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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 IMPERIALINE

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-LRCDAWNTSA-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

Imperialine is a steroidal alkaloid first isolated from the bulb of Fritillaria imperialis L. (Liliaceae). Bulbs of Fritillaria have been used in many Asian countries for a long time to treat pulmonary diseases, such as cough, expectoration, and asthma. Imperialine is one of the biologically active constituents in Fritillaria. It acts as a selective antagonist at muscarinic M2 receptors. It exerts antitussive, expectorant, and anti-inflammatory properties. In addition, imperialine demonstrated antineoplastic potential in vitro.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Rats: 3.5 or 7 mg/kg
Route of Administration: Intragastric
In Vitro Use Guide
50-400 uM peiminine (imperialine) induces apoptosis and autophagy in HCT-116 cells