TOMATIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H45NO2
Molecular Weight	415.6517
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]2[C@H](C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]23C)O[C@@]16CC[C@H](C)CN6

InChI

InChIKey=XYNPYHXGMWJBLV-VXPJTDKGSA-N

InChI=1S/C27H45NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28-29H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H45NO2
Molecular Weight	415.6517
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/24719321 | https://www.ncbi.nlm.nih.gov/pubmed/26338703

Tomatidine is a steroidal alkaloid derived from green tomato. Tomatitidine has been identified as a potential therapeutic agent or lead compound for the treatment of skeletal muscle atrophy. It has been shown to increase skeletal muscle mTORC1 signaling, reduce skeletal muscle atrophy, enhance recovery from skeletal muscle atrophy, stimulate skeletal muscle hypertrophy, and increase strength and exercise capacity. In addition, tomatidine has been identified as a potential therapeutic agent or lead compound for reducing the activity of Activating Transcription Factor 4 (ATF4).

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
mTORC1 signaling 2 Target ID: mTORC1 signaling Sources: https://www.ncbi.nlm.nih.gov/pubmed/24719321	Activator 1447
Sphingomyelin phosphodiesterase 7 Target ID: P17405 Gene ID: 6609.0 Gene Symbol: SMPD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21909365	Inhibitor 8504
NF-kappa B signaling pathway 87 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18544347	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skeletal muscle atrophy 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24719321	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression.	2013-05-25	23566884
Gli2 expression and human bladder transitional carcinoma cell invasiveness.	2010-07	20488474
Distortion of trichome morphology by the hairless mutation of tomato affects leaf surface chemistry.	2010-02	20018901
Smoothened as a new therapeutic target for human osteosarcoma.	2010-01-12	20067614
Chemoprotective Effect of Sobatum against Lithium-Induced Oxidative Damage in Rats.	2010-01	21331195
Resistance of wild Solanum accessions to aphids and other potato pests in Quebec field conditions.	2010	21054161
Plant antimicrobial agents and their effects on plant and human pathogens.	2009-07-31	20111686
Tomatine-containing green tomato extracts inhibit growth of human breast, colon, liver, and stomach cancer cells.	2009-07-08	19514731
Hedgehog signaling regulates the survival of gastric cancer cells by regulating the expression of Bcl-2.	2009-07-06	19742123
Evidence for allosteric interactions of antagonist binding to the smoothened receptor.	2009-06	19304771
Hedgehog signalling is essential for maintenance of cancer stem cells in myeloid leukaemia.	2009-04-09	19169242
Cross talk between hedgehog and epithelial-mesenchymal transition pathways in gastric pit cells and in diffuse-type gastric cancers.	2009-01-27	19107131
Musashi1 modulates cell proliferation genes in the medulloblastoma cell line Daoy.	2008-09-30	18826648
Autonomous Hedgehog signalling is undetectable in PC-3 prostate cancer cells.	2008-08-15	18544338
Tomatidine inhibits iNOS and COX-2 through suppression of NF-kappaB and JNK pathways in LPS-stimulated mouse macrophages.	2008-07-09	18544347
Simultaneously cycled NMR spectroscopy.	2008-04-09	18338896
Heterologous expression of Fusarium oxysporum tomatinase in Saccharomyces cerevisiae increases its resistance to saponins and improves ethanol production during the fermentation of Agave tequilana Weber var. azul and Agave salmiana must.	2008-03	17896184
Diosgenin, a naturally occurring steroid, suppresses fatty acid synthase expression in HER2-overexpressing breast cancer cells through modulating Akt, mTOR and JNK phosphorylation.	2007-12-22	18022396
Hedgehog signaling pathway is inactive in colorectal cancer cell lines.	2007-12-15	17683069
Efficient conversion of tomatidine into neuritogenic pregnane derivative.	2007-07	17603206
Wnt and Hedgehog are critical mediators of cigarette smoke-induced lung cancer.	2006-12-20	17183725
Identification of a tomatinase in the tomato-pathogenic actinomycete Clavibacter michiganensis subsp. michiganensis NCPPB382.	2005-10	16255248
Influence of incorporated wild Solanum genomes on potato properties in terms of starch nanostructure and glycoalkaloid content.	2005-06-29	15969512
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
A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum.	2005-01	15821879
Activation of the hedgehog pathway in advanced prostate cancer.	2004-10-13	15482598
Tomatidine and lycotetraose, hydrolysis products of alpha-tomatine by Fusarium oxysporum tomatinase, suppress induced defense responses in tomato cells.	2004-07-30	15280013
Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.	2004-05-19	15137822
Dehydrotomatine and alpha-tomatine content in tomato fruits and vegetative plant tissues.	2004-04-07	15053555
Hedgehog signalling within airway epithelial progenitors and in small-cell lung cancer.	2003-03-20	12629553
Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice.	2003-01	12453729
Determination of glycoalkaloids and relative aglycones by nonaqueous capillary electrophoresis coupled with electrospray ionization-ion trap mass spectrometry.	2002-09	12207298
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
Inhibitory effect of steroidal alkaloids on drug transport and multidrug resistance in human cancer cells.	2001-06-09	11396162

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

To test this hypothesis, we incubated C2C12 myotubes with 1 μm tomatidine for 1 h. We found that tomatidine increased phosphorylation of a key mTORC1 substrate, S6 kinase (S6K) (Fig. 3A). In addition, tomatidine increased protein synthesis (Fig. 3B) and IGF1 and PGC-1α1 mRNAs (Fig. 3C). To determine if mTORC1 signaling is required for tomatidine-mediated cell growth, we tested the effect of an mTORC1 inhibitor, rapamycin. As expected, rapamycin abolished the effect of tomatidine on S6K phosphorylation (Fig. 3D). Moreover, rapamycin inhibited tomatidine-mediated protein accretion and myotube growth (Fig. 3, E and F). Collectively, these data indicate that tomatidine stimulates muscle cell growth by activating mTORC1 signaling.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:44:23 GMT 2025` Edited by `admin` on `Mon Mar 31 22:44:23 GMT 2025`
Record UNII	2B73S48786
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TOMATIDINE

Common Name

English

TOMATIDIN

Preferred Name

English

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

Common Name

English

NSC-27592

Code

English

5.ALPHA.-TOMATIDAN-3.BETA.-OL

Common Name

English

TOMATIDINE [MI]

Common Name

English

NSC-226903

Code

English

Code System Code Type Description

FDA UNII

2B73S48786