NSC689857 is a potent inhibitor of EGFR and SCFSKP2 with IC50 of 36 μM for Skp2-Cks1. NSC689857 inhibits p27 phosphorylation (IC50=30 μM). NSC689857 has varying activities in different cancer types, with higher activity against leukemia cell lines than other cancer/tumor cells.

Physicochemical Properties

Molecular Formula	C25H29NO4
Molecular Weight	407.502067327499
Exact Mass	407.209
CAS #	241127-79-7
PubChem CID	391131
Appearance	White to off-white solid powder
LogP	5.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Heavy Atom Count	30
Complexity	573
Defined Atom Stereocenter Count	0
SMILES	O(C(C1C=CC(=CC=1)NCC1C=C(C=CC=1O)O)=O)CC12CC3CC(CC(C3)C1)C2
InChi Key	MXKHJVTZHIIIMQ-UHFFFAOYSA-N
InChi Code	InChI=1S/C25H29NO4/c27-22-5-6-23(28)20(10-22)14-26-21-3-1-19(2-4-21)24(29)30-15-25-11-16-7-17(12-25)9-18(8-16)13-25/h1-6,10,16-18,26-28H,7-9,11-15H2
Chemical Name	1-adamantylmethyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate
Synonyms	NSC-689857 NSC689857 NSC 689857
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

[1]. High-Throughput Screen for Inhibitors of Androgen Receptor-RUNX2 Transcriptional Regulation in Prostate Cancer. J Pharmacol Exp Ther. 2016 Nov;359(2):256-261. [2]. Chemical probes of Skp2-mediated p27 ubiquitylation and degradation. Medchemcomm. 2018 Jun 11;9(7):1093-1104.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~245.40 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.13 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.13 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (6.13 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.4540 mL	12.2699 mL	24.5399 mL
	5 mM	0.4908 mL	2.4540 mL	4.9080 mL
	10 mM	0.2454 mL	1.2270 mL	2.4540 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.