CYP3A4 fluorogenic substrate F8   Click here for help

GtoPdb Ligand ID: 12659

Synonyms: compound F8 [PMID: 37145039]
Compound class: Synthetic organic
Comment: This compound is selectively metabolised to the fluorescent product (4-OH F8) by cytochrome P450 3A4 (CYP3A4) [1]. It is not converted by other P450 isozymes, and its metabolism is inhibited by small molecules that are active against CYP3A/CYP3A4 but not other CYPs. F8 is proposed as a molecular tool for monitoring CYP3A4 activities in living cells and tissue preparations.

CYP3A4 fluorogenic substrate F8 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 3
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 37.38
Molecular weight 305.3
XLogP 1.69
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 C1=CC2=C3C(=C1)C=CC=C3C(=O)N(CC4=CC=C(C=C4)F)C2=O
Isomeric SMILES FC1=CC=C(CN2C(=O)C3=CC=CC4=C3C(=CC=C4)C2=O)C=C1
InChI InChI=1S/C19H12FNO2/c20-14-9-7-12(8-10-14)11-21-18(22)15-5-1-3-13-4-2-6-16(17(13)15)19(21)23/h1-10H,11H2
InChI Key JVHUQBLLHSIOMR-UHFFFAOYSA-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/)
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form CYP3A4 fluorescent probe 4-OH F8
IUPAC Name Click here for help
2-[(4-fluorophenyl)methyl]benzo[de]isoquinoline-1,3-dione
Synonyms Click here for help
compound F8 [PMID: 37145039]
Database Links Click here for help
BindingDB Ligand 50070431
ChEMBL Ligand CHEMBL3408793
GtoPdb PubChem SID 483123207
PubChem CID 10614509
Search Google for chemical match using the InChIKey JVHUQBLLHSIOMR-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JVHUQBLLHSIOMR
UniChem Compound Search for chemical match using the InChIKey JVHUQBLLHSIOMR-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JVHUQBLLHSIOMR-UHFFFAOYSA-N

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MedChemExpress
hCYP3A4 Fluorogenic substrate 1 (links to external site)
Cat. No. HY-155002