Compound Detail

CHEMBL2059499

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CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[C@@H]5O[C@H](COS(=O)(=O)[O-])[C@@H](O[C@H]6O[C@H](COS(=O)(=O)[O-])[C@@H](O[C@H]7O[C@H](COS(=O)(=O)[O-])[C@@H](O[C@H]8O[C@H](COS(=O)(=O)[O-])[C@@H](OS(=O)(=O)[O-])[C@H](OS(=O)(=O)[O-])[C@H]8OS(=O)(=O)[O-])[C@H](OS(=O)(=O)[O-])[C@H]7OS(=O)(=O)[O-])[C@H](OS(=O)(=O)[O-])[C@H]6OS(=O)(=O)[O-])[C@H](OS(=O)(=O)[O-])[C@H]5OS(=O)(=O)[O-])CC[C@]4(C)[C@H]3CC[C@]12C.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2059499
Phase	Preclinical
Structure Type	MOL
InChI Key	PHIUHBOJEMIHQZ-YAPWIAIGSA-A
Parent Compound	CHEMBL2078841
Active Moiety	CHEMBL2078841

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

2078.1

MW (Da)

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C51H75Na13O60S13
MW	2363.84

Activity Summary

IC50 6 meas. best 6.91

Kd 4 meas. best 8.1

Ki 1 meas. best 8.21

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Heparanase CHEMBL3921	Ki	8.21	8.21	6.1	1
Fibroblast growth factor 1 CHEMBL2120	Kd	8.1	8.1	8.0	1
Unchecked CHEMBL612545	Kd	7.54	7.54	28.9	1
Heparanase CHEMBL3921	IC50	6.91	6.91	123.0	1
Fibroblast growth factor 2 CHEMBL3107	Kd	6.41	6.41	390.0	1
HUVEC CHEMBL613979	IC50	6.3	6.02	500.0	4
Aorta CHEMBL613606	IC50	5.96	5.96	1100.0	1
Spike glycoprotein CHEMBL4662936	Kd	5.04	5.04	9120.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	50.0	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Heparanase	Ki	=	6.1	nM	8.21	Inhibition of human recombinant heparanase after 2 to 24 hrs by WST1 dye based f...	22458531
Fibroblast growth factor 1	Kd	=	8.0	nM	8.1	Binding affinity to FGF-1 by surface plasmon resonance assay	22458531
Unchecked	Kd	=	28.9	nM	7.54	Binding affinity to VEGFR by surface plasmon resonance assay	22458531
Heparanase	IC50	=	123.0	nM	6.91	Inhibition of recombinant human heparanase expressed in Insect cells assessed as...	38995734
Fibroblast growth factor 2	Kd	=	390.0	nM	6.41	Binding affinity to FGF-2 by surface plasmon resonance assay	22458531
HUVEC	IC50	=	500.0	nM	6.3	Antiangiogenic activity in VEGF-stimulated HUVEC cells after 72 hrs by CellTiter...	22458531
HUVEC	IC50	=	700.0	nM	6.16	Antiangiogenic activity in FGF2-stimulated HUVEC cells after 72 hrs by CellTiter...	22458531
Aorta	IC50	=	1100.0	nM	5.96	Antiangiogenic activity in Sprague-Dawley rat aorta assessed as inhibition of tu...	22458531
HUVEC	IC50	=	1210.0	nM	5.92	Antiangiogenic activity in FGF1-stimulated HUVEC cells after 72 hrs by CellTiter...	22458531
HUVEC	IC50	=	2000.0	nM	5.7	Antiangiogenic activity in HUVEC cells assessed as inhibition of tube formation ...	22458531
Spike glycoprotein	Kd	=	9120.0	nM	5.04	Binding affinity to RBD domain of SARS-CoV-2 spike protein assessed as dissociat...	38995734

Literature References

PubMed	DOI	Target Context	# Activities
22458531	10.1021/jm201708h	HUVEC	10
22458531	10.1021/jm201708h	Aorta	5
38995734	10.1021/acs.jmedchem.4c00487	Spike glycoprotein	3
22458531	10.1021/jm201708h	NON-PROTEIN TARGET	3
38995734	10.1021/acs.jmedchem.4c00487	SARS-CoV-2	2
22458531	10.1021/jm201708h	Plasma	2
37981443	10.1016/j.ejmech.2023.115923	Respiratory syncytial virus	1
38995734	10.1021/acs.jmedchem.4c00487	Vero C1008	1
38995734	10.1021/acs.jmedchem.4c00487	Heparanase	1
38995734	10.1021/acs.jmedchem.4c00487	Human alphaherpesvirus 2	1
38995734	10.1021/acs.jmedchem.4c00487	Respiratory syncytial virus	1
37981443	10.1016/j.ejmech.2023.115923	SARS-CoV-2	1
37981443	10.1016/j.ejmech.2023.115923	Spike glycoprotein/Angiotensin-converting enzyme 2	1
22458531	10.1021/jm201708h	Heparanase	1
22458531	10.1021/jm201708h	Unchecked	1
22458531	10.1021/jm201708h	Fibroblast growth factor 2	1
22458531	10.1021/jm201708h	Fibroblast growth factor 1	1
22458531	10.1021/jm201708h	Rattus norvegicus	1

Data from ChEMBL 36 via Core Engine