Compound Detail

CHEMBL403233

MANZAMINE A

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O[C@]12C=C(c3nccc4c3[nH]c3ccccc34)[C@@H]3CCN(CCCC/C=C\CC1)C[C@@]31C[C@@H]3/C=C\CCCCN3[C@H]12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL403233
Name	MANZAMINE A
Phase	Preclinical
Structure Type	MOL
InChI Key	FUCSLKWLLSEMDQ-MKYGIPPKSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

548.8

MW (Da)

6.86

ALogP

HBA

HBD

55.4

PSA (Å²)

0.33

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	C36H44N4O
MW	548.78
Aromatic Rings	3
Heavy Atoms	41
NP-Likeness	2.07

Activity Summary

IC50 57 meas. best 8.1

EC50 2 meas. best 6.23

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Plasmodium falciparum CHEMBL364	IC50	8.1	7.8825	8.0	4
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.0	5.708	100.0	10
Mycobacterium intracellulare CHEMBL612640	IC50	6.75	6.47	180.0	2
Staphylococcus aureus CHEMBL352	IC50	6.75	6.75	180.0	1
Vero CHEMBL391	IC50	6.3	6.3	501.0	1
Human immunodeficiency virus 1 CHEMBL378	EC50	6.23	5.805	590.0	2
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	5.82	5.82	1500.0	1
C-33-A CHEMBL2366313	IC50	5.8	5.5867	1600.0	3
RAW264.7 CHEMBL612557	IC50	5.8	5.422	1600.0	5
Cryptococcus neoformans CHEMBL365	IC50	5.73	5.65	1848.0	2
Unchecked CHEMBL612545	IC50	5.7	5.47	2000.0	2
Candida albicans CHEMBL366	IC50	5.44	5.115	3656.0	2
HeLa CHEMBL399	IC50	5.4	5.125	4000.0	4
SiHa CHEMBL612542	IC50	5.39	5.03	4100.0	3
Human immunodeficiency virus 1 CHEMBL378	IC50	5.38	5.38	4200.0	1
Sterol O-acyltransferase 2 CHEMBL4465	IC50	5.32	5.32	4800.0	1
K562 CHEMBL385	IC50	5.28	5.28	5200.0	1
A549 CHEMBL392	IC50	5.24	5.24	5800.0	1
Sterol O-acyltransferase 1 CHEMBL2782	IC50	5.21	5.2	6200.0	2
Ca-Ski CHEMBL1075403	IC50	5.03	4.7333	9400.0	3
Glycogen synthase kinase-3 beta CHEMBL262	IC50	5.0	4.976	10000.0	5
Glycogen synthase kinase-3 alpha CHEMBL2850	IC50	4.6	4.6	25000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Plasmodium falciparum	IC50	=	8.0	nM	8.1	Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 inf...	19833520
Plasmodium falciparum	IC50	=	11.0	nM	7.96	Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 inf...	19833520
Plasmodium falciparum	IC50	=	17.0	nM	7.77	Antimalarial activity after 72 hrs against chloroquine-sensitive Plasmodium falc...	18595720
Plasmodium falciparum	IC50	=	20.0	nM	7.7	Antimalarial activity after 72 hrs against chloroquine-resistant Plasmodium falc...	18595720
NON-PROTEIN TARGET	IC50	=	100.0	nM	7.0	Antineuroinflammatory activity in LPS-stimulated rat neonatal microglia assessed...	20017491
Staphylococcus aureus	IC50	=	180.0	nM	6.75	Antimicrobial activity against methicillin-resistant Staphylococcus aureus ATCC ...	18595720
Mycobacterium intracellulare	IC50	=	180.0	nM	6.75	Antimicrobial activity against Mycobacterium intracellular ATCC 23068	18595720
Vero	IC50	=	501.0	nM	6.3	Cytotoxicity against african green monkey Vero cells after 48 hrs by neutral red...	18595720
Human immunodeficiency virus 1	EC50	=	590.0	nM	6.23	Antiviral activity against HIV1 in human PBM cells	12828469
Mycobacterium intracellulare	IC50	=	640.0	nM	6.19	Antibacterial activity against Mycobacterium intracellular by alamar blue assay	19833520
NON-PROTEIN TARGET	IC50	=	1100.0	nM	5.96	Cytotoxicity against human NCI-H441 cells assessed as decrease in cell viability...	27650927
Cyclin-dependent kinase 5/CDK5 activator 1	IC50	=	1500.0	nM	5.82	Inhibition of human recombinant CDK5/p35	17708655
NON-PROTEIN TARGET	IC50	=	1500.0	nM	5.82	Cytotoxicity against human NCI-H1299 cells assessed as decrease in cell viabilit...	27650927
C-33-A	IC50	=	1600.0	nM	5.8	Antiproliferative activity against human C33A cells assessed as reduction in cel...	32022559
RAW264.7	IC50	=	1600.0	nM	5.8	Antiproliferative activity against mouse differentiated RAW 264.7 osteoclast cel...	38383319
NON-PROTEIN TARGET	IC50	=	1600.0	nM	5.8	Cytotoxicity against human NCI-H2009 cells assessed as decrease in cell viabilit...	27650927
Cryptococcus neoformans	IC50	=	1848.0	nM	5.73	Antifungal activity against Cryptococcus neoformans by modified NCCLS method	19833520
RAW264.7	IC50	=	1900.0	nM	5.72	Antiproliferative activity against mouse RAW 264.7 preosteoclast cells assessed ...	38383319
Unchecked	IC50	=	2000.0	nM	5.7	Inhibition of chymotrypsin-like activity of rat liver proteasome using fluorogen...	24902064
NON-PROTEIN TARGET	IC50	=	2100.0	nM	5.68	Cytotoxicity against human NCI-H1373 cells assessed as decrease in cell viabilit...	27650927

Literature References

PubMed	DOI	Target Context	# Activities
20017491	10.1021/jm900672t	Plasmodium berghei	67
38383319	10.1021/acs.jnatprod.3c01097	RAW264.7	34
32022559	10.1021/acs.jnatprod.9b00577	C-33-A	25
32022559	10.1021/acs.jnatprod.9b00577	SiHa	22
32022559	10.1021/acs.jnatprod.9b00577	Ca-Ski	22
32022559	10.1021/acs.jnatprod.9b00577	HeLa	21
20017491	10.1021/jm900672t	HeLa	13
32022559	10.1021/acs.jnatprod.9b00577	Homeobox protein SIX1	8
32022559	10.1021/acs.jnatprod.9b00577	Casein kinase II subunit alpha	8
20017491	10.1021/jm900672t	Mus musculus	8
-	10.1007/s00044-004-0054-2	MCF7	7
27650927	10.1016/j.bmcl.2016.09.030	NON-PROTEIN TARGET	7
23665143	10.1016/j.bmc.2013.04.025	Unchecked	6
32022559	10.1021/acs.jnatprod.9b00577	Protein E6	6
38383319	10.1021/acs.jnatprod.3c01097	Unchecked	6
23665143	10.1016/j.bmc.2013.04.025	NON-PROTEIN TARGET	5
23665143	10.1016/j.bmc.2013.04.025	Mus musculus	5
23665143	10.1016/j.bmc.2013.04.025	Sterol O-acyltransferase 1	4
32022559	10.1021/acs.jnatprod.9b00577	Protein E7	4
23665143	10.1016/j.bmc.2013.04.025	ADMET	3

Data from ChEMBL 36 via Core Engine