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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 19:37:59 UTC

Update Date

2022-03-07 02:54:13 UTC

HMDB ID

HMDB0034731

Secondary Accession Numbers

HMDB34731

Metabolite Identification

Common Name

Tomatidine

Description

Tomatidine 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 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241215182D          

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M  END

HMDB0034731
     RDKit          3D
Tomatidine
 75 80  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 02241215182D          

 30 35  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0034731

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0034731
     RDKit          3D
Tomatidine
 75 80  0  0  0  0  0  0  0  0999 V2000
    7.0963    0.0368    1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4191    1.3281    0.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1026    1.3155   -0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1291    0.1468   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8208    0.5635   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9808    1.6238    0.5362 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0855    1.4360    1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145    1.0372   -1.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8755    0.1853   -1.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5069    0.6483   -1.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2494   -0.5073   -1.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856   -0.3659   -0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1800    0.5185   -2.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5317    1.1096   -1.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4231    0.1647   -1.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7525    0.8642   -0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5737    0.0681    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8490    0.6697    0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9395    0.1145    1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4656    0.3804    1.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7886   -0.2672    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9545   -1.7455    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3164    0.1580    0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6627   -0.3173    1.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2104   -0.0424    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902   -0.7350    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5398   -2.2010    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -0.0579    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0671   -0.6135    0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239   -1.8167   -0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8492    0.1429    1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3250   -0.6842    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5620   -0.4666    0.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0904    2.1754    0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0101    1.2005   -1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254    2.2641   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1090    0.0069   -2.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5964   -0.7104   -0.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9397    2.5696    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9298    0.5268    2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1477    2.2838    2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486   -0.7710   -1.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404    1.6182   -1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    0.5880   -2.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269   -1.4024   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725   -1.3667   -1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150   -0.1047   -3.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4966    1.3694   -2.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    2.0912   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0264    1.3396   -2.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5929   -0.7175   -1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5448    1.8974   -0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2168    0.9831   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6356   -0.9671   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1920    0.7407   -0.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1978   -0.8295    1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4179    0.9275    2.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0395   -0.1603    2.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2449    1.4539    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5769   -2.1839   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312   -2.3228    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5250   -2.0352    1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3187    1.2640    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9479   -1.3375    1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0652    0.3446    2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2784   -0.4379    2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0582    1.0566    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523   -2.4893    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073   -2.4517    1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360   -2.8618   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373    0.9966    0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4019   -0.7167    1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0545   -1.6068   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920   -2.4221   -0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594   -2.4938    0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
  7  2  1  0
 28  9  1  0
 29  5  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 22 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 29 72  1  0
 30 73  1  0
 30 74  1  0
 30 75  1  0
M  END

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

COMPND    HMDB0034731
HETATM    1  C1  UNL     1       7.096   0.037   1.070  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.419   1.328   0.699  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.103   1.315  -0.786  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.129   0.147  -0.997  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.821   0.563  -0.426  1.00  0.00           C  
HETATM    6  N1  UNL     1       3.981   1.624   0.536  1.00  0.00           N  
HETATM    7  C6  UNL     1       5.085   1.436   1.423  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.915   1.037  -1.413  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.876   0.185  -1.449  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.507   0.648  -1.715  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.249  -0.507  -1.026  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.686  -0.366  -0.980  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.180   0.519  -2.135  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.532   1.110  -1.809  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.423   0.165  -1.057  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.752   0.864  -0.852  1.00  0.00           C  
HETATM   17  C15 UNL     1      -6.574   0.068   0.105  1.00  0.00           C  
HETATM   18  O2  UNL     1      -7.849   0.670   0.177  1.00  0.00           O  
HETATM   19  C16 UNL     1      -5.939   0.114   1.454  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.466   0.380   1.438  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.789  -0.267   0.237  1.00  0.00           C  
HETATM   22  C19 UNL     1      -3.955  -1.746   0.374  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.316   0.158   0.261  1.00  0.00           C  
HETATM   24  C21 UNL     1      -1.663  -0.317   1.525  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.210  -0.042   1.453  1.00  0.00           C  
HETATM   26  C23 UNL     1       0.490  -0.735   0.286  1.00  0.00           C  
HETATM   27  C24 UNL     1       0.540  -2.201   0.641  1.00  0.00           C  
HETATM   28  C25 UNL     1       1.736  -0.058   0.076  1.00  0.00           C  
HETATM   29  C26 UNL     1       3.067  -0.613   0.250  1.00  0.00           C  
HETATM   30  C27 UNL     1       3.424  -1.817  -0.546  1.00  0.00           C  
HETATM   31  H1  UNL     1       7.849   0.143   1.860  1.00  0.00           H  
HETATM   32  H2  UNL     1       6.325  -0.684   1.463  1.00  0.00           H  
HETATM   33  H3  UNL     1       7.562  -0.467   0.197  1.00  0.00           H  
HETATM   34  H4  UNL     1       7.090   2.175   0.966  1.00  0.00           H  
HETATM   35  H5  UNL     1       7.010   1.200  -1.398  1.00  0.00           H  
HETATM   36  H6  UNL     1       5.625   2.264  -1.094  1.00  0.00           H  
HETATM   37  H7  UNL     1       5.109   0.007  -2.112  1.00  0.00           H  
HETATM   38  H8  UNL     1       5.596  -0.710  -0.474  1.00  0.00           H  
HETATM   39  H9  UNL     1       3.940   2.570   0.125  1.00  0.00           H  
HETATM   40  H10 UNL     1       4.930   0.527   2.035  1.00  0.00           H  
HETATM   41  H11 UNL     1       5.148   2.284   2.108  1.00  0.00           H  
HETATM   42  H12 UNL     1       2.049  -0.771  -1.976  1.00  0.00           H  
HETATM   43  H13 UNL     1       0.240   1.618  -1.277  1.00  0.00           H  
HETATM   44  H14 UNL     1       0.318   0.588  -2.816  1.00  0.00           H  
HETATM   45  H15 UNL     1       0.027  -1.402  -1.662  1.00  0.00           H  
HETATM   46  H16 UNL     1      -2.173  -1.367  -1.188  1.00  0.00           H  
HETATM   47  H17 UNL     1      -2.315  -0.105  -3.056  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.497   1.369  -2.314  1.00  0.00           H  
HETATM   49  H19 UNL     1      -3.413   2.091  -1.304  1.00  0.00           H  
HETATM   50  H20 UNL     1      -4.026   1.340  -2.787  1.00  0.00           H  
HETATM   51  H21 UNL     1      -4.593  -0.717  -1.721  1.00  0.00           H  
HETATM   52  H22 UNL     1      -5.545   1.897  -0.492  1.00  0.00           H  
HETATM   53  H23 UNL     1      -6.217   0.983  -1.853  1.00  0.00           H  
HETATM   54  H24 UNL     1      -6.636  -0.967  -0.258  1.00  0.00           H  
HETATM   55  H25 UNL     1      -8.192   0.741  -0.738  1.00  0.00           H  
HETATM   56  H26 UNL     1      -6.198  -0.829   1.983  1.00  0.00           H  
HETATM   57  H27 UNL     1      -6.418   0.927   2.057  1.00  0.00           H  
HETATM   58  H28 UNL     1      -4.039  -0.160   2.334  1.00  0.00           H  
HETATM   59  H29 UNL     1      -4.245   1.454   1.464  1.00  0.00           H  
HETATM   60  H30 UNL     1      -4.577  -2.184  -0.460  1.00  0.00           H  
HETATM   61  H31 UNL     1      -3.031  -2.323   0.395  1.00  0.00           H  
HETATM   62  H32 UNL     1      -4.525  -2.035   1.305  1.00  0.00           H  
HETATM   63  H33 UNL     1      -2.319   1.264   0.262  1.00  0.00           H  
HETATM   64  H34 UNL     1      -1.948  -1.337   1.814  1.00  0.00           H  
HETATM   65  H35 UNL     1      -2.065   0.345   2.349  1.00  0.00           H  
HETATM   66  H36 UNL     1       0.278  -0.438   2.369  1.00  0.00           H  
HETATM   67  H37 UNL     1      -0.058   1.057   1.420  1.00  0.00           H  
HETATM   68  H38 UNL     1       1.452  -2.489   1.194  1.00  0.00           H  
HETATM   69  H39 UNL     1      -0.307  -2.452   1.348  1.00  0.00           H  
HETATM   70  H40 UNL     1       0.336  -2.862  -0.243  1.00  0.00           H  
HETATM   71  H41 UNL     1       1.737   0.997   0.491  1.00  0.00           H  
HETATM   72  H42 UNL     1       3.402  -0.717   1.299  1.00  0.00           H  
HETATM   73  H43 UNL     1       4.055  -1.607  -1.455  1.00  0.00           H  
HETATM   74  H44 UNL     1       2.592  -2.422  -0.911  1.00  0.00           H  
HETATM   75  H45 UNL     1       4.059  -2.494   0.078  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    7   34
CONECT    3    4   35   36
CONECT    4    5   37   38
CONECT    5    6    8   29
CONECT    6    7   39
CONECT    7   40   41
CONECT    8    9
CONECT    9   10   28   42
CONECT   10   11   43   44
CONECT   11   12   26   45
CONECT   12   13   23   46
CONECT   13   14   47   48
CONECT   14   15   49   50
CONECT   15   16   21   51
CONECT   16   17   52   53
CONECT   17   18   19   54
CONECT   18   55
CONECT   19   20   56   57
CONECT   20   21   58   59
CONECT   21   22   23
CONECT   22   60   61   62
CONECT   23   24   63
CONECT   24   25   64   65
CONECT   25   26   66   67
CONECT   26   27   28
CONECT   27   68   69   70
CONECT   28   29   71
CONECT   29   30   72
CONECT   30   73   74   75
END

HMDB0034731
     RDKit          3D
Tomatidine
 75 80  0  0  0  0  0  0  0  0999 V2000
    7.0963    0.0368    1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4191    1.3281    0.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1026    1.3155   -0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1291    0.1468   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8208    0.5635   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9808    1.6238    0.5362 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0855    1.4360    1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145    1.0372   -1.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8755    0.1853   -1.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5069    0.6483   -1.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2494   -0.5073   -1.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856   -0.3659   -0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1800    0.5185   -2.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5317    1.1096   -1.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4231    0.1647   -1.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7525    0.8642   -0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5737    0.0681    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8490    0.6697    0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9395    0.1145    1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4656    0.3804    1.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7886   -0.2672    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9545   -1.7455    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3164    0.1580    0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6627   -0.3173    1.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2104   -0.0424    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902   -0.7350    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5398   -2.2010    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -0.0579    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0671   -0.6135    0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239   -1.8167   -0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8492    0.1429    1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3250   -0.6842    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5620   -0.4666    0.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0904    2.1754    0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0101    1.2005   -1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254    2.2641   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1090    0.0069   -2.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5964   -0.7104   -0.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9397    2.5696    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9298    0.5268    2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1477    2.2838    2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486   -0.7710   -1.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404    1.6182   -1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    0.5880   -2.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269   -1.4024   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725   -1.3667   -1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150   -0.1047   -3.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4966    1.3694   -2.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    2.0912   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0264    1.3396   -2.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5929   -0.7175   -1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5448    1.8974   -0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2168    0.9831   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6356   -0.9671   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1920    0.7407   -0.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1978   -0.8295    1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4179    0.9275    2.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0395   -0.1603    2.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2449    1.4539    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5769   -2.1839   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312   -2.3228    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5250   -2.0352    1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3187    1.2640    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9479   -1.3375    1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0652    0.3446    2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2784   -0.4379    2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0582    1.0566    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523   -2.4893    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073   -2.4517    1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360   -2.8618   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373    0.9966    0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4019   -0.7167    1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0545   -1.6068   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920   -2.4221   -0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594   -2.4938    0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
  7  2  1  0
 28  9  1  0
 29  5  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 22 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 29 72  1  0
 30 73  1  0
 30 74  1  0
 30 75  1  0
M  END

View in JSmol View Stereo Labels

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
Soladulcidine	MeSH
Tomatidine, (3beta,5alpha,22alpha,25R)-isomer	MeSH
5 alpha,20 beta(F),22 alpha(F),25 beta(F),27- Azaspirostan-3 beta-ol	MeSH

Chemical Formula

C₂₇H₄₅NO₂

Average Molecular Weight

415.6517

Monoisotopic Molecular Weight

415.345029689

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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0034731)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034731)

Source

Exogenous

Exogenous (HMDB: HMDB0034731)

Food

Food (HMDB: HMDB0034731)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Fruit vegetable

Garden tomato (FooDB: FOOD00171)
Garden tomato (var.) (FooDB: FOOD00173)

Tomato (HMDB: HMDB0034731)

Endogenous

Endogenous (HMDB: HMDB0034731)

Plant

Plant (HMDB: HMDB0034731)

Animal

Animal (HMDB: HMDB0034731)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034731)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034731)

Lipid metabolism pathway (HMDB: HMDB0034731)

Cellular process

Cell signaling (HMDB: HMDB0034731)

Biochemical process

Lipid transport (HMDB: HMDB0034731)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034731)
Anti feedant (HMDB: HMDB0034731)

Molecular messenger

Signaling molecule (HMDB: HMDB0034731)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034731)

Agriculture

Pesticide (HMDB: HMDB0034731)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 - 211 °C	Not Available
Boiling Point	527.20 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.031 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.150 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00019 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	197.482	31661259
DarkChem	[M-H]-	191.786	31661259
DeepCCS	[M-2H]-	238.47	30932474
DeepCCS	[M+Na]+	214.188	30932474
AllCCS	[M+H]+	209.5	32859911
AllCCS	[M+H-H2O]+	207.4	32859911
AllCCS	[M+NH4]+	211.4	32859911
AllCCS	[M+Na]+	211.9	32859911
AllCCS	[M-H]-	204.9	32859911
AllCCS	[M+Na-2H]-	206.6	32859911
AllCCS	[M+HCOO]-	208.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.84 minutes	32390414
Predicted by Siyang on May 30, 2022	13.7468 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.08 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	95.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2620.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	180.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	217.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	564.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	553.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	284.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1062.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	532.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1510.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	269.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	346.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	25.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tomatidine	CC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1	2741.1	Standard polar	33892256
Tomatidine	CC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1	3234.2	Standard non polar	33892256
Tomatidine	CC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1	3436.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tomatidine,1TMS,isomer #1	CC1CCC2(NC1)OC1CC3C4CCC5CC(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C	3459.1	Semi standard non polar	33892256
Tomatidine,1TMS,isomer #2	CC1CCC2(OC3CC4C5CCC6CC(O)CCC6(C)C5CCC4(C)C3C2C)N([Si](C)(C)C)C1	3447.4	Semi standard non polar	33892256
Tomatidine,2TMS,isomer #1	CC1CCC2(OC3CC4C5CCC6CC(O[Si](C)(C)C)CCC6(C)C5CCC4(C)C3C2C)N([Si](C)(C)C)C1	3403.1	Semi standard non polar	33892256
Tomatidine,2TMS,isomer #1	CC1CCC2(OC3CC4C5CCC6CC(O[Si](C)(C)C)CCC6(C)C5CCC4(C)C3C2C)N([Si](C)(C)C)C1	3427.8	Standard non polar	33892256
Tomatidine,1TBDMS,isomer #1	CC1CCC2(NC1)OC1CC3C4CCC5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C	3693.6	Semi standard non polar	33892256
Tomatidine,1TBDMS,isomer #2	CC1CCC2(OC3CC4C5CCC6CC(O)CCC6(C)C5CCC4(C)C3C2C)N([Si](C)(C)C(C)(C)C)C1	3650.8	Semi standard non polar	33892256
Tomatidine,2TBDMS,isomer #1	CC1CCC2(OC3CC4C5CCC6CC(O[Si](C)(C)C(C)(C)C)CCC6(C)C5CCC4(C)C3C2C)N([Si](C)(C)C(C)(C)C)C1	3834.3	Semi standard non polar	33892256
Tomatidine,2TBDMS,isomer #1	CC1CCC2(OC3CC4C5CCC6CC(O[Si](C)(C)C(C)(C)C)CCC6(C)C5CCC4(C)C3C2C)N([Si](C)(C)C(C)(C)C)C1	3960.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tomatidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zg0-1129200000-5d9e624514d0944e171c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tomatidine GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-2215900000-9b8851953955b216ad28	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tomatidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 10V, Positive-QTOF	splash10-014j-0009600000-59abef74949d70a8cafc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 20V, Positive-QTOF	splash10-0avj-0198200000-9c90978a91bba76ca55a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 40V, Positive-QTOF	splash10-05fr-5269000000-c49d77f03cb7c42696cd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 10V, Positive-QTOF	splash10-014j-0009600000-59abef74949d70a8cafc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 20V, Positive-QTOF	splash10-0avj-0198200000-9c90978a91bba76ca55a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 40V, Positive-QTOF	splash10-05fr-5269000000-c49d77f03cb7c42696cd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 10V, Negative-QTOF	splash10-03di-0002900000-0177947b1b0afba7dd49	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 20V, Negative-QTOF	splash10-03di-0009600000-594f89795c2e81f4b990	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 40V, Negative-QTOF	splash10-052f-3119000000-96f892c1d44b480cfcca	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 10V, Negative-QTOF	splash10-03di-0002900000-0177947b1b0afba7dd49	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 20V, Negative-QTOF	splash10-03di-0009600000-594f89795c2e81f4b990	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 40V, Negative-QTOF	splash10-052f-3119000000-96f892c1d44b480cfcca	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 10V, Positive-QTOF	splash10-014i-0002900000-c098f83c1fc2f2160cf3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 20V, Positive-QTOF	splash10-014j-3579800000-be21ff49c8422a55ae65	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 40V, Positive-QTOF	splash10-059y-3950000000-8454b0799a2b0fd68bfa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 10V, Negative-QTOF	splash10-03di-0000900000-713eea1f92e6cf59257a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 20V, Negative-QTOF	splash10-03di-0001900000-a98be16fc6ee5b3252a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tomatidine 40V, Negative-QTOF	splash10-03di-0239800000-e6773abcff13370b5fc4	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tomatidine

METLIN ID

Not Available

PubChem Compound

312827

PDB ID

Not Available

ChEBI ID

9629

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1698601

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Tomatidine (HMDB0034731)

MOL for HMDB0034731 (Tomatidine)

3D MOL for HMDB0034731 (Tomatidine)

3D SDF for HMDB0034731 (Tomatidine)

3D-SDF for HMDB0034731 (Tomatidine)

PDB for HMDB0034731 (Tomatidine)

3D PDB for HMDB0034731 (Tomatidine)

SMILES for HMDB0034731 (Tomatidine)

INCHI for HMDB0034731 (Tomatidine)

Structure for HMDB0034731 (Tomatidine)

3D Structure for HMDB0034731 (Tomatidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra