ISOPTEROPODINE

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 Search

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	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16042336 | https://www.ncbi.nlm.nih.gov/pubmed/16445836 | https://www.ncbi.nlm.nih.gov/pubmed/12191580 | https://www.ncbi.nlm.nih.gov/pubmed/11197086

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

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M1 168 Target ID: CHEMBL3733 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12191580	Activator 1447	9.92 µM [EC50]
Serotonin 2 (5-HT2) receptor 90 Target ID: CHEMBL2096671 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12191580	Activator 1447	14.5 µM [EC50]
Apoptosis 156 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20032400	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
T-cell lymphoblastic leukaemia 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16445836	Primary		Basic research	Unknown Approved Use Unknown
Medullary thyroid carcinoma 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20032400	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells.	2006-03	16445836
Antimicrobial activity of isopteropodine.	2005-07-27	16042336
Pteropodine and isopteropodine positively modulate the function of rat muscarinic M(1) and 5-HT(2) receptors expressed in Xenopus oocyte.	2002-05-24	12191580
Two stereoisomeric pentacyclic oxindole alkaloids from Uncaria tomentosa: uncarine C and uncarine E.	2001-04	11313600
Effects of Uncaria tomentosa total alkaloid and its components on experimental amnesia in mice: elucidation using the passive avoidance test.	2000-12	11197086
Bioactive indole alkaloids from the bark of Uncaria guianensis.	1999-12	10630124

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 `Mon Mar 31 23:25:48 GMT 2025` Edited by `admin` on `Mon Mar 31 23:25:48 GMT 2025`
Record UNII	J9IZ1U593L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-601678

Preferred Name

English

ISOPTEROPODINE

Common Name

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