cholesterol   Click here for help

GtoPdb Ligand ID: 2718

Synonyms: cholest-5-en-3β-ol
PDB Ligand
Compound class: Metabolite
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 1
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 20.23
Molecular weight 386.35
XLogP 10.52
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 CC(CCCC(C1CCC2C1(C)CCC1C2CC=C2C1(C)CCC(C2)O)C)C
Isomeric SMILES CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C)C
InChI InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI Key HVYWMOMLDIMFJA-DPAQBDIFSA-N
Natural/Endogenous Targets
Target
RAR-related orphan receptor-α
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
RAR-related orphan receptor-α Ligand is endogenous in the given species Hs Agonist Agonist - - - 2,5
⤷ [2,5]
Targets where the ligand is described in the comment field
Target Comment
CYP11A1 Converts cholesterol to pregnenolone plus 4-methylpentanal.
CYP7A1 Converts cholesterol to 7α-hydroxycholesterol [4].
CYP46A1 Converts cholesterol to 24(S)-hydroxycholesterol.
CYP27A1 Converts cholesterol to 27-hydroxycholesterol. Autosomal-recessive mutations in CYP27A1 cause the bile acid metabolism disorder cerebrotendinous xanthomatosis (CTX, cerebral cholesterosis) [1,3]. An adenovirus vector encoding human CYP27A1 (VTX-806; Vivet Therapeutics) is being trialled as a gene replacement therapy for CTX. VTX-806 was granted Orphan Drug Designation by the EMA in September 2024 for this rare disease.
Ligand mentioned in the following text fields
1F. Retinoic acid-related orphans overview
Bile acid receptor overview
Class Frizzled GPCRs comments