Compound Detail

CHEMBL404811

DIGITONIN

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C[C@@H]1CC[C@@]2(OC1)O[C@H]1[C@@H](O)[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)C(O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)C[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL404811
Name	DIGITONIN
Phase	Preclinical
Structure Type	MOL
InChI Key	UVYVLBIGDKGWPX-YCCXZQINSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

1229.3

MW (Da)

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C56H92O29
MW	1229.32

Activity Summary

IC50 7 meas. best 5.41

Ki 2 meas. best 6.0

EC50 1 meas. best 5.1

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Vascular endothelial growth factor receptor 1 CHEMBL1868	Ki	6.0	6.0	1001.0	1
Melanocortin receptor 5 CHEMBL4608	Ki	5.44	5.44	3639.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	5.41	5.41	3859.0	1
Melanocortin receptor 5 CHEMBL4608	IC50	5.41	5.41	3880.0	1
HT-29 CHEMBL384	IC50	5.25	5.25	5600.0	1
No relevant target CHEMBL2362975	EC50	5.1	5.1	8000.0	1
HCT-116 CHEMBL394	IC50	5.06	5.06	8700.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.02	5.02	9600.0	1
ECV-304 CHEMBL614035	IC50	4.89	4.855	13000.0	2

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Vascular endothelial growth factor receptor 1	Ki	=	1001.0	nM	6.0	DRUGMATRIX: Vascular Endothelial Growth Factor (VEGF) radioligand binding (ligan...	-
Melanocortin receptor 5	Ki	=	3639.0	nM	5.44	DRUGMATRIX: Melanocortin MC5 radioligand binding (ligand: [125I] NDP-alpha-MSH)	-
Melanocortin receptor 5	IC50	=	3880.0	nM	5.41	DRUGMATRIX: Melanocortin MC5 radioligand binding (ligand: [125I] NDP-alpha-MSH)	-
Vascular endothelial growth factor receptor 1	IC50	=	3859.0	nM	5.41	DRUGMATRIX: Vascular Endothelial Growth Factor (VEGF) radioligand binding (ligan...	-
HT-29	IC50	=	5600.0	nM	5.25	Cytotoxicity against human HT-29 cells after 72 hrs by FMCA method	19894733
No relevant target	EC50	=	8000.0	nM	5.1	Reduction in surface tension in 0.1 M PBS after 10 mins by Wilhelmy plate method...	22503361
HCT-116	IC50	=	8700.0	nM	5.06	Cytotoxicity against human HCT116 cells after 72 hrs by FMCA method	19894733
NON-PROTEIN TARGET	IC50	=	9600.0	nM	5.02	Cytotoxicity against human CC20 cells after 72 hrs by FMCA method	19894733
ECV-304	IC50	=	13000.0	nM	4.89	Cytotoxicity against human ECV304 cells after 72 hrs by Hoechst 33258 staining b...	22503361
ECV-304	IC50	=	15000.0	nM	4.82	Membranolytic activity in human ECV304 cells assessed as leakage of intracellula...	22503361

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5303300	U2OS	304
-	10.6019/CHEMBL5303300	Fibroblast	304
-	10.6019/CHEMBL5303300	HEK-293T	304
-	10.6019/CHEMBL3885881	Rattus norvegicus	214
-	10.6019/CHEMBL5303304	U2OS	9
-	10.6019/CHEMBL5303304	Fibroblast	8
-	10.6019/CHEMBL5303304	HEK-293T	5
21717567	10.1002/ps.2235	Acyrthosiphon pisum	3
23454223	10.1016/j.bmc.2013.01.061	ADMET	3
23454223	10.1016/j.bmc.2013.01.061	ECV-304	3
23454223	10.1016/j.bmc.2013.01.061	Unchecked	2
7783116	10.1021/jm00011a003	ADMET	2
22503361	10.1016/j.bmc.2012.03.032	No relevant target	2
22503361	10.1016/j.bmc.2012.03.032	ECV-304	2
19894733	10.1021/np900210m	HT-29	2
19894733	10.1021/np900210m	HCT-116	2
19894733	10.1021/np900210m	NON-PROTEIN TARGET	2
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B1	1
-	10.6019/CHEMBL5308504	Bromodomain-containing protein 4	1
10346941	10.1021/np9803068	ADMET	1

Data from ChEMBL 36 via Core Engine