vacquinol-1   Click here for help

GtoPdb Ligand ID: 8373

Synonyms: NSC13316
Compound class: Synthetic organic
Comment: We represent this molecule with no stereochemical assignments to represent the racemic mixture ariisng from the presence of two steroecentres. The compound can exist as RS (PubChem CID 36691047), SR (PubChem CID 36691042), RR (PubChem CID 36691044) or SS (PubChem CID 3246043) enantiomers. The compound is contained in the National Cancer Institute (NCI) Diversity Set II which is a freely accessible compound repository maintained as part of the Developmental Therapeutics Program (DTP). The DTP provides online, open access to screening data and compound structural details for small molecules that may be of use in anti-cancer (and anti-HIV) drug discovery programmes.
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 3
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 45.15
Molecular weight 352.13
XLogP 4.58
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 Clc1ccc(cc1)c1cc(C(C2CCCCN2)O)c2c(n1)cccc2
Isomeric SMILES Clc1ccc(cc1)c1cc(C(C2CCCCN2)O)c2c(n1)cccc2
InChI InChI=1S/C21H21ClN2O/c22-15-10-8-14(9-11-15)20-13-17(16-5-1-2-6-18(16)24-20)21(25)19-7-3-4-12-23-19/h1-2,5-6,8-11,13,19,21,23,25H,3-4,7,12H2
InChI Key VKLJPGAHSLIQKH-UHFFFAOYSA-N
Bioactivity Comments
Vacquinol-1 is reported to selectively reduce viability of patient-derived glioblastoma cells, with an IC50 of 2.36µM [1].