5α-pregnan-3α-ol-20-one   Click here for help

GtoPdb Ligand ID: 4108

Synonyms: 3α,5α-tetrahydroprogesterone | 3α,5α-THP | allopregnanolone | SAGE-547 | SAGE547 | Zulresso®
Approved drug PDB Ligand
5α-pregnan-3α-ol-20-one is an approved drug (FDA (2019))
Compound class: Metabolite
Comment: This steroidal compound behaves as a neuroactive agent with anti-depressant activity in mood disorders [2-3]. Pharmacologically it is a positive allosteric modulator of GABAA receptors.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 37.3
Molecular weight 318.26
XLogP 6.1
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OC1CCC2(C(C1)CCC1C2CCC2(C1CCC2C(=O)C)C)C
Isomeric SMILES O[C@@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
InChI 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
InChI Key AURFZBICLPNKBZ-SYBPFIFISA-N
Natural/Endogenous Targets
Target
GABAA receptor α1 subunit
GABAA receptor α2 subunit
GABAA receptor α3 subunit
GABAA receptor α4 subunit
GABAA receptor α5 subunit
GABAA receptor α6 subunit
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
GABAA receptor α1 subunit Ligand is endogenous in the given species Hs Allosteric modulator Potentiation - - -
GABAA receptor α2 subunit Ligand is endogenous in the given species Hs Allosteric modulator Potentiation - - -
GABAA receptor α3 subunit Ligand is endogenous in the given species Hs Allosteric modulator Potentiation - - -
GABAA receptor α4 subunit Ligand is endogenous in the given species Hs Allosteric modulator Potentiation - - -
GABAA receptor α5 subunit Ligand is endogenous in the given species Hs Allosteric modulator Potentiation - - -
GABAA receptor α6 subunit Ligand is endogenous in the given species Hs Allosteric modulator Potentiation - - -
Ligand mentioned in the following text fields