AC-480

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Synonyms
Status
Molecule Category Free-form
UNII 2252724U5N
EPA CompTox DTXSID60221714

Structure

InChI Key LUJZZYWHBDHDQX-QFIPXVFZSA-N
Smiles Cc1c(NC(=O)OC[C@@H]2COCCN2)cn2ncnc(Nc3ccc4c(cnn4Cc4cccc(F)c4)c3)c12
InChI
InChI=1S/C27H27FN8O3/c1-17-23(34-27(37)39-15-22-14-38-8-7-29-22)13-36-25(17)26(30-16-32-36)33-21-5-6-24-19(10-21)11-31-35(24)12-18-3-2-4-20(28)9-18/h2-6,9-11,13,16,22,29H,7-8,12,14-15H2,1H3,(H,34,37)(H,30,32,33)/t22-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H27FN8O3
Molecular Weight 530.56
AlogP 3.86
Hydrogen Bond Acceptor 10.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 7.0
Polar Surface Area 119.63
Molecular species NEUTRAL
Aromatic Rings 5.0
Heavy Atoms 39.0

Bioactivity

Mechanism of Action Action Reference
Epidermal growth factor receptor erbB1 inhibitor INHIBITOR PubMed PubMed
Protein: Epidermal growth factor receptor erbB1
Description: Epidermal growth factor receptor
Organism : Homo sapiens
P00533 ENSG00000146648
Protein: Receptor protein-tyrosine kinase erbB-2
Description: Receptor tyrosine-protein kinase erbB-2
Organism : Homo sapiens
P04626 ENSG00000141736
Protein: Receptor protein-tyrosine kinase erbB-4
Description: Receptor tyrosine-protein kinase erbB-4
Organism : Homo sapiens
Q15303 ENSG00000178568
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 10000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 12000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 1600-12000 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
- 22-23 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 4000 - - -
Assay Description Organism Bioactivity Reference
Inhibition of human recombinant HER1 expressed in Sf9 cells by liquid scintillation counting Homo sapiens 32.0 nM
Inhibition of human recombinant HER2 expressed in Sf9 cells by liquid scintillation counting Homo sapiens 22.0 nM
Antiproliferative activity against human BT474 cells after 72 hrs by MTT assay Homo sapiens 310.0 nM
Antiproliferative activity against human NCI-N87 cells after 72 hrs by MTT assay Homo sapiens 450.0 nM
Antiproliferative activity against mouse SAL2 cells after 72 hrs by MTT assay Mus musculus 240.0 nM
Inhibition of human recombinant HER4 expressed in Sf9 cells by liquid scintillation counting Homo sapiens 190.0 nM
Inhibition of EGFR None 32.0 nM
Inhibition of HER2 None 23.0 nM
Antiproliferative activity against human NCI-N87 cells Homo sapiens 450.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 3.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 76.42 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 19.1 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -1.28 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 15.67 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.19 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.05 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.28 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.05 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.28 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.19 %

Cross References

Resources Reference
ChEMBL CHEMBL1645462
DrugBank DB12318
FDA SRS 2252724U5N
Guide to Pharmacology 7647
SureChEMBL SCHEMBL12065349
ZINC ZINC000006717782
CONTENTS