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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H24N2O4
Molecular Weight 368.4271
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOPTEROPODINE

SMILES

C[C@@]1([H])[C@]2([H])CN3CC[C@]4(c5ccccc5N=C4O)[C@]3([H])C[C@]2([H])C(=CO1)C(=O)OC

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 368.4271
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Bioactive indole alkaloids from the bark of Uncaria guianensis.
1999 Dec
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

Mice: 20 mg/kg
Route of Administration: Intraperitoneal
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 Sat Jun 26 10:19:55 UTC 2021
Edited
by admin
on Sat Jun 26 10:19:55 UTC 2021
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
FDA UNII
J9IZ1U593L
Created by admin on Sat Jun 26 10:19:55 UTC 2021 , Edited by admin on Sat Jun 26 10:19:55 UTC 2021
PRIMARY
PUBCHEM
9885603
Created by admin on Sat Jun 26 10:19:55 UTC 2021 , Edited by admin on Sat Jun 26 10:19:55 UTC 2021
PRIMARY
USP_CATALOG
1351107
Created by admin on Sat Jun 26 10:19:55 UTC 2021 , Edited by admin on Sat Jun 26 10:19:55 UTC 2021
PRIMARY USP-RS
CAS
5171-37-9
Created by admin on Sat Jun 26 10:19:55 UTC 2021 , Edited by admin on Sat Jun 26 10:19:55 UTC 2021
PRIMARY
Related Record Type Details
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