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

[H][C@@]12C[C@]3([H])C(=CO[C@@H](C)[C@]3([H])CN1CC[C@@]24C(=O)NC5=C4C=CC=C5)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	368.4263
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 169 Target ID: CHEMBL3733 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12191580	Activator 1430	9.92 µM [EC50]
Serotonin 2 (5-HT2) receptor 87 Target ID: CHEMBL2096671 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12191580	Activator 1430	14.5 µM [EC50]
Apoptosis 155 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20032400	Activator 1430

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

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 `Sat Dec 16 10:45:50 GMT 2023` Edited by `admin` on `Sat Dec 16 10:45:50 GMT 2023`
Record UNII	J9IZ1U593L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOPTEROPODINE

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