Compound Detail

CHEMBL83747

PSAMMAPLIN A

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O=C(NCCSSCCNC(=O)/C(Cc1ccc(O)c(Br)c1)=N/O)/C(Cc1ccc(O)c(Br)c1)=N/O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL83747
Name	PSAMMAPLIN A
Phase	Preclinical
Structure Type	MOL
InChI Key	LMAFSGDNHVBIHU-XUIWWLCJSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

664.4

MW (Da)

3.68

ALogP

HBA

HBD

163.8

PSA (Å²)

0.06

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C22H24Br2N4O6S2
MW	664.40
Aromatic Rings	2
Heavy Atoms	36
NP-Likeness	0.27

Activity Summary

IC50 33 meas. best 8.4

EC50 5 meas. best 6.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histone deacetylase CHEMBL2093865	IC50	8.4	7.85	4.0	2
Unchecked CHEMBL612545	IC50	8.38	6.938	4.2	5
Histone deacetylase 1 CHEMBL325	IC50	8.1	7.6767	8.0	3
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) CHEMBL2111363	IC50	7.91	7.91	12.4	1
DNA (cytosine-5)-methyltransferase 1 CHEMBL1993	IC50	7.73	7.73	18.6	1
Histone deacetylase 2 CHEMBL1937	IC50	7.48	7.48	33.0	1
Human immunodeficiency virus 1 CHEMBL378	EC50	6.7	6.7	200.0	1
Histone deacetylase 6 CHEMBL1865	IC50	6.51	5.87	311.0	3
SNU-638 CHEMBL614935	IC50	6.25	6.25	560.0	1
HCT-116 CHEMBL394	IC50	6.21	5.865	610.0	2
CHO-K1 CHEMBL614031	EC50	6.05	6.05	900.0	1
A549 CHEMBL392	IC50	5.93	5.84	1180.0	2
SK-HEP1 CHEMBL614912	IC50	5.89	5.89	1290.0	1
MDA-MB-231 CHEMBL400	IC50	5.88	5.88	1310.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.79	5.79	1620.0	1
Molecular identity unknown CHEMBL612546	IC50	5.58	5.045	2640.0	2
Trypanosoma brucei CHEMBL612849	EC50	5.58	5.58	2600.0	2
Mycothiol S-conjugate amidase CHEMBL3703	IC50	5.55	5.55	2800.0	3
UDP-glucose 4-epimerase CHEMBL5843	IC50	5.44	5.44	3600.0	1
MCF7 CHEMBL387	IC50	5.3	5.3	5000.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	EC50	5.24	5.24	5700.0	1
Adenosine receptor A1 CHEMBL318	IC50	4.7	4.7	20000.0	1
Sortase A CHEMBL5362	IC50	4.32	4.32	47400.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histone deacetylase	IC50	=	4.0	nM	8.4	Inhibitory concentration against isolated Histone deacetylase	14613312
Unchecked	IC50	=	4.2	nM	8.38	Inhibition of HDAC in cell-free system	21215647
Unchecked	IC50	=	4.2	nM	8.38	Inhibition of HDAC in cell extract based assay	22280363
Histone deacetylase 1	IC50	=	8.0	nM	8.1	Inhibition of recombinant full length C-terminal FLAG/His-tagged human HDAC1 exp...	33488962
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	IC50	=	12.4	nM	7.91	Inhibition of C-terminal His-tagged recombinant human HDAC3 (1 to 428 residues)/...	33488962
Unchecked	IC50	=	18.6	nM	7.73	Inhibition of DNMT in cell-free system	21215647
DNA (cytosine-5)-methyltransferase 1	IC50	=	18.6	nM	7.73	Inhibition of semi-purified DNMT1	22280363
Histone deacetylase 1	IC50	=	26.0	nM	7.58	Inhibition of recombinant human HDAC1 using Boc-Lys(Ac)-AMC as substrate preincu...	38851056
Histone deacetylase 2	IC50	=	33.0	nM	7.48	Inhibition of recombinant full length C-terminal FLAG-tagged human HDAC2 express...	33488962
Histone deacetylase 1	IC50	=	45.0	nM	7.35	Inhibition of human recombinant HDAC1 using Boc-lys(Ac)-AMC as substrate preincu...	22280363
Histone deacetylase	IC50	=	50.0	nM	7.3	Inhibition of HDAC in human HeLa cells using Fluor deLys as substrate assessed a...	27460171
Human immunodeficiency virus 1	EC50	=	200.0	nM	6.7	Reactivation of latent HIV1 NL4-3-Luc expression in human naive CD4+ T cells tre...	24495105
Histone deacetylase 6	IC50	=	311.0	nM	6.51	Inhibition of recombinant full length C-terminal FLAG-tagged human HDAC6 express...	33488962
SNU-638	IC50	=	560.0	nM	6.25	Cytotoxicity against human SNU-638 cells assessed as reduction in cell viability...	33636429
HCT-116	IC50	=	610.0	nM	6.21	Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability...	33636429
CHO-K1	EC50	=	900.0	nM	6.05	Cytotoxicity against CHO-K1 cells by Alamar blue assay	16962325
A549	IC50	=	1180.0	nM	5.93	Cytotoxicity against human A549 cells by SRB assay	25884112
SK-HEP1	IC50	=	1290.0	nM	5.89	Cytotoxicity against human SK-HEP1 cells assessed as reduction in cell viability...	33636429
MDA-MB-231	IC50	=	1310.0	nM	5.88	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil...	33636429
NON-PROTEIN TARGET	IC50	=	1620.0	nM	5.79	Cytotoxicity against human HCT116 cells by SRB assay	25884112

Literature References

PubMed	DOI	Target Context	# Activities
33488962	10.1021/acsmedchemlett.0c00369	HL-60	17
38851056	10.1016/j.ejmech.2024.116541	HCT-116	16
38632902	10.1021/acs.jnatprod.4c00153	SH-SY5Y	7
16643023	10.1021/np050397q	MCF7	6
38632902	10.1021/acs.jnatprod.4c00153	Peroxisome proliferator-activated receptor gamma	6
22280363	10.1021/jm2016182	Unchecked	5
33636429	10.1016/j.bmc.2021.116072	Histone-lysine N-methyltransferase, H3 lysine-79 specific	5
21215647	10.1016/j.bmc.2010.12.026	U-937	4
16643023	10.1021/np050397q	Peroxisome proliferator-activated receptor gamma	3
33488962	10.1021/acsmedchemlett.0c00369	Unchecked	3
33636429	10.1016/j.bmc.2021.116072	MDA-MB-231	3
33488962	10.1021/acsmedchemlett.0c00369	ADMET	2
22280363	10.1021/jm2016182	Histone deacetylase 6	2
27460171	10.1016/j.bmcl.2015.12.094	Histone deacetylase	2
33488962	10.1021/acsmedchemlett.0c00369	Histone deacetylase 2	2
22280363	10.1021/jm2016182	Histone deacetylase 1	2
25884112	10.1016/j.ejmech.2015.04.001	Histone deacetylase	2
16962325	10.1016/j.bmcl.2006.08.091	Unchecked	2
16134928	10.1021/jm050524f	Mycothiol S-conjugate amidase	2
33488962	10.1021/acsmedchemlett.0c00369	Histone deacetylase 1	2

Data from ChEMBL 36 via Core Engine