VERTICINE

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 Search

SMILES

C[C@H]1CC[C@@H]2N(C1)C[C@H]3[C@@H]4C[C@H]5[C@@H](C[C@H](O)[C@H]6C[C@@H](O)CC[C@]56C)[C@@H]4CC[C@@H]3[C@]2(C)O

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27033404 | https://www.ncbi.nlm.nih.gov/pubmed/12865981 | https://www.ncbi.nlm.nih.gov/pubmed/28282785 | https://www.ncbi.nlm.nih.gov/pubmed/26926170

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 Target	Pharmacology	Potency
Angiotensin-converting enzyme 94 Target ID: CHEMBL2625 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12865981	Inhibitor 8504	312.8 µM [IC50]
I-kappaB kinase/NF-kappaB signaling 4 Target ID: GO:0007249 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23944357	Blocker 555
MAPK signaling pathway 26 Target ID: map04010 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23944357	Blocker 555
HERG 99 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28282785	Inhibitor 8504	43.7 µM [IC50]
Sodium channel protein type IX alpha subunit 21 Target ID: CHEMBL4296 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27033404	Blocker 555	47.2 µM [IC50]
Voltage-gated potassium channel subunit Kv1.3 7 Target ID: CHEMBL4633 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27033404	Inhibitor 8504	142.1 µM [IC50]
Voltage-gated potassium channel subunit Kv1.2 3 Target ID: CHEMBL2086 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27033404	Inhibitor 8504	472.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cough 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21958967	Preventing	Preclinical	Unknown Approved Use Unknown
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27033404	Primary	Basic research	Unknown Approved Use Unknown
Inflammation 105 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27033404	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Peimine inhibits hERG potassium channels through the channel inactivation states.	2017-05	28282785
Peimine, a main active ingredient of Fritillaria, exhibits anti-inflammatory and pain suppression properties at the cellular level.	2016-06	27033404
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.	2016-02-15	26926170
Imperialine and Verticinone from Bulbs of Fritillaria wabuensis Inhibit Pro-inflammatory Mediators in LPS-stimulated RAW 264.7 Macrophages.	2015-07	26132855
Pharmacokinetics, tissue distribution and excretion of verticinone from F. hupehensis in rats.	2014-12-10	25514053
Angiotensin converting enzyme (ACE) inhibitory alkaloids from Fritillaria ussuriensis.	2003-06	12865981

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:24:05 GMT 2025` Edited by `admin` on `Mon Mar 31 22:24:05 GMT 2025`
Record UNII	34QDF8UFSY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VERTICINE

Common Name

English

5.ALPHA.-CEVANE-3.BETA.,6.ALPHA.,20-TRIOL

Preferred Name

English

CEVANE-3,6,20-TRIOL, (3.BETA.,5.ALPHA.,6.ALPHA.)-

Systematic Name

English

PEIMINE

Common Name

English

6.ALPHA.-DIHYDROISOIMPERIALINE

Common Name

English

VERTICINE [MI]

Common Name

English

Code System Code Type Description

FDA UNII

34QDF8UFSY