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

CO[C@@H]1[C@@H](O)[C@H](C)O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]5(C)[C@H](CC[C@]45O)C6=CC(=O)OC6)C2)[C@H]1O

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

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 34 Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1966653	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
A review of the natural history, toxinology, diagnosis and clinical management of Nerium oleander (common oleander) and Thevetia peruviana (yellow oleander) poisoning.	2010-09-01	20438743
Double lethal coconut crab (Birgus latro L.) poisoning.	2010-01	19591858
Management of yellow oleander poisoning.	2009-03	19306191
Cutaneous absorption of Oleander: Fact or fiction.	2009-01	19561955
A screen for drugs that protect against the cytotoxicity of polyglutamine-expanded androgen receptor.	2004-02-15	14709594

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.

Name

Type

Language

NERIIFOLIN

Common Name

English

NSC-123976

Preferred Name

English

NERIIFOLIN [MI]

Common Name

English

17.BETA.-NERIIFOLIN

Common Name

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