77-59-8,MFCD00075644
Catalog No.:AA00G2PL

77-59-8 | TOMATIDINE

Pack Size
Purity
Availability
Price(USD)
Quantity
  
5mg
98%
1 week  
$130.00   $91.00
- +
10mg
98%
1 week  
$162.00   $113.00
- +
25mg
98%
1 week  
$273.00   $191.00
- +
50mg
98%
1 week  
$400.00   $280.00
- +
100mg
98%
1 week  
$606.00   $424.00
- +
  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA00G2PL
Chemical Name:
TOMATIDINE
CAS Number:
77-59-8
Molecular Formula:
C27H45NO2
Molecular Weight:
415.6517
MDL Number:
MFCD00075644
SMILES:
CC1CCC2(NC1)OC1C(C2C)C2(C(C1)C1CCC3C(C1CC2)(C)CCC(C3)O)C
Properties
Computed Properties
 
Complexity:
696  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
12  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
0  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
6.2  

Literature

Title: Neurotoxicity of the steroidal alkaloids tomatine and tomatidine is RIP1 kinase- and caspase-independent and involves the eIF2α branch of the endoplasmic reticulum.

Journal: The Journal of steroid biochemistry and molecular biology 20170701

Title: Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression.

Journal: Chemico-biological interactions 20130525

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Tomatidine promotes the inhibition of 24-alkylated sterol biosynthesis and mitochondrial dysfunction in Leishmania amazonensis promastigotes.

Journal: Parasitology 20120901

Title: Structure-activity relationships of α-, β(1)-, γ-, and δ-tomatine and tomatidine against human breast (MDA-MB-231), gastric (KATO-III), and prostate (PC3) cancer cells.

Journal: Journal of agricultural and food chemistry 20120418

Title: Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT).

Journal: Journal of agricultural and food chemistry 20120314

Title: Tomatidine acts in synergy with aminoglycoside antibiotics against multiresistant Staphylococcus aureus and prevents virulence gene expression.

Journal: The Journal of antimicrobial chemotherapy 20120301

Title: The side population in human lung cancer cell line NCI-H460 is enriched in stem-like cancer cells.

Journal: PloS one 20120101

Title: Footprinting of inhibitor interactions of in silico identified inhibitors of trypanothione reductase of Leishmania parasite.

Journal: TheScientificWorldJournal 20120101

Title: ABCG2 is a direct transcriptional target of hedgehog signaling and involved in stroma-induced drug tolerance in diffuse large B-cell lymphoma.

Journal: Oncogene 20111208

Title: GLYCOALKALOID METABOLISM1 is required for steroidal alkaloid glycosylation and prevention of phytotoxicity in tomato.

Journal: The Plant cell 20111201

Title: Targeting GLI1 expression in human inflammatory breast cancer cells enhances apoptosis and attenuates migration.

Journal: British journal of cancer 20110510

Title: Identification of candidate small-molecule therapeutics to cancer by gene-signature perturbation in connectivity mapping.

Journal: PloS one 20110101

Title: Sonic hedgehog pathway is essential for maintenance of cancer stem-like cells in human gastric cancer.

Journal: PloS one 20110101

Title: Identification of novel functional inhibitors of acid sphingomyelinase.

Journal: PloS one 20110101

Title: Gli2 expression and human bladder transitional carcinoma cell invasiveness.

Journal: The Journal of urology 20100701

Title: Distortion of trichome morphology by the hairless mutation of tomato affects leaf surface chemistry.

Journal: Journal of experimental botany 20100201

Title: Smoothened as a new therapeutic target for human osteosarcoma.

Journal: Molecular cancer 20100101

Title: Resistance of wild Solanum accessions to aphids and other potato pests in Quebec field conditions.

Journal: Journal of insect science (Online) 20100101

Title: Chemoprotective Effect of Sobatum against Lithium-Induced Oxidative Damage in Rats.

Journal: Journal of young pharmacists : JYP 20100101

Title: Plant antimicrobial agents and their effects on plant and human pathogens.

Journal: International journal of molecular sciences 20090801

Title: Tomatine-containing green tomato extracts inhibit growth of human breast, colon, liver, and stomach cancer cells.

Journal: Journal of agricultural and food chemistry 20090708

Title: Hedgehog signaling regulates the survival of gastric cancer cells by regulating the expression of Bcl-2.

Journal: International journal of molecular sciences 20090701

Title: Evidence for allosteric interactions of antagonist binding to the smoothened receptor.

Journal: The Journal of pharmacology and experimental therapeutics 20090601

Title: Hedgehog signalling is essential for maintenance of cancer stem cells in myeloid leukaemia.

Journal: Nature 20090409

Title: Cross talk between hedgehog and epithelial-mesenchymal transition pathways in gastric pit cells and in diffuse-type gastric cancers.

Journal: British journal of cancer 20090127

Title: Autonomous Hedgehog signalling is undetectable in PC-3 prostate cancer cells.

Journal: Biochemical and biophysical research communications 20080815

Title: Tomatidine inhibits iNOS and COX-2 through suppression of NF-kappaB and JNK pathways in LPS-stimulated mouse macrophages.

Journal: FEBS letters 20080709

Title: Simultaneously cycled NMR spectroscopy.

Journal: Journal of the American Chemical Society 20080409

Title: 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.

Journal: Antonie van Leeuwenhoek 20080301

Title: Musashi1 modulates cell proliferation genes in the medulloblastoma cell line Daoy.

Journal: BMC cancer 20080101

Title: Diosgenin, a naturally occurring steroid, suppresses fatty acid synthase expression in HER2-overexpressing breast cancer cells through modulating Akt, mTOR and JNK phosphorylation.

Journal: FEBS letters 20071222

Title: Hedgehog signaling pathway is inactive in colorectal cancer cell lines.

Journal: International journal of cancer 20071215

Title: Efficient conversion of tomatidine into neuritogenic pregnane derivative.

Journal: Chemical & pharmaceutical bulletin 20070701

Title: Wnt and Hedgehog are critical mediators of cigarette smoke-induced lung cancer.

Journal: PloS one 20060101

Title: Identification of a tomatinase in the tomato-pathogenic actinomycete Clavibacter michiganensis subsp. michiganensis NCPPB382.

Journal: Molecular plant-microbe interactions : MPMI 20051001

Title: Influence of incorporated wild Solanum genomes on potato properties in terms of starch nanostructure and glycoalkaloid content.

Journal: Journal of agricultural and food chemistry 20050629

Title: Glycoalkaloid aglycone accumulations associated with infection by Clavibacter michiganensis ssp. sepedonicus in potato species Solanum acaule and Solanum tuberosum and their interspecific somatic hybrids.

Journal: Plant cell reports 20050301

Title: A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum.

Journal: Plant molecular biology 20050101

Title: Tomatidine and lycotetraose, hydrolysis products of alpha-tomatine by Fusarium oxysporum tomatinase, suppress induced defense responses in tomato cells.

Journal: FEBS letters 20040730

Title: Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.

Journal: Journal of agricultural and food chemistry 20040519

Title: Dehydrotomatine and alpha-tomatine content in tomato fruits and vegetative plant tissues.

Journal: Journal of agricultural and food chemistry 20040407

Title: Activation of the hedgehog pathway in advanced prostate cancer.

Journal: Molecular cancer 20040101

Title: Hedgehog signalling within airway epithelial progenitors and in small-cell lung cancer.

Journal: Nature 20030320

Title: Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030101

Title: Determination of glycoalkaloids and relative aglycones by nonaqueous capillary electrophoresis coupled with electrospray ionization-ion trap mass spectrometry.

Journal: Electrophoresis 20020901

Title: Non-aqueous capillary electrophoresis with diode array and electrospray mass spectrometric detection for the analysis of selected steroidal alkaloids in plant extracts.

Journal: Journal of chromatography. A 20010713

Title: Inhibitory effect of steroidal alkaloids on drug transport and multidrug resistance in human cancer cells.

Journal: Anticancer research 20010101

Title: Chiu FL, et al. Tomatidine inhibits iNOS and COX-2 through suppression of NF-kappaB and JNK pathways in LPS-stimulated mouse macrophages. FEBS Lett. 2008 Jul 9;582(16):2407-12.

Title: Anil Ahsan, et al. Tomatidine Protects Against Ischemic Neuronal Injury by Improving Lysosomal Function. Eur J Pharmacol. 2020 Jun 21;173280.

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SDS
Tags:77-59-8 Molecular Formula|77-59-8 MDL|77-59-8 SMILES|77-59-8 TOMATIDINE
Catalog No.: AA00G2PL
77-59-8,MFCD00075644
77-59-8 | TOMATIDINE
Pack Size: 5mg
Purity: 98%
1 week
$130.00 $91.00
Pack Size: 10mg
Purity: 98%
1 week
$162.00 $113.00
Pack Size: 25mg
Purity: 98%
1 week
$273.00 $191.00
Pack Size: 50mg
Purity: 98%
1 week
$400.00 $280.00
Pack Size: 100mg
Purity: 98%
1 week
$606.00 $424.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA00G2PL
Chemical Name: TOMATIDINE
CAS Number: 77-59-8
Molecular Formula: C27H45NO2
Molecular Weight: 415.6517
MDL Number: MFCD00075644
SMILES: CC1CCC2(NC1)OC1C(C2C)C2(C(C1)C1CCC3C(C1CC2)(C)CCC(C3)O)C
Properties
Complexity: 696  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 12  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 30  
Hydrogen Bond Acceptor Count: 3  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 0  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 6.2  
Literature fold

Title: Neurotoxicity of the steroidal alkaloids tomatine and tomatidine is RIP1 kinase- and caspase-independent and involves the eIF2α branch of the endoplasmic reticulum.

Journal: The Journal of steroid biochemistry and molecular biology20170701

Title: Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression.

Journal: Chemico-biological interactions20130525

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry20121115

Title: Tomatidine promotes the inhibition of 24-alkylated sterol biosynthesis and mitochondrial dysfunction in Leishmania amazonensis promastigotes.

Journal: Parasitology20120901

Title: Structure-activity relationships of α-, β(1)-, γ-, and δ-tomatine and tomatidine against human breast (MDA-MB-231), gastric (KATO-III), and prostate (PC3) cancer cells.

Journal: Journal of agricultural and food chemistry20120418

Title: Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT).

Journal: Journal of agricultural and food chemistry20120314

Title: Tomatidine acts in synergy with aminoglycoside antibiotics against multiresistant Staphylococcus aureus and prevents virulence gene expression.

Journal: The Journal of antimicrobial chemotherapy20120301

Title: The side population in human lung cancer cell line NCI-H460 is enriched in stem-like cancer cells.

Journal: PloS one20120101

Title: Footprinting of inhibitor interactions of in silico identified inhibitors of trypanothione reductase of Leishmania parasite.

Journal: TheScientificWorldJournal20120101

Title: ABCG2 is a direct transcriptional target of hedgehog signaling and involved in stroma-induced drug tolerance in diffuse large B-cell lymphoma.

Journal: Oncogene20111208

Title: GLYCOALKALOID METABOLISM1 is required for steroidal alkaloid glycosylation and prevention of phytotoxicity in tomato.

Journal: The Plant cell20111201

Title: Targeting GLI1 expression in human inflammatory breast cancer cells enhances apoptosis and attenuates migration.

Journal: British journal of cancer20110510

Title: Identification of candidate small-molecule therapeutics to cancer by gene-signature perturbation in connectivity mapping.

Journal: PloS one20110101

Title: Sonic hedgehog pathway is essential for maintenance of cancer stem-like cells in human gastric cancer.

Journal: PloS one20110101

Title: Identification of novel functional inhibitors of acid sphingomyelinase.

Journal: PloS one20110101

Title: Gli2 expression and human bladder transitional carcinoma cell invasiveness.

Journal: The Journal of urology20100701

Title: Distortion of trichome morphology by the hairless mutation of tomato affects leaf surface chemistry.

Journal: Journal of experimental botany20100201

Title: Smoothened as a new therapeutic target for human osteosarcoma.

Journal: Molecular cancer20100101

Title: Resistance of wild Solanum accessions to aphids and other potato pests in Quebec field conditions.

Journal: Journal of insect science (Online)20100101

Title: Chemoprotective Effect of Sobatum against Lithium-Induced Oxidative Damage in Rats.

Journal: Journal of young pharmacists : JYP20100101

Title: Plant antimicrobial agents and their effects on plant and human pathogens.

Journal: International journal of molecular sciences20090801

Title: Tomatine-containing green tomato extracts inhibit growth of human breast, colon, liver, and stomach cancer cells.

Journal: Journal of agricultural and food chemistry20090708

Title: Hedgehog signaling regulates the survival of gastric cancer cells by regulating the expression of Bcl-2.

Journal: International journal of molecular sciences20090701

Title: Evidence for allosteric interactions of antagonist binding to the smoothened receptor.

Journal: The Journal of pharmacology and experimental therapeutics20090601

Title: Hedgehog signalling is essential for maintenance of cancer stem cells in myeloid leukaemia.

Journal: Nature20090409

Title: Cross talk between hedgehog and epithelial-mesenchymal transition pathways in gastric pit cells and in diffuse-type gastric cancers.

Journal: British journal of cancer20090127

Title: Autonomous Hedgehog signalling is undetectable in PC-3 prostate cancer cells.

Journal: Biochemical and biophysical research communications20080815

Title: Tomatidine inhibits iNOS and COX-2 through suppression of NF-kappaB and JNK pathways in LPS-stimulated mouse macrophages.

Journal: FEBS letters20080709

Title: Simultaneously cycled NMR spectroscopy.

Journal: Journal of the American Chemical Society20080409

Title: 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.

Journal: Antonie van Leeuwenhoek20080301

Title: Musashi1 modulates cell proliferation genes in the medulloblastoma cell line Daoy.

Journal: BMC cancer20080101

Title: Diosgenin, a naturally occurring steroid, suppresses fatty acid synthase expression in HER2-overexpressing breast cancer cells through modulating Akt, mTOR and JNK phosphorylation.

Journal: FEBS letters20071222

Title: Hedgehog signaling pathway is inactive in colorectal cancer cell lines.

Journal: International journal of cancer20071215

Title: Efficient conversion of tomatidine into neuritogenic pregnane derivative.

Journal: Chemical & pharmaceutical bulletin20070701

Title: Wnt and Hedgehog are critical mediators of cigarette smoke-induced lung cancer.

Journal: PloS one20060101

Title: Identification of a tomatinase in the tomato-pathogenic actinomycete Clavibacter michiganensis subsp. michiganensis NCPPB382.

Journal: Molecular plant-microbe interactions : MPMI20051001

Title: Influence of incorporated wild Solanum genomes on potato properties in terms of starch nanostructure and glycoalkaloid content.

Journal: Journal of agricultural and food chemistry20050629

Title: Glycoalkaloid aglycone accumulations associated with infection by Clavibacter michiganensis ssp. sepedonicus in potato species Solanum acaule and Solanum tuberosum and their interspecific somatic hybrids.

Journal: Plant cell reports20050301

Title: A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum.

Journal: Plant molecular biology20050101

Title: Tomatidine and lycotetraose, hydrolysis products of alpha-tomatine by Fusarium oxysporum tomatinase, suppress induced defense responses in tomato cells.

Journal: FEBS letters20040730

Title: Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.

Journal: Journal of agricultural and food chemistry20040519

Title: Dehydrotomatine and alpha-tomatine content in tomato fruits and vegetative plant tissues.

Journal: Journal of agricultural and food chemistry20040407

Title: Activation of the hedgehog pathway in advanced prostate cancer.

Journal: Molecular cancer20040101

Title: Hedgehog signalling within airway epithelial progenitors and in small-cell lung cancer.

Journal: Nature20030320

Title: Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association20030101

Title: Determination of glycoalkaloids and relative aglycones by nonaqueous capillary electrophoresis coupled with electrospray ionization-ion trap mass spectrometry.

Journal: Electrophoresis20020901

Title: Non-aqueous capillary electrophoresis with diode array and electrospray mass spectrometric detection for the analysis of selected steroidal alkaloids in plant extracts.

Journal: Journal of chromatography. A20010713

Title: Inhibitory effect of steroidal alkaloids on drug transport and multidrug resistance in human cancer cells.

Journal: Anticancer research20010101

Title: Chiu FL, et al. Tomatidine inhibits iNOS and COX-2 through suppression of NF-kappaB and JNK pathways in LPS-stimulated mouse macrophages. FEBS Lett. 2008 Jul 9;582(16):2407-12.

Title: Anil Ahsan, et al. Tomatidine Protects Against Ischemic Neuronal Injury by Improving Lysosomal Function. Eur J Pharmacol. 2020 Jun 21;173280.

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