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Showing metabocard for beta-Carotene-15,15'-epoxide (HMDB0060443)

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enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:21:12 UTC
Update Date2022-03-07 03:17:45 UTC
HMDB IDHMDB0060443
Secondary Accession Numbers
  • HMDB60443
Metabolite Identification
Common Namebeta-Carotene-15,15'-epoxide
Descriptionbeta-Carotene-15,15'-epoxide, also known as 15,15'-epoxy-b,b-carotene or 15-ebbct, belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. beta-Carotene-15,15'-epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866061
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060443 (beta-Carotene-15,15'-epoxide)


  Mrv0541 05161318212D          

 41 43  0  0  0  0            999 V2000
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   11.9744   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D MOL for HMDB0060443 (beta-Carotene-15,15'-epoxide)

HMDB0060443
     RDKit          3D
beta-Carotene-15,15'-epoxide
 97 99  0  0  0  0  0  0  0  0999 V2000
  -11.8574    2.5694   -0.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D SDF for HMDB0060443 (beta-Carotene-15,15'-epoxide)


  Mrv0541 05161318212D          

 41 43  0  0  0  0            999 V2000
    9.3987   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151    6.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572    8.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9862    6.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2717    5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0060443

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C1OC1\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H56O/c1-29(21-23-35-33(5)19-13-25-39(35,7)8)15-11-17-31(3)27-37-38(41-37)28-32(4)18-12-16-30(2)22-24-36-34(6)20-14-26-40(36,9)10/h11-12,15-18,21-24,27-28,37-38H,13-14,19-20,25-26H2,1-10H3/b17-11+,18-12+,23-21+,24-22+,29-15+,30-16+,31-27+,32-28+

> <INCHI_KEY>
AULCUSCIZQQSMU-WDJSDFAOSA-N

> <FORMULA>
C40H56O

> <MOLECULAR_WEIGHT>
552.872

> <EXACT_MASS>
552.433116414

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
72.78145977318309

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-bis[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]oxirane

> <ALOGPS_LOGP>
9.11

> <JCHEM_LOGP>
10.497899115000001

> <ALOGPS_LOGS>
-6.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.262660506248616

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
189.70809999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-bis[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]oxirane

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0060443 (beta-Carotene-15,15'-epoxide)

HMDB0060443
     RDKit          3D
beta-Carotene-15,15'-epoxide
 97 99  0  0  0  0  0  0  0  0999 V2000
  -11.8574    2.5694   -0.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2348    1.4917    0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6391    0.1419   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
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 40 95  1  0
 41 96  1  0
 41 97  1  0
M  END
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PDB for HMDB0060443 (beta-Carotene-15,15'-epoxide)

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0      17.544  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.442  12.114   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.877   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.774   7.494   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.213  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.107  16.734   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.352  -6.067   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.362  -4.353   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.624  17.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.635  16.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.544   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.774  10.574   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.546  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.774  19.814   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.878  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.774  12.114   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.544   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.441   9.804   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.546  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.441  19.044   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.212  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.108  14.424   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.545  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.774  15.194   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.213  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.108  19.044   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.211   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.107   7.494   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.878  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.108  12.884   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.211   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.441   8.264   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      24.213  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.441  17.504   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.879  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.774  16.734   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.877   4.620   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.107   5.954   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      22.879  -4.620   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      18.108  17.504   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
CONECT    1   29                                                            
CONECT    2   30                                                            
CONECT    3   31                                                            
CONECT    4   32                                                            
CONECT    5   33                                                            
CONECT    6   34                                                            
CONECT    7   39                                                            
CONECT    8   39                                                            
CONECT    9   40                                                            
CONECT   10   40                                                            
CONECT   11   15   17                                                       
CONECT   12   16   18                                                       
CONECT   13   19   25                                                       
CONECT   14   20   26                                                       
CONECT   15   11   29                                                       
CONECT   16   12   30                                                       
CONECT   17   11   31                                                       
CONECT   18   12   32                                                       
CONECT   19   13   33                                                       
CONECT   20   14   34                                                       
CONECT   21   23   29                                                       
CONECT   22   24   30                                                       
CONECT   23   21   35                                                       
CONECT   24   22   36                                                       
CONECT   25   13   39                                                       
CONECT   26   14   40                                                       
CONECT   27   31   37                                                       
CONECT   28   32   38                                                       
CONECT   29    1   15   21                                                  
CONECT   30    2   16   22                                                  
CONECT   31    3   17   27                                                  
CONECT   32    4   18   28                                                  
CONECT   33    5   19   35                                                  
CONECT   34    6   20   36                                                  
CONECT   35   23   33   39                                                  
CONECT   36   24   34   40                                                  
CONECT   37   27   38   41                                                  
CONECT   38   28   37   41                                                  
CONECT   39    7    8   25   35                                             
CONECT   40    9   10   26   36                                             
CONECT   41   37   38                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END
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3D PDB for HMDB0060443 (beta-Carotene-15,15'-epoxide)

COMPND    HMDB0060443
HETATM    1  C1  UNL     1     -11.857   2.569  -0.911  1.00  0.00           C  
HETATM    2  C2  UNL     1     -12.235   1.492   0.058  1.00  0.00           C  
HETATM    3  C3  UNL     1     -11.329   0.584   0.464  1.00  0.00           C  
HETATM    4  C4  UNL     1      -9.991   0.725  -0.096  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.953  -0.042   0.138  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.639   0.142  -0.438  1.00  0.00           C  
HETATM    7  C7  UNL     1      -7.314   1.245  -1.343  1.00  0.00           C  
HETATM    8  C8  UNL     1      -6.628  -0.706  -0.148  1.00  0.00           C  
HETATM    9  C9  UNL     1      -5.315  -0.510  -0.730  1.00  0.00           C  
HETATM   10  C10 UNL     1      -4.317  -1.323  -0.459  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.990  -1.119  -1.051  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.696  -0.014  -2.020  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.992  -1.937  -0.758  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.651  -1.669  -1.397  1.00  0.00           C  
HETATM   15  O1  UNL     1      -0.305  -0.302  -1.383  1.00  0.00           O  
HETATM   16  C15 UNL     1       0.398  -1.124  -0.483  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.824  -1.332  -0.864  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.779  -0.774  -0.120  1.00  0.00           C  
HETATM   19  C18 UNL     1       2.309   0.006   1.043  1.00  0.00           C  
HETATM   20  C19 UNL     1       4.149  -0.938  -0.539  1.00  0.00           C  
HETATM   21  C20 UNL     1       5.200  -0.415   0.119  1.00  0.00           C  
HETATM   22  C21 UNL     1       6.518  -0.623  -0.365  1.00  0.00           C  
HETATM   23  C22 UNL     1       7.648  -0.317  -0.072  1.00  0.00           C  
HETATM   24  C23 UNL     1       7.025   0.632   1.404  1.00  0.00           C  
HETATM   25  C24 UNL     1       8.975   0.046   0.275  1.00  0.00           C  
HETATM   26  C25 UNL     1       9.995  -0.390  -0.544  1.00  0.00           C  
HETATM   27  C26 UNL     1      11.389  -0.094  -0.294  1.00  0.00           C  
HETATM   28  C27 UNL     1      12.239  -0.597  -1.213  1.00  0.00           C  
HETATM   29  C28 UNL     1      11.690  -1.388  -2.376  1.00  0.00           C  
HETATM   30  C29 UNL     1      13.703  -0.419  -1.133  1.00  0.00           C  
HETATM   31  C30 UNL     1      13.901   0.952  -0.472  1.00  0.00           C  
HETATM   32  C31 UNL     1      13.348   0.782   0.921  1.00  0.00           C  
HETATM   33  C32 UNL     1      11.820   0.675   0.876  1.00  0.00           C  
HETATM   34  C33 UNL     1      11.309   2.081   0.790  1.00  0.00           C  
HETATM   35  C34 UNL     1      11.448  -0.021   2.182  1.00  0.00           C  
HETATM   36  C35 UNL     1     -11.625  -0.482   1.435  1.00  0.00           C  
HETATM   37  C36 UNL     1     -10.706  -0.277   2.647  1.00  0.00           C  
HETATM   38  C37 UNL     1     -11.383  -1.875   0.911  1.00  0.00           C  
HETATM   39  C38 UNL     1     -13.066  -0.426   1.945  1.00  0.00           C  
HETATM   40  C39 UNL     1     -13.555   1.005   2.002  1.00  0.00           C  
HETATM   41  C40 UNL     1     -13.616   1.454   0.546  1.00  0.00           C  
HETATM   42  H1  UNL     1     -11.390   2.172  -1.822  1.00  0.00           H  
HETATM   43  H2  UNL     1     -12.791   3.069  -1.227  1.00  0.00           H  
HETATM   44  H3  UNL     1     -11.214   3.339  -0.448  1.00  0.00           H  
HETATM   45  H4  UNL     1      -9.775   1.555  -0.798  1.00  0.00           H  
HETATM   46  H5  UNL     1      -9.095  -0.899   0.828  1.00  0.00           H  
HETATM   47  H6  UNL     1      -6.885   0.770  -2.281  1.00  0.00           H  
HETATM   48  H7  UNL     1      -6.430   1.836  -0.949  1.00  0.00           H  
HETATM   49  H8  UNL     1      -8.102   1.951  -1.588  1.00  0.00           H  
HETATM   50  H9  UNL     1      -6.877  -1.507   0.527  1.00  0.00           H  
HETATM   51  H10 UNL     1      -5.154   0.322  -1.381  1.00  0.00           H  
HETATM   52  H11 UNL     1      -4.427  -2.177   0.208  1.00  0.00           H  
HETATM   53  H12 UNL     1      -3.636   0.242  -2.555  1.00  0.00           H  
HETATM   54  H13 UNL     1      -2.033  -0.414  -2.847  1.00  0.00           H  
HETATM   55  H14 UNL     1      -2.284   0.869  -1.532  1.00  0.00           H  
HETATM   56  H15 UNL     1      -2.065  -2.773  -0.105  1.00  0.00           H  
HETATM   57  H16 UNL     1      -0.428  -2.175  -2.330  1.00  0.00           H  
HETATM   58  H17 UNL     1       0.178  -0.955   0.567  1.00  0.00           H  
HETATM   59  H18 UNL     1       2.056  -1.911  -1.715  1.00  0.00           H  
HETATM   60  H19 UNL     1       1.989  -0.684   1.857  1.00  0.00           H  
HETATM   61  H20 UNL     1       3.068   0.706   1.425  1.00  0.00           H  
HETATM   62  H21 UNL     1       1.440   0.628   0.732  1.00  0.00           H  
HETATM   63  H22 UNL     1       4.367  -1.506  -1.420  1.00  0.00           H  
HETATM   64  H23 UNL     1       4.908   0.137   1.002  1.00  0.00           H  
HETATM   65  H24 UNL     1       6.595  -1.289  -1.355  1.00  0.00           H  
HETATM   66  H25 UNL     1       6.503   1.321   0.798  1.00  0.00           H  
HETATM   67  H26 UNL     1       6.681  -0.231   1.875  1.00  0.00           H  
HETATM   68  H27 UNL     1       7.967   1.007   1.712  1.00  0.00           H  
HETATM   69  H28 UNL     1       9.359   0.613   1.078  1.00  0.00           H  
HETATM   70  H29 UNL     1       9.639  -0.974  -1.388  1.00  0.00           H  
HETATM   71  H30 UNL     1      10.948  -0.786  -2.935  1.00  0.00           H  
HETATM   72  H31 UNL     1      11.128  -2.290  -2.029  1.00  0.00           H  
HETATM   73  H32 UNL     1      12.502  -1.626  -3.083  1.00  0.00           H  
HETATM   74  H33 UNL     1      14.187  -0.377  -2.102  1.00  0.00           H  
HETATM   75  H34 UNL     1      14.161  -1.157  -0.424  1.00  0.00           H  
HETATM   76  H35 UNL     1      13.304   1.692  -1.062  1.00  0.00           H  
HETATM   77  H36 UNL     1      14.945   1.271  -0.470  1.00  0.00           H  
HETATM   78  H37 UNL     1      13.631   1.639   1.536  1.00  0.00           H  
HETATM   79  H38 UNL     1      13.770  -0.177   1.320  1.00  0.00           H  
HETATM   80  H39 UNL     1      10.633   2.282  -0.063  1.00  0.00           H  
HETATM   81  H40 UNL     1      10.819   2.379   1.763  1.00  0.00           H  
HETATM   82  H41 UNL     1      12.131   2.850   0.664  1.00  0.00           H  
HETATM   83  H42 UNL     1      10.865  -0.962   1.990  1.00  0.00           H  
HETATM   84  H43 UNL     1      12.340  -0.374   2.749  1.00  0.00           H  
HETATM   85  H44 UNL     1      10.933   0.690   2.854  1.00  0.00           H  
HETATM   86  H45 UNL     1     -10.132  -1.185   2.894  1.00  0.00           H  
HETATM   87  H46 UNL     1     -11.321  -0.065   3.557  1.00  0.00           H  
HETATM   88  H47 UNL     1     -10.008   0.536   2.426  1.00  0.00           H  
HETATM   89  H48 UNL     1     -10.705  -2.444   1.595  1.00  0.00           H  
HETATM   90  H49 UNL     1     -10.986  -1.912  -0.120  1.00  0.00           H  
HETATM   91  H50 UNL     1     -12.334  -2.456   0.918  1.00  0.00           H  
HETATM   92  H51 UNL     1     -13.693  -0.978   1.240  1.00  0.00           H  
HETATM   93  H52 UNL     1     -13.116  -0.833   2.949  1.00  0.00           H  
HETATM   94  H53 UNL     1     -14.515   1.034   2.507  1.00  0.00           H  
HETATM   95  H54 UNL     1     -12.834   1.659   2.553  1.00  0.00           H  
HETATM   96  H55 UNL     1     -14.260   0.795  -0.039  1.00  0.00           H  
HETATM   97  H56 UNL     1     -14.059   2.480   0.563  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3    3   41
CONECT    3    4   36
CONECT    4    5    5   45
CONECT    5    6   46
CONECT    6    7    8    8
CONECT    7   47   48   49
CONECT    8    9   50
CONECT    9   10   10   51
CONECT   10   11   52
CONECT   11   12   13   13
CONECT   12   53   54   55
CONECT   13   14   56
CONECT   14   15   16   57
CONECT   15   16
CONECT   16   17   58
CONECT   17   18   18   59
CONECT   18   19   20
CONECT   19   60   61   62
CONECT   20   21   21   63
CONECT   21   22   64
CONECT   22   23   23   65
CONECT   23   24   25
CONECT   24   66   67   68
CONECT   25   26   26   69
CONECT   26   27   70
CONECT   27   28   28   33
CONECT   28   29   30
CONECT   29   71   72   73
CONECT   30   31   74   75
CONECT   31   32   76   77
CONECT   32   33   78   79
CONECT   33   34   35
CONECT   34   80   81   82
CONECT   35   83   84   85
CONECT   36   37   38   39
CONECT   37   86   87   88
CONECT   38   89   90   91
CONECT   39   40   92   93
CONECT   40   41   94   95
CONECT   41   96   97
END
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SMILES for HMDB0060443 (beta-Carotene-15,15'-epoxide)

C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C1OC1\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
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INCHI for HMDB0060443 (beta-Carotene-15,15'-epoxide)

InChI=1S/C40H56O/c1-29(21-23-35-33(5)19-13-25-39(35,7)8)15-11-17-31(3)27-37-38(41-37)28-32(4)18-12-16-30(2)22-24-36-34(6)20-14-26-40(36,9)10/h11-12,15-18,21-24,27-28,37-38H,13-14,19-20,25-26H2,1-10H3/b17-11+,18-12+,23-21+,24-22+,29-15+,30-16+,31-27+,32-28+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
15,15'-Epoxy-15,15'-dihydro-beta,beta-caroteneChEBI
15,15'-Epoxy-beta,beta-caroteneChEBI
15,15'-Epoxy-beta-caroteneChEBI
15-EbbctChEBI
beta-Carotene 15,15' epoxideChEBI
15,15'-Epoxy-15,15'-dihydro-b,b-caroteneGenerator
15,15'-Epoxy-15,15'-dihydro-β,β-caroteneGenerator
15,15'-Epoxy-b,b-caroteneGenerator
15,15'-Epoxy-β,β-caroteneGenerator
15,15'-Epoxy-b-caroteneGenerator
15,15'-Epoxy-β-caroteneGenerator
b-Carotene 15,15' epoxideGenerator
Β-carotene 15,15' epoxideGenerator
b-Carotene-15,15'-epoxideGenerator
Β-carotene-15,15'-epoxideGenerator
Chemical FormulaC40H56O
Average Molecular Weight552.872
Monoisotopic Molecular Weight552.433116414
IUPAC Name2,3-bis[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]oxirane
Traditional Name2,3-bis[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]oxirane
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C1OC1\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C40H56O/c1-29(21-23-35-33(5)19-13-25-39(35,7)8)15-11-17-31(3)27-37-38(41-37)28-32(4)18-12-16-30(2)22-24-36-34(6)20-14-26-40(36,9)10/h11-12,15-18,21-24,27-28,37-38H,13-14,19-20,25-26H2,1-10H3/b17-11+,18-12+,23-21+,24-22+,29-15+,30-16+,31-27+,32-28+
InChI KeyAULCUSCIZQQSMU-WDJSDFAOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Retinoid skeleton
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00045 g/LALOGPS
logP9.11ALOGPS
logP10.5ChemAxon
logS-6.1ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity189.71 m³·mol⁻¹ChemAxon
Polarizability72.78 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+242.24431661259
DarkChem[M-H]-239.39831661259
DeepCCS[M+H]+258.0930932474
DeepCCS[M-H]-256.26530932474
DeepCCS[M-2H]-289.50730932474
DeepCCS[M+Na]+263.69630932474
AllCCS[M+H]+255.232859911
AllCCS[M+H-H2O]+253.532859911
AllCCS[M+NH4]+256.832859911
AllCCS[M+Na]+257.332859911
AllCCS[M-H]-228.132859911
AllCCS[M+Na-2H]-231.732859911
AllCCS[M+HCOO]-235.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.6.55 minutes32390414
Predicted by Siyang on May 30, 202245.5178 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.75 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid5867.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid1368.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid509.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid817.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid700.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid1817.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid1512.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)129.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid3968.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid1293.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid2494.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid1621.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid946.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate640.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA1206.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water11.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-Carotene-15,15'-epoxideC\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C1OC1\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C5461.6Standard polar33892256
beta-Carotene-15,15'-epoxideC\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C1OC1\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C4303.9Standard non polar33892256
beta-Carotene-15,15'-epoxideC\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C1OC1\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C4441.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - beta-Carotene-15,15'-epoxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-3190180000-18fa5fe375427a90ed932017-09-20Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carotene-15,15'-epoxide 10V, Positive-QTOFsplash10-0udi-0443390000-b86b444d8de208d46aaa2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carotene-15,15'-epoxide 20V, Positive-QTOFsplash10-02aa-0984620000-2682c6f17feedeb9332d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carotene-15,15'-epoxide 40V, Positive-QTOFsplash10-029i-3894710000-ef12554b6332cee19bed2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carotene-15,15'-epoxide 10V, Negative-QTOFsplash10-0udi-0010090000-fec996a718d809f6d4f82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carotene-15,15'-epoxide 20V, Negative-QTOFsplash10-0udi-1050090000-bcba82082e0652fa9ae12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carotene-15,15'-epoxide 40V, Negative-QTOFsplash10-00kr-1192020000-eea6310dad0468f80d932017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031284
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC20331
BioCyc IDCPD-14386
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6449945
PDB IDNot Available
ChEBI ID67227
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details
1. Beta,beta-carotene 15,15'-monooxygenase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Symmetrically cleaves beta-carotene into two molecules of retinal. The reaction proceeds in three stages, epoxidation of the 15,15'-double bond, hydration of the double bond leading to ring opening, and oxidative cleavage of the diol formed.
Gene Name:
BCMO1
Uniprot ID:
Q9HAY6
Molecular weight:
62636.69
Reactions
beta-Carotene + Oxygen + Reduced acceptor → beta-Carotene-15,15'-epoxide + Water + Acceptordetails
beta-Carotene-15,15'-epoxide + Water → 15,15'-Dihydroxy-beta-carotenedetails