Structure Database (LMSD)

Common Name
3beta-hydroxy-5alpha-pregnan-20-one
Systematic Name
3β-hydroxy-5α-pregnan-20-one
Synonyms
  • (3beta,5alpha)-3-hydroxypregnan-20-one
  • 3beta-hydroxy-5alpha-pregnane-20-one
  • 5alpha-pregnan-3beta-ol-20-one
  • allopregnan-3beta-ol-20-one
LM ID
LMST02030173
Formula
C21H34O2
Exact Mass
Calculate m/z
318.25588
Sum Composition
ST 21:1;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]

Biological Context

Isopregnanolone is an analytical reference standard categorized as a steroid metabolite.1 Isopregnanolone is a metabolite of progesterone. Isopregnanolone is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.

This information has been provided by Cayman Chemical

References

1. Murphy, B.E.P., Abbott, F.V., Allison, C.M., et al. Elevated levels of some neuroactive progesterone metabolites, particularly isopregnanolone, in women with chronic fatigue syndrome. Psychoneuroendocrinology 29(2), 245-268 (2004).

String Representations

InChiKey (Click to copy)
AURFZBICLPNKBZ-FZCSVUEKSA-N
InChi (Click to copy)
InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16-,17+,18-,19-,20-,21+/m0/s1
SMILES (Click to copy)
C1C[C@H](O)C[C@]2([H])CC[C@]3([H])[C@@]([H])([C@]21C)CC[C@]1(C)[C@@]([H])(C(=O)C)CC[C@]13[H]

Other Databases

KEGG ID
C15484
HMDB ID
HMDB0001455
CHEBI ID
11909
PubChem CID
92787
SwissLipids ID
SLM:000485663
Cayman ID
32708

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 4
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 337.36
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 4.88
Molar Refractivity 92.42

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Updated at
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