draflazine   Click here for help

GtoPdb Ligand ID: 4590

Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 104.69
Molecular weight 603.2
XLogP 4.8
No. Lipinski's rules broken 1
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Canonical SMILES O=C(Nc1c(Cl)cc(cc1Cl)N)CN1CCN(CC1C(=O)N)CCCCC(c1ccc(cc1)F)c1ccc(cc1)F
Isomeric SMILES O=C(Nc1c(Cl)cc(cc1Cl)N)CN1CCN(CC1C(=O)N)CCCCC(c1ccc(cc1)F)c1ccc(cc1)F
InChI InChI=1S/C30H33Cl2F2N5O2/c31-25-15-23(35)16-26(32)29(25)37-28(40)18-39-14-13-38(17-27(39)30(36)41)12-2-1-3-24(19-4-8-21(33)9-5-19)20-6-10-22(34)11-7-20/h4-11,15-16,24,27H,1-3,12-14,17-18,35H2,(H2,36,41)(H,37,40)
1. Daniels G, Ballif BA, Helias V, Saison C, Grimsley S, Mannessier L, Hustinx H, Lee E, Cartron JP, Peyrard T et al.. (2015)
Lack of the nucleoside transporter ENT1 results in the Augustine-null blood type and ectopic mineralization.
Blood, 125 (23): 3651-4. [PMID:25896650]
2. Grañe-Boladeras N, Williams D, Tarmakova Z, Stevanovic K, Villani LA, Mehrabi P, Siu KWM, Pastor-Anglada M, Coe IR. (2019)
Oligomerization of equilibrative nucleoside transporters: a novel regulatory and functional mechanism involving PKC and PP1.
FASEB J, 33 (3): 3841-3850. [PMID:30521377]
3. Hammond JR. (2000)
Interaction of a series of draflazine analogues with equilibrative nucleoside transporters: species differences and transporter subtype selectivity.
Naunyn Schmiedebergs Arch Pharmacol, 361 (4): 373-82. [PMID:10763851]
4. Hammond JR, Archer RG. (2004)
Interaction of the novel adenosine uptake inhibitor 3-[1-(6,7-diethoxy-2-morpholinoquinazolin-4-yl)piperidin-4-yl]-1,6-dimethyl-2,4(1H,3H)-quinazolinedione hydrochloride (KF24345) with the es and ei subtypes of equilibrative nucleoside transporters.
J Pharmacol Exp Ther, 308 (3): 1083-93. [PMID:14634039]
5. Sundaram M, Yao SY, Ng AM, Griffiths M, Cass CE, Baldwin SA, Young JD. (1998)
Chimeric constructs between human and rat equilibrative nucleoside transporters (hENT1 and rENT1) reveal hENT1 structural domains interacting with coronary vasoactive drugs.
J Biol Chem, 273 (34): 21519-25. [PMID:9705281]
6. Warraich S, Bone DB, Quinonez D, Ii H, Choi DS, Holdsworth DW, Drangova M, Dixon SJ, Séguin CA, Hammond JR. (2013)
Loss of equilibrative nucleoside transporter 1 in mice leads to progressive ectopic mineralization of spinal tissues resembling diffuse idiopathic skeletal hyperostosis in humans.
J Bone Miner Res, 28 (5): 1135-49. [PMID:23184610]
7. Wright NJ, Lee SY. (2019)
Structures of human ENT1 in complex with adenosine reuptake inhibitors.
Nat Struct Mol Biol, 26 (7): 599-606. [PMID:31235912]
8. Yao SY, Ng AM, Cass CE, Baldwin SA, Young JD. (2011)
Nucleobase transport by human equilibrative nucleoside transporter 1 (hENT1).
J Biol Chem, 286 (37): 32552-62. [PMID:21795683]