PHORBOL MYRISTATE ACETATE

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Synonyms
Status
Molecule Category UNKNOWN
UNII NI40JAQ945
EPA CompTox DTXSID5023798

Structure

InChI Key PHEDXBVPIONUQT-RGYGYFBISA-N
Smiles CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@@H](C=C(CO)C[C@]3(O)C(=O)C(C)=C[C@@H]23)[C@@H]2C(C)(C)[C@]12OC(C)=O
InChI
InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C36H56O8
Molecular Weight 616.84
AlogP 5.75
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 15.0
Polar Surface Area 130.36
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 44.0
Assay Description Organism Bioactivity Reference
Inhibition of [3H]PDBu binding to murine brain PKC (protein kinase C) Mus musculus 10.0 nM
Inhibition of [3H]-phorbol 12,13-dibutyrate (PDBu) binding to human recombinant protein kinase C alpha Homo sapiens 2.5 nM
Inhibition of [3H]-phorbol 12,13-dibutyrate (PDBu) binding to human recombinant protein kinase C epsilon Homo sapiens 0.45 nM
Inhibition of [3H]-phorbol 12,13-dibutyrate (PDBu) binding to human recombinant protein kinase C delta Homo sapiens 0.8 nM
Inhibition of [3H]-phorbol 12,13-dibutyrate (PDBu) binding to human recombinant protein kinase C beta Homo sapiens 1.8 nM
Inhibition of [3H]-phorbol 12,13-dibutyrate (PDBu) binding to human recombinant protein kinase C gamma Homo sapiens 4.9 nM
Inhibition of cell proliferation in WEHI231 cell line after 48 hrs Mus musculus 0.85 nM
Induction of attachment of U937 cells after 48 hrs Homo sapiens 0.45 nM
Displacement of [3H]PDBu from partially purified rabbit brain PKC Oryctolagus cuniculus 15.0 nM
Activation of PKC signaling in human HUES8 cells assessed as increase in Pdx1-expressing cells at 14 nM after 4 days by immunocytochemistry pregrown in medium with Wnt3a, activin A, FGF10, KAAD-cyclopamine and retinoic acid relative to ILV treated cells Homo sapiens 21.3 %
Activation of PKC signaling in human HUES8 definitive endoderm cells assessed as increase in Pdx1-expressing cells at 14 nM after 4 days by immunocytochemistry (Rvb = 2.8+/-0.6%) Homo sapiens 18.3 %
Displacement of [3H]PDBu from human recombinant PKCalpha after 20 mins by liquid scintillation counting Homo sapiens 6.4 nM
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus 19.61 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus -6.35 %
Antiviral activity against Chikungunya virus 899 infected in african green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect incubated for 6 to 7 days by MTS assay Chikungunya virus 2.9 nM
Displacement of [3H]PDBu from phorbol ester receptor in ICR mouse brain after 60 mins Mus musculus 0.59 nM Displacement of [3H]PDBu from phorbol ester receptor in ICR mouse brain after 60 mins Mus musculus 0.79 nM
Displacement of [3H]PDBu from phorbol ester receptor in ICR mouse brain at 10 uM after 60 mins relative to control Mus musculus -1.0 %
Antiviral activity against chikungunya virus Indian ocean strain 899 infected in Vero cells assessed as virus-induced cytopathic effect after 6 to 7 days Chikungunya virus 2.9 nM
Antiviral activity against HIV1 3B infected in MT4 cells assessed as cell viability after 5 days by MTT assay Human immunodeficiency virus 1 0.9 nM
Antiviral activity against HIV2 ROD infected in MT4 cells assessed as cell viability after 5 days by MTT assay Human immunodeficiency virus type 2 (ISOLATE ROD) 0.7 nM
Activation of PKC in human platelet assessed as induction of platelet aggregation measured within 15 mins by tribidimetric method Homo sapiens 9.5 nM
Antiviral activity against Chikungunya virus Indian ocean strain 899 infected in African green monkey Vero cells assessed as reduction in virus-induced cytopathic effect by MTS assay Chikungunya virus 2.9 nM
Activation of GFP-tagged RasGRP3 (unknown origin) expressed in HEK293 cells after 30 mins by immunoblot method Homo sapiens 82.0 nM
Activation of PKCdelta (unknown origin) expressed in HEK293 cells harboring GFP-tagged RasGRP3 assessed as phosphorylation at ser299 residues after 30 mins by immunoblot method Homo sapiens 290.0 nM
Activation of firefly luciferase activity expressed in HEK293T cells after 6 hrs by luminescence assay Photinus pyralis 10.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.07 %
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 12.61 % 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 12.61 %

Related Entries

Cross References

Resources Reference
ChEBI 37537
ChEMBL CHEMBL279115
FDA SRS NI40JAQ945
Guide to Pharmacology 2341
KEGG C05151
SureChEMBL SCHEMBL115567
ZINC ZINC000008214783
CONTENTS