NP-MRD: Showing NP-Card for Tomatidine (NP0048057)

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Record Information

Version

1.0

Created at

2022-03-17 20:50:24 UTC

Updated at

2022-03-17 20:50:24 UTC

NP-MRD ID

NP0048057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tomatidine

Description

Tomatidine, also known as spirosolan-3-ol, 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. Tomatidine is a very strong basic compound (based on its pKa). Outside of the human body, Tomatidine has been detected, but not quantified in, a few different foods, such as garden tomato, garden tomato (var.), And potato. This could make tomatidine a potential biomarker for the consumption of these foods. 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. 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 is the aglycone derivative of tomatine. Red, ripe tomatoes have somewhat reduced amounts of tomatine and tomatidine. 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 ). 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). Tomatidine is found in Lycianthes biflora, Lycopersicon pimpinellifolium , Solanum aculeastrum, Solanum brevidens, Solanum demissum, Solanum donianum, Solanum dulcamara , Solanum dunalianum, Solanum kieseritzkii, Solanum lyratum , Solanum megacarpum, Solanum pimpinellifolium Jusl.Mill. and Solanum polyadenium. It was first documented in 2000 (PMID: 11413487). Tomatidine belongs to the chemical family known as Spirosolanes and Derivatives (PMID: 16902246) (PMID: 24877760) (PMID: 24719321) (PMID: 22224814).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241215182D          

 30 35  0  0  0  0            999 V2000
    0.0780   -1.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0780   -0.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -0.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3968   -0.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    0.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7758    0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8538    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6294    2.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286    1.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261    2.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7254    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7254    0.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261    0.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2505    0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830   -0.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6977    0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187    0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537   -0.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748   -0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643   -1.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4245    2.1343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179    0.0383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3286   -0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262   -0.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -0.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -1.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245   -2.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9497   -1.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3286   -1.5912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 16  1  0  0  0  0
  2 19  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 30  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END


  Mrv0541 02241215182D          

 30 35  0  0  0  0            999 V2000
    0.0780   -1.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0780   -0.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -0.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3968   -0.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    0.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7758    0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8538    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6294    2.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286    1.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261    2.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7254    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7254    0.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261    0.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2505    0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830   -0.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6977    0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187    0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537   -0.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748   -0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643   -1.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4245    2.1343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179    0.0383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3286   -0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262   -0.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -0.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -1.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245   -2.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9497   -1.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3286   -1.5912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 16  1  0  0  0  0
  2 19  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 30  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
XYNPYHXGMWJBLV-UHFFFAOYSA-N

> <FORMULA>
C27H45NO2

> <MOLECULAR_WEIGHT>
415.6517

> <EXACT_MASS>
415.345029689

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
51.094339528721754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]-16-ol

> <ALOGPS_LOGP>
4.72

> <JCHEM_LOGP>
5.015457028666667

> <ALOGPS_LOGS>
-6.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2963963211217

> <JCHEM_PKA_STRONGEST_BASIC>
9.541647886074307

> <JCHEM_POLAR_SURFACE_AREA>
41.49

> <JCHEM_REFRACTIVITY>
121.09680000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.89e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tomatidine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.146  -2.102   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.146  -0.509   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.302  -1.088   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.607  -0.509   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.753   1.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.448   1.811   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.594   3.259   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.041   3.838   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.347   2.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.649   3.838   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.954   3.259   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.954   1.665   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.649   1.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.201   1.519   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.635  -0.072   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.302   1.519   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.462   0.506   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.594  -0.797   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.753  -1.811   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.173  -3.262   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -8.259   3.984   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.767   0.072   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.347  -1.522   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.649  -1.088   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.954  -1.668   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.954  -3.116   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.259  -3.984   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.506  -3.696   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       4.347  -2.970   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   16   19                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    5    9   13   15                                             
CONECT   15   14                                                            
CONECT   16    2    6   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19    2   18   20                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20                                                            
CONECT   22   11                                                            
CONECT   23   18   24                                                       
CONECT   24   20   23   25   30                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   24   29                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Value	Source
(22S,25S)-5alpha-Spirosolan-3beta-ol	HMDB
(3beta,5alpha,22beta,25S)-Spirosolan-3-ol	HMDB
(3beta,5alpha,25S)-Spirosolan-3-ol	HMDB
5a-Tomatidan-3b-ol, 8ci	HMDB
5alpha -Tomatidan-3beta -ol	HMDB
5alpha-Tomatidan-3beta-ol	HMDB
5alpha-Tomatidan-3beta-ol (8ci)	HMDB
Spirosolan-3-ol	HMDB
Spirosolan-3-ol, (3alpha ,22alpha -tomatidan-3beta -ol	HMDB
Spirosolan-3-ol, (3beta,5alpha,22beta,25S)- (9ci)	HMDB
Tomatidin	HMDB
Tomatidine, (3beta,5alpha,22alpha,25R)-isomer	MeSH
5 alpha,20 beta(F),22 alpha(F),25 beta(F),27- Azaspirostan-3 beta-ol	MeSH
Soladulcidine	MeSH

Chemical Formula

C₂₇H₄₅NO₂

Average Mass

415.6517 Da

Monoisotopic Mass

415.34503 Da

IUPAC Name

5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]-16-ol

Traditional Name

tomatidine

CAS Registry Number

77-59-8

SMILES

CC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1

InChI Identifier

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

InChI Key

XYNPYHXGMWJBLV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lycianthes biflora	LOTUS Database	35616633
Lycopersicon pimpinellifolium	Plant	KNApSAcK
Solanum aculeastrum	LOTUS Database	35616633
Solanum brevidens	Plant	KNApSAcK
Solanum demissum	Plant	KNApSAcK
Solanum donianum	LOTUS Database	35616633
Solanum dulcamara	Plant	KNApSAcK
Solanum dunalianum	LOTUS Database	35616633
Solanum kieseritzkii	Plant	KNApSAcK
Solanum lycopersicum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum lyratum	Plant	KNApSAcK
Solanum megacarpum	Plant	KNApSAcK
Solanum pimpinellifolium Jusl.Mill.	Plant	KNApSAcK
Solanum polyadenium	LOTUS Database	35616633
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Spirosolanes 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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.72	ALOGPS
logP	5.02	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	121.1 m³·mol⁻¹	ChemAxon
Polarizability	51.09 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034731

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

312827

PDB ID

Not Available

ChEBI ID

9629

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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. [PubMed:16902246 ]
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. [PubMed:24877760 ]
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. [PubMed:24719321 ]
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. [PubMed:22224814 ]

Showing NP-Card for Tomatidine (NP0048057)

MOL for NP0048057 (Tomatidine)

3D MOL for NP0048057 (Tomatidine)

3D SDF for NP0048057 (Tomatidine)

3D-SDF for NP0048057 (Tomatidine)

PDB for NP0048057 (Tomatidine)

3D PDB for NP0048057 (Tomatidine)

SMILES for NP0048057 (Tomatidine)

INCHI for NP0048057 (Tomatidine)

Structure for NP0048057 (Tomatidine)

3D Structure for NP0048057 (Tomatidine)