GITOXIGENIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H34O5
Molecular Weight	390.5131
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
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]([C@@H](O)C[C@]34O)C5=CC(=O)OC5)[C@@]1(C)CC[C@H](O)C2

InChI

InChIKey=PVAMXWLZJKTXFW-VQMOFDJESA-N

InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-16(21)6-8-22(2)20(13-9-19(26)28-12-13)18(25)11-23(17,22)27/h9,14-18,20,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16+,17-,18+,20+,21+,22-,23+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895 | https://www.ncbi.nlm.nih.gov/pubmed/27031987

Gitoxigenin is a 16β-substituted digitoxigenin which may act as a Na+/K+-ATPase inhibitor. Cardiac glycosides (CGs), inhibitors of Na+/K+-ATPase (NKA), used clinically to treat heart failure, have garnered recent attention as potential anti-cancer and anti-viral agents. A high-throughput phenotypic screen designed to identify modulators of promyelocytic leukemia protein (PML) nuclear body (NB) formation revealed the CG gitoxigenin as a potent activator of PML.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14531018	Activator 1430
Sodium/potassium-transporting ATPase subunit alpha-1 16 Target ID: P05023\|\|\|Q9UJ20 Gene ID: 476.0 Gene Symbol: ATP1A1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895 \| https://link.springer.com/article/10.1007/BF00518481	Inhibitor 8297	500.0 nM [Kd]
Protein PML 1 Target ID: P29590\|\|\|Q8WUA0\|\|\|Q9BZY0 Gene ID: 5371.0 Gene Symbol: PML Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27031987	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14531018 https://www.ncbi.nlm.nih.gov/pubmed/27031987	Primary		Basic research	Unknown Approved Use Unknown
Cardiac insufficiency 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13820624 http://google.com/patents/US3862931	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Simultaneous determination of cardenolides by sonic spray ionization liquid chromatography-ion trap mass spectrometry--a fatal case of oleander poisoning.	2002 May-Jun	12054363
Anti-tumour activity of Digitalis purpurea L. subsp. heywoodii.	2003 Aug	14531018
Analysis of sterol and other components present in unsaponifiable matters of mahua, sal and mango kernel oil.	2010	20299763

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Gitoxigenin inhibited A549 cells with IC50 value of 1.72 uM.

Name

Type

Language

GITOXIGENIN

Common Name

English

GITOXIGENIN [MI]

Common Name

English

16.BETA.-HYDROXYDIGITOXIGENIN

Common Name

English

NSC-407807

Code

English

5.BETA.-CARD-20(22)-ENOLIDE, 3.BETA.,14,16.BETA.-TRIHYDROXY-

Systematic Name

English

CARD-20(22)-ENOLIDE, 3,14,16-TRIHYDROXY-, (3.BETA.,5.BETA.,16.BETA.)-

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID20878642