Reaction participants Show >> << Hide
- Name help_outline O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline prostaglandin I2 Identifier CHEBI:57403 (Beilstein: 8135954) help_outline Charge -1 Formula C20H31O5 InChIKeyhelp_outline KAQKFAOMNZTLHT-OZUDYXHBSA-M SMILEShelp_outline [H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])C\C(O2)=C\CCCC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
reduced [NADPH—hemoprotein reductase]
Identifier
RHEA-COMP:11964
Reactive part
help_outline
- Name help_outline FMNH2 Identifier CHEBI:57618 (Beilstein: 6258176) help_outline Charge -2 Formula C17H21N4O9P InChIKeyhelp_outline YTNIXZGTHTVJBW-SCRDCRAPSA-L SMILEShelp_outline Cc1cc2Nc3c([nH]c(=O)[nH]c3=O)N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])([O-])=O)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 771 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 19-hydroxy-prostaglandin I2 Identifier CHEBI:137987 Charge -1 Formula C20H31O6 InChIKeyhelp_outline PGRXDTJFXIPRSO-QAQUDUTNSA-M SMILEShelp_outline O1/C(/C[C@]2([C@@]1(C[C@H]([C@@H]2/C=C/[C@H](CCCC(C)O)O)O)[H])[H])=C\CCCC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
oxidized [NADPH—hemoprotein reductase]
Identifier
RHEA-COMP:11965
Reactive part
help_outline
- Name help_outline FMN Identifier CHEBI:58210 Charge -3 Formula C17H18N4O9P InChIKeyhelp_outline ANKZYBDXHMZBDK-SCRDCRAPSA-K SMILEShelp_outline C12=NC([N-]C(C1=NC=3C(N2C[C@@H]([C@@H]([C@@H](COP(=O)([O-])[O-])O)O)O)=CC(=C(C3)C)C)=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 781 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:53932 | RHEA:53933 | RHEA:53934 | RHEA:53935 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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On the mechanism of biosynthesis of 19-hydroxyprostaglandins of human seminal fluid and expression of cyclooxygenase-2, PGH 19-hydroxylase (CYP4F8) and microsomal PGE synthase-1 in seminal vesicles and vas deferens.
Stark K., Bylund J., Toermae H., Sahlen G., Oliw E.H.
The predominating prostaglandins of human seminal fluid are 19R-hydroxyprostaglandins E1 and E2, conceivably formed sequentially by prostaglandin H (PGH) synthase-2, PGH 19-hydroxylase (CYP4F8), and microsomal PGE synthase-1 of seminal vesicles. Our aim was to study this enzyme system. Quantificat ... >> More
The predominating prostaglandins of human seminal fluid are 19R-hydroxyprostaglandins E1 and E2, conceivably formed sequentially by prostaglandin H (PGH) synthase-2, PGH 19-hydroxylase (CYP4F8), and microsomal PGE synthase-1 of seminal vesicles. Our aim was to study this enzyme system. Quantification by real-time PCR suggested that the transcripts of PGH synthase-2, CYP4F8, and microsomal PGE synthase-1 were abundant and correlated in seminal vesicles of seven patients (p < 0.05). The three enzymes were detected in seminal vesicles by Western blot analysis, and immunohistological analysis confirmed the localization to the epithelia of seminal vesicles and distal vas deferens. Immunofluorescence analysis showed co-localization of the three enzymes in epithelial cells of seminal vesicles and vas deferens. 19-Hydroxy-PGE compounds were detected by mass spectrometry in the mucosa of distal vas deferens. Recombinant CYP4F8 catalyzes n-2 hydroxylation of PGH1 and PGH2 and n-3 hydroxylation of arachidonic acid. Arachidonic acid was oxidized to 18-hydroxyarachidonic acid and to PGE2 and by microsomes of seminal vesicles in the presence of NADPH and GSH, and to relatively small amounts of 19-hydroxy-PGE2. We conclude that PGH synthase-2, CYP4F8, and PGE synthase-1 likely forms 19-hydroxy-PGE compounds in seminal vesicles and vas deferens, but the catalytic properties of CYP4F8 suggest additional biological functions. Recombinant CYP4F8 was also found to catalyze n-2 hydroxylation of PGI2 and carbaprostacyclin (Km to approximately 40 microM), and n-2 and n-3 hydroxylation of carbocyclic TXA2. << Less
Prostaglandins Other Lipid Mediat. 75:47-64(2005) [PubMed] [EuropePMC]
This publication is cited by 4 other entries.