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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O4
Molecular Weight 382.4537
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ISOCORYNOXEINE

SMILES

C=C[C@@]1([H])CN2CC[C@]3(c4ccccc4N=C3O)[C@]2([H])C[C@]1([H])/C(=C(/[H])\OC)/C(=O)OC

InChI

InChIKey=MUVGVMUWMAGNSY-VKCGGMIFSA-N
InChI=1S/C22H26N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h4-8,13-15,19H,1,9-12H2,2-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H26N2O4
Molecular Weight 382.4537
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Isocorynoxeine is one of four bioactive tetracyclic oxinole alkaloids which can be isolated from Uncaria hooks used in traditional Chinese and Kampo medicines. The traditional remedies are claimed to have sedative and anti-spasmodic effects, however, isocorynoxeine does not appear to cross the blood-brain barrier. It is suspected that one or more metabolites of isocorynoxeine produce the effect of lower blood pressure, vasodilation and protection against ischemic neural damage. Furthermore, isocoynoxine has also shown reduce the viability of multi-drug resistant cancer cells when used in conjunction with doxycycline

CNS Activity

Curator's Comment:: referenced study was conducted in rat

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
13.6999999999999993 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
[Anti-convulsion effects of choto-san and chotoko (Uncariae Uncis cam Ramlus) in mice, and identification of the active principles].
1997 Dec
Uncaria alkaloids reverse ABCB1-mediated cancer multidrug resistance.
2017 Jul
Patents

Sample Use Guides

An oral dose of 40 mg/kg of isocorynoxeine was fed to rats. After dosing bile was drained and analyzed by LC-MS in order to identify metabolites of isocorynoxeine.
Route of Administration: Oral
Isocorynooxeine and several metabolites were tested for the ability to protect against 3 mM glutamate-induced cell death in immortalized an HT22-cell line. HT22 cells were cultured in DMEM supplemented with 10% FBS at 37 deg-C in a 5% CO2 and 95% air atmosphere. Cells were incubated 24 hours before being treated with 1 - 100 micro-M of each test sample and 3 mM glutamate. Isocorynoxeine exhibited significant neuroprotective effects against glutamate-induced cell death at the maximum concentration of 100 micro-M. However little neuroprotection was observed for the tested metabolites.
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:50:22 UTC 2021
Edited
by admin
on Sat Jun 26 07:50:22 UTC 2021
Record UNII
J18B596D11
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOCORYNOXEINE
Common Name English
SPIRO(3H-INDOLE-3,1'(5'H)-INDOLIZINE)-7'-ACETIC ACID, 6'-ETHENYL-1,2,2',3',6',7',8',8'A-OCTAHYDRO-.ALPHA.-(METHOXYMETHYLENE)-2-OXO-, METHYL ESTER, (.ALPHA.E,1'S,6'R,7'S,8'AS)-
Systematic Name English
7-ISOCORYNOXEINE
Common Name English
CORYNOXAN-16-CARBOXYLIC ACID, 16,17,18,19-TETRADEHYDRO-17-METHOXY-2-OXO-, METHYL ESTER, (16E,20.ALPHA.)-
Common Name English
Code System Code Type Description
PUBCHEM
3037448
Created by admin on Sat Jun 26 07:50:22 UTC 2021 , Edited by admin on Sat Jun 26 07:50:22 UTC 2021
PRIMARY
CAS
51014-29-0
Created by admin on Sat Jun 26 07:50:22 UTC 2021 , Edited by admin on Sat Jun 26 07:50:22 UTC 2021
PRIMARY
FDA UNII
J18B596D11
Created by admin on Sat Jun 26 07:50:22 UTC 2021 , Edited by admin on Sat Jun 26 07:50:22 UTC 2021
PRIMARY
Related Record Type Details
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