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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Physico-chemical Properties
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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
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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
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]