Structure Database (LMSD)
Common Name
Allopregnanolone
Systematic Name
3α-hydroxy-5α-pregnane-20-one
Synonyms
- (3alpha,5alpha)-3-hydroxypregnan-20-one
- allopregnan-3alpha-ol-20-one
- brexanolone
LM ID
LMST02030130
Formula
Exact Mass
Calculate m/z
318.25588
Sum Composition
Status
Curated
3D model of Allopregnanolone
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Allopregnanolone is an analytical reference standard categorized as a GABAA and GABAC receptor positive allosteric modulator.1,2 Allopregnanolone has anxiolytic-like and anticonvulsant activities in rodents.3,4 Formulations containing allopregnanolone have been used in the treatment of postpartum depression. Allopregnanolone 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. Fernández-Guasti, A., and Picazo, O. Flumazenil blocks the anxiolytic action of allopregnanolone. Eur. J. Pharmacol. 281(1), 113-115 (1995).
2. Alvarez, L.D., Pecci, A., and Estrin, D.A. In search of GABAA receptor’s neurosteroid binding sites. J. Med. Chem. 62(11), 5250-5260 (2019).
Reactions
Filter by species:
ⓘ
Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).

References
String Representations
InChiKey (Click to copy)
AURFZBICLPNKBZ-SYBPFIFISA-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)
[C@@]12([H])CC[C@@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@H](C(=O)C)CC[C@@]21[H]
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID
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
Admin
Created at
-
Updated at
15th Dec 2020