saxitoxin   Click here for help

GtoPdb Ligand ID: 2625

PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 6
Rotatable bonds 3
Topological polar surface area 184.81
Molecular weight 299.13
XLogP -2.59
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES NC(=O)OCC1N=C(N)N2C3(C1NC(=N3)N)C(O)(O)CC2
Isomeric SMILES NC(=O)OC[C@@H]1N=C(N)N2[C@@]3([C@H]1NC(=N3)N)C(O)(O)CC2
InChI InChI=1S/C10H17N7O4/c11-6-15-5-4(3-21-8(13)18)14-7(12)17-2-1-9(19,20)10(5,17)16-6/h4-5,19-20H,1-3H2,(H2,12,14)(H2,13,18)(H3,11,15,16)/t4-,5-,10-/m0/s1
InChI Key RPQXVSUAYFXFJA-HGRQIUPRSA-N
References
1. Bricelj VM, Connell L, Konoki K, Macquarrie SP, Scheuer T, Catterall WA, Trainer VL. (2005)
Sodium channel mutation leading to saxitoxin resistance in clams increases risk of PSP.
Nature, 434 (7034): 763-7. [PMID:15815630]
2. Cribbs LL, Satin J, Fozzard HA, Rogart RB. (1990)
Functional expression of the rat heart I Na+ channel isoform. Demonstration of properties characteristic of native cardiac Na+ channels.
FEBS Lett., 275 (1-2): 195-200. [PMID:2175715]
3. Penzotti JL, Lipkind G, Fozzard HA, Dudley Jr SC. (2001)
Specific neosaxitoxin interactions with the Na+ channel outer vestibule determined by mutant cycle analysis.
Biophys. J., 80 (2): 698-706. [PMID:11159437]
4. Walker JR, Novick PA, Parsons WH, McGregor M, Zablocki J, Pande VS, Du Bois J. (2012)
Marked difference in saxitoxin and tetrodotoxin affinity for the human nociceptive voltage-gated sodium channel (Nav1.7) [corrected].
Proc. Natl. Acad. Sci. U.S.A., 109 (44): 18102-7. [PMID:23077250]
5. Zeng D, Kyle JW, Martin RL, Ambler KS, Hanck DA. (1996)
Cardiac sodium channels expressed in a peripheral neurotumor-derived cell line, RT4-B8.
Am. J. Physiol., 270 (5 Pt 1): C1522-31. [PMID:8967455]