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.
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/)
References
1. He RJ, Tian ZH, Huang J, Sun MR, Wei F, Li CY, Zeng HR, Zhang F, Guan XQ, Feng Y et al.. (2023)
Rationally Engineered CYP3A4 Fluorogenic Substrates for Functional Imaging Analysis and Drug-Drug Interaction Studies.
J Med Chem, 66 (10): 6743-6755. [PMID:37145039]