VERTICINONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H43NO3
Molecular Weight	429.6352
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@]3([H])[C@@]([H])(CC(=O)[C@@]4([H])C[C@@H](O)CC[C@]34C)[C@]1([H])CC[C@@]5([H])[C@@]2([H])CN6C[C@@H](C)CC[C@@]6([H])[C@@]5(C)O

InChI

InChIKey=IQDIERHFZVCNRZ-YUYPDVIUSA-N

InChI=1S/C27H43NO3/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/h15-23,25,29,31H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-,22-,23+,25-,26+,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H43NO3
Molecular Weight	429.6352
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28496003 | https://www.ncbi.nlm.nih.gov/pubmed/21881221 | https://www.ncbi.nlm.nih.gov/pubmed/25514053 | https://www.ncbi.nlm.nih.gov/pubmed/21958967

Verticinone is a major alkaloid isolated from the bulbus of Fritillaria ussuriensis. Verticinone was rapidly absorbed, widely distributed in most tissues, and metabolized extensively before excretion. Verticinone has antitumor effects - treatment with verticinone can induce cancer cell apoptosis and autophagy via modulating the production of metabolites, which are supportive of carcinoma cell proliferation. Due to the potent antitussive activity and no addictive effect, verticinone seems to be a promising potential antitussive drug. Verticinone is expected to become a potentially novel sedative-analgesic agent without producing tolerance and dependence.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Angiotensin-converting enzyme 97 Target ID: CHEMBL2625 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12865981	Inhibitor 8297	165.0 µM [IC50]
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28496003	Activator 1430
autophagy 17 Target ID: GO:0006914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28496003	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Cough 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21958967	Preventing	Preclinical	Unknown Approved Use Unknown
Promyelocytic leukemia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12419949	Primary	Basic research	Unknown Approved Use Unknown
Colorectal cancer 101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28496003	Primary	Basic research	Unknown Approved Use Unknown
Oral cancer 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18058993	Primary	Basic research	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21881221	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Differentiation-inducing effects of verticinone, an isosteroidal alkaloid isolated from the bulbus of Fritillaria ussuriensis, on human promyelocytic leukemia HL-60 cells.	2002 Nov	12419949
Verticinone induces cell cycle arrest and apoptosis in immortalized and malignant human oral keratinocytes.	2008 Mar	18058993
Antitussive, expectorant and anti-inflammatory alkaloids from Bulbus Fritillariae Cirrhosae.	2011 Dec	21958967
Pharmacokinetics, tissue distribution and excretion of verticinone from F. hupehensis in rats.	2014 Dec 10	25514053

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 3 mg/kg

Route of Administration: Oral

In Vitro Use Guide

When HL-60 cells were incubated with 7.5 uM of verticinone for 4 d, 44% of the cells became nitroblue tetrazolium (NBT) positive.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:05:28 UTC 2023` Edited by `admin` on `Sat Dec 16 10:05:28 UTC 2023`
Record UNII	QUB07U6VTQ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

VERTICINONE

Common Name

English

CEVAN-6-ONE, 3,20-DIHYDROXY-, (3.BETA.,5.ALPHA.)-

Systematic Name

English

FRITILLARINE

Common Name

English

OSNOVANINE

Common Name

English

PEIMININE

Common Name

English

RADDEANINE

Common Name

English

IMPERIALINE [MI]

Common Name

English

Code System Code Type Description

FDA UNII

QUB07U6VTQ