Compound Detail

CHEMBL222863

OUABAIN

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C[C@@H]1O[C@@H](O[C@H]2C[C@@H](O)[C@]3(CO)[C@H]4[C@H](O)C[C@]5(C)[C@@H](C6=CC(=O)OC6)CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)[C@H](O)[C@H](O)[C@H]1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL222863
Name	OUABAIN
Phase	Preclinical
Structure Type	MOL
InChI Key	LPMXVESGRSUGHW-HBYQJFLCSA-N
Therapeutic	✓ Yes

Known Names

Acocantherin Gratus strophanthin NSC-25485 Ouabain Strophantin-g

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

584.7

MW (Da)

-1.51

ALogP

HBA

HBD

206.6

PSA (Å²)

0.14

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula	C29H44O12
MW	584.66
Aromatic Rings	0
Heavy Atoms	41
NP-Likeness	3.21

Activity Summary

IC50 40 meas. best 8.74

EC50 4 meas. best 7.19

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
N+/K+ ATPase alpha-4/beta-3 CHEMBL4106166	IC50	8.74	8.74	1.8	1
N+/K+ ATPase alpha-4/beta-1 CHEMBL4106165	IC50	8.37	8.37	4.3	1
ADMET CHEMBL612558	IC50	8.22	6.235	6.0	2
A549 CHEMBL392	IC50	7.57	7.57	27.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.55	7.33	28.0	2
Na+/K+ ATPase alpha-3/beta-1 CHEMBL4106149	IC50	7.51	7.51	31.0	1
Unchecked CHEMBL612545	IC50	7.4	6.0	40.0	14
PC-3 CHEMBL390	IC50	7.37	7.37	43.0	1
Unchecked CHEMBL612545	EC50	7.19	7.1233	64.0	3
Hs-578T CHEMBL614645	IC50	6.96	5.495	110.0	2
MCF7 CHEMBL387	IC50	6.88	5.925	133.0	2
Krueppel-like factor 5 CHEMBL1293249	IC50	6.78	6.78	164.6	1
Na+/K+ ATPase alpha-2/beta-1 CHEMBL4106148	IC50	6.77	6.77	170.0	1
SK-MEL-28 CHEMBL614919	IC50	6.68	6.68	211.0	1
Vaccinia virus CHEMBL613493	EC50	6.6	6.6	250.0	1
T47D CHEMBL614361	IC50	6.42	6.42	385.0	1
SK-BR-3 CHEMBL613834	IC50	6.39	6.39	403.0	1
Signal transducer and activator of transcription 3 CHEMBL4026	IC50	5.94	5.94	1154.0	1
Na+/K+ ATPase alpha-1/beta-1 CHEMBL4106147	IC50	5.37	5.37	4300.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.24	5.24	5800.0	1
Sodium/potassium-transporting ATPase CHEMBL2095186	IC50	5.22	5.2	6000.0	2
Plasmodium falciparum CHEMBL364	IC50	4.9	4.9	12589.2	2

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	0.2567	hr	-
T1/2	0.2633	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
N+/K+ ATPase alpha-4/beta-3	IC50	=	1.8	nM	8.74	Inhibition of recombinant rat Na+/K+-ATPase alpha4/beta3 expressed in baculoviru...	29291372
N+/K+ ATPase alpha-4/beta-1	IC50	=	4.3	nM	8.37	Inhibition of recombinant rat Na+/K+-ATPase alpha4/beta1 expressed in baculoviru...	29291372
ADMET	IC50	=	6.0	nM	8.22	Cytotoxicity against human Hs578Bst cells after 72 hrs by CellTiter-Glo assay	22316168
A549	IC50	=	27.0	nM	7.57	Cytotoxicity against human A549 cells after 3 days by MTT assay	23706005
NON-PROTEIN TARGET	IC50	=	28.0	nM	7.55	Cytotoxicity against human Hs683 cells after 3 days by MTT assay	23706005
Na+/K+ ATPase alpha-3/beta-1	IC50	=	31.0	nM	7.51	Inhibition of recombinant rat Na+/K+-ATPase alpha3/beta1 expressed in baculoviru...	29291372
Unchecked	IC50	=	40.0	nM	7.4	Inhibition of rat brain sodium/potassium-transporting ATPase after 10 mins in pr...	141522
PC-3	IC50	=	43.0	nM	7.37	Cytotoxicity against human PC3 cells after 3 days by MTT assay	23706005
Unchecked	EC50	=	64.0	nM	7.19	PUBCHEM_BIOASSAY: Luminescence Cell-Based HTS Dose Confirmation to Identify Inhi...	-
NON-PROTEIN TARGET	IC50	=	77.0	nM	7.11	Cytotoxicity against human U373 cells after 3 days by MTT assay	23706005
Unchecked	EC50	=	80.0	nM	7.1	PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response to Identify Inhibitors o...	-
Unchecked	EC50	=	84.0	nM	7.08	PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response to Identify Inhibitors o...	-
Hs-578T	IC50	=	110.0	nM	6.96	Cytotoxicity against human Hs578T cells after 72 hrs by CellTiter-Glo assay	22316168
MCF7	IC50	=	133.0	nM	6.88	Cytotoxicity against human MCF7 cells after 3 days by MTT assay	23706005
Unchecked	IC50	=	150.0	nM	6.82	Inhibition of Na+/K+ ATPase	18588282
Krueppel-like factor 5	IC50	=	164.55	nM	6.78	PUBCHEM_BIOASSAY: Luminescence-based dose response cell-based high throughput sc...	-
Na+/K+ ATPase alpha-2/beta-1	IC50	=	170.0	nM	6.77	Inhibition of recombinant rat Na+/K+-ATPase alpha2/beta1 expressed in baculoviru...	29291372
Unchecked	IC50	=	200.0	nM	6.7	Inhibition of calf heart Na+-K+ dependent ATPase preincubated for 30 mins measur...	152813
SK-MEL-28	IC50	=	211.0	nM	6.68	Cytotoxicity against human SK-MEL-28 cells after 3 days by MTT assay	23706005
Vaccinia virus	EC50	=	250.0	nM	6.6	Antiviral activity against Vaccinia virus infected in African green monkey CV-1 ...	36961984

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	290
38352829	10.1021/acsmedchemlett.3c00517	Unchecked	8
20553004	10.1021/np9005212	NON-PROTEIN TARGET	6
12109909	10.1021/jm0102811	Monoclonal antibody (mAb)	5
18805699	10.1016/j.bmc.2008.09.007	Unchecked	4
24900847	10.1021/ml400529q	HFF	3
152813	10.1021/jm00210a021	Unchecked	3
23706005	10.1021/np400034d	NON-PROTEIN TARGET	3
152813	10.1021/jm00210a021	NON-PROTEIN TARGET	3
17339374	10.1128/aac.01544-06	Trypanosoma cruzi	2
18066055	10.1038/nchembio.2007.53	HeLa	2
23379671	10.1021/jf305164m	Meloidogyne incognita	2
19734910	10.1038/nchembio.215	Plasmodium falciparum	2
22316168	10.1021/np2008076	ADMET	2
24828374	10.1021/np500156n	Unchecked	2
17339374	10.1128/aac.01544-06	Trypanosoma brucei rhodesiense	2
20739103	10.1016/j.ejmech.2010.07.050	Saccharomyces cerevisiae	2
20739103	10.1016/j.ejmech.2010.07.050	Unchecked	2
7143360	10.1021/jm00352a025	ADMET	2
9632674	10.1074/jbc.273.26.16184	Solute carrier organic anion transporter family member 1A1	2

Data from ChEMBL 36 via Core Engine