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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 of VERTICINONE

SMILES

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

Description

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 TargetPharmacologyConditionPotency
165.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

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.