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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:02:42 UTC

Update Date

2022-03-07 02:54:43 UTC

HMDB ID

HMDB0035984

Secondary Accession Numbers

HMDB35984

Metabolite Identification

Common Name

Zapoterin

Description

Zapoterin belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Based on a literature review a small amount of articles have been published on Zapoterin.

Structure

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

  Mrv0541 02241219102D          

 34 39  0  0  0  0            999 V2000
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    1.3157   -2.0692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157    1.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157    0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008    0.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1128    0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0035984
     RDKit          3D
Zapoterin
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M  END

  Mrv0541 02241219102D          

 34 39  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0035984

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CC(O)C3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O8/c1-22(2)15-10-16(28)25(5)18(23(15,3)8-6-17(29)33-22)14(27)11-24(4)19(13-7-9-31-12-13)32-21(30)20-26(24,25)34-20/h6-9,12,14-15,18-20,27H,10-11H2,1-5H3

> <INCHI_KEY>
OZGKITZRRFNYRV-UHFFFAOYSA-N

> <FORMULA>
C26H30O8

> <MOLECULAR_WEIGHT>
470.5116

> <EXACT_MASS>
470.194067936

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
48.05923142827898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(furan-3-yl)-10-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.5735543583333342

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.348872050156228

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.854343021490454

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8617751406045553

> <JCHEM_POLAR_SURFACE_AREA>
115.57000000000001

> <JCHEM_REFRACTIVITY>
117.77889999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(furan-3-yl)-10-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035984
     RDKit          3D
Zapoterin
 64 69  0  0  0  0  0  0  0  0999 V2000
   -4.9157   -1.4429    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -0.1141    0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3804    0.7101    1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8764    0.3937   -0.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5880    0.2821   -2.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5169    0.2366   -3.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2339    0.2098   -2.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0651    0.2702   -2.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8401    0.4370   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503    1.9005   -0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.5295   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3085   -1.1558    1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9357   -1.6201    0.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6263   -2.7579    1.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110   -0.5192    0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129    0.3863    1.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883    0.2086   -0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4731    1.4372   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    2.3065   -1.5760 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232    1.1613   -0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950   -0.1595   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -0.9508   -1.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5668    0.1146    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7850    0.5106    0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7561   -0.2891   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7044    0.5137   -1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3398    1.7419   -0.8433 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2207    1.8053   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9086   -0.9618    1.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3059   -2.2011    1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8849   -3.2989    1.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -2.1570    1.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581   -2.4625    0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3914   -1.0538    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9834   -1.3677    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9388   -1.6333    1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4625   -2.2676   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1182    1.5195    1.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8894    0.1640    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5069    1.1833    1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682    0.0873   -3.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2019    0.1925   -2.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0768    2.5164   -1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7606    2.3722    0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306    2.0179   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8469   -1.4369   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3964   -0.4997    2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9539   -2.0400    1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0079   -0.3222    2.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    0.9858    2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379    0.9521    2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408   -0.4390   -1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2273    1.9847    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720    3.2287   -1.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    2.0117    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371    1.3063   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.8603   -0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7085   -0.3293   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069   -1.2777   -1.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2476    0.9653    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8002   -1.3562   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5938    0.1811   -1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067    2.7063    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2708   -2.4973    2.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 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  2  0
 26 27  1  0
 27 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 11  2  1  0
 34 15  1  0
 17  9  1  0
 34 21  1  0
 28 24  2  0
 34 32  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  7 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 16 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 18 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 25 61  1  0
 26 62  1  0
 28 63  1  0
 32 64  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      -1.545  -3.093   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.211  -3.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.121  -3.093   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.456  -3.863   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.456   2.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.456   0.757   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.121   1.527   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.211   0.757   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.211  -0.783   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.545  -1.553   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.429  -0.015   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.543   3.973   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.790   3.067   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.035   3.973   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.560   5.438   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.021   5.438   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.790   1.527   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.123   0.757   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.123  -0.783   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.457  -1.553   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.749  -0.590   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.250  -0.934   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.917  -2.323   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.250  -3.709   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -6.457  -2.323   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.891  -2.887   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.121  -1.553   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.456  -0.783   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.790  -1.553   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.456  -2.323   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.416  -5.438   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.749  -4.052   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.545  -5.012   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.545   1.527   0.000  0.00  0.00           O+0
CONECT    1    2   10   32                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    5    7   17   28                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   34                                                  
CONECT    9    8   10   27                                                  
CONECT   10    1    9   11   21                                             
CONECT   11   10                                                            
CONECT   12   13   16                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15                                                       
CONECT   17    6   13   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19                                                            
CONECT   21   10   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   32                                                       
CONECT   25   23                                                            
CONECT   26   27                                                            
CONECT   27    3    9   26   28                                             
CONECT   28    6   27   29   30                                             
CONECT   29   19   28   30                                                  
CONECT   30   28   29                                                       
CONECT   31   32                                                            
CONECT   32    1   24   31   33                                             
CONECT   33   32                                                            
CONECT   34    8                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

COMPND    HMDB0035984
HETATM    1  C1  UNL     1      -4.916  -1.443   0.464  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.166  -0.114   0.183  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.380   0.710   1.414  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.876   0.394  -0.943  1.00  0.00           O  
HETATM    5  C4  UNL     1      -4.588   0.282  -2.276  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.517   0.237  -3.093  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.234   0.210  -2.834  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.065   0.270  -2.226  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.840   0.437  -0.731  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.250   1.900  -0.520  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.769  -0.530  -0.093  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.309  -1.156   1.212  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.936  -1.620   0.994  1.00  0.00           C  
HETATM   14  O3  UNL     1      -0.626  -2.758   1.023  1.00  0.00           O  
HETATM   15  C12 UNL     1       0.011  -0.519   0.736  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.013   0.386   1.952  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.388   0.209  -0.531  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.473   1.437  -0.516  1.00  0.00           C  
HETATM   19  O4  UNL     1       0.213   2.306  -1.576  1.00  0.00           O  
HETATM   20  C16 UNL     1       1.923   1.161  -0.538  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.395  -0.160  -0.050  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.008  -0.951  -1.218  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.567   0.115   0.873  1.00  0.00           C  
HETATM   24  C20 UNL     1       4.785   0.511   0.125  1.00  0.00           C  
HETATM   25  C21 UNL     1       5.756  -0.289  -0.451  1.00  0.00           C  
HETATM   26  C22 UNL     1       6.704   0.514  -1.043  1.00  0.00           C  
HETATM   27  O5  UNL     1       6.340   1.742  -0.843  1.00  0.00           O  
HETATM   28  C23 UNL     1       5.221   1.805  -0.163  1.00  0.00           C  
HETATM   29  O6  UNL     1       3.909  -0.962   1.709  1.00  0.00           O  
HETATM   30  C24 UNL     1       3.306  -2.201   1.572  1.00  0.00           C  
HETATM   31  O7  UNL     1       3.885  -3.299   1.618  1.00  0.00           O  
HETATM   32  C25 UNL     1       1.821  -2.157   1.348  1.00  0.00           C  
HETATM   33  O8  UNL     1       1.358  -2.463   0.096  1.00  0.00           O  
HETATM   34  C26 UNL     1       1.391  -1.054   0.590  1.00  0.00           C  
HETATM   35  H1  UNL     1      -5.983  -1.368   0.178  1.00  0.00           H  
HETATM   36  H2  UNL     1      -4.939  -1.633   1.577  1.00  0.00           H  
HETATM   37  H3  UNL     1      -4.462  -2.268  -0.090  1.00  0.00           H  
HETATM   38  H4  UNL     1      -5.118   1.519   1.142  1.00  0.00           H  
HETATM   39  H5  UNL     1      -4.889   0.164   2.254  1.00  0.00           H  
HETATM   40  H6  UNL     1      -3.507   1.183   1.851  1.00  0.00           H  
HETATM   41  H7  UNL     1      -3.168   0.087  -3.918  1.00  0.00           H  
HETATM   42  H8  UNL     1      -1.202   0.192  -2.867  1.00  0.00           H  
HETATM   43  H9  UNL     1      -2.077   2.516  -1.455  1.00  0.00           H  
HETATM   44  H10 UNL     1      -1.761   2.372   0.330  1.00  0.00           H  
HETATM   45  H11 UNL     1      -3.331   2.018  -0.375  1.00  0.00           H  
HETATM   46  H12 UNL     1      -2.847  -1.437  -0.776  1.00  0.00           H  
HETATM   47  H13 UNL     1      -2.396  -0.500   2.078  1.00  0.00           H  
HETATM   48  H14 UNL     1      -2.954  -2.040   1.389  1.00  0.00           H  
HETATM   49  H15 UNL     1       0.008  -0.322   2.834  1.00  0.00           H  
HETATM   50  H16 UNL     1       0.912   0.986   2.064  1.00  0.00           H  
HETATM   51  H17 UNL     1      -0.938   0.952   2.068  1.00  0.00           H  
HETATM   52  H18 UNL     1       0.041  -0.439  -1.357  1.00  0.00           H  
HETATM   53  H19 UNL     1       0.227   1.985   0.434  1.00  0.00           H  
HETATM   54  H20 UNL     1       0.372   3.229  -1.249  1.00  0.00           H  
HETATM   55  H21 UNL     1       2.427   2.012   0.017  1.00  0.00           H  
HETATM   56  H22 UNL     1       2.337   1.306  -1.583  1.00  0.00           H  
HETATM   57  H23 UNL     1       3.522  -1.860  -0.870  1.00  0.00           H  
HETATM   58  H24 UNL     1       3.709  -0.329  -1.770  1.00  0.00           H  
HETATM   59  H25 UNL     1       2.207  -1.278  -1.918  1.00  0.00           H  
HETATM   60  H26 UNL     1       3.248   0.965   1.557  1.00  0.00           H  
HETATM   61  H27 UNL     1       5.800  -1.356  -0.455  1.00  0.00           H  
HETATM   62  H28 UNL     1       7.594   0.181  -1.579  1.00  0.00           H  
HETATM   63  H29 UNL     1       4.707   2.706   0.134  1.00  0.00           H  
HETATM   64  H30 UNL     1       1.271  -2.497   2.239  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    4   11
CONECT    3   38   39   40
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8    8   41
CONECT    8    9   42
CONECT    9   10   11   17
CONECT   10   43   44   45
CONECT   11   12   46
CONECT   12   13   47   48
CONECT   13   14   14   15
CONECT   15   16   17   34
CONECT   16   49   50   51
CONECT   17   18   52
CONECT   18   19   20   53
CONECT   19   54
CONECT   20   21   55   56
CONECT   21   22   23   34
CONECT   22   57   58   59
CONECT   23   24   29   60
CONECT   24   25   28   28
CONECT   25   26   26   61
CONECT   26   27   62
CONECT   27   28
CONECT   28   63
CONECT   29   30
CONECT   30   31   31   32
CONECT   32   33   34   64
CONECT   33   34
END

HMDB0035984
     RDKit          3D
Zapoterin
 64 69  0  0  0  0  0  0  0  0999 V2000
   -4.9157   -1.4429    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -0.1141    0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3804    0.7101    1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8764    0.3937   -0.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5880    0.2821   -2.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5169    0.2366   -3.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2339    0.2098   -2.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0651    0.2702   -2.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8401    0.4370   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503    1.9005   -0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.5295   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3085   -1.1558    1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9357   -1.6201    0.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6263   -2.7579    1.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110   -0.5192    0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129    0.3863    1.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883    0.2086   -0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4731    1.4372   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    2.3065   -1.5760 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232    1.1613   -0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950   -0.1595   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -0.9508   -1.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5668    0.1146    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7850    0.5106    0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7561   -0.2891   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7044    0.5137   -1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3398    1.7419   -0.8433 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2207    1.8053   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9086   -0.9618    1.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3059   -2.2011    1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8849   -3.2989    1.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -2.1570    1.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581   -2.4625    0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3914   -1.0538    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9834   -1.3677    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9388   -1.6333    1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4625   -2.2676   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1182    1.5195    1.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8894    0.1640    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5069    1.1833    1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682    0.0873   -3.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2019    0.1925   -2.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0768    2.5164   -1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7606    2.3722    0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306    2.0179   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8469   -1.4369   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3964   -0.4997    2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9539   -2.0400    1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0079   -0.3222    2.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    0.9858    2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379    0.9521    2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408   -0.4390   -1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2273    1.9847    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720    3.2287   -1.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    2.0117    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371    1.3063   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.8603   -0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7085   -0.3293   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069   -1.2777   -1.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2476    0.9653    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8002   -1.3562   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5938    0.1811   -1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067    2.7063    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2708   -2.4973    2.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 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  2  0
 26 27  1  0
 27 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 11  2  1  0
 34 15  1  0
 17  9  1  0
 34 21  1  0
 28 24  2  0
 34 32  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  7 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 16 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 18 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 25 61  1  0
 26 62  1  0
 28 63  1  0
 32 64  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₈

Average Molecular Weight

470.5116

Monoisotopic Molecular Weight

470.194067936

IUPAC Name

7-(furan-3-yl)-10-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione

Traditional Name

7-(furan-3-yl)-10-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione

CAS Registry Number

35796-71-5

SMILES

CC12CC(O)C3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1

InChI Identifier

InChI=1S/C26H30O8/c1-22(2)15-10-16(28)25(5)18(23(15,3)8-6-17(29)33-22)14(27)11-24(4)19(13-7-9-31-12-13)32-21(30)20-26(24,25)34-20/h6-9,12,14-15,18-20,27H,10-11H2,1-5H3

InChI Key

OZGKITZRRFNYRV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Naphthopyran
Naphthalene
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
Dicarboxylic acid or derivatives
Pyran
Oxane
Cyclic alcohol
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Furan
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Ether
Oxirane
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035984)

Source

Endogenous

Endogenous (HMDB: HMDB0035984)

Plant

Plant (HMDB: HMDB0035984)

Animal

Animal (HMDB: HMDB0035984)

Exogenous

Food

Food (HMDB: HMDB0035984)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Exogenous (HMDB: HMDB0035984)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035984)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035984)

Lipid metabolism pathway (HMDB: HMDB0035984)

Cellular process

Cell signaling (HMDB: HMDB0035984)

Biochemical process

Lipid transport (HMDB: HMDB0035984)

Role

Biological role

Energy source (HMDB: HMDB0035984)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035984)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	257 - 259 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.063 g/L	ALOGPS
logP	2.53	ALOGPS
logP	2.57	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	14.85	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	115.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	117.78 m³·mol⁻¹	ChemAxon
Polarizability	48.06 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	207.926	31661259
DarkChem	[M-H]-	196.562	31661259
DeepCCS	[M-2H]-	237.234	30932474
DeepCCS	[M+Na]+	212.658	30932474
AllCCS	[M+H]+	208.9	32859911
AllCCS	[M+H-H2O]+	206.9	32859911
AllCCS	[M+NH4]+	210.8	32859911
AllCCS	[M+Na]+	211.4	32859911
AllCCS	[M-H]-	214.4	32859911
AllCCS	[M+Na-2H]-	215.4	32859911
AllCCS	[M+HCOO]-	216.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zapoterin	CC12CC(O)C3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1	4283.1	Standard polar	33892256
Zapoterin	CC12CC(O)C3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1	3087.2	Standard non polar	33892256
Zapoterin	CC12CC(O)C3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1	4005.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zapoterin,1TMS,isomer #1	CC1(C)OC(=O)C=CC2(C)C1CC(=O)C1(C)C2C(O[Si](C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC321	3734.4	Semi standard non polar	33892256
Zapoterin,1TMS,isomer #2	CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C)C1(C)C2C(O)CC2(C)C(C3=COC=C3)OC(=O)C3OC321	3707.9	Semi standard non polar	33892256
Zapoterin,2TMS,isomer #1	CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C)C1(C)C2C(O[Si](C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC321	3627.0	Semi standard non polar	33892256
Zapoterin,2TMS,isomer #1	CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C)C1(C)C2C(O[Si](C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC321	3223.2	Standard non polar	33892256
Zapoterin,1TBDMS,isomer #1	CC1(C)OC(=O)C=CC2(C)C1CC(=O)C1(C)C2C(O[Si](C)(C)C(C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC321	3991.3	Semi standard non polar	33892256
Zapoterin,1TBDMS,isomer #2	CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2C(O)CC2(C)C(C3=COC=C3)OC(=O)C3OC321	3964.5	Semi standard non polar	33892256
Zapoterin,2TBDMS,isomer #1	CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2C(O[Si](C)(C)C(C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC321	4082.3	Semi standard non polar	33892256
Zapoterin,2TBDMS,isomer #1	CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2C(O[Si](C)(C)C(C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC321	3642.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zapoterin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2940600000-bea5563117b9b750e651	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zapoterin GC-MS (1 TMS) - 70eV, Positive	splash10-004l-7716390000-7e216cb7159042ed2569	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zapoterin 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 - Zapoterin 10V, Positive-QTOF	splash10-0uk9-0000900000-4cde74236abc79abcaa1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 20V, Positive-QTOF	splash10-0udr-0002900000-44b148a8c069fe339c2c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 40V, Positive-QTOF	splash10-0012-9316200000-3ddc75aa649d56e95bd5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 10V, Negative-QTOF	splash10-00or-0000900000-aa9d019b2cd90495cd51	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 20V, Negative-QTOF	splash10-0v00-0001900000-2e6ef8e31a6bd3dc3b49	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 40V, Negative-QTOF	splash10-014j-9005100000-b243bcfc26af56f060a2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 10V, Positive-QTOF	splash10-00di-0000900000-4a4297bf0283c5dc2794	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 20V, Positive-QTOF	splash10-0fki-0051900000-989cc41e7465d5a16516	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 40V, Positive-QTOF	splash10-003f-3571900000-7ccb0375f22da397c51f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 10V, Negative-QTOF	splash10-014i-0000900000-3ea147f9e912d29f22fb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 20V, Negative-QTOF	splash10-014i-0001900000-029a95cbe20e4011a4f8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapoterin 40V, Negative-QTOF	splash10-000i-0092300000-e0c35ece0c03bb5d591e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

METLIN ID

Not Available

PubChem Compound

4482275

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1852961

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]
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 Zapoterin (HMDB0035984)

MOL for HMDB0035984 (Zapoterin)

3D MOL for HMDB0035984 (Zapoterin)

3D SDF for HMDB0035984 (Zapoterin)

3D-SDF for HMDB0035984 (Zapoterin)

PDB for HMDB0035984 (Zapoterin)

3D PDB for HMDB0035984 (Zapoterin)

SMILES for HMDB0035984 (Zapoterin)

INCHI for HMDB0035984 (Zapoterin)

Structure for HMDB0035984 (Zapoterin)

3D Structure for HMDB0035984 (Zapoterin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra