Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H36O7 |
Molecular Weight | 412.517 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CC[C@]3([H])[C@@](C[C@@]1(C)O)(C[C@@H](O)[C@@]4(O)[C@@]([H])(C[C@H](O)C4(C)C)[C@]3(C)O)[C@@H]2OC(C)=O
InChI
InChIKey=NXCYBYJXCJWMRY-VGBBEZPXSA-N
InChI=1S/C22H36O7/c1-11(23)29-17-12-6-7-13-20(5,27)14-8-15(24)18(2,3)22(14,28)16(25)9-21(13,17)10-19(12,4)26/h12-17,24-28H,6-10H2,1-5H3/t12-,13+,14+,15+,16-,17-,19-,20-,21+,22+/m1/s1
Molecular Formula | C22H36O7 |
Molecular Weight | 412.517 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.sciencedirect.com/topics/page/Grayanotoxin | https://www.ncbi.nlm.nih.gov/pubmed/6839060Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/10620699
https://www.ncbi.nlm.nih.gov/pubmed/7854342
https://www.ncbi.nlm.nih.gov/pubmed/8389862
Sources: http://www.sciencedirect.com/topics/page/Grayanotoxin | https://www.ncbi.nlm.nih.gov/pubmed/6839060
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/10620699
https://www.ncbi.nlm.nih.gov/pubmed/7854342
https://www.ncbi.nlm.nih.gov/pubmed/8389862
Grayanotoxin I is found in the leaves of plants belonging to the family Ericaceae (Leucothoe, Rhododendron, Andromeda, Kalmia). It binds to the sodium channel in its open state and upon binding the sodium channel gating is altered. A shift occurs in the activation of the sodium channel to the hyperpolarizing direction, leading to its persistent opening even at resting potentials (ranging from −70 to −100mV). In addition, the inactivation process of these modified sodium channels is suppressed. The resulting massive influx of Na+ ions will cause excitation followed by complete inexcitability of nerve cells. These lipid-soluble neurotoxins may modify sodium channels gating by causing immobilization of S6 segments during gating transitions and thereby during depolarization the channels ‘are freezed’ in the open state. In the guineapig atria, Grayanotoxin I produces a membrane depolarization, positive inotropic effects and arrhythmias.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
31.0 µM [EC50] | |||
Target ID: GO:0050432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6261866 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Mechanism of nerve membrane depolarization caused by grayanotoxin I. | 1974 Oct |
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Cytotoxic principles from the sap of Kalmia latifolia. | 1979 Sep-Oct |
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Further evidence for the involvement of Na+ channels in the release of adrenal catecholamine: the effect of scorpion venom and grayanotoxin I. | 1981 Jan |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2864640
Grayanotoxin I at 1 X 10(-5) mol/l depolarized the membrane of ventricular muscles from dogs and guinea pigs only when they were stimulated, but it caused depolarization in Purkinje fibres in both stimulated and rested conditions
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:03:52 GMT 2023
by
admin
on
Sat Dec 16 02:03:52 GMT 2023
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Record UNII |
W4E6HC3T2B
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Record Status |
Validated (UNII)
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Record Version |
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