spermine   Click here for help

GtoPdb Ligand ID: 710

PDB Ligand
Compound class: Metabolite or derivative
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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]