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
SMILES
[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@]6(CC[C@H](C)CN6)O2
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
Molecular Formula | C27H45NO2 |
Molecular Weight | 415.6517 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 11 / 12 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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Target ID: mTORC1 signaling Sources: https://www.ncbi.nlm.nih.gov/pubmed/24719321 |
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Target ID: P17405 Gene ID: 6609.0 Gene Symbol: SMPD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21909365 |
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Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18544347 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Dehydrotomatine and alpha-tomatine content in tomato fruits and vegetative plant tissues. | 2004 Apr 7 |
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A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum. | 2005 Jan |
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Wnt and Hedgehog are critical mediators of cigarette smoke-induced lung cancer. | 2006 Dec 20 |
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Hedgehog signaling pathway is inactive in colorectal cancer cell lines. | 2007 Dec 15 |
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Efficient conversion of tomatidine into neuritogenic pregnane derivative. | 2007 Jul |
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Hedgehog signalling is essential for maintenance of cancer stem cells in myeloid leukaemia. | 2009 Apr 9 |
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Cross talk between hedgehog and epithelial-mesenchymal transition pathways in gastric pit cells and in diffuse-type gastric cancers. | 2009 Jan 27 |
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Hedgehog signaling regulates the survival of gastric cancer cells by regulating the expression of Bcl-2. | 2009 Jul 6 |
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Resistance of wild Solanum accessions to aphids and other potato pests in Quebec field conditions. | 2010 |
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Chemoprotective Effect of Sobatum against Lithium-Induced Oxidative Damage in Rats. | 2010 Jan |
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Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression. | 2013 May 25 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24719321
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
Edited
Sat Dec 16 09:35:11 GMT 2023
by
admin
on
Sat Dec 16 09:35:11 GMT 2023
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Record UNII |
2B73S48786
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Record Status |
Validated (UNII)
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Record Version |
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Tomatidine
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