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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H24N2O4
Molecular Weight 368.4263
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOPTEROPODINE

SMILES

COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CC[C@]4([C@@H]3C[C@H]12)C(=O)NC5=C4C=CC=C5

InChI

InChIKey=JMIAZDVHNCCPDM-PFDNRQJHSA-N
InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14-,18-,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H24N2O4
Molecular Weight 368.4263
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Isopteropodine is an Uncaria pentacyclic oxindol alkaloid. It is exhibited antibacterial activity against Gram-positive bacteria. The moderate anti-proliferative effect of isopteropodine was demonstrated on the acute lymphoblastic leukaemia cells. Isopteropodine positively modulate the function of rat muscarinic M1 and 5-HT2 receptors expressed in Xenopus oocyte but further studies are necessary to elucidate the exact mechanism by which isopteropodine positively modulates muscarinic M1 and 5-HT2 receptor functions. Isopteropodine blocked the impairment of passive avoidance performance caused by the nicotinic receptor antagonist mecamylamine and the N-methyl-D-aspartate (NMDA) receptor antagonist (+/-)-3-(2-carboxypiperazin-4-yl)- propyl-1-phosphonic acid (CPP) in mouse model. Moreover, it is possible that the glutamatergic systems are implicated in the anti-amnesic effect of isopteropodine.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Effects of Uncaria tomentosa total alkaloid and its components on experimental amnesia in mice: elucidation using the passive avoidance test.
2000 Dec
Two stereoisomeric pentacyclic oxindole alkaloids from Uncaria tomentosa: uncarine C and uncarine E.
2001 Apr
Pteropodine and isopteropodine positively modulate the function of rat muscarinic M(1) and 5-HT(2) receptors expressed in Xenopus oocyte.
2002 May 24
Antimicrobial activity of isopteropodine.
2005 May-Jun
Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells.
2006 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Mice: 20 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
The Isopteropodine showed moderate cytotoxicity to several mammalian cell lines (BALB/c 3T3 (mouse fibroblasts); H460 (human non-small cell lung carcinoma); MEI8O (human cervical carcinoma); DU145 (human prostate carcinoma); LSR (mouse reticular lymphosarcoma); C678 (mouse C3H stomach carcinoma), with IC50 values ranging from 17—51 ug/mL. These activities are significantly less than those shown by camptothecin and streptonigrin.
Substance Class Chemical
Created
by admin
on Tue Oct 22 17:29:29 UTC 2019
Edited
by admin
on Tue Oct 22 17:29:29 UTC 2019
Record UNII
J9IZ1U593L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOPTEROPODINE
USP-RS  
Common Name English
NSC-601678
Code English
SPIRO(3H-INDOLE-3,6'(4'AH)-(1H)PYRANO(3,4-F)INDOLIZINE)-4'-CARBOXYLIC ACID, 1,2,5',5'A,7',8',10',10'A-OCTAHYDRO-1'-METHYL-2-OXO-, METHYL ESTER, (1'S,3S,4'AS,5'AS,10'AS)-
Systematic Name English
ISOPTEROPODINE [USP-RS]
Common Name English
ISOPTEROPODIN
Common Name English
ISOPTEROPODINE (UNCARINE A) (CONSTITUENT OF CAT'S CLAW) [DSC]
Common Name English
UNCARINE E
Common Name English
FORMOSANAN-16-CARBOXYLIC ACID, 19-METHYL-2-OXO-, METHYL ESTER, (7.ALPHA.,19.ALPHA.,20.ALPHA.)-
Systematic Name English
ALLO-ISOPTEROPODINE
Common Name English
7-ISOPTEROPODINE
Common Name English
Code System Code Type Description
PUBCHEM
9885603
Created by admin on Tue Oct 22 17:29:29 UTC 2019 , Edited by admin on Tue Oct 22 17:29:29 UTC 2019
PRIMARY
CAS
5171-37-9
Created by admin on Tue Oct 22 17:29:29 UTC 2019 , Edited by admin on Tue Oct 22 17:29:29 UTC 2019
PRIMARY
Related Record Type Details
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