Compound Detail

CHEMBL279115

PHORBOL MYRISTATE ACETATE

🧪 Phase II

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🧪 Phase II

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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL279115
Name	PHORBOL MYRISTATE ACETATE
Phase	Phase II
Structure Type	MOL
InChI Key	PHEDXBVPIONUQT-RGYGYFBISA-N

Known Names

NSC-262244 Phorbol 12-myristate 13-acetate Phorbol 12-myristate 13-acetate diester Phorbol myristate acetate Pma (phorbol ester) Tetradecanoylphorbol acetate Tpa (phorbol ester)

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

616.8

MW (Da)

5.75

ALogP

HBA

HBD

130.4

PSA (Å²)

0.12

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula	C36H56O8
MW	616.84
Aromatic Rings	0
Heavy Atoms	44
NP-Likeness	2.38

Indications

Leukemia Leukemia, Myeloid, Acute Myelodysplastic Syndromes

Activity Summary

EC50 16 meas. best 9.35

IC50 10 meas. best 9.1

Ki 7 meas. best 9.35

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
U-937 CHEMBL612794	EC50	9.35	9.35	0.5	1
Protein kinase C epsilon type CHEMBL3582	Ki	9.35	9.35	0.5	1
Unchecked CHEMBL612545	Ki	9.23	9.23	0.6	1
Human immunodeficiency virus 2 CHEMBL380	EC50	9.15	9.15	0.7	1
Protein kinase C delta type CHEMBL2996	Ki	9.1	9.1	0.8	1
Unchecked CHEMBL612545	IC50	9.1	8.3067	0.8	3
NON-PROTEIN TARGET CHEMBL3879801	EC50	9.07	8.7167	0.8	3
Human immunodeficiency virus 1 CHEMBL378	EC50	9.05	9.05	0.9	1
Protein kinase C beta type CHEMBL3045	Ki	8.74	8.74	1.8	1
Protein kinase C alpha type CHEMBL299	Ki	8.6	8.395	2.5	2
Chikungunya virus CHEMBL4296563	EC50	8.54	8.54	2.9	1
Protein kinase C gamma type CHEMBL2938	Ki	8.31	8.31	4.9	1
Protein kinase C (PKC) CHEMBL2093867	EC50	8.02	8.02	9.5	1
Luciferin 4-monooxygenase CHEMBL5567	EC50	8.0	8.0	10.0	1
Ras guanyl-releasing protein 3 CHEMBL3638	EC50	7.09	7.09	82.0	1
Protein kinase C delta type CHEMBL2996	EC50	6.54	5.915	290.0	2
Sindbis virus CHEMBL613725	EC50	5.66	5.66	2200.0	1
Protein kinase C theta type CHEMBL3920	EC50	5.5	5.5	3190.0	1
Protein kinase C epsilon type CHEMBL3582	EC50	5.25	5.25	5560.0	1
Plasmodium falciparum CHEMBL364	IC50	5.2	5.0286	6309.6	7

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
U-937	EC50	=	0.45	nM	9.35	Induction of attachment of U937 cells after 48 hrs	17284021
Protein kinase C epsilon type	Ki	=	0.45	nM	9.35	Inhibition of [3H]-phorbol 12,13-dibutyrate (PDBu) binding to human recombinant ...	11327599
Unchecked	Ki	=	0.59	nM	9.23	Displacement of [3H]PDBu from phorbol ester receptor in ICR mouse brain after 60...	23403082
Human immunodeficiency virus 2	EC50	=	0.7	nM	9.15	Antiviral activity against HIV2 ROD infected in MT4 cells assessed as cell viabi...	25970561
Protein kinase C delta type	Ki	=	0.8	nM	9.1	Inhibition of [3H]-phorbol 12,13-dibutyrate (PDBu) binding to human recombinant ...	11327599
Unchecked	IC50	=	0.79	nM	9.1	Displacement of [3H]PDBu from phorbol ester receptor in ICR mouse brain after 60...	23403082
NON-PROTEIN TARGET	EC50	=	0.85	nM	9.07	Inhibition of cell proliferation in WEHI231 cell line after 48 hrs	17284021
Human immunodeficiency virus 1	EC50	=	0.9	nM	9.05	Antiviral activity against HIV1 3B infected in MT4 cells assessed as cell viabil...	25970561
Protein kinase C beta type	Ki	=	1.8	nM	8.74	Inhibition of [3H]-phorbol 12,13-dibutyrate (PDBu) binding to human recombinant ...	11327599
Protein kinase C alpha type	Ki	=	2.5	nM	8.6	Inhibition of [3H]-phorbol 12,13-dibutyrate (PDBu) binding to human recombinant ...	11327599
NON-PROTEIN TARGET	EC50	=	2.9	nM	8.54	Antiviral activity against Chikungunya virus 899 infected in african green monke...	23215460
NON-PROTEIN TARGET	EC50	=	2.9	nM	8.54	Antiviral activity against chikungunya virus Indian ocean strain 899 infected in...	25970561
Chikungunya virus	EC50	=	2.9	nM	8.54	Antiviral activity against Chikungunya virus Indian ocean strain 899 infected in...	28925702
Protein kinase C gamma type	Ki	=	4.9	nM	8.31	Inhibition of [3H]-phorbol 12,13-dibutyrate (PDBu) binding to human recombinant ...	11327599
Protein kinase C alpha type	Ki	=	6.4	nM	8.19	Displacement of [3H]PDBu from human recombinant PKCalpha after 20 mins by liquid...	21596562
Protein kinase C (PKC)	EC50	=	9.5	nM	8.02	Activation of PKC in human platelet assessed as induction of platelet aggregatio...	27731641
Unchecked	IC50	=	10.0	nM	8.0	Inhibition of [3H]PDBu binding to murine brain PKC (protein kinase C)	2362276
Luciferin 4-monooxygenase	EC50	=	10.0	nM	8.0	Activation of firefly luciferase activity expressed in HEK293T cells after 6 hrs...	30600206
Unchecked	IC50	=	15.0	nM	7.82	Displacement of [3H]PDBu from partially purified rabbit brain PKC	10075762
Ras guanyl-releasing protein 3	EC50	=	82.0	nM	7.09	Activation of GFP-tagged RasGRP3 (unknown origin) expressed in HEK293 cells afte...	29860841

Literature References

PubMed	DOI	Target Context	# Activities
27731641	10.1021/acs.jnatprod.6b00603	Protein kinase C (PKC)	19
38840407	10.1021/acs.jnatprod.4c00395	Unchecked	11
21596562	10.1016/j.bmcl.2011.04.108	Protein kinase C alpha type	8
8904648	10.1111/j.1476-5381.1996.tb15733.x	Unchecked	8
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
-	10.6019/CHEMBL5303304	Fibroblast	7
-	10.6019/CHEMBL5303304	U2OS	6
30413535	10.1074/jbc.ra118.005798	ACH-2 cell line	4
20817520	10.1016/j.bmcl.2010.08.051	Unchecked	4
-	10.1007/s00044-012-0048-4	Unchecked	4
-	10.6019/CHEMBL5303304	HEK-293T	4
30413535	10.1074/jbc.ra118.005798	U1	4
20817520	10.1016/j.bmcl.2010.08.051	Raji	4
22625994	10.1021/jm300566h	Mus musculus	3
25808573	10.1021/acs.jnatprod.5b00094	U-937	3
24794745	10.1016/j.bmc.2014.04.024	Ras guanyl-releasing protein 3	3
25970561	10.1021/acs.jnatprod.5b00073	Unchecked	3
23403082	10.1016/j.bmcl.2013.01.025	Unchecked	3
30445266	10.1016/j.ejmech.2018.10.071	MCF7	3
28213283	10.1016/j.ejmech.2017.02.008	MCF7	3

Data from ChEMBL 36 via Core Engine