SOTRASTAURIN

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
UNII 7I279E1NZ8

Structure

InChI Key OAVGBZOFDPFGPJ-UHFFFAOYSA-N
Smiles CN1CCN(c2nc(C3=C(c4c[nH]c5ccccc45)C(=O)NC3=O)c3ccccc3n2)CC1
InChI
InChI=1S/C25H22N6O2/c1-30-10-12-31(13-11-30)25-27-19-9-5-3-7-16(19)22(28-25)21-20(23(32)29-24(21)33)17-14-26-18-8-4-2-6-15(17)18/h2-9,14,26H,10-13H2,1H3,(H,29,32,33)

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H22N6O2
Molecular Weight 438.49
AlogP 2.43
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 3.0
Polar Surface Area 94.22
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 33.0

Bioactivity

Mechanism of Action Action Reference
Protein kinase C (PKC) inhibitor INHIBITOR PubMed
Protein: Protein kinase C (PKC)
Description: Serine/threonine-protein kinase D3
Organism : Homo sapiens
O94806 ENSG00000115825
Protein: Protein kinase C (PKC)
Description: Protein kinase C gamma type
Organism : Homo sapiens
P05129 ENSG00000126583
Protein: Protein kinase C (PKC)
Description: Protein kinase C beta type
Organism : Homo sapiens
P05771 ENSG00000166501
Protein: Protein kinase C (PKC)
Description: Protein kinase C alpha type
Organism : Homo sapiens
P17252 ENSG00000154229
Protein: Protein kinase C (PKC)
Description: Protein kinase C eta type
Organism : Homo sapiens
P24723 ENSG00000027075
Protein: Protein kinase C (PKC)
Description: Protein kinase C iota type
Organism : Homo sapiens
P41743 ENSG00000163558
Protein: Protein kinase C (PKC)
Description: Protein kinase C epsilon type
Organism : Homo sapiens
Q02156 ENSG00000171132
Protein: Protein kinase C (PKC)
Description: Protein kinase C theta type
Organism : Homo sapiens
Q04759 ENSG00000065675
Protein: Protein kinase C (PKC)
Description: Protein kinase C zeta type
Organism : Homo sapiens
Q05513 ENSG00000067606
Protein: Protein kinase C (PKC)
Description: Protein kinase C delta type
Organism : Homo sapiens
Q05655 ENSG00000163932
Protein: Protein kinase C (PKC)
Description: Serine/threonine-protein kinase D1
Organism : Homo sapiens
Q15139 ENSG00000184304
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - 2900 -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC alpha subfamily
- 2-2 - - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC delta subfamily
- 1-81 - - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC eta subfamily
- 6-6 - - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC iota subfamily
- 5400 - - -
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase PDHK subfamily
- 6700 - - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase PIM family
- 50 - - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase CDK family CMGC protein kinase CDC2 subfamily
- 2300 - - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase GSK family
- 870 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Abl family
- 3300 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Axl family
- 9100 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Fak family
- 8300 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakA family
- 1500 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakB family
- 1500 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- 5500 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase VEGFR family
- 3900 - - -
Other cytosolic protein
- 2300 - - -
Assay Description Organism Bioactivity Reference
Inhibition of PKCalpha by SPA None 2.1 nM
Inhibition of PKCbeta1 by SPA None 2.0 nM
Inhibition of PKCdelta by SPA None 1.3 nM
Inhibition of PKCepsilon by SPA None 6.2 nM
Inhibition of PKCeta by SPA None 6.1 nM
Inhibition of PKCtheta by SPA None 1.0 nM
Inhibition of TCR/CD28-mediated human T cell activation in Jurkat cells expressing human IL2 promoter by luciferase reporter gene assay Homo sapiens 54.0 nM
Immunosuppressive activity in BALB/c mouse splenocytes assessed as inhibition of [3H]thymidine incorporation after 4 days by allogenic mixed lymphocyte reaction assay Mus musculus 128.0 nM
Immunosuppressive activity in human splenocytes assessed as inhibition of [3H]thymidine incorporation after 4 days by allogenic mixed lymphocyte reaction assay Homo sapiens 34.0 nM
Inhibition of human recombinant GSK3-beta Homo sapiens 870.0 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: MAP4K4 None 158.49 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: MST1R None 158.49 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: STK3 None 125.89 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PRKCQ None 0.631 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: RPS6KA3 None 125.89 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PRKCZ None 63.1 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PRKG1 None 794.33 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PRKAA1 None 630.96 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: RPS6KB1 None 158.49 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: CAMK2G None 79.43 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: CDK2 None 125.89 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PIM1 None 158.49 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: CAMK2D None 31.62 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: JAK3 None 630.96 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PKN2 None 251.19 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PIM3 None 316.23 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PRKCG None 12.59 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: GSK3A None 158.49 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: ERBB2 None 794.33 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: KDR None 398.11 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: GPRK5 None 630.96 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: SGK None 630.96 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: MINK None 7.943 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PRKCI None 398.11 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: AKT1 None 501.19 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: MAP4K5 None 158.49 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: FLT4 None 316.23 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: FER None 316.23 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PIM2 None 1.585 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: SLK None 125.89 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: PLK1 None 63.1 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: GSK3B None 199.53 nM
Inhibition of PKCalpha by scintillation proximity assay None 2.1 nM
Inhibition of PKCbeta-1 by scintillation proximity assay None 2.0 nM
Inhibition of PKCdelta by scintillation proximity assay None 1.3 nM
Inhibition of PKCepsilon by scintillation proximity assay None 6.2 nM
Inhibition of PKCeta by scintillation proximity assay None 6.1 nM
Inhibition of PKCtheta by scintillation proximity assay None 1.0 nM
Immunosuppressive activity in mouse lymphocytes assessed as alloantigen-induced T cell proliferation by mixed lymphocyte reaction assay Mus musculus 150.0 nM
Immunosuppressive activity in human lymphocytes assessed as alloantigen-induced T cell proliferation by mixed lymphocyte reaction assay Homo sapiens 37.0 nM
Inhibition of human Jurkat cell activation assessed as TCR/CD28 stimulated inhibition of IL-2 secretion Homo sapiens 54.0 nM
Inhibition of PIM1 (unknown origin) Homo sapiens 50.12 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 121.0 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 709.0 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 41.0 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 13.0 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 24.0 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 5.0 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 16.0 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 13.0 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 38.0 nM
Inhibition of PKCeta (unknown origin) after 60 mins in presence of [gamma33P]ATP by scintillation proximity assay Homo sapiens 6.1 nM
Inhibition of PKCalpha (unknown origin) after 60 mins in presence of [gamma33P]ATP by scintillation proximity assay Homo sapiens 2.1 nM
Inhibition of PKCbeta1 (unknown origin) after 60 mins in presence of [gamma33P]ATP by scintillation proximity assay Homo sapiens 2.0 nM
Inhibition of PKCdelta (unknown origin) after 60 mins in presence of [gamma33P]ATP by scintillation proximity assay Homo sapiens 1.3 nM
Inhibition of PKCepsilon (unknown origin) after 60 mins in presence of [gamma33P]ATP by scintillation proximity assay Homo sapiens 6.2 nM
Inhibition of PKCtheta (unknown origin) after 60 mins in presence of [gamma33P]ATP by scintillation proximity assay Homo sapiens 1.0 nM
Inhibition of PKCtheta in human Jurkat T cells assessed as reduction in anti-CD3/CD28 antibody-induced T-cell activation by measuring decrease in IL-2 secretion after 5 hrs by luciferase reporter gene assay Homo sapiens 81.0 nM
Inhibition of human PBMC proliferation assessed as decrease in [3H]-TdR uptake after 6 days by mixed lymphocyte reaction assay Homo sapiens 28.0 nM
Inhibition of PKCbeta in mouse B cells assessed as reduction in IgM-stimulated cell proliferation Mus musculus 234.0 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 -5.03 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 36.94 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 24.0 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.885 %
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 0.7 % 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 -0.01 % 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 -0.18 % 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 -0.18 % 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 0.7 % 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 -0.01 %
Inhibition of activation of T cells in C57BL/6 mouse allogenic spleen cells injected B6D2F1 mouse graft versus host disease mouse model assessed as reduction of popliteal lymph node size increase at 100 mg/kg, po twice daily treated 30 mins after allogenic challenge measured on day 4 relative to control Mus musculus 48.0 %

Cross References

Resources Reference
ChEBI 90531
ChEMBL CHEMBL565612
DrugBank DB12369
FDA SRS 7I279E1NZ8
Guide to Pharmacology 7946
PDB LW4
PubChem 10296883
SureChEMBL SCHEMBL2500835
ZINC ZINC000003973984
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