Details of the Drug

General Information of Drug (ID: DMXSWF6)

Drug Name

grayanotoxin III

Synonyms

grayanotoxin III; UNII-ZKR09NT58C; Andromedol; ZKR09NT58C; Deacylasebotoxin I; Deacetylandromedotoxin; 4678-45-9; NSC 323778; BRN 2059374; Grayanotoxane-3,5,6,10,14,16-hexol, (3-beta,6-beta,14R)-; grayanotoxin-III; (3beta,6beta,14R)-Grayanotoxane-3,5,6,10,14,16-hexol; GTPL2628; CHEMBL454313; SCHEMBL1008212; 7,9a-Methano-9aH-cyclopenta(b)heptalene-2,4,8,11,11a,12(1H)-hexol, dodecahydro-1,1,4,8-tetramethyl-, (2S,3as,4R,4ar,7R,8R,9as,11R,11aR,12R)-; ZINC33913426; Grayanotoxane-3,5,6,10,14,16-hexol, (3beta,6beta,14R)- (9CI)

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

370.5

Topological Polar Surface Area (xlogp)

0.3

Rotatable Bond Count (rotbonds)

0

Hydrogen Bond Donor Count (hbonddonor)

6

Hydrogen Bond Acceptor Count (hbondacc)

6

Chemical Identifiers

Formula: C20H34O6
IUPAC Name: (1S,3R,4R,6S,8S,9R,10R,13R,14R,16R)-5,5,9,14-tetramethyltetracyclo[11.2.1.01,10.04,8]hexadecane-3,4,6,9,14,16-hexol
Canonical SMILES: C[C@]1(C[C@@]23C[C@H]([C@]4([C@@H](C[C@@H](C4(C)C)O)[C@]([C@@H]2CC[C@@H]1[C@H]3O)(C)O)O)O)O
InChI: InChI=1S/C20H34O6/c1-16(2)13(21)7-12-18(4,25)11-6-5-10-15(23)19(11,9-17(10,3)24)8-14(22)20(12,16)26/h10-15,21-26H,5-9H2,1-4H3/t10-,11+,12+,13+,14-,15-,17-,18-,19+,20+/m1/s1
InChIKey: BWMFRQKICHXLSH-FIRPSQKQSA-N

Cross-matching ID

PubChem CID: 11057730
CAS Number: 4678-45-9
TTD ID: D0YA8J

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Voltage-gated sodium channel alpha Nav1.4 (SCN4A)	TT84DRB	SCN4A_HUMAN	Activator	[2]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2628).
2	Novel site on sodium channel alpha-subunit responsible for the differential sensitivity of grayanotoxin in skeletal and cardiac muscle. Mol Pharmacol. 2001 Oct;60(4):865-72.
3	Tolperisone-type drugs inhibit spinal reflexes via blockade of voltage-gated sodium and calcium channels. J Pharmacol Exp Ther. 2005 Dec;315(3):1237-46.
4	Oxadiazolylindazole sodium channel modulators are neuroprotective toward hippocampal neurones. J Med Chem. 2009 May 14;52(9):2694-707.
5	3-(4-phenoxyphenyl)pyrazoles: a novel class of sodium channel blockers. J Med Chem. 2004 Mar 11;47(6):1547-52.
6	Point mutations in segment I-S6 render voltage-gated Na+ channels resistant to batrachotoxin. Proc Natl Acad Sci U S A. 1998 Mar 3;95(5):2653-8.
7	Structure/function characterization of micro-conotoxin KIIIA, an analgesic, nearly irreversible blocker of mammalian neuronal sodium channels. J Biol Chem. 2007 Oct 19;282(42):30699-706.