pregnenolone   Click here for help

GtoPdb Ligand ID: 2376

Approved drug PDB Ligand
pregnenolone is an approved drug
Compound class: Metabolite
Comment: Pregnenolone is an endogenous steroid hormone and is the precursor of the progestogens, mineralocorticoids, glucocorticoids, androgens, estrogens and neuroactive steroids.

pregnenolone is commercially available from our sponsors

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 316.24
XLogP 4.83
No. Lipinski's rules broken 0

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(=CCC3C2CCC2(C3CCC2C(=O)C)C)C1)C
Isomeric SMILES O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2C(=O)C)C)C1)C
InChI InChI=1S/C21H32O2/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/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
InChI Key ORNBQBCIOKFOEO-QGVNFLHTSA-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/)
No information available.
Summary of Clinical Use Click here for help
In the brain pregnenolone acts as a neurosteroid [3-4] with synaptic function, neuroprotective and myelinization enhancing properties. Based on this activity pregnenolone and its sulphate ester (PubChem CID 105074) have been investigated as potential nootropics [5], and pregnenolone was also considered as an anti-schizophrenic [3].
The only clinical approval for pregnenolone appears to be a combination formulation with androstenedione available in Japan.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Pregnenolone sulfate has been reported to act as an activator of the TRPM1 and TRPM3 channels [1].