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.
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 316.24
XLogP 4.83
No. Lipinski's rules broken 0
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 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
Classification Click here for help
Compound class Metabolite
Approved drug? Yes
IUPAC Name Click here for help
1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
International Nonproprietary Names Click here for help
INN number INN
4178 pregnenolone
Database Links Click here for help
CAS Registry No. 145-13-1 (source: SciFinder)
ChEBI CHEBI:16581
ChEMBL Ligand CHEMBL253363
DrugBank Ligand DB02789
GtoPdb PubChem SID 135651548
LIPID MAPS LMST02030088
PubChem CID 8955
RCSB PDB Ligand PLO
Search Google for chemical match using the InChIKey ORNBQBCIOKFOEO-QGVNFLHTSA-N
Search Google for chemicals with the same backbone ORNBQBCIOKFOEO
Search PubMed clinical trials pregnenolone
Search PubMed titles pregnenolone
Search PubMed titles/abstracts pregnenolone
UniChem Compound Search for chemical match using the InChIKey ORNBQBCIOKFOEO-QGVNFLHTSA-N
UniChem Connectivity Search for chemical match using the InChIKey ORNBQBCIOKFOEO-QGVNFLHTSA-N
Wikipedia Pregnenolone