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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H45NO3.ClH
Molecular Weight 468.112
Optical Activity UNSPECIFIED
Defined Stereocenters 13 / 13
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VERTICINE HYDROCHLORIDE

SMILES

Cl.[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=RDNDJVJNDWTGGV-LOGDSNHLSA-N
InChI=1S/C27H45NO3.ClH/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;1H/t15-,16-,17+,18+,19-,20-,21-,22-,23+,24-,25-,26+,27-;/m0./s1

HIDE SMILES / InChI
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

Curator's Comment: Fukuda: Sci. Rep. Res. Inst. Tohoku Univ. Ser. A 18, 323 (1929)

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

Mice: 3 mg/kg
Route of Administration: Oral
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.
Name Type Language
VERTICINE HYDROCHLORIDE
MI  
Common Name English
PEIMINE HYDROCHLORIDE
Common Name English
VERTICINIUM CHLORIDE
Common Name English
CEVANE-3,6,20-TRIOL, HYDROCHLORIDE, (3.BETA.,5.ALPHA.,6.ALPHA.)-
Systematic Name English
VERTICINE HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
MERCK INDEX
m11435
Created by admin on Sat Dec 16 19:05:08 GMT 2023 , Edited by admin on Sat Dec 16 19:05:08 GMT 2023
PRIMARY Merck Index
FDA UNII
GL32ZJ6868
Created by admin on Sat Dec 16 19:05:08 GMT 2023 , Edited by admin on Sat Dec 16 19:05:08 GMT 2023
PRIMARY
PUBCHEM
90479089
Created by admin on Sat Dec 16 19:05:08 GMT 2023 , Edited by admin on Sat Dec 16 19:05:08 GMT 2023
PRIMARY
CAS
104578-56-5
Created by admin on Sat Dec 16 19:05:08 GMT 2023 , Edited by admin on Sat Dec 16 19:05:08 GMT 2023
PRIMARY