20alpha-Hydroxycholesterol (BioCAD00000003199)

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Metabolite Card

Formula: C27H46O2 (402.3498)
SMILES: CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Synonyms [en]

20-hydroxycholesterol; 20alpha-hydroxycholesterol; (20S)-20-hydroxycholesterol; 20(S)-hydroxycholesterol; cholest-5-ene-3beta,20-diol; 20(S)-OHC

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

20alpha-Hydroxycholesterol. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000003199). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

20 alpha-hydroxycholesterol participates in C21-Steroid hormone metabolism. 20 alpha-hydroxycholesterol is produced by the reaction between cholesterol and the enzyme, cholesterol monooxygenase (side-chain-cleaving) [EC:1.14.15.6].

Extracellular Membrane Mitochondria
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 516-72-3
  • PubChem: 121935
  • PubChem: 24779600
  • PubChem: 440711
  • ChEBI: ChEBI:1296
  • ChEBI: ChEBI:166801
  • HMDB: HMDB0006283
  • LipidMaps: LMST01010201
  • LipidMaps: LMST01010211
  • KEGG: C05500
  • BioCyc: 2-HYDROXY-CHOLESTEROL
  • NCBI MeSH: 20-hydroxycholesterol
  • Wikipedia: 20S-Hydroxycholesterol
  • DrugBank: DB04704
  • RefMet: RM0018306
  • RefMet: RM0135688
  • Metlin: METLIN_24053
  • Coconut NaturalProduct: CNP0347064.1
  • Coconut NaturalProduct: CNP0347064.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01454 1.14.15.6 cholesterol:oxygen oxidoreductase (side-chain-cleaving)
KEGG:R04853 1.14.14.19 20alpha-hydroxycholesterol,NADPH-hemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating)
KEGG:R04854 1.14.15.6 20alpha-hydroxycholesterol:oxygen oxidoreductase (side-chain-cleaving)
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Organism Source

Taxonomy Source

  1. Homo sapiens [ncbi taxid: 9606]
  2. Mus musculus [ncbi taxid: 10090]

Pathway Synthetic

pathway id name
PathBank:SMP0120690 Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH
PathBank:SMP0120858 11-beta-Hydroxylase Deficiency (CYP11B1)
PathBank:SMP0120641 Corticosterone Methyl Oxidase I Deficiency (CMO I)
PathBank:SMP0120649 Apparent Mineralocorticoid Excess Syndrome
PathBank:SMP0000373 Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency
PathBank:SMP0000576 21-Hydroxylase Deficiency (CYP21)
PathBank:SMP0000718 3-beta-Hydroxysteroid Dehydrogenase Deficiency
PathBank:SMP0087238 Steroidogenesis
PathBank:SMP0120849 17-alpha-Hydroxylase Deficiency (CYP17)
PathBank:SMP0120861 Corticosterone Methyl Oxidase II Deficiency (CMO II)
PathBank:SMP0120869 3-beta-Hydroxysteroid Dehydrogenase Deficiency
PathBank:SMP0120451 Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency
PathBank:SMP0120640 21-Hydroxylase Deficiency (CYP21)
PathBank:SMP0000575 11-beta-Hydroxylase Deficiency (CYP11B1)
PathBank:SMP0000717 Apparent Mineralocorticoid Excess Syndrome
PathBank:SMP0063672 Steroidogenesis
PathBank:SMP0120672 Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency
PathBank:SMP0120860 Corticosterone Methyl Oxidase I Deficiency (CMO I)
PathBank:SMP0120868 Apparent Mineralocorticoid Excess Syndrome
PathBank:SMP0120630 17-alpha-Hydroxylase Deficiency (CYP17)
View All Pathways