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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:05 UTC

Update Date

2022-03-07 02:49:16 UTC

HMDB ID

HMDB0002710

Secondary Accession Numbers

HMDB0005078
HMDB02710
HMDB05078

Metabolite Identification

Common Name

Prostaglandin J2

Description

Prostaglandin J2 (PGJ2) is an endogenous product of inflammation in humans. It induces neuronal death and the accumulation of ubiquitinated proteins into distinct aggregates. It may play a role in neurodegenerative disorders inducing a chain of events that culminates in neuronal cell death. An altered expression of enzymes in PGJ2 synthesis may represent a novel pathogenic mechanism in human obesity. The peroxisome proliferator-activated receptor gamma (PPARγ) has a fundamental role in glucose homeostasis and adipocyte differentiation. Besides linoleate, linolenate and arachidonate, the most notable PPAR ligand is 15-deoxy-delta12-14-prostaglandin J2, a natural derivative of prostaglandin D2 and PGJ2. It is therefore plausible that the production of 15d-PGJ2 within adipose tissue may act as an endogenous mediator of adipocyte differentiation. PGJ2 disrupts the cytoskeleton in neuronal cells. This cyclopentenone prostaglandin triggered endoplasmic reticulum (ER) collapse and the redistribution of ER proteins, such as calnexin and catechol-O-methyltransferase, into a large centrosomal aggregate containing ubiquitinated proteins and alpha-synuclein. The PGJ2-dependent cytoskeletal rearrangement paralleled the development of the large centrosomal aggregate. Supporting a mechanism by which, upon PGJ2 treatment, cytoskeleton/ER collapse coincides with the relocation of ER proteins, other potentially neighboring proteins, and ubiquitinated proteins into centrosomal aggregates. Development of these large perinuclear aggregates is associated with disruption of the microtubule/ER network. This aberrant protein deposition, triggered by a product of inflammation, may be common to other compounds that disrupt microtubules and induce protein aggregation, such as MPP+ and rotenone, found to be associated with neurodegeneration. Many neurodegenerative disorders, such as Parkinson disease, exhibit inclusion bodies containing ubiquitinated proteins. Concentrations of PGJ2 in biofluids have not been established, since this prostaglandin is further metabolized into delta12-PGJ2, and 15-deoxy-delta12,14-PGJ2. (PMID: 16737963 , 16842938 , 16774923 )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

HMDB0002710
     RDKit          3D
Prostaglandin J2
 54 54  0  0  0  0  0  0  0  0999 V2000
    7.0982   -2.1104   -0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1364   -0.9002    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9147    0.3531   -0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5788    0.3427   -1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597    0.2375   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150    0.2244   -0.9129 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8701    1.3797   -1.6583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587    0.1329    0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -0.0360   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2852   -0.1377    0.7652 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0021    0.0194    2.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0169   -0.2042    2.8431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2455    0.5340    2.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    1.0781    1.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172    0.9761    0.5539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2130    0.6982   -0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9844   -0.5364   -0.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3037   -0.5211   -0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1540    0.6649   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0344    0.7465    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9151   -0.4420    0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8865   -0.6860   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5795   -1.7255   -0.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0462    0.2107   -1.3276 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628   -2.4947   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7860   -2.8658   -0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4150   -1.8082   -1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1542   -0.8106    0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4306   -0.9676    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9103    1.2104    0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7334    0.4851   -1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    1.3449   -1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5066   -0.4902   -1.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4912    1.0485    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -0.7268    0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9756   -0.6603   -1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667    1.1592   -2.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844    0.2174    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5570   -0.1096   -1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8600   -1.1039    0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4721    0.4510    3.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    1.5158    2.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7756    1.9232    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314    1.5992   -0.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    0.5084   -1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5255   -1.5180   -0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8676   -1.4810   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6680    1.6282   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8067    0.5793   -1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4101    0.8424    1.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6324    1.6951    0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5282   -0.3201    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2912   -1.3504    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8986    0.2005   -1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  1
 13 41  1  0
 14 42  1  0
 15 43  1  6
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END


  Mrv0541 02231219342D          

 24 24  0  0  1  0            999 V2000
   20.5874  -13.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1352  -10.7113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2015  -10.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7599  -12.1416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4678  -13.6713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1352  -13.1864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.6831  -13.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7227  -14.4560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8027  -13.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1352  -12.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5477  -14.4560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8497  -11.1238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5642  -10.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8497  -11.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5642   -9.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0701  -13.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2787   -9.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2787   -8.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2854  -13.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1139  -12.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3292  -12.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9932   -8.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1577  -11.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3731  -11.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
 12  2  1  1  0  0  0
  3 24  1  0  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  6  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  1  0  0  0
  7 16  1  0  0  0  0
  8 11  2  0  0  0  0
  9 11  1  0  0  0  0
 10 14  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  2  0  0  0  0
 17 18  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002710

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-2-3-6-10-17(21)13-14-18-16(12-15-19(18)22)9-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-13+/t16-,17-,18+/m0/s1

> <INCHI_KEY>
UQOQENZZLBSFKO-POPPZSFYSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.4498

> <EXACT_MASS>
334.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.62729638841884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
4.375950963666667

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.998309190507722

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6842788055026645

> <JCHEM_PKA_STRONGEST_BASIC>
-1.59725889520801

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
99.08989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prostaglandin J2

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002710
     RDKit          3D
Prostaglandin J2
 54 54  0  0  0  0  0  0  0  0999 V2000
    7.0982   -2.1104   -0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1364   -0.9002    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9147    0.3531   -0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5788    0.3427   -1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597    0.2375   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150    0.2244   -0.9129 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8701    1.3797   -1.6583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587    0.1329    0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -0.0360   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2852   -0.1377    0.7652 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0021    0.0194    2.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0169   -0.2042    2.8431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2455    0.5340    2.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    1.0781    1.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172    0.9761    0.5539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2130    0.6982   -0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9844   -0.5364   -0.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3037   -0.5211   -0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1540    0.6649   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0344    0.7465    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9151   -0.4420    0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8865   -0.6860   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5795   -1.7255   -0.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0462    0.2107   -1.3276 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628   -2.4947   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7860   -2.8658   -0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4150   -1.8082   -1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1542   -0.8106    0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4306   -0.9676    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9103    1.2104    0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7334    0.4851   -1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    1.3449   -1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5066   -0.4902   -1.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4912    1.0485    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -0.7268    0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9756   -0.6603   -1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667    1.1592   -2.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844    0.2174    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5570   -0.1096   -1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8600   -1.1039    0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4721    0.4510    3.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    1.5158    2.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7756    1.9232    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314    1.5992   -0.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    0.5084   -1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5255   -1.5180   -0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8676   -1.4810   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6680    1.6282   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8067    0.5793   -1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4101    0.8424    1.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6324    1.6951    0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5282   -0.3201    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2912   -1.3504    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8986    0.2005   -1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  1
 13 41  1  0
 14 42  1  0
 15 43  1  6
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  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      38.430 -25.044   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.719 -19.994   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      26.509 -20.128   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      25.685 -22.664   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      34.473 -25.520   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.719 -24.615   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.008 -25.044   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.949 -26.985   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      36.965 -25.520   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.719 -23.074   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.489 -26.985   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.053 -20.764   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.387 -19.994   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.053 -22.304   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      38.387 -18.454   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.864 -26.074   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      39.720 -17.684   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.720 -16.144   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.399 -25.599   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.079 -24.092   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.615 -23.616   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      41.054 -15.374   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.294 -22.110   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.830 -21.634   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   12                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    6    7    8                                                  
CONECT    6    5    9   10                                                  
CONECT    7    5   16                                                       
CONECT    8    5   11                                                       
CONECT    9    1    6   11                                                  
CONECT   10    6   14                                                       
CONECT   11    8    9                                                       
CONECT   12    2   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   10   12                                                       
CONECT   15   13   17                                                       
CONECT   16    7   19                                                       
CONECT   17   15   18                                                       
CONECT   18   17   22                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   23                                                       
CONECT   22   18                                                            
CONECT   23   21   24                                                       
CONECT   24    3    4   23                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0002710
HETATM    1  C1  UNL     1       7.098  -2.110  -0.666  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.136  -0.900   0.243  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.915   0.353  -0.565  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.579   0.343  -1.272  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.460   0.237  -0.259  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.115   0.224  -0.913  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.870   1.380  -1.658  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.059   0.133   0.150  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.812  -0.036  -0.177  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.285  -0.138   0.765  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.002   0.019   2.189  1.00  0.00           C  
HETATM   12  O2  UNL     1       1.017  -0.204   2.843  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.246   0.534   2.773  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.992   1.078   1.832  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.317   0.976   0.554  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.213   0.698  -0.633  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.984  -0.536  -0.522  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.304  -0.521  -0.536  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.154   0.665  -0.657  1.00  0.00           C  
HETATM   20  C18 UNL     1      -6.034   0.747   0.592  1.00  0.00           C  
HETATM   21  C19 UNL     1      -6.915  -0.442   0.776  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.886  -0.686  -0.299  1.00  0.00           C  
HETATM   23  O3  UNL     1      -8.579  -1.726  -0.277  1.00  0.00           O  
HETATM   24  O4  UNL     1      -8.046   0.211  -1.328  1.00  0.00           O  
HETATM   25  H1  UNL     1       6.063  -2.495  -0.728  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.786  -2.866  -0.222  1.00  0.00           H  
HETATM   27  H3  UNL     1       7.415  -1.808  -1.684  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.154  -0.811   0.703  1.00  0.00           H  
HETATM   29  H5  UNL     1       6.431  -0.968   1.079  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.910   1.210   0.159  1.00  0.00           H  
HETATM   31  H7  UNL     1       7.733   0.485  -1.292  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.467   1.345  -1.756  1.00  0.00           H  
HETATM   33  H9  UNL     1       5.507  -0.490  -1.984  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.491   1.049   0.478  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.564  -0.727   0.292  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.976  -0.660  -1.557  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.367   1.159  -2.493  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.384   0.217   1.158  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.557  -0.110  -1.248  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.860  -1.104   0.659  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.472   0.451   3.848  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.965   1.516   2.089  1.00  0.00           H  
HETATM   43  H19 UNL     1      -0.776   1.923   0.332  1.00  0.00           H  
HETATM   44  H20 UNL     1      -2.731   1.599  -0.935  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.475   0.508  -1.485  1.00  0.00           H  
HETATM   46  H22 UNL     1      -2.525  -1.518  -0.426  1.00  0.00           H  
HETATM   47  H23 UNL     1      -4.868  -1.481  -0.451  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.668   1.628  -0.739  1.00  0.00           H  
HETATM   49  H25 UNL     1      -5.807   0.579  -1.571  1.00  0.00           H  
HETATM   50  H26 UNL     1      -5.410   0.842   1.503  1.00  0.00           H  
HETATM   51  H27 UNL     1      -6.632   1.695   0.554  1.00  0.00           H  
HETATM   52  H28 UNL     1      -7.528  -0.320   1.720  1.00  0.00           H  
HETATM   53  H29 UNL     1      -6.291  -1.350   0.994  1.00  0.00           H  
HETATM   54  H30 UNL     1      -8.899   0.200  -1.894  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    8   36
CONECT    7   37
CONECT    8    9    9   38
CONECT    9   10   39
CONECT   10   11   15   40
CONECT   11   12   12   13
CONECT   13   14   14   41
CONECT   14   15   42
CONECT   15   16   43
CONECT   16   17   44   45
CONECT   17   18   18   46
CONECT   18   19   47
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22   52   53
CONECT   22   23   23   24
CONECT   24   54
END

HMDB0002710
     RDKit          3D
Prostaglandin J2
 54 54  0  0  0  0  0  0  0  0999 V2000
    7.0982   -2.1104   -0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1364   -0.9002    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9147    0.3531   -0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5788    0.3427   -1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597    0.2375   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150    0.2244   -0.9129 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8701    1.3797   -1.6583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587    0.1329    0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -0.0360   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2852   -0.1377    0.7652 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0021    0.0194    2.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0169   -0.2042    2.8431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2455    0.5340    2.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    1.0781    1.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172    0.9761    0.5539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2130    0.6982   -0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9844   -0.5364   -0.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3037   -0.5211   -0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1540    0.6649   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0344    0.7465    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9151   -0.4420    0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8865   -0.6860   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5795   -1.7255   -0.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0462    0.2107   -1.3276 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628   -2.4947   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7860   -2.8658   -0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4150   -1.8082   -1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1542   -0.8106    0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4306   -0.9676    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9103    1.2104    0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7334    0.4851   -1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    1.3449   -1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5066   -0.4902   -1.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4912    1.0485    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -0.7268    0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9756   -0.6603   -1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667    1.1592   -2.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844    0.2174    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5570   -0.1096   -1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8600   -1.1039    0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4721    0.4510    3.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    1.5158    2.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7756    1.9232    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314    1.5992   -0.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    0.5084   -1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5255   -1.5180   -0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8676   -1.4810   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6680    1.6282   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8067    0.5793   -1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4101    0.8424    1.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6324    1.6951    0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5282   -0.3201    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2912   -1.3504    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8986    0.2005   -1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  1
 13 41  1  0
 14 42  1  0
 15 43  1  6
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-Deoxy-delta-9-PGD2	ChEBI
9-Deoxy-delta-9-prostaglandin D2	ChEBI
PGJ2	ChEBI
9-Deoxy-δ-9-PGD2	Generator
9-Deoxy-δ-9-prostaglandin D2	Generator
11-oxo-15S-Hydroxy-5Z,8Z,13E-prostatrienoate	HMDB
11-oxo-15S-Hydroxy-5Z,8Z,13E-prostatrienoic acid	HMDB

Chemical Formula

C₂₀H₃₀O₄

Average Molecular Weight

334.4498

Monoisotopic Molecular Weight

334.214409448

IUPAC Name

(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid

Traditional Name

prostaglandin J2

CAS Registry Number

60203-57-8

SMILES

CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O

InChI Identifier

InChI=1S/C20H30O4/c1-2-3-6-10-17(21)13-14-18-16(12-15-19(18)22)9-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-13+/t16-,17-,18+/m0/s1

InChI Key

UQOQENZZLBSFKO-POPPZSFYSA-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
Fatty acid
Unsaturated fatty acid
Ketone
Cyclic ketone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins J (CHEBI:27485 )
Prostaglandins (C05957 )
Prostaglandins (LMFA03010019 )

Ontology

Not Available

Neuron (HMDB: HMDB0002710)

Hematocyte

Platelet (HMDB: HMDB0002710)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Cellular substructure

Membrane (HMDB: HMDB0002710)
Extracellular (HMDB: HMDB0002710)

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

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arachidonic Acid Metabolism (HMDB: HMDB0002710)

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0000353)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium Salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-Choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-Sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

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	0.02 g/L	ALOGPS
logP	4.1	ALOGPS
logP	4.38	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	99.09 m³·mol⁻¹	ChemAxon
Polarizability	38.63 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]+	188.866	30932474
DeepCCS	[M-H]-	186.471	30932474
DeepCCS	[M-2H]-	220.183	30932474
DeepCCS	[M+Na]+	195.37	30932474
AllCCS	[M+H]+	187.9	32859911
AllCCS	[M+H-H2O]+	185.1	32859911
AllCCS	[M+NH4]+	190.6	32859911
AllCCS	[M+Na]+	191.3	32859911
AllCCS	[M-H]-	187.9	32859911
AllCCS	[M+Na-2H]-	189.2	32859911
AllCCS	[M+HCOO]-	190.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin J2	CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O	4408.3	Standard polar	33892256
Prostaglandin J2	CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O	2586.1	Standard non polar	33892256
Prostaglandin J2	CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O	2776.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin J2,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2796.6	Semi standard non polar	33892256
Prostaglandin J2,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2737.8	Semi standard non polar	33892256
Prostaglandin J2,1TMS,isomer #3	CCCCC[C@H](O)/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O	2885.5	Semi standard non polar	33892256
Prostaglandin J2,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2754.9	Semi standard non polar	33892256
Prostaglandin J2,2TMS,isomer #2	CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2911.3	Semi standard non polar	33892256
Prostaglandin J2,2TMS,isomer #3	CCCCC[C@H](O)/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2858.9	Semi standard non polar	33892256
Prostaglandin J2,3TMS,isomer #1	CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2887.8	Semi standard non polar	33892256
Prostaglandin J2,3TMS,isomer #1	CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2741.4	Standard non polar	33892256
Prostaglandin J2,3TMS,isomer #1	CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3087.8	Standard polar	33892256
Prostaglandin J2,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3039.4	Semi standard non polar	33892256
Prostaglandin J2,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2983.3	Semi standard non polar	33892256
Prostaglandin J2,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O	3112.0	Semi standard non polar	33892256
Prostaglandin J2,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3241.2	Semi standard non polar	33892256
Prostaglandin J2,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3344.9	Semi standard non polar	33892256
Prostaglandin J2,2TBDMS,isomer #3	CCCCC[C@H](O)/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3326.9	Semi standard non polar	33892256
Prostaglandin J2,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3570.7	Semi standard non polar	33892256
Prostaglandin J2,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3289.9	Standard non polar	33892256
Prostaglandin J2,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3274.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin J2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-067u-5392000000-9b45d3f37955c67682bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin J2 GC-MS (2 TMS) - 70eV, Positive	splash10-00bi-9212200000-d9dcb4c0bb23a56c81d0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin J2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin J2 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOF	splash10-01b9-0089000000-78fdf4aa71747b22d9f5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOF	splash10-00xr-0097000000-d507bda3b27e80eb9966	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOF	splash10-00di-0094000000-f6f67078fe3ecda59341	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOF	splash10-00di-0091000000-240dba66bc1f4401b0c1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOF	splash10-00di-0090000000-1cb619054c8aa83a868d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOF	splash10-0fk9-0190000000-505725a881b9d2e93ec9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOF	splash10-0uk9-0290000000-de982b17f44086e4d4ae	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOF	splash10-0udi-0590000000-8f4c01a7293ad0cf7235	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOF	splash10-0uka-0950000000-219ff8b09fa3a4091f0e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 10V, Positive-QTOF	splash10-014j-0069000000-a381e76c384ef4a00dd2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 20V, Positive-QTOF	splash10-01bj-2592000000-31c78f2cc310297d596e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 40V, Positive-QTOF	splash10-05to-9320000000-0ffe9cf3d89d02767050	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 10V, Negative-QTOF	splash10-001i-0019000000-09381487459f4a98eaef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 20V, Negative-QTOF	splash10-0159-2159000000-e8aa48903843629c8575	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 40V, Negative-QTOF	splash10-0a4i-9330000000-ccd52bfaf256d7ac2024	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 10V, Negative-QTOF	splash10-00lr-0009000000-3a01c9a41ab9915ff411	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 20V, Negative-QTOF	splash10-00si-0297000000-26f532b6f59ff7845c98	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 40V, Negative-QTOF	splash10-0911-7930000000-05c866b3a6adf47ee471	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 10V, Positive-QTOF	splash10-00kk-0596000000-3753a6f26d8178114c13	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 20V, Positive-QTOF	splash10-05mt-5971000000-9fb5b5e59d1fca621a86	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin J2 40V, Positive-QTOF	splash10-0a4i-9810000000-3362a9f0c438d0c276a7	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Neuron
Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000027 +/- 0.000003 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.000072 +/- 0.000065 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	<0.0003 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	<0.0003 uM	Adult (>18 years old)	Both	Normal	21359215	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023049

KNApSAcK ID

Not Available

Chemspider ID

4444407

KEGG Compound ID

C05957

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3464

PubChem Compound

5280884

PDB ID

Not Available

ChEBI ID

27485

Food Biomarker Ontology

Not Available

VMH ID

C05957

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Zanoni, Giuseppe; Porta, Alessio; De Toma, Quintino; Castronovo, Francesca; Vidari, Giovanni. First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J2. Journal of Organic Chemistry (2003), 68(16), 6437-6439.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ogburn KD, Bottiglieri T, Wang Z, Figueiredo-Pereira ME: Prostaglandin J2 reduces catechol-O-methyltransferase activity and enhances dopamine toxicity in neuronal cells. Neurobiol Dis. 2006 May;22(2):294-301. Epub 2006 Jan 5. [PubMed:16406650 ]
Fukushima S, Takeuchi Y, Kishimoto S, Yamashita S, Uetsuki K, Shirakawa S, Suzuki M, Furuta K, Noyori R, Sasaki H, Kikuchi Y, Kita T, Yamori T, Sawada J, Kojima M, Hazato A, Kurozumi S, Fukushima M: Antitumor activity, optimum administration method and pharmacokinetics of 13,14-dihydro-15-deoxy-deoxy-Delta7 -prostaglandin A1 methyl ester (TEI-9826) integrated in lipid microspheres (Lipo TEI-9826). Anticancer Drugs. 2001 Mar;12(3):221-34. [PubMed:11290870 ]
Coyle AT, O'Keeffe MB, Kinsella BT: 15-deoxy Delta12,14-prostaglandin J2 suppresses transcription by promoter 3 of the human thromboxane A2 receptor gene through peroxisome proliferator-activated receptor gamma in human erythroleukemia cells. FEBS J. 2005 Sep;272(18):4754-73. [PubMed:16156795 ]
Wang Z, Aris VM, Ogburn KD, Soteropoulos P, Figueiredo-Pereira ME: Prostaglandin J2 alters pro-survival and pro-death gene expression patterns and 26 S proteasome assembly in human neuroblastoma cells. J Biol Chem. 2006 Jul 28;281(30):21377-86. Epub 2006 May 30. [PubMed:16737963 ]
Quinkler M, Bujalska IJ, Tomlinson JW, Smith DM, Stewart PM: Depot-specific prostaglandin synthesis in human adipose tissue: a novel possible mechanism of adipogenesis. Gene. 2006 Oct 1;380(2):137-43. Epub 2006 Jun 10. [PubMed:16842938 ]
Ogburn KD, Figueiredo-Pereira ME: Cytoskeleton/endoplasmic reticulum collapse induced by prostaglandin J2 parallels centrosomal deposition of ubiquitinated protein aggregates. J Biol Chem. 2006 Aug 11;281(32):23274-84. Epub 2006 Jun 14. [PubMed:16774923 ]

Showing metabocard for Prostaglandin J2 (HMDB0002710)

MOL for HMDB0002710 (Prostaglandin J2)

3D MOL for HMDB0002710 (Prostaglandin J2)

3D SDF for HMDB0002710 (Prostaglandin J2)

3D-SDF for HMDB0002710 (Prostaglandin J2)

PDB for HMDB0002710 (Prostaglandin J2)

3D PDB for HMDB0002710 (Prostaglandin J2)

SMILES for HMDB0002710 (Prostaglandin J2)

INCHI for HMDB0002710 (Prostaglandin J2)

Structure for HMDB0002710 (Prostaglandin J2)

3D Structure for HMDB0002710 (Prostaglandin J2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra