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5122   -9.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2200  -11.3560    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8874  -10.8711    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.4749  -12.1406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5548  -11.3560    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2999  -12.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4353  -11.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8874  -10.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8223  -11.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6019   -9.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0376  -11.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6019   -8.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8661  -10.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3163   -8.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3163   -7.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0814  -10.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0309   -7.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9099   -9.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0309   -6.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7453   -5.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1253   -9.2743    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
  3 16  2  0  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 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  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 25  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005077

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(=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/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17+,18-,19+/m0/s1

> <INCHI_KEY>
LOLJEILMPWPILA-RLXHZABYSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.7692467664877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
3.0223929053333323

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.513644380756794

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.35529359589066

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8720111602020335

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
99.5733

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-iso-15-keto-PGF2α

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005077
     RDKit          3D
8-iso-15-keto-PGF2a
 57 57  0  0  0  0  0  0  0  0999 V2000
    6.4787    2.5384   -1.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8282    1.5029   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2036    0.1647   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6909    0.2059   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2302   -1.2156   -0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7595   -1.3481   -0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -1.4404   -2.0351 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577   -1.3722    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6491   -1.5022    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622   -1.5401    1.4021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2727   -0.3814    1.3733 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8296   -0.1057    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -1.2820   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145   -1.2139   -0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6992   -0.0523   -0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2661    0.2963   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1582    1.5101   -1.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2499    1.2061   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1467    1.2970    0.3304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4864    0.7887   -1.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    0.7054    1.9824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1393    1.8646    2.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0224   -0.0044    3.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -1.4039    2.7582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3703   -2.2730    3.6530 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4155    2.8749   -1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7311    2.1764   -2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0267    3.4153   -0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6116    1.8501    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9420    1.3159   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6255   -0.1823   -1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4794   -0.5383    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2786    0.9362   -1.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790    0.5240    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -1.8648   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7244   -1.6227   -1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -1.2811    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2139   -1.5926   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -2.4605    1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -0.5941    2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9364    0.0768   -0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657    0.8362    0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0392   -2.2368   -0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2888   -2.1442   -1.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6275   -0.3978   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3001    0.8672   -0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4678    0.4667   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9478   -0.5373   -2.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5695    1.8814   -2.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5264    2.2856   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8396   -0.1456   -1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4952    0.8980    1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900    2.5424    1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197    0.5118    3.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8206    0.0083    4.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.6051    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -3.2088    3.3042 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  2  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
  8 37  1  0
  9 38  1  0
 10 39  1  1
 11 40  1  1
 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  6
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  6
 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      31.715 -23.908   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      36.100 -20.722   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      33.390 -15.673   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      24.180 -15.806   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      23.356 -18.343   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      32.144 -21.198   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.390 -20.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.620 -22.662   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.636 -21.198   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.160 -22.662   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.679 -20.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.390 -18.753   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.535 -21.752   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.724 -17.983   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.070 -21.277   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.724 -16.443   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.750 -19.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.057 -15.673   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.057 -14.133   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.285 -19.294   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.391 -13.363   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.965 -17.788   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.391 -11.823   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      38.725 -11.053   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.501 -17.312   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   16                                                            
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   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16    3   14   18                                                  
CONECT   17   15   20                                                       
CONECT   18   16   19                                                       
CONECT   19   18   21                                                       
CONECT   20   17   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   25                                                       
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25    4    5   22                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0005077
HETATM    1  C1  UNL     1       6.479   2.538  -1.300  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.828   1.503  -0.281  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.204   0.165  -0.567  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.691   0.206  -0.604  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.230  -1.216  -0.876  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.759  -1.348  -0.942  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.184  -1.440  -2.035  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.958  -1.372   0.288  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.649  -1.502   0.281  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.262  -1.540   1.402  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.273  -0.381   1.373  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.830  -0.106   0.031  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.539  -1.282  -0.472  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.815  -1.214  -0.780  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.699  -0.052  -0.690  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.266   0.296  -2.077  1.00  0.00           C  
HETATM   17  C16 UNL     1      -6.158   1.510  -1.871  1.00  0.00           C  
HETATM   18  C17 UNL     1      -7.250   1.206  -0.931  1.00  0.00           C  
HETATM   19  O2  UNL     1      -7.147   1.297   0.330  1.00  0.00           O  
HETATM   20  O3  UNL     1      -8.486   0.789  -1.443  1.00  0.00           O  
HETATM   21  C18 UNL     1      -0.434   0.705   1.982  1.00  0.00           C  
HETATM   22  O4  UNL     1      -1.139   1.865   2.256  1.00  0.00           O  
HETATM   23  C19 UNL     1       0.022  -0.004   3.263  1.00  0.00           C  
HETATM   24  C20 UNL     1       0.311  -1.404   2.758  1.00  0.00           C  
HETATM   25  O5  UNL     1      -0.370  -2.273   3.653  1.00  0.00           O  
HETATM   26  H1  UNL     1       7.416   2.875  -1.818  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.731   2.176  -2.013  1.00  0.00           H  
HETATM   28  H3  UNL     1       6.027   3.415  -0.750  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.612   1.850   0.758  1.00  0.00           H  
HETATM   30  H5  UNL     1       7.942   1.316  -0.289  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.625  -0.182  -1.542  1.00  0.00           H  
HETATM   32  H7  UNL     1       6.479  -0.538   0.240  1.00  0.00           H  
HETATM   33  H8  UNL     1       4.279   0.936  -1.307  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.379   0.524   0.424  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.617  -1.865  -0.048  1.00  0.00           H  
HETATM   36  H11 UNL     1       4.724  -1.623  -1.794  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.411  -1.281   1.262  1.00  0.00           H  
HETATM   38  H13 UNL     1       0.214  -1.593  -0.729  1.00  0.00           H  
HETATM   39  H14 UNL     1      -0.865  -2.461   1.345  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.080  -0.594   2.120  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.936   0.077  -0.652  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.366   0.836   0.032  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.039  -2.237  -0.601  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.289  -2.144  -1.155  1.00  0.00           H  
HETATM   45  H20 UNL     1      -5.628  -0.398  -0.136  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.300   0.867  -0.295  1.00  0.00           H  
HETATM   47  H22 UNL     1      -4.468   0.467  -2.795  1.00  0.00           H  
HETATM   48  H23 UNL     1      -5.948  -0.537  -2.363  1.00  0.00           H  
HETATM   49  H24 UNL     1      -6.569   1.881  -2.817  1.00  0.00           H  
HETATM   50  H25 UNL     1      -5.526   2.286  -1.364  1.00  0.00           H  
HETATM   51  H26 UNL     1      -8.840  -0.146  -1.189  1.00  0.00           H  
HETATM   52  H27 UNL     1       0.495   0.898   1.405  1.00  0.00           H  
HETATM   53  H28 UNL     1      -0.990   2.542   1.552  1.00  0.00           H  
HETATM   54  H29 UNL     1       0.920   0.512   3.649  1.00  0.00           H  
HETATM   55  H30 UNL     1      -0.821   0.008   4.001  1.00  0.00           H  
HETATM   56  H31 UNL     1       1.356  -1.605   2.918  1.00  0.00           H  
HETATM   57  H32 UNL     1      -0.209  -3.209   3.304  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    7    8
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

HMDB0005077
     RDKit          3D
8-iso-15-keto-PGF2a
 57 57  0  0  0  0  0  0  0  0999 V2000
    6.4787    2.5384   -1.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8282    1.5029   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2036    0.1647   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6909    0.2059   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2302   -1.2156   -0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7595   -1.3481   -0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -1.4404   -2.0351 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577   -1.3722    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6491   -1.5022    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622   -1.5401    1.4021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2727   -0.3814    1.3733 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8296   -0.1057    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -1.2820   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145   -1.2139   -0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6992   -0.0523   -0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2661    0.2963   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1582    1.5101   -1.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2499    1.2061   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1467    1.2970    0.3304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4864    0.7887   -1.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    0.7054    1.9824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1393    1.8646    2.2559 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0224   -0.0044    3.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -1.4039    2.7582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3703   -2.2730    3.6530 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4155    2.8749   -1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7311    2.1764   -2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0267    3.4153   -0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6116    1.8501    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9420    1.3159   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6255   -0.1823   -1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4794   -0.5383    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2786    0.9362   -1.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790    0.5240    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -1.8648   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7244   -1.6227   -1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -1.2811    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2139   -1.5926   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -2.4605    1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -0.5941    2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9364    0.0768   -0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657    0.8362    0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0392   -2.2368   -0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2888   -2.1442   -1.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6275   -0.3978   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3001    0.8672   -0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4678    0.4667   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9478   -0.5373   -2.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5695    1.8814   -2.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5264    2.2856   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8396   -0.1456   -1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4952    0.8980    1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900    2.5424    1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197    0.5118    3.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8206    0.0083    4.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.6051    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -3.2088    3.3042 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  2  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
  8 37  1  0
  9 38  1  0
 10 39  1  1
 11 40  1  1
 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  6
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  6
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8b,9a,11a,13E)-9,11-Dihydroxy-15-oxo-prosta-5,13-dien-1-Oate	HMDB
(5Z,8b,9a,11a,13E)-9,11-Dihydroxy-15-oxo-prosta-5,13-dien-1-Oic acid	HMDB
8-Iso-15-keto-PGF2alpha	HMDB
9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoate	HMDB
9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoic acid	HMDB
9S,11R-Dihydroxy-15-oxo-5Z,13E-prostadienoic acid-cyclo[8S,12R]	HMDB
8-Iso-15-keto-PGF2α	HMDB
8-Iso-15-keto-PGF2a	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)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

Traditional Name

8-iso-15-keto-PGF2α

CAS Registry Number

191919-01-4

SMILES

CCCCCC(=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/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17+,18-,19+/m0/s1

InChI Key

LOLJEILMPWPILA-RLXHZABYSA-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
Unsaturated fatty acid
Fatty acid
Enone
Acryloyl-group
Cyclic alcohol
Alpha,beta-unsaturated ketone
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Isoprostanes (LMFA03110005 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0005077)
Membrane (HMDB: HMDB0005077)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

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	0.093 g/L	ALOGPS
logP	3.03	ALOGPS
logP	3.02	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	99.57 m³·mol⁻¹	ChemAxon
Polarizability	40.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	199.522	30932474
DeepCCS	[M-H]-	197.126	30932474
DeepCCS	[M-2H]-	230.826	30932474
DeepCCS	[M+Na]+	205.75	30932474
AllCCS	[M+H]+	192.6	32859911
AllCCS	[M+H-H2O]+	189.9	32859911
AllCCS	[M+NH4]+	195.0	32859911
AllCCS	[M+Na]+	195.7	32859911
AllCCS	[M-H]-	191.1	32859911
AllCCS	[M+Na-2H]-	192.5	32859911
AllCCS	[M+HCOO]-	194.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-iso-15-keto-PGF2a	CCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O	4596.6	Standard polar	33892256
8-iso-15-keto-PGF2a	CCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O	2639.5	Standard non polar	33892256
8-iso-15-keto-PGF2a	CCCCCC(=O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O	2948.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-iso-15-keto-PGF2a,1TMS,isomer #1	CCCCCC(=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	2758.3	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,1TMS,isomer #2	CCCCCC(=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	2753.6	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,1TMS,isomer #3	CCCCCC(=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	2839.3	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,1TMS,isomer #4	CCCCC=C(/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	3159.9	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TMS,isomer #1	CCCCCC(=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	2724.7	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TMS,isomer #2	CCCCCC(=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	2700.5	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TMS,isomer #3	CCCCC=C(/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	3046.3	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TMS,isomer #4	CCCCCC(=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	2726.2	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TMS,isomer #5	CCCCC=C(/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	3034.3	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TMS,isomer #6	CCCCC=C(/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	3078.6	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,3TMS,isomer #1	CCCCCC(=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	2696.6	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,3TMS,isomer #2	CCCCC=C(/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	2998.7	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,3TMS,isomer #3	CCCCC=C(/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	3006.4	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,3TMS,isomer #4	CCCCC=C(/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	2984.9	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,4TMS,isomer #1	CCCCC=C(/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	2964.5	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,4TMS,isomer #1	CCCCC=C(/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	2751.3	Standard non polar	33892256
8-iso-15-keto-PGF2a,4TMS,isomer #1	CCCCC=C(/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	2956.4	Standard polar	33892256
8-iso-15-keto-PGF2a,1TBDMS,isomer #1	CCCCCC(=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	2984.7	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,1TBDMS,isomer #2	CCCCCC(=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	2985.2	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,1TBDMS,isomer #3	CCCCCC(=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	3113.6	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,1TBDMS,isomer #4	CCCCC=C(/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	3400.4	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #1	CCCCCC(=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	3225.6	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #2	CCCCCC(=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	3185.1	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #3	CCCCC=C(/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	3480.8	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #4	CCCCCC(=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	3225.2	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #5	CCCCC=C(/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	3478.3	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,2TBDMS,isomer #6	CCCCC=C(/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	3568.2	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,3TBDMS,isomer #1	CCCCCC(=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	3401.9	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,3TBDMS,isomer #2	CCCCC=C(/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	3701.3	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,3TBDMS,isomer #3	CCCCC=C(/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	3647.7	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,3TBDMS,isomer #4	CCCCC=C(/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	3690.8	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,4TBDMS,isomer #1	CCCCC=C(/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	3844.9	Semi standard non polar	33892256
8-iso-15-keto-PGF2a,4TBDMS,isomer #1	CCCCC=C(/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	3447.5	Standard non polar	33892256
8-iso-15-keto-PGF2a,4TBDMS,isomer #1	CCCCC=C(/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	3218.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-15-keto-PGF2a GC-MS (Non-derivatized) - 70eV, Positive	splash10-0570-4498000000-cc0a6152c4c014df4b6f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-15-keto-PGF2a GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-5100980000-6257b72a2aa9de720f36	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-iso-15-keto-PGF2a 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-15-keto-PGF2a 10V, Positive-QTOF	splash10-00kr-0019000000-910369cab5e253b484e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 20V, Positive-QTOF	splash10-00kr-2295000000-e2c04166a9405e56f2fc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 40V, Positive-QTOF	splash10-00dr-9160000000-23fb78d0cc03202e3212	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 10V, Negative-QTOF	splash10-0ue9-0009000000-e05daa9da0040142e39c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 20V, Negative-QTOF	splash10-0f8i-2069000000-8c098522c3791b504d19	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 40V, Negative-QTOF	splash10-0a4i-9441000000-d1759dfb65fcc9f9b470	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 10V, Negative-QTOF	splash10-0udi-0039000000-db45ea43b0b32962d543	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 20V, Negative-QTOF	splash10-0fri-0094000000-e560b2602cb2e45b3c66	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 40V, Negative-QTOF	splash10-052p-9151000000-c46a461dbc0a557352d5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 10V, Positive-QTOF	splash10-014r-0019000000-e81e2e2f5abdc4bb9c39	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 20V, Positive-QTOF	splash10-014r-9356000000-a519ec47287e412b92ed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-iso-15-keto-PGF2a 40V, Positive-QTOF	splash10-00kf-9100000000-fb5ea9c2e3392b9c6014	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

FDB023618

KNApSAcK ID

Not Available

Chemspider ID

4446336

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283215

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

Janssen LJ: Isoprostanes: generation, pharmacology, and roles in free-radical-mediated effects in the lung. Pulm Pharmacol Ther. 2000;13(4):149-55. [PubMed:10930353 ]

Showing metabocard for 8-iso-15-keto-PGF2a (HMDB0005077)

MOL for HMDB0005077 (8-iso-15-keto-PGF2a)

3D MOL for HMDB0005077 (8-iso-15-keto-PGF2a)

3D SDF for HMDB0005077 (8-iso-15-keto-PGF2a)

3D-SDF for HMDB0005077 (8-iso-15-keto-PGF2a)

PDB for HMDB0005077 (8-iso-15-keto-PGF2a)

3D PDB for HMDB0005077 (8-iso-15-keto-PGF2a)

SMILES for HMDB0005077 (8-iso-15-keto-PGF2a)

INCHI for HMDB0005077 (8-iso-15-keto-PGF2a)

Structure for HMDB0005077 (8-iso-15-keto-PGF2a)

3D Structure for HMDB0005077 (8-iso-15-keto-PGF2a)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra