DEMISSIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H45NO
Molecular Weight	399.6523
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1[C@H]2CC[C@H](C)CN2[C@H]3C[C@H]4[C@@H]5CC[C@H]6C[C@@H](O)CC[C@]6(C)[C@H]5CC[C@]4(C)[C@@H]13

InChI

InChIKey=JALVTHFTYRPDMB-HRRTYWNUSA-N

InChI=1S/C27H45NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h16-25,29H,5-15H2,1-4H3/t16-,17+,18-,19-,20+,21-,22-,23+,24-,25-,26-,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H45NO
Molecular Weight	399.6523
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/15137822 | https://www.ncbi.nlm.nih.gov/pubmed/18833031 | https://www.ncbi.nlm.nih.gov/pubmed/9491766 | https://www.ncbi.nlm.nih.gov/pubmed/27232858

Demissidine was isolated from several potato species including Solanum demissum, Solanum acaule and Solanum tuberosum. Demissidine was synthesized from the related steroidal alkaloid dihydrotomatidine. Demissidine is an alkaloid that inhibits the growth of human colon and liver cancer cells in culture, though less actively than glycoalkaloid dehydrocommersonine. Demissidine is a growth inhibitor of Trypanosoma cruzi.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Colon cancer 66 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15137822	Primary		Basic research	Unknown Approved Use Unknown
Liver cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15137822	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Elucidation of the mass fragmentation pathways of potato glycoalkaloids and aglycons using Orbitrap mass spectrometry.	2010-09	20641001
Alkaloids induce programmed cell death in bloodstream forms of trypanosomes (Trypanosoma b. brucei).	2008-10-03	18833031
Compartmentalization of oxidative stress and antioxidant defense in the larval gut of Spodoptera littoralis.	2006-09	16921519
Glycoalkaloid aglycone accumulations associated with infection by Clavibacter michiganensis ssp. sepedonicus in potato species Solanum acaule and Solanum tuberosum and their interspecific somatic hybrids.	2005-03	15365763
Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.	2004-05-19	15137822
Non-aqueous capillary electrophoresis with diode array and electrospray mass spectrometric detection for the analysis of selected steroidal alkaloids in plant extracts.	2001-07-13	11486878

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Alkaloid demissidine induced apoptosis at a concentration of 100 uM in Trypanosoma brucei. EC50 value was 14 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:01:19 GMT 2025` Edited by `admin` on `Mon Mar 31 19:01:19 GMT 2025`
Record UNII	VG66W0726Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEMISSIDINE

Common Name

English

NSC-409074

Preferred Name

English

(22R,25S)-5.ALPHA.-SOLANIDAN-3.BETA.-OL

Common Name

English

SOLANINE D

Common Name

English

DIHYDROSOLANIDINE

Common Name

English

SOLANIDAN-3-OL, (3.BETA.,5.ALPHA.)-

Common Name

English

Code System Code Type Description

FDA UNII

VG66W0726Y