5-Dehydroepisterol
5-Dehydroepisterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 5-dehydroepisterol is considered to be a sterol lipid molecule. 5-Dehydroepisterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Dehydroepisterol is an intermediate in the biosynthesis of steroids and is converted from episterol via the enzyme lathosterol oxidase (EC 1.14.21.6). It is then converted into 24-methylenecholesterol via the enzyme 7-dehydrocholesterol reductase (EC 1.3.1.21).
| ID | EC Number | Name |
|---|---|---|
| KEGG:R07491 | 1.14.19.20 | episterol,ferrocytochrome b5:oxygen oxidoreductase 5,6-dehydrogenating |
| KEGG:R07492 | 1.3.1.21 | C15780<=>C15781 |
| KEGG:R07506 | 1.14.19.41 | ergosta-5,7,24(28)-trien-3beta-ol,NADPH:oxygen oxidoreductase (22,23-dehydrogenating) |
| Rhea:RHEA:33464 | episterol + NADPH + O2 + H+ => 5-dehydroepisterol + NADP+ + 2 H2O | |
| Rhea:RHEA:33465 | 5-dehydroepisterol + NADP+ + 2 H2O => episterol + NADPH + O2 + H+ | |
| Rhea:RHEA:33466 | episterol + NADPH + O2 + H+ <=> 5-dehydroepisterol + NADP+ + 2 H2O | |
| Rhea:RHEA:33468 | 1.14.19.41 | 5-dehydroepisterol + NADPH + O2 + H+ => ergosta-5,7,22,24(28)-tetraen-3β-ol + NADP+ + 2 H2O |
| Rhea:RHEA:33469 | 1.14.19.41 | ergosta-5,7,22,24(28)-tetraen-3β-ol + NADP+ + 2 H2O => 5-dehydroepisterol + NADPH + O2 + H+ |
| Rhea:RHEA:33470 | 1.14.19.41 | 5-dehydroepisterol + NADPH + O2 + H+ <=> ergosta-5,7,22,24(28)-tetraen-3β-ol + NADP+ + 2 H2O |
| Rhea:RHEA:34008 | 7-dehydrodesmosterol + S-adenosyl-L-methionine => 5-dehydroepisterol + S-adenosyl-L-homocysteine + H+ | |
| Rhea:RHEA:34009 | 5-dehydroepisterol + S-adenosyl-L-homocysteine + H+ => 7-dehydrodesmosterol + S-adenosyl-L-methionine | |
| Rhea:RHEA:34010 | 7-dehydrodesmosterol + S-adenosyl-L-methionine <=> 5-dehydroepisterol + S-adenosyl-L-homocysteine + H+ | |
| Rhea:RHEA:34012 | 5-dehydroepisterol + NADP+ + 2 H2O => ergosta-5,7-dien-3βbeta-ol + NADPH + O2 + H+ | |
| Rhea:RHEA:34013 | ergosta-5,7-dien-3βbeta-ol + NADPH + O2 + H+ => 5-dehydroepisterol + NADP+ + 2 H2O | |
| Rhea:RHEA:34014 | 5-dehydroepisterol + NADP+ + 2 H2O <=> ergosta-5,7-dien-3βbeta-ol + NADPH + O2 + H+ | |
| Rhea:RHEA:46561 | 1.14.19.20 | episterol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ => 5-dehydroepisterol + 2 Fe(III)-[cytochrome b5] + 2 H2O |
| Rhea:RHEA:46562 | 1.14.19.20 | 5-dehydroepisterol + 2 Fe(III)-[cytochrome b5] + 2 H2O => episterol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ |
| Rhea:RHEA:46563 | 1.14.19.20 | episterol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ <=> 5-dehydroepisterol + 2 Fe(III)-[cytochrome b5] + 2 H2O |