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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 of TOMATIDINE

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

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P17405
Gene ID: 6609.0
Gene Symbol: SMPD1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Dehydrotomatine and alpha-tomatine content in tomato fruits and vegetative plant tissues.
2004 Apr 7
A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum.
2005 Jan
Wnt and Hedgehog are critical mediators of cigarette smoke-induced lung cancer.
2006 Dec 20
Hedgehog signaling pathway is inactive in colorectal cancer cell lines.
2007 Dec 15
Efficient conversion of tomatidine into neuritogenic pregnane derivative.
2007 Jul
Hedgehog signalling is essential for maintenance of cancer stem cells in myeloid leukaemia.
2009 Apr 9
Cross talk between hedgehog and epithelial-mesenchymal transition pathways in gastric pit cells and in diffuse-type gastric cancers.
2009 Jan 27
Hedgehog signaling regulates the survival of gastric cancer cells by regulating the expression of Bcl-2.
2009 Jul 6
Resistance of wild Solanum accessions to aphids and other potato pests in Quebec field conditions.
2010
Chemoprotective Effect of Sobatum against Lithium-Induced Oxidative Damage in Rats.
2010 Jan
Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression.
2013 May 25

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Sat Dec 16 09:35:11 GMT 2023
Edited
by admin
on Sat Dec 16 09:35:11 GMT 2023
Record UNII
2B73S48786
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TOMATIDINE
MI  
Common Name English
SPIROSOLAN-3-OL, (3.BETA.,5.ALPHA.,22.BETA.,25S)-
Common Name English
TOMATIDIN
Brand 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
Created by admin on Sat Dec 16 09:35:11 GMT 2023 , Edited by admin on Sat Dec 16 09:35:11 GMT 2023
PRIMARY
CHEBI
9629
Created by admin on Sat Dec 16 09:35:11 GMT 2023 , Edited by admin on Sat Dec 16 09:35:11 GMT 2023
PRIMARY
MERCK INDEX
m10973
Created by admin on Sat Dec 16 09:35:11 GMT 2023 , Edited by admin on Sat Dec 16 09:35:11 GMT 2023
PRIMARY Merck Index
NSC
27592
Created by admin on Sat Dec 16 09:35:11 GMT 2023 , Edited by admin on Sat Dec 16 09:35:11 GMT 2023
PRIMARY
WIKIPEDIA
Tomatidine
Created by admin on Sat Dec 16 09:35:11 GMT 2023 , Edited by admin on Sat Dec 16 09:35:11 GMT 2023
PRIMARY
CAS
77-59-8
Created by admin on Sat Dec 16 09:35:11 GMT 2023 , Edited by admin on Sat Dec 16 09:35:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID0037102
Created by admin on Sat Dec 16 09:35:11 GMT 2023 , Edited by admin on Sat Dec 16 09:35:11 GMT 2023
PRIMARY
NSC
226903
Created by admin on Sat Dec 16 09:35:11 GMT 2023 , Edited by admin on Sat Dec 16 09:35:11 GMT 2023
PRIMARY
PUBCHEM
65576
Created by admin on Sat Dec 16 09:35:11 GMT 2023 , Edited by admin on Sat Dec 16 09:35:11 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-040-3
Created by admin on Sat Dec 16 09:35:11 GMT 2023 , Edited by admin on Sat Dec 16 09:35:11 GMT 2023
PRIMARY