spermine   Click here for help

GtoPdb Ligand ID: 710

PDB Ligand
Compound class: Metabolite
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 4
Rotatable bonds 11
Topological polar surface area 76.1
Molecular weight 202.22
XLogP -0.68
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES NCCCNCCCCNCCCN
Isomeric SMILES NCCCNCCCCNCCCN
InChI InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
InChI Key PFNFFQXMRSDOHW-UHFFFAOYSA-N
References
1. Haber MT, Fukui T, Lebowitz MS, Lowenstein JM. (1991)
Activation of phosphoinositide-specific phospholipase C delta from rat liver by polyamines and basic proteins.
Arch Biochem Biophys, 288 (1): 243-9. [PMID:1654825]
2. Hiasa M, Miyaji T, Haruna Y, Takeuchi T, Harada Y, Moriyama S, Yamamoto A, Omote H, Moriyama Y. (2014)
Identification of a mammalian vesicular polyamine transporter.
Sci Rep, 4: 6836. [PMID:25355561]
3. Homma Y, Emori Y. (1995)
A dual functional signal mediator showing RhoGAP and phospholipase C-delta stimulating activities.
EMBO J, 14 (2): 286-91. [PMID:7835339]
4. Ishihara K, Hiraoka M, Ochi R. (1996)
The tetravalent organic cation spermine causes the gating of the IRK1 channel expressed in murine fibroblast cells.
J Physiol (Lond.), 491 ( Pt 2): 367-81. [PMID:8866861]
5. Kozak JA, Kerschbaum HH, Cahalan MD. (2002)
Distinct properties of CRAC and MIC channels in RBL cells.
J Gen Physiol, 120 (2): 221-35. [PMID:12149283]
6. Lopatin AN, Makhina EN, Nichols CG. (1994)
Potassium channel block by cytoplasmic polyamines as the mechanism of intrinsic rectification.
Nature, 372 (6504): 366-9. [PMID:7969496]
7. Murthy SN, Lomasney JW, Mak EC, Lorand L. (1999)
Interactions of G(h)/transglutaminase with phospholipase Cdelta1 and with GTP.
Proc Natl Acad Sci USA, 96 (21): 11815-9. [PMID:10518533]
8. Nilius B, Prenen J, Voets T, Droogmans G. (2004)
Intracellular nucleotides and polyamines inhibit the Ca2+-activated cation channel TRPM4b.
Pflugers Arch, 448 (1): 70-5. [PMID:14758478]
9. Park D, Jhon DY, Lee CW, Lee KH, Rhee SG. (1993)
Activation of phospholipase C isozymes by G protein beta gamma subunits.
J Biol Chem, 268 (7): 4573-6. [PMID:8383116]
10. Quinn SJ, Ye CP, Diaz R, Kifor O, Bai M, Vassilev P, Brown E. (1997)
The Ca2+-sensing receptor: a target for polyamines.
Am J Physiol, 273 (4): C1315-23. [PMID:9357776]
11. Ullrich ND, Voets T, Prenen J, Vennekens R, Talavera K, Droogmans G, Nilius B. (2005)
Comparison of functional properties of the Ca2+-activated cation channels TRPM4 and TRPM5 from mice.
Cell Calcium, 37 (3): 267-78. [PMID:15670874]
12. Yang J, Jan YN, Jan LY. (1995)
Control of rectification and permeation by residues in two distinct domains in an inward rectifier K+ channel.
Neuron, 14 (5): 1047-54. [PMID:7748552]