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
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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Search Google for chemical match using the InChIKey AURFZBICLPNKBZ-YZRLXODZSA-N
Search Google for chemicals with the same backbone AURFZBICLPNKBZ
Search PubMed clinical trials eltanolone
Search PubMed titles eltanolone
Search PubMed titles/abstracts eltanolone
Search UniChem for chemical match using the InChIKey AURFZBICLPNKBZ-YZRLXODZSA-N
Search UniChem for chemicals with the same backbone AURFZBICLPNKBZ