eltanolone   Click here for help

GtoPdb Ligand ID: 11534

Synonyms: 3α,5β-tetrahydroprogesterone | 3α,5β-THP | 3α-hydroxy-5β-pregnan-20-one | Pregnan-3alpha-ol-20-one | pregnanolone
PDB Ligand
Compound class: Metabolite or derivative
Comment: Eltanolone (pregnanolone) is an endogenous neurosteroid that is derived from progesterone. It is a stereoisomer of 5α-pregnan-3α-ol-20-one (allopregnanolone). Like allopregnanolone it behaves as a positive allosteric modulator of GABAA receptors. It is often formulated as the sulphate salt. Eltanolone induces sedative, anxiolytic, anesthetic, and anticonvulsant effects.
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 CDK toolkit. 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
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.

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Canonical 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
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-/m1/s1
InChI Key AURFZBICLPNKBZ-YZRLXODZSA-N
Classification Click here for help
Compound class Metabolite or derivative
IUPAC Name Click here for help
1-[(3R,5R,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
6781 eltanolone
Synonyms Click here for help
3α,5β-tetrahydroprogesterone | 3α,5β-THP | 3α-hydroxy-5β-pregnan-20-one | Pregnan-3alpha-ol-20-one | pregnanolone
Database Links Click here for help
CAS Registry No. 128-20-1 (source: WHO INN record)
DrugBank Ligand DB12308
GtoPdb PubChem SID 441604906
PubChem CID 31402
RCSB PDB Ligand P9N
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UniChem Compound Search for chemical match using the InChIKey AURFZBICLPNKBZ-YZRLXODZSA-N
UniChem Connectivity Search for chemical match using the InChIKey AURFZBICLPNKBZ-YZRLXODZSA-N