Structure Database (LMSD)

Common Name
(20R)-17,20-dihydroxypregn-4-en-3-one
Systematic Name
17α,20R-dihydroxypregn-4-en-3-one
Synonyms
  • 17-DHP
  • 17alpha,20beta-dihydroxypregn-4-en-3-one
  • 17alpha-hydroxy-20beta-dihydroprogesterone
LM ID
LMST02030149
Formula
Exact Mass
Calculate m/z
332.235146
Sum Composition
Status
Curated

Classification

Biological Context

17α,20β-Dihydroxy-4-pregnen-3-one (17α,20β-DHP) is an endogenous, maturation-inducing steroid that stimulates oocyte maturation in females of several teleost species. For example, 1 µg/ml of 17α,20β-DHP applied to Persian sturgeon oocytes has been shown to effectively induce germinal vesicle breakdown, an essential step during oocyte maturation.1 Gonadotropin-releasing hormone and the gonadotropins, follicle-stimulating hormone and luteinizing hormone, have been shown to stimulate the production of 17α,20β-DHP either in vivo or in vitro.2 17α,20β-DHP has also been reported to influence spermiation by stimulating milt production when administered at 5 mg/kg to various male teleosts.1

This information has been provided by Cayman Chemical

References

2. Planas, J.V., and Swanson, P. Maturation-associated changes in the response of the salmon testis to the steroidogenic actions of gonadotropins (GTH I and GTH II) in vitro. Biol. Reprod. 52(3), 697-704 (1995).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Carassius auratus (#7957)
Actinopteri (#186623)
A steroid sex pheromone synchronizes male–female spawning readiness in goldfish,
Nature, 1987

String Representations

InChiKey (Click to copy)
MASCESDECGBIBB-FSHQYNQFSA-N
InChi (Click to copy)
InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12-13,16-18,22,24H,4-11H2,1-3H3/t13-,16-,17+,18+,19+,20+,21+/m1/s1
SMILES (Click to copy)
C1CC2[C@@](C)([C@@]3([H])CC[C@@]4(C)[C@@]([H])(CC[C@@]4([C@@H](C)O)O)[C@]13[H])CCC(=O)C=2

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 4
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 343.51
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 4.20
Molar Refractivity 94.36

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Created at
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Updated at
7th Apr 2025