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TOMATIDINE

CAS No.:
77-59-8
Catalog Number:
AG00G2SD
Molecular Formula:
C27H45NO2
Molecular Weight:
415.6517
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
25mg
98%
1 week
United States
$140
- +
50mg
98%
1 week
United States
$190
- +
100mg
98%
1 week
United States
$290
- +
Product Description
Catalog Number:
AG00G2SD
Chemical Name:
TOMATIDINE
CAS Number:
77-59-8
Molecular Formula:
C27H45NO2
Molecular Weight:
415.6517
MDL Number:
MFCD00075644
IUPAC Name:
(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-ol
InChI:
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
InChI Key:
XYNPYHXGMWJBLV-VXPJTDKGSA-N
SMILES:
CC1CCC2(NC1)OC1C(C2C)C2(C(C1)C1CCC3C(C1CC2)(C)CCC(C3)O)C
EC Number:
201-040-3
UNII:
2B73S48786
Properties
Complexity:
696  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
12  
Defined Bond Stereocenter Count:
0
Exact Mass:
415.345g/mol
Formal Charge:
0
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
415.662g/mol
Monoisotopic Mass:
415.345g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
41.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.2  
Literature
Title Journal
Neurotoxicity of the steroidal alkaloids tomatine and tomatidine is RIP1 kinase- and caspase-independent and involves the eIF2α branch of the endoplasmic reticulum. The Journal of steroid biochemistry and molecular biology 20170701
Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression. Chemico-biological interactions 20130525
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. Bioorganic & medicinal chemistry 20121115
Tomatidine promotes the inhibition of 24-alkylated sterol biosynthesis and mitochondrial dysfunction in Leishmania amazonensis promastigotes. Parasitology 20120901
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 of agricultural and food chemistry 20120418
Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT). Journal of agricultural and food chemistry 20120314
Tomatidine acts in synergy with aminoglycoside antibiotics against multiresistant Staphylococcus aureus and prevents virulence gene expression. The Journal of antimicrobial chemotherapy 20120301
The side population in human lung cancer cell line NCI-H460 is enriched in stem-like cancer cells. PloS one 20120101
Footprinting of inhibitor interactions of in silico identified inhibitors of trypanothione reductase of Leishmania parasite. TheScientificWorldJournal 20120101
ABCG2 is a direct transcriptional target of hedgehog signaling and involved in stroma-induced drug tolerance in diffuse large B-cell lymphoma. Oncogene 20111208
GLYCOALKALOID METABOLISM1 is required for steroidal alkaloid glycosylation and prevention of phytotoxicity in tomato. The Plant cell 20111201
Targeting GLI1 expression in human inflammatory breast cancer cells enhances apoptosis and attenuates migration. British journal of cancer 20110510
Identification of candidate small-molecule therapeutics to cancer by gene-signature perturbation in connectivity mapping. PloS one 20110101
Sonic hedgehog pathway is essential for maintenance of cancer stem-like cells in human gastric cancer. PloS one 20110101
Identification of novel functional inhibitors of acid sphingomyelinase. PloS one 20110101
Gli2 expression and human bladder transitional carcinoma cell invasiveness. The Journal of urology 20100701
Distortion of trichome morphology by the hairless mutation of tomato affects leaf surface chemistry. Journal of experimental botany 20100201
Smoothened as a new therapeutic target for human osteosarcoma. Molecular cancer 20100101
Resistance of wild Solanum accessions to aphids and other potato pests in Quebec field conditions. Journal of insect science (Online) 20100101
Chemoprotective Effect of Sobatum against Lithium-Induced Oxidative Damage in Rats. Journal of young pharmacists : JYP 20100101
Plant antimicrobial agents and their effects on plant and human pathogens. International journal of molecular sciences 20090801
Tomatine-containing green tomato extracts inhibit growth of human breast, colon, liver, and stomach cancer cells. Journal of agricultural and food chemistry 20090708
Hedgehog signaling regulates the survival of gastric cancer cells by regulating the expression of Bcl-2. International journal of molecular sciences 20090701
Evidence for allosteric interactions of antagonist binding to the smoothened receptor. The Journal of pharmacology and experimental therapeutics 20090601
Hedgehog signalling is essential for maintenance of cancer stem cells in myeloid leukaemia. Nature 20090409
Cross talk between hedgehog and epithelial-mesenchymal transition pathways in gastric pit cells and in diffuse-type gastric cancers. British journal of cancer 20090127
Autonomous Hedgehog signalling is undetectable in PC-3 prostate cancer cells. Biochemical and biophysical research communications 20080815
Tomatidine inhibits iNOS and COX-2 through suppression of NF-kappaB and JNK pathways in LPS-stimulated mouse macrophages. FEBS letters 20080709
Simultaneously cycled NMR spectroscopy. Journal of the American Chemical Society 20080409
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. Antonie van Leeuwenhoek 20080301
Musashi1 modulates cell proliferation genes in the medulloblastoma cell line Daoy. BMC cancer 20080101
Diosgenin, a naturally occurring steroid, suppresses fatty acid synthase expression in HER2-overexpressing breast cancer cells through modulating Akt, mTOR and JNK phosphorylation. FEBS letters 20071222
Hedgehog signaling pathway is inactive in colorectal cancer cell lines. International journal of cancer 20071215
Efficient conversion of tomatidine into neuritogenic pregnane derivative. Chemical & pharmaceutical bulletin 20070701
Wnt and Hedgehog are critical mediators of cigarette smoke-induced lung cancer. PloS one 20060101
Identification of a tomatinase in the tomato-pathogenic actinomycete Clavibacter michiganensis subsp. michiganensis NCPPB382. Molecular plant-microbe interactions : MPMI 20051001
Influence of incorporated wild Solanum genomes on potato properties in terms of starch nanostructure and glycoalkaloid content. Journal of agricultural and food chemistry 20050629
Glycoalkaloid aglycone accumulations associated with infection by Clavibacter michiganensis ssp. sepedonicus in potato species Solanum acaule and Solanum tuberosum and their interspecific somatic hybrids. Plant cell reports 20050301
A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum. Plant molecular biology 20050101
Tomatidine and lycotetraose, hydrolysis products of alpha-tomatine by Fusarium oxysporum tomatinase, suppress induced defense responses in tomato cells. FEBS letters 20040730
Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells. Journal of agricultural and food chemistry 20040519
Dehydrotomatine and alpha-tomatine content in tomato fruits and vegetative plant tissues. Journal of agricultural and food chemistry 20040407
Activation of the hedgehog pathway in advanced prostate cancer. Molecular cancer 20040101
Hedgehog signalling within airway epithelial progenitors and in small-cell lung cancer. Nature 20030320
Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030101
Determination of glycoalkaloids and relative aglycones by nonaqueous capillary electrophoresis coupled with electrospray ionization-ion trap mass spectrometry. Electrophoresis 20020901
Non-aqueous capillary electrophoresis with diode array and electrospray mass spectrometric detection for the analysis of selected steroidal alkaloids in plant extracts. Journal of chromatography. A 20010713
Inhibitory effect of steroidal alkaloids on drug transport and multidrug resistance in human cancer cells. Anticancer research 20010101
Properties