HELVETICOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H42O9
Molecular Weight	534.6384
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(C[C@H](O)[C@H](O)[C@@H](C)O1)O[C@H]2CC[C@]3(C=O)[C@@]4([H])CC[C@]5(C)[C@H](CC[C@]5(O)[C@]4([H])CC[C@]3(O)C2)C6=CC(=O)OC6

InChI

InChIKey=QBILRDAMJUPXCX-AGAUEGNUSA-N

InChI=1S/C29H42O9/c1-16-25(33)22(31)12-24(37-16)38-18-3-8-27(15-30)20-4-7-26(2)19(17-11-23(32)36-14-17)6-10-29(26,35)21(20)5-9-28(27,34)13-18/h11,15-16,18-22,24-25,31,33-35H,3-10,12-14H2,1-2H3/t16-,18+,19-,20+,21-,22+,24+,25-,26-,27+,28+,29+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C29H42O9
Molecular Weight	534.6384
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26384484
Curator's Comment: Description was created based on several sources, including

Helveticoside is a well-known digitalis-like cardiac glycosidic constituent of ELA (Lepidium apetalum). It increased atrial stroke volume and pulse pressure without changes in cAMP efflux. Helveticoside inhibited lung cancer cell line A549 with IC50 35 nm.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
A549 13 Target ID: CHEMBL392 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26384484	Inhibitor 8297		35.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lung cancer 69 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26384484	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antiherpes activity of glucoevatromonoside, a cardenolide isolated from a Brazilian cultivar of Digitalis lanata.	2011 Oct	21763352

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Helveticoside (2 x 10-5 M) increased atrial stroke volume and pulse pressure without changes in cAMP efflux in beating rabbit atria

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:09:36 GMT 2023` Edited by `admin` on `Sat Dec 16 10:09:36 GMT 2023`
Record UNII	52OAE3C457
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HELVETICOSIDE

Common Name

English

ERYSIMIN

Common Name

English

STROPHANTHIDIN DIGITOXOSIDE

Common Name

English

DEGLUCOERYSIMOSIDE

Common Name

English

CARD-20(22)-ENOLIDE, 3-((2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-5,14-DIHYDROXY-19-OXO-, (3.BETA.,5.BETA.)-

Systematic Name

English

HELVETICOSIDE [MI]

Common Name

English

ERYSIMOTOXIN

Common Name

English

STROPHANTHIDIN 3.BETA.-DIGITOXOSIDE

Common Name

English

Code System Code Type Description

MERCK INDEX

m5937