Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H45NO3 |
| Molecular Weight | 431.6511 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 13 / 13 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@]3([H])[C@@]([H])(CN4C[C@@H](C)CC[C@@]4([H])[C@@]3(C)O)[C@]1([H])C[C@@]5([H])[C@@]2([H])C[C@H](O)[C@@]6([H])C[C@@H](O)CC[C@]56C
InChI
InChIKey=IUKLSMSEHKDIIP-BZMYINFQSA-N
InChI=1S/C27H45NO3/c1-15-4-7-25-27(3,31)21-6-5-17-18(20(21)14-28(25)13-15)11-22-19(17)12-24(30)23-10-16(29)8-9-26(22,23)2/h15-25,29-31H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-,22-,23+,24-,25-,26+,27-/m0/s1
| Molecular Formula | C27H45NO3 |
| Molecular Weight | 431.6511 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 13 / 13 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Verticine is a steroidal alkaloid compound extracted from the Fritillaria species of medicinal plants. Verticine was not only able to block the Nav1.7 ion channel but also preferably inhibited the Kv1.3 ion channel. It inhibits the production of inflammatory cytokines induced by LPS through blocking MAPKs and NF-κB signaling pathways. Verticine inhibited the hERG peak tail currents in a concentration dependent manner. Verticine exhibits anti-inflammatory, antitussive, antihypertensive and pain suppression properties.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2625 |
312.8 µM [IC50] | ||
Target ID: GO:0007249 |
|||
Target ID: map04010 |
|||
Target ID: CHEMBL240 |
43.7 µM [IC50] | ||
Target ID: CHEMBL4296 |
47.2 µM [IC50] | ||
Target ID: CHEMBL4633 |
142.1 µM [IC50] | ||
Target ID: CHEMBL2086 |
472.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacokinetics, tissue distribution and excretion of verticinone from F. hupehensis in rats. | 2014 Dec 10 |
|
| Imperialine and Verticinone from Bulbs of Fritillaria wabuensis Inhibit Pro-inflammatory Mediators in LPS-stimulated RAW 264.7 Macrophages. | 2015 Jul |
|
| Verticine, ebeiedine and suchengbeisine isolated from the bulbs of Fritillaria thunbergii Miq. inhibited the gene expression and production of MUC5AC mucin from human airway epithelial cells. | 2016 Feb 15 |
|
| Peimine, a main active ingredient of Fritillaria, exhibits anti-inflammatory and pain suppression properties at the cellular level. | 2016 Jun |
|
| Peimine inhibits hERG potassium channels through the channel inactivation states. | 2017 May |
Patents
Sample Use Guides
Verticine significantly inhibited EGF-induced MUC5AC production from NCI-H292 cells, at the highest concentration. The amounts of mucin in the cells of verticine-treated cultures were 100 ± 8%, 212 ± 10%, 217 ± 8%, 221 ± 4%, 187 ± 3% and 93 ± 4% for control, 25 ng/ml of EGF alone, EGF plus verticine 10–6 M, EGF plus verticine 2 × 10−6 M, EGF plus verticine 5 × 10–6 M and EGF plus verticine 10–5 M, respectively.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:57:31 GMT 2023
by
admin
on
Sat Dec 16 08:57:31 GMT 2023
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| Record UNII |
34QDF8UFSY
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| Record Status |
Validated (UNII)
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| Record Version |
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m11435
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| Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
