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

Molecular Formula	C23H34O5
Molecular Weight	390.5131
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:31:26 GMT 2023` Edited by `admin` on `Sat Dec 16 08:31:26 GMT 2023`
Record UNII	G36K2H8SME
Record Status	`Validated (UNII)`
Record Version

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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