5α-Dihydrocortisol

5α-Dihydrocortisol (5α-DHF), also known as hydrallostane or as allodihydrocortisol,[1] is a metabolite of cortisol that is formed by 5α-reductase.[2][3] It is present in the aqueous humor of the eye, is produced in the lens of the eye, and be involved in regulating the formation of the aqueous humor.[2] 5α-DHF can be further metabolized into 3α,5α-tetrahydrocortisol by 3α-hydroxysteroid dehydrogenase.[3]

5α-Dihydrocortisol
Names
IUPAC name
11β,17α,21-Trihydroxy-5α-pregnane-3,20-dione
Systematic IUPAC name
(1R,3aS,3bS,5aS,9aS,9bS,10S,11aS)-1,10-Dihydroxy-1-(hydroxyacetyl)-9a,11a-dimethylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one
Other names
Hydrallostane; 5α-DHF; Allodihydrocortisol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12,14-16,18,22,24,26H,3-11H2,1-2H3/t12-,14-,15-,16-,18+,19-,20-,21-/m0/s1
    Key: ACSFOIGNUQUIGE-SERXDUEGSA-N
  • C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O
Properties
C21H32O5
Molar mass 364.482 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. "Hydrallostane".
  2. Azzouni F, Godoy A, Li Y, Mohler J (2012). "The 5 alpha-reductase isozyme family: a review of basic biology and their role in human diseases". Adv Urol. 2012: 530121. doi:10.1155/2012/530121. PMC 3253436. PMID 22235201.
  3. Wilson JD (2001). "The role of 5alpha-reduction in steroid hormone physiology". Reprod. Fertil. Dev. 13 (7–8): 673–8. doi:10.1071/RD01074. PMID 11999320.



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