22R-Hydroxycholesterol (original) (raw)
22R-Hydroxycholesterol, or (3β)-cholest-5-ene-3,22-diol is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol. Cholesterol ((3β)-cholest-5-en-3-ol) is hydroxylated by cholesterol side-chain cleavage enzyme (P450scc) to form 22R-hydroxycholesterol, which is subsequently hydroxylated again by P450scc to form 20α,22R-dihydroxycholesterol, and finally the bond between carbons 20 and 22 is cleaved by P450scc to form pregnenolone ((3β)-3-hydroxypregn-5-en-20-one), the precursor to the steroid hormones. It is an agonist of the liver X receptor.
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| dbo:abstract | 22R-Hydroxycholesterol, or (3β)-cholest-5-ene-3,22-diol is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol. Cholesterol ((3β)-cholest-5-en-3-ol) is hydroxylated by cholesterol side-chain cleavage enzyme (P450scc) to form 22R-hydroxycholesterol, which is subsequently hydroxylated again by P450scc to form 20α,22R-dihydroxycholesterol, and finally the bond between carbons 20 and 22 is cleaved by P450scc to form pregnenolone ((3β)-3-hydroxypregn-5-en-20-one), the precursor to the steroid hormones. It is an agonist of the liver X receptor. (en) Le 22R-hydroxycholestérol est un intermédiaire métabolique endogène de la biosynthèse des hormones stéroïdiennes à partir du cholestérol. C'est le produit de la première étape de la conversion du cholestérol en prégnénolone par l'enzyme de clivage de la chaîne latérale du cholestérol, ou P450scc. (fr) 22R-하이드록시콜레스테롤(영어: 22R-hydroxycholesterol)은 콜레스테롤로부터 스테로이드 호르몬의 생합성 과정에서의 내인성 대사 중간생성물이다. 콜레스테롤은 (P450scc)에 의해 하이드록실화되어 22R-하이드록시콜레스테롤을 형성한다. 이어서 22R-하이드록시콜레스테롤은 콜레스테롤 곁사슬 절단효소에 의해 다시 하이드록실화되어 20α,22R-다이하이드록시콜레스테롤을 형성한다. 마지막으로 20α,22R-다이하이드록시콜레스테롤의 20번 탄소와 22번 탄소 사이의 결합은 콜레스테롤 곁사슬 절단효소에 의해 분해되어 스테로이드 호르몬의 전구체인 을 형성한다. 22R-하이드록시콜레스테롤은 의 작용제이다. (ko) 22R-羟基胆固醇（英語：22R-Hydroxycholesterol）是一种内源性的胆固醇代谢中间产物，参与甾体激素的生物合成。 胆固醇被细胞色素P450家族的CYP11A1胆固醇侧链裂解酶（P450scc）羟基化形成22R-羟基胆固醇，之后再次被P450scc 羟基化为20α,22R-二羟基胆固醇，最后再被P450scc裂解20和22号碳原子之间的C-C键成为21个碳原子的孕烯醇酮，作为甾体激素的前体物质。 22R-羟基胆固醇也是肝X受体的激动剂。 (zh) |
| dbo:iupacName | (3β)-Cholest-5-ene-3,22-diol (en) (1R,3aS,3bS,7S,9aR,9bS,11aS)-1-[(2S,3R)-3-Hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol (en) |
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| dbo:wikiPageWikiLink | dbr:Pregnenolone dbr:Metabolic_intermediate dbc:Cholestanes dbr:Hydroxylated dbc:Sterols dbr:Cholesterol_side-chain_cleavage_enzyme dbr:20α,22R-Dihydroxycholesterol dbr:27-Hydroxycholesterol dbr:Agonist dbr:Endogenous dbr:Precursor_(chemistry) dbr:Cholesterol dbr:Biosynthesis dbr:20α,22R-dihydroxycholesterol dbr:Bond_cleavage dbr:Liver_X_receptor dbr:Steroid_hormone |
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| dbp:iupacname | -Cholest-5-ene-3,22-diol (en) |
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| dcterms:subject | dbc:Cholestanes dbc:Sterols |
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| rdfs:comment | 22R-Hydroxycholesterol, or (3β)-cholest-5-ene-3,22-diol is an endogenous, metabolic intermediate in the biosynthesis of the steroid hormones from cholesterol. Cholesterol ((3β)-cholest-5-en-3-ol) is hydroxylated by cholesterol side-chain cleavage enzyme (P450scc) to form 22R-hydroxycholesterol, which is subsequently hydroxylated again by P450scc to form 20α,22R-dihydroxycholesterol, and finally the bond between carbons 20 and 22 is cleaved by P450scc to form pregnenolone ((3β)-3-hydroxypregn-5-en-20-one), the precursor to the steroid hormones. It is an agonist of the liver X receptor. (en) Le 22R-hydroxycholestérol est un intermédiaire métabolique endogène de la biosynthèse des hormones stéroïdiennes à partir du cholestérol. C'est le produit de la première étape de la conversion du cholestérol en prégnénolone par l'enzyme de clivage de la chaîne latérale du cholestérol, ou P450scc. (fr) 22R-하이드록시콜레스테롤(영어: 22R-hydroxycholesterol)은 콜레스테롤로부터 스테로이드 호르몬의 생합성 과정에서의 내인성 대사 중간생성물이다. 콜레스테롤은 (P450scc)에 의해 하이드록실화되어 22R-하이드록시콜레스테롤을 형성한다. 이어서 22R-하이드록시콜레스테롤은 콜레스테롤 곁사슬 절단효소에 의해 다시 하이드록실화되어 20α,22R-다이하이드록시콜레스테롤을 형성한다. 마지막으로 20α,22R-다이하이드록시콜레스테롤의 20번 탄소와 22번 탄소 사이의 결합은 콜레스테롤 곁사슬 절단효소에 의해 분해되어 스테로이드 호르몬의 전구체인 을 형성한다. 22R-하이드록시콜레스테롤은 의 작용제이다. (ko) 22R-羟基胆固醇（英語：22R-Hydroxycholesterol）是一种内源性的胆固醇代谢中间产物，参与甾体激素的生物合成。 胆固醇被细胞色素P450家族的CYP11A1胆固醇侧链裂解酶（P450scc）羟基化形成22R-羟基胆固醇，之后再次被P450scc 羟基化为20α,22R-二羟基胆固醇，最后再被P450scc裂解20和22号碳原子之间的C-C键成为21个碳原子的孕烯醇酮，作为甾体激素的前体物质。 22R-羟基胆固醇也是肝X受体的激动剂。 (zh) |
| rdfs:label | 22R-Hydroxycholesterol (en) 22R-Hydroxycholestérol (fr) 22R-하이드록시콜레스테롤 (ko) 22R-羟基胆固醇 (zh) |
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