Structure Database (LMSD)

Common Name
delta-12-PGJ2
Systematic Name
11-oxo-15S-hydroxy-5Z,9Z,12E-prostatrienoic acid
Synonyms
  • delta-12-Prostaglandin J2
LM ID
LMFA03010020
Formula
C20H30O4
Exact Mass
Calculate m/z
334.21441
Sum Composition
FA 20:5;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Prostaglandins [FA0301]

Biological Context

Δ12-Prostaglandin J2 (Δ12-PGJ2) is a decomposition product of PGD2 in aqueous media in the presence of albumin.1 It has antitumor and antiviral activity, inhibiting growth of cultured L1210 cells at with an IC50 value of 0.7 µg/ml.2 Δ12-PGJ2 is present in normal human urine with a 24 hour excretion rate of 50-150 ng.3 It is also a moderately potent PPARγ ligand.4

This information has been provided by Cayman Chemical

References

1. Kato, T., Fukushima, M., Kurozumi, S., et al. Antitumor activity of Δ7-prostaglandin A1 and Δ12-prostaglandin J2 in vitro and in vivo. Cancer Res. 46(7), 3538-3542 (1986).
2. Hirata, Y., Hayashi, H., Ito, S., et al. Occurrence of 9-deoxy-Δ9,Δ12-13,14-dihydroprostaglandin D2 in human urine. The Journal of Biological Chemisty 263(32), 16619-16625 (1988).
3. Forman, B.M., Tontonoz, P., Chen, J., et al. 15-Deoxy-Δ12,14-prostaglandin J2 is a ligand for the adipocyte determination factor PPARγ. Cell 83(5), 803-812 (1995).
4. Fitzpatrick, F.A., and Wynalda, M.A. Albumin-catalyzed metabolism of prostaglandin D2. Identification of products formed in vitro. The Journal of Biological Chemisty 258(19), 11713-11718 (1983).

Reactions

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References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Albumin-catalyzed metabolism of prostaglandin D2. Identification of products formed in vitro.,
J Biol Chem, 1983
Pubmed ID: 6578214

String Representations

InChiKey (Click to copy)
TUXFWOHFPFBNEJ-GJGHEGAFSA-N
InChi (Click to copy)
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/h4,7,12,14-17,21H,2-3,5-6,8-11,13H2,1H3,(H,23,24)/b7-4-,18-14+/t16-,17-/m0/s1
SMILES (Click to copy)
C1(=C/C[C@@H](O)CCCCC)\C(=O)C=C[C@@H]\1C/C=C\CCCC(=O)O

Other Databases

KEGG ID
C05958
HMDB ID
HMDB0004238
CHEBI ID
28130
LIPIDBANK ID
XPR1726
PubChem CID
5280885
Cayman ID
18550
GuidePharm ID
1876

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 1
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 364.16
Topological Polar Surface Area 74.60
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 4.49
Molar Refractivity 96.24

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Created at
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Updated at
12th Feb 2024