Tomatidine (CHEM028747)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:40:01 UTC
Update Date2016-11-09 01:18:45 UTC
Accession NumberCHEM028747
Identification
Common NameTomatidine
ClassSmall Molecule
DescriptionTomatidine is the aglycone derivative of tomatine. Tomatidine belongs to the chemical family known as Spirosolanes and Derivatives. These are steroidal alkaloids whose structure contains a spirosolane skeleton. Tomatine (the glycosylated form of tomatidine) is a mildly toxic glycoalkaloid or glycospirosolane found in the stems and leaves of tomato plants as well as in the fruit of unripened (green) tomatoes (up to 500 mg/kg). Red, ripe tomatoes have somewhat reduced amounts of tomatine and tomatidine. Both tomatine and tomatidine possess antimicrobial, antifungal and antiviral properties. Tomatidine has been shown to exhibit anti-virulence activity against normal strains of Staphylococcus aureus as well as the ability to potentiate the effect of aminoglycoside antibiotics (PMID: 24877760). Recent studies have shown that tomatidine stimulates mTORC1 signaling and anabolism, leading to accumulation of protein and mitochondria, and ultimately, cell growth. Furthermore, in mice, tomatidine 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 (PMID: 24719321). Tomatidine has also been shown to significantly inhibit cholesterol ester accumulation induced by acetylated LDL in human monocyte-derived macrophages in a dose-dependent manner. Tomatidine also inhibits cholesterol ester formation in Chinese hamster ovary cells overexpressing acyl-CoA:cholesterol acyl-transferase (ACAT)-1 or ACAT-2, suggesting that tomatidine suppresses both ACAT-1 and ACAT-2 activities. The oral administration of tomatidine to apoE-deficient mice significantly reduces levels of serum cholesterol, LDL-cholesterol, and the size of atherosclerotic lesions (PMID: 22224814).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(22S,25S)-5alpha-Spirosolan-3beta-olHMDB
(3beta,5alpha,22beta,25S)-Spirosolan-3-olHMDB
(3beta,5alpha,25S)-Spirosolan-3-olHMDB
5a-Tomatidan-3b-ol, 8ciHMDB
5alpha -Tomatidan-3beta -olHMDB
5alpha-Tomatidan-3beta-olHMDB
5alpha-Tomatidan-3beta-ol (8ci)HMDB
Spirosolan-3-olHMDB
Spirosolan-3-ol, (3alpha ,22alpha -tomatidan-3beta -olHMDB
Spirosolan-3-ol, (3beta,5alpha,22beta,25S)- (9ci)HMDB
TomatidinHMDB
SoladulcidineMeSH
Tomatidine, (3beta,5alpha,22alpha,25R)-isomerMeSH
5 alpha,20 beta(F),22 alpha(F),25 beta(F),27- Azaspirostan-3 beta-olMeSH
Chemical FormulaC27H45NO2
Average Molecular Mass415.652 g/mol
Monoisotopic Mass415.345 g/mol
CAS Registry Number77-59-8
IUPAC Name5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]-16-ol
Traditional Nametomatidine
SMILESCC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1
InChI IdentifierInChI=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
InChI KeyXYNPYHXGMWJBLV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4',5']indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal alkaloids
Direct ParentSpirosolanes and derivatives
Alternative Parents
Substituents
  • Spirosolane skeleton
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Azasteroid
  • Azaspirodecane
  • Alkaloid or derivatives
  • Piperidine
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Hemiaminal
  • Organoheterocyclic compound
  • Oxacycle
  • Secondary amine
  • Azacycle
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
logP4.72ALOGPS
logP5.02ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity121.1 m³·mol⁻¹ChemAxon
Polarizability51.09 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zg0-1129200000-5d9e624514d0944e171cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-2215900000-9b8851953955b216ad28Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0009600000-59abef74949d70a8cafcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avj-0198200000-9c90978a91bba76ca55aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-5269000000-c49d77f03cb7c42696cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0009600000-59abef74949d70a8cafcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avj-0198200000-9c90978a91bba76ca55aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-5269000000-c49d77f03cb7c42696cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-0177947b1b0afba7dd49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009600000-594f89795c2e81f4b990Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-3119000000-96f892c1d44b480cfccaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-0177947b1b0afba7dd49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009600000-594f89795c2e81f4b990Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-3119000000-96f892c1d44b480cfccaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0002900000-c098f83c1fc2f2160cf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-3579800000-be21ff49c8422a55ae65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059y-3950000000-8454b0799a2b0fd68bfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-713eea1f92e6cf59257aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0001900000-a98be16fc6ee5b3252a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0239800000-e6773abcff13370b5fc4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034731
FooDB IDFDB013270
Phenol Explorer IDNot Available
KNApSAcK IDC00029023
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTomatidine
Chemspider ID276680
ChEBI ID9629
PubChem Compound ID312827
Kegg Compound IDC10826
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Chagnon F, Guay I, Bonin MA, Mitchell G, Bouarab K, Malouin F, Marsault E: Unraveling the structure-activity relationship of tomatidine, a steroid alkaloid with unique antibiotic properties against persistent forms of Staphylococcus aureus. Eur J Med Chem. 2014 Jun 10;80:605-20. doi: 10.1016/j.ejmech.2013.11.019.
2. Dyle MC, Ebert SM, Cook DP, Kunkel SD, Fox DK, Bongers KS, Bullard SA, Dierdorff JM, Adams CM: Systems-based discovery of tomatidine as a natural small molecule inhibitor of skeletal muscle atrophy. J Biol Chem. 2014 May 23;289(21):14913-24. doi: 10.1074/jbc.M114.556241. Epub 2014 Apr 9.
3. Fujiwara Y, Kiyota N, Tsurushima K, Yoshitomi M, Horlad H, Ikeda T, Nohara T, Takeya M, Nagai R: Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT). J Agric Food Chem. 2012 Mar 14;60(10):2472-9. doi: 10.1021/jf204197r. Epub 2012 Feb 28.
4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
9. The lipid handbook with CD-ROM