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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
Structure of VERTICINE

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

HIDE SMILES / InChI

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
312.8 µM [IC50]
43.7 µM [IC50]
47.2 µM [IC50]
142.1 µM [IC50]
472.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Mice: 3 mg/kg
Route of Administration: Oral
In Vitro Use Guide
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.