20alpha,22beta-Dihydroxycholesterol (BioCAD00000003200)

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Metabolite Card

Formula: C27H46O3 (418.3447)
SMILES: [H][C@@]12CC[C@]([H])([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)CC[C@]12C

Synonyms [en]

20alpha,22beta-Dihydroxycholesterol; (20R,22R)-20,22-dihydroxycholesterol; 20a,22b-Dihydroxycholesterol; 20-a-22-b-dihydroxycholesterol; (22R)-cholest-5-ene-3beta,20,22-triol; 20,22-dihydroxycholesterol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

20alpha,22beta-Dihydroxycholesterol. 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: BioCAD00000003200). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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).

Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 15234-55-6
  • CAS Registry Number: 596-94-1
  • PubChem: 171035483
  • PubChem: 53477897
  • PubChem: 6453841
  • PubChem: 71777104
  • PubChem: 9802154
  • ChEBI: ChEBI:1294
  • ChEBI: ChEBI:190409
  • HMDB: HMDB0006763
  • LipidMaps: LMST01010200
  • KEGG: C05501
  • BioCyc: 20A-20B-DIHYDROXY-CHOLESTEROL
  • NCBI MeSH: 20,22-dihydroxycholesterol
  • Wikipedia: 20%CE%B1,22R-Dihydroxycholesterol
  • RefMet: RM0135687
  • Metlin: METLIN_57643
  • Coconut NaturalProduct: CNP0212278.1
  • Coconut NaturalProduct: CNP0212278.2
  • Coconut NaturalProduct: CNP0248357.3
  • Coconut NaturalProduct: CNP0323856.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03933 1.14.15.6 20alpha,22beta-dihydroxycholesterol,ferredoxin:oxygen oxidoreductase (side-chain-cleaving)
KEGG:R04854 1.14.15.6 20alpha-hydroxycholesterol:oxygen oxidoreductase (side-chain-cleaving)
KEGG:R04855 1.14.15.6 22beta-hydroxycholesterol:oxygen oxidoreductase (side-chain-cleaving)
Rhea:RHEA:34340 (22R)-hydroxycholesterol + 2 reduced [adrenodoxin] + O2 + 2 H+ => (20R,22R)-20,22-dihydroxycholesterol + 2 oxidized [adrenodoxin] + H2O
Rhea:RHEA:34341 (20R,22R)-20,22-dihydroxycholesterol + 2 oxidized [adrenodoxin] + H2O => (22R)-hydroxycholesterol + 2 reduced [adrenodoxin] + O2 + 2 H+
Rhea:RHEA:34342 (22R)-hydroxycholesterol + 2 reduced [adrenodoxin] + O2 + 2 H+ <=> (20R,22R)-20,22-dihydroxycholesterol + 2 oxidized [adrenodoxin] + H2O
Rhea:RHEA:34344 (20R,22R)-20,22-dihydroxycholesterol + 2 reduced [adrenodoxin] + O2 + 2 H+ => 4-methylpentanal + pregnenolone + 2 oxidized [adrenodoxin] + 2 H2O
Rhea:RHEA:34345 4-methylpentanal + pregnenolone + 2 oxidized [adrenodoxin] + 2 H2O => (20R,22R)-20,22-dihydroxycholesterol + 2 reduced [adrenodoxin] + O2 + 2 H+
Rhea:RHEA:34346 (20R,22R)-20,22-dihydroxycholesterol + 2 reduced [adrenodoxin] + O2 + 2 H+ <=> 4-methylpentanal + pregnenolone + 2 oxidized [adrenodoxin] + 2 H2O
BioCyc:RXN66-338 22-β-hydroxycholesterol 20-α-hydroxylation
BioCyc:RXN66-339 20A-20B-DIHYDROXY-CHOLESTEROL + OXYGEN-MOLECULE + 2 Reduced-adrenal-ferredoxins + 2 PROTON --> PREGNENOLONE + 4-METHYLPENTANAL + 2 Oxidized-adrenal-ferredoxins + 2 WATER
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Organism Source

Taxonomy Source

  1. Nonomuraea roseoviolacea [ncbi taxid: 103837]

Pathway Synthetic

pathway id name
WikiPathways:WP3604 Biochemical pathways: part I
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
View All Pathways