NERIIFOLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H46O8
Molecular Weight	534.6814
Optical Activity	UNSPECIFIED
Defined Stereocenters	13 / 13
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@H](CC[C@]34O)C5=CC(=O)OC5)[C@@]1(C)CC[C@@H](C2)O[C@]6([H])O[C@@H](C)[C@H](O)[C@@H](OC)[C@@H]6O

InChI

InChIKey=VPUNMTHWNSJUOG-BAOINKAISA-N

InChI=1S/C30H46O8/c1-16-24(32)26(35-4)25(33)27(37-16)38-19-7-10-28(2)18(14-19)5-6-22-21(28)8-11-29(3)20(9-12-30(22,29)34)17-13-23(31)36-15-17/h13,16,18-22,24-27,32-34H,5-12,14-15H2,1-4H3/t16-,18+,19-,20+,21-,22+,24-,25-,26+,27-,28-,29+,30-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C30H46O8
Molecular Weight	534.6814
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	13 / 13
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25075041
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21459134 | https://www.ncbi.nlm.nih.gov/pubmed/20438743 | https://www.ncbi.nlm.nih.gov/pubmed/16793926

Neriifolin is a cardenolide glycoside that is digitoxigenin in which the hydroxy goup at position 3 has been converted to its 6-deoxy-3-O-methyl-alpha-L-glucopyranoside derivative. Found in the seeds of Cerbera odollamand in Thevetia ahouia and Thevitia neriifolia. Neriifolin reduced viability of cancer cells, induced S and G2/M phase arrests of the cell cycle, and stimulated apoptosis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/potassium-transporting ATPase 39 Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1966653	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Management of yellow oleander poisoning.	2009 Mar	19306191
Double lethal coconut crab (Birgus latro L.) poisoning.	2010 Jan	19591858
A review of the natural history, toxinology, diagnosis and clinical management of Nerium oleander (common oleander) and Thevetia peruviana (yellow oleander) poisoning.	2010 Sep 1	20438743

Patents

Sample Use Guides

In Vivo Use Guide

Pilot studies determined that up to 3 mg/kg neriifolin could be given i.v. without substantive changes in arterial blood pressure. Rats were then randomly assigned to receive vehicle (10% acetic acid) or neriifolin (0.75 mg/kg or 1.5 mg/kg i.v.) at middle cerebral artery occlusion (MCAO) onset. Cerebral infarct sizes measured at 24 h after MCAO were reduced in a dose-dependent manner by neriifolin

Route of Administration: Intravenous

In Vitro Use Guide

The SKOV-3 ovarian cancer cells were treated with 0.01 mkM 17βH-neriifolin respectively, for 4, 6, 12 and 24 hours prior to terminal deoxynucleotidyl transferase dUTP nick-end labeling (TUNEL) assay. Another set of experiment was also conducted to study the effect of different concentrations of 17βH-neriifolin (0.001, 0.01, 0.1 μM) incubated for 24 hours. Results from TUNEL assay indicated that 17βH-neriifolin caused apoptosis in SKOV-3 cells in a dose-dependent manner.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:57:17 GMT 2023` Edited by `admin` on `Sat Dec 16 07:57:17 GMT 2023`
Record UNII	5RD2ADS9WV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NERIIFOLIN

Common Name

English

NERIIFOLIN [MI]

Common Name

English

17.BETA.-NERIIFOLIN

Common Name

English

NSC-123976

Code

English

CARD-20(22)-ENOLIDE, 3-((6-DEOXY-3-O-METHYL-.ALPHA.-L-GLUCOPYRANOSYL)OXY)-14-HYDROXY-, (3.BETA.,5.BETA.)-

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

207-372-5