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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.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Metabolite
Approved drug? Yes. US FDA (2019)
IUPAC Name Click here for help
1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
International Nonproprietary Names Click here for help
INN number INN
10446 brexanolone
Synonyms Click here for help
3α,5α-tetrahydroprogesterone | 3α,5α-THP | allopregnanolone | SAGE-547 | SAGE547 | Zulresso®
Database Links Click here for help
CAS Registry No. 516-54-1 (source: Scifinder)
ChEBI CHEBI:50169
ChEMBL Ligand CHEMBL207538
GtoPdb PubChem SID 178100930
LIPID MAPS LMST02030130
PubChem CID 92786
RCSB PDB Ligand Y4B
Search Google for chemical match using the InChIKey AURFZBICLPNKBZ-SYBPFIFISA-N
Search Google for chemicals with the same backbone AURFZBICLPNKBZ
Search PubMed clinical trials brexanolone
Search PubMed titles brexanolone
Search PubMed titles/abstracts brexanolone
UniChem Compound Search for chemical match using the InChIKey AURFZBICLPNKBZ-SYBPFIFISA-N
UniChem Connectivity Search for chemical match using the InChIKey AURFZBICLPNKBZ-SYBPFIFISA-N
Wikipedia Allopregnanolone