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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17NO4
Molecular Weight 323.3426
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STYLOPINE

SMILES

[H][C@]12CC3=CC=C4OCOC4=C3CN1CCC5=CC6=C(OCO6)C=C25

InChI

InChIKey=UXYJCYXWJGAKQY-OAHLLOKOSA-N
InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m1/s1

HIDE SMILES / InChI
Stylopine is a major component of the leaf of Chelidonium majus L. (Papaveraceae) which has been used for the removal of warts, papillomas, and condylomas, as well as the treatment of liver disease in oriental countries. It was shown that stylopine might contribute to the anti-inflammatory activity of Chelidonium majus by means of suppressing NO and PGE2 production. Stylopine has also been highlighted as a model compound for the design and future development of structurally related AKR1C3 inhibitors.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P42330|||Q9UII3
Gene ID: 8644.0
Gene Symbol: AKR1C3
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Isoquinoline alkaloids as a novel type of AKR1C3 inhibitors.
2014 Sep
Patents

Patents

Sample Use Guides

Different doses of aerial parts of F. capreolata (AFC) (25, 50 and 100mg/kg) were assayed in the DNBS model of experimental colitis in mice, and the colonic damage was evaluated both histologically and biochemically. AFC containS 1.3% of stylopine and 0.9% of protopine
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Stylopine per se had no cytotoxic effect in unstimulated RAW 264.7 cells, but concentration-dependently reduced nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor-alpha (TNF-alpha) and interleukin-1beta (IL-1beta), and the IL-6 production and cyclooxygenase-2 (COX-2) activity caused by the LPS stimulation.
Unknown
Name Type Language
STYLOPINE
Common Name English
STYLOPIN
Brand Name English
2,3:9,10-BIS(METHYLENEDIOXY)-(-)-TETRAHYDROBERBERINE
Common Name English
(S)-STYLOPINE
Common Name English
STYLOPINE [MI]
Common Name English
13A.ALPHA.-BERBINE, 2,3:9,10-BIS(METHYLENEDIOXY)-
Common Name English
(-)-TETRAHYDROCOPTISINE
Common Name English
NSC-110382
Code English
(-)-STYLOPINE
Common Name English
4H-BIS(1,3)BENZODIOXOLO(5,6-A:4',5'-G)QUINOLIZINE, 6,7,12B,13-TETRAHYDRO-, (12BS)-
Systematic Name English
Code System Code Type Description
FDA UNII
J0JS75Q12Z
Created by admin on Sat Dec 16 07:32:21 GMT 2023 , Edited by admin on Sat Dec 16 07:32:21 GMT 2023
PRIMARY
MERCK INDEX
m10258
Created by admin on Sat Dec 16 07:32:21 GMT 2023 , Edited by admin on Sat Dec 16 07:32:21 GMT 2023
PRIMARY
CAS
84-39-9
Created by admin on Sat Dec 16 07:32:21 GMT 2023 , Edited by admin on Sat Dec 16 07:32:21 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
CHEBI
18285
Created by admin on Sat Dec 16 07:32:21 GMT 2023 , Edited by admin on Sat Dec 16 07:32:21 GMT 2023
PRIMARY
PUBCHEM
697545
Created by admin on Sat Dec 16 07:32:21 GMT 2023 , Edited by admin on Sat Dec 16 07:32:21 GMT 2023
PRIMARY
NSC
110382
Created by admin on Sat Dec 16 07:32:21 GMT 2023 , Edited by admin on Sat Dec 16 07:32:21 GMT 2023
PRIMARY
WIKIPEDIA
Tetrahydrocoptisine
Created by admin on Sat Dec 16 07:32:21 GMT 2023 , Edited by admin on Sat Dec 16 07:32:21 GMT 2023
PRIMARY
CAS
4312-32-7
Created by admin on Sat Dec 16 07:32:21 GMT 2023 , Edited by admin on Sat Dec 16 07:32:21 GMT 2023
PRIMARY