20a,22b-Dihydroxycholesterol (BioDeep_00000005852)
Main id: BioDeep_00000636711
human metabolite Endogenous
代谢物信息卡片
化学式: C27H46O3 (418.34467659999996)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C)CCC(C(C)(C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O)O
InChI: InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19-,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1
描述信息
20alpha,22beta-Dihydroxycholesterol is an intermediate in C21-Steroid hormone metabolism. 20alpha,22beta-Dihydroxycholesterol is the 8th to last step in the synthesis of 3alpha,11beta,21-Trihydroxy-20-oxo-5beta-pregnan-18-al and is converted from 20alpha-Hydroxycholesterol via the enzyme cytochrome P450 (EC 1.14.15.6). It is then converted to Pregnenolone via the enzyme cytochrome P450 (EC 1.14.15.6). [HMDB]
20alpha,22beta-Dihydroxycholesterol is an intermediate in C21-Steroid hormone metabolism. 20alpha,22beta-Dihydroxycholesterol is the 8th to last step in the synthesis of 3alpha,11beta,21-Trihydroxy-20-oxo-5beta-pregnan-18-al and is converted from 20alpha-Hydroxycholesterol via the enzyme cytochrome P450 (EC 1.14.15.6). It is then converted to Pregnenolone via the enzyme cytochrome P450 (EC 1.14.15.6).
同义名列表
9 个代谢物同义名
(2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol; 2-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylheptane-2,3-diol; (20R,22R)-20,22-Dihydroxycholesterol;(22R)-20alpha,22-Dihydroxycholesterol; (22R)-cholest-5-ene-3beta,20,22-triol; (20R,22R)-20,22-dihydroxycholesterol; 20alpha,22beta-Dihydroxycholesterol; 20alpha,22R-Dihydroxycholesterol; 20a,22b-Dihydroxycholesterol; 20,22-Dihydroxycholesterol
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:190409
- ChEBI: CHEBI:1294
- KEGG: C05501
- PubChem: 53477897
- PubChem: 6453841
- PubChem: 5118785
- HMDB: HMDB0006763
- Metlin: METLIN57643
- ChEMBL: CHEMBL560194
- foodb: FDB024066
- CAS: 15234-55-6
- CAS: 596-94-1
- PMhub: MS000018750
- PubChem: 7854
- LipidMAPS: LMST01010200
- PDB-CCD: 2DC
- 3DMET: B05066
- NIKKAJI: J401.177E
分类词条
相关代谢途径
Reactome(13)
- Metabolism
- Biological oxidations
- Phase I - Functionalization of compounds
- Disease
- Metabolism of lipids
- Metabolism of steroids
- Diseases of metabolism
- Cytochrome P450 - arranged by substrate type
- Endogenous sterols
- Metabolic disorders of biological oxidation enzymes
- Metabolism of steroid hormones
- Pregnenolone biosynthesis
- Defective CYP11A1 causes AICSR
BioCyc(0)
PlantCyc(0)
代谢反应
116 个相关的代谢反应过程信息。
Reactome(81)
- Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of lipids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of steroids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of steroid hormones:
17aHPROG + H+ + Oxygen + TPNH ⟶ 11-deoxycortisol + H2O + TPN
- Pregnenolone biosynthesis:
STAR:CHOL ⟶ CHOL + STAR
- Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Cytochrome P450 - arranged by substrate type:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Endogenous sterols:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of steroids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of steroid hormones:
17aHPROG + H+ + Oxygen + TPNH ⟶ 11-deoxycortisol + H2O + TPN
- Pregnenolone biosynthesis:
STAR:CHOL ⟶ CHOL + STAR
- Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Cytochrome P450 - arranged by substrate type:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Endogenous sterols:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of steroids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of steroid hormones:
17aHPROG + H+ + Oxygen + TPNH ⟶ 11-deoxycortisol + H2O + TPN
- Pregnenolone biosynthesis:
STAR:CHOL ⟶ CHOL + star
- Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Cytochrome P450 - arranged by substrate type:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Endogenous sterols:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of steroids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of steroid hormones:
17aHPROG + H+ + Oxygen + TPNH ⟶ 11-deoxycortisol + H2O + TPN
- Pregnenolone biosynthesis:
STAR:CHOL ⟶ CHOL + STAR
- Biological oxidations:
H+ + Oxygen + TPNH + progesterone ⟶ 11DCORST + H2O + TPN
- Phase I - Functionalization of compounds:
H+ + Oxygen + TPNH + progesterone ⟶ 11DCORST + H2O + TPN
- Cytochrome P450 - arranged by substrate type:
H+ + Oxygen + TPNH + progesterone ⟶ 11DCORST + H2O + TPN
- Endogenous sterols:
H+ + Oxygen + TPNH + progesterone ⟶ 11DCORST + H2O + TPN
- Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of steroids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of steroid hormones:
11-deoxycortisol ⟶ 11DCORT
- Pregnenolone biosynthesis:
STAR:CHOL ⟶ CHOL + STAR
- Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Cytochrome P450 - arranged by substrate type:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Endogenous sterols:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of steroids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of steroid hormones:
17aHPROG + H+ + Oxygen + TPNH ⟶ 11-deoxycortisol + H2O + TPN
- Pregnenolone biosynthesis:
STAR:CHOL ⟶ CHOL + Star
- Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Cytochrome P450 - arranged by substrate type:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Endogenous sterols:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of steroids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of steroid hormones:
17aHPROG + H+ + Oxygen + TPNH ⟶ 11-deoxycortisol + H2O + TPN
- Pregnenolone biosynthesis:
STAR:CHOL ⟶ CHOL + Star
- Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Cytochrome P450 - arranged by substrate type:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Endogenous sterols:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Metabolism of lipids:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Metabolism of steroids:
17aHPROG + H+ + Oxygen + TPNH ⟶ 11-deoxycortisol + H2O + TPN
- Metabolism of steroid hormones:
17aHPROG + H+ + Oxygen + TPNH ⟶ 11-deoxycortisol + H2O + TPN
- Pregnenolone biosynthesis:
H+ + ISCAL + TPNH ⟶ MePeOH + TPN
- Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Cytochrome P450 - arranged by substrate type:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Endogenous sterols:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of steroids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of steroid hormones:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Pregnenolone biosynthesis:
STAR:CHOL ⟶ CHOL + STAR
- Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Cytochrome P450 - arranged by substrate type:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
- Endogenous sterols:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
BioCyc(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(34)
- Steroidogenesis:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 17-alpha-Hydroxylase Deficiency (CYP17):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 11-beta-Hydroxylase Deficiency (CYP11B1):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 21-Hydroxylase Deficiency (CYP21):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Corticosterone Methyl Oxidase I Deficiency (CMO I):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Corticosterone Methyl Oxidase II Deficiency (CMO II):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Apparent Mineralocorticoid Excess Syndrome:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 3-beta-Hydroxysteroid Dehydrogenase Deficiency:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Steroidogenesis:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 17-alpha-Hydroxylase Deficiency (CYP17):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 11-beta-Hydroxylase Deficiency (CYP11B1):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 21-Hydroxylase Deficiency (CYP21):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Corticosterone Methyl Oxidase I Deficiency (CMO I):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Corticosterone Methyl Oxidase II Deficiency (CMO II):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Apparent Mineralocorticoid Excess Syndrome:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 3-beta-Hydroxysteroid Dehydrogenase Deficiency:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Steroidogenesis:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Steroidogenesis:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 17-alpha-Hydroxylase Deficiency (CYP17):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 11-beta-Hydroxylase Deficiency (CYP11B1):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 21-Hydroxylase Deficiency (CYP21):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Corticosterone Methyl Oxidase I Deficiency (CMO I):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Corticosterone Methyl Oxidase II Deficiency (CMO II):
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- Apparent Mineralocorticoid Excess Syndrome:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
- 3-beta-Hydroxysteroid Dehydrogenase Deficiency:
Cortexolone + Oxygen + Reduced adrenal ferredoxin ⟶ Cortisol + Oxidized adrenal ferredoxin + Water
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Feng Wang, Frank Stappenbeck, William Matsui, Farhad Parhami. Inhibition of Pancreatic Cancer Cell-Induced Paracrine Hedgehog Signaling by Liver X Receptor Agonists and Oxy16, a Naturally Occurring Oxysterol.
Journal of cellular biochemistry.
2017 03; 118(3):499-509. doi:
10.1002/jcb.25668
. [PMID: 27490478] - Anna Meljon, Spyridon Theofilopoulos, Cedric H L Shackleton, Gordon L Watson, Norman B Javitt, Hans-Joachim Knölker, Ratni Saini, Ernest Arenas, Yuqin Wang, William J Griffiths. Analysis of bioactive oxysterols in newborn mouse brain by LC/MS.
Journal of lipid research.
2012 Nov; 53(11):2469-83. doi:
10.1194/jlr.d028233
. [PMID: 22891291]