Hmdb loader

Showing metabocard for (5R,5'R,6S,8'R)-Luteochrome (HMDB0035316)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:16:38 UTC
Update Date2022-03-07 02:54:27 UTC
HMDB IDHMDB0035316
Secondary Accession Numbers
  • HMDB35316
Metabolite Identification
Common Name(5R,5'R,6S,8'R)-Luteochrome
Description(5R,5'R,6S,8'R)-Luteochrome 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. Based on a literature review a small amount of articles have been published on (5R,5'R,6S,8'R)-Luteochrome.
Structure
Data?1563862699
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0035316 ((5R,5'R,6S,8'R)-Luteochrome)


  Mrv0541 02241210482D          

 42 45  0  0  0  0            999 V2000
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M  END
Download

3D MOL for HMDB0035316 ((5R,5'R,6S,8'R)-Luteochrome)

HMDB0035316
     RDKit          3D
(5R,5'R,6S,8'R)-Luteochrome
 98101  0  0  0  0  0  0  0  0999 V2000
   -7.2025    1.1169    1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D SDF for HMDB0035316 ((5R,5'R,6S,8'R)-Luteochrome)


  Mrv0541 02241210482D          

 42 45  0  0  0  0            999 V2000
    1.7223    0.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1229    0.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0035316

> <DATABASE_NAME>
hmdb

> <SMILES>
C/C(/C=C/C=C(/C)\C=C/C12OC1(C)CCCC2(C)C)=C\C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CCCC(C)(C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C40H56O2/c1-30(19-13-20-32(3)23-28-40-37(7,8)25-16-27-39(40,10)42-40)17-11-12-18-31(2)21-14-22-33(4)34-29-35-36(5,6)24-15-26-38(35,9)41-34/h11-14,17-23,28-29,34H,15-16,24-27H2,1-10H3/b12-11-,19-13+,21-14+,28-23-,30-17+,31-18+,32-20-,33-22-

> <INCHI_KEY>
HSOIPJLINDKQOV-VCAYJPBHSA-N

> <FORMULA>
C40H56O2

> <MOLECULAR_WEIGHT>
568.8714

> <EXACT_MASS>
568.428031036

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
72.14029168699116

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,4,7a-trimethyl-2-[(2Z,4E,6E,8Z,10E,12E,14Z,16Z)-6,11,15-trimethyl-17-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}heptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-2,4,5,6,7,7a-hexahydro-1-benzofuran

> <ALOGPS_LOGP>
9.59

> <JCHEM_LOGP>
9.90540959

> <ALOGPS_LOGS>
-6.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9764348451859504

> <JCHEM_POLAR_SURFACE_AREA>
21.759999999999998

> <JCHEM_REFRACTIVITY>
188.95000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.76e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4,7a-trimethyl-2-[(2Z,4E,6E,8Z,10E,12E,14Z,16Z)-6,11,15-trimethyl-17-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}heptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-2,5,6,7-tetrahydro-1-benzofuran

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0035316 ((5R,5'R,6S,8'R)-Luteochrome)

HMDB0035316
     RDKit          3D
(5R,5'R,6S,8'R)-Luteochrome
 98101  0  0  0  0  0  0  0  0999 V2000
   -7.2025    1.1169    1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.7927    0.4148   -0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
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 42 31  1  0
 12  5  1  0
 40 33  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  3 46  1  0
  4 47  1  0
  8 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
  9 52  1  0
 10 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 13 57  1  0
 13 58  1  0
 13 59  1  0
 14 60  1  0
 14 61  1  0
 14 62  1  0
 15 63  1  0
 16 64  1  0
 17 65  1  0
 19 66  1  0
 19 67  1  0
 19 68  1  0
 20 69  1  0
 21 70  1  0
 22 71  1  0
 23 72  1  0
 25 73  1  0
 25 74  1  0
 25 75  1  0
 26 76  1  0
 27 77  1  0
 28 78  1  0
 30 79  1  0
 30 80  1  0
 30 81  1  0
 31 82  1  0
 32 83  1  0
 35 84  1  0
 35 85  1  0
 35 86  1  0
 36 87  1  0
 36 88  1  0
 36 89  1  0
 37 90  1  0
 37 91  1  0
 38 92  1  0
 38 93  1  0
 39 94  1  0
 39 95  1  0
 41 96  1  0
 41 97  1  0
 41 98  1  0
M  END
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PDB for HMDB0035316 ((5R,5'R,6S,8'R)-Luteochrome)

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       3.215   0.448   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.963   1.794   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.916   2.991   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.570   2.243   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.065  -1.645   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.570  -1.645   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.523  -0.449   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.570   0.598   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.076   1.346   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.113  -4.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.262  -2.991   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.364  -1.645   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.963  -0.300   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.608  -0.150   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.018   4.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.514   3.888   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.113   2.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.215   1.197   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.672  -3.289   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.168  -3.439   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.065  -4.635   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.168  -5.832   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.513  -6.729   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.158  -2.093   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.262  -0.747   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.608   0.150   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.561  -6.879   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.514  -5.832   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.168  -6.580   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.673  -6.580   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.523  -5.682   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.270  -7.028   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.009   4.635   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.513   4.337   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.466   5.533   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.971   5.234   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.074   6.281   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.720   5.832   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.767   7.028   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.971  -2.841   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.374  -4.336   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.869  -4.336   0.000  0.00  0.00           C+0
CONECT    1    2    8   25                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    8                                                       
CONECT    5    6   25                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    1    4    7    9                                             
CONECT    9    8                                                            
CONECT   10   11   28                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13                                                            
CONECT   15   16   38                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   13   17                                                       
CONECT   19   20   41                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31   32                                             
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25    1    5   24   26                                             
CONECT   26   25                                                            
CONECT   27   28                                                            
CONECT   28   10   27   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   22   30   32   41                                             
CONECT   32   22   31                                                       
CONECT   33   34                                                            
CONECT   34    3   33   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   15   37   39                                                  
CONECT   39   38                                                            
CONECT   40   41                                                            
CONECT   41   19   31   40   42                                             
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END
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3D PDB for HMDB0035316 ((5R,5'R,6S,8'R)-Luteochrome)

COMPND    HMDB0035316
HETATM    1  C1  UNL     1      -7.202   1.117   1.633  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.725   0.434   0.366  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.485  -0.111  -0.670  1.00  0.00           C  
HETATM    4  C4  UNL     1      -8.735  -0.161  -0.941  1.00  0.00           C  
HETATM    5  C5  UNL     1      -9.793   0.415  -0.127  1.00  0.00           C  
HETATM    6  O1  UNL     1      -9.656   0.227   1.292  1.00  0.00           O  
HETATM    7  C6  UNL     1     -10.802  -0.275   0.545  1.00  0.00           C  
HETATM    8  C7  UNL     1     -10.910  -1.779   0.689  1.00  0.00           C  
HETATM    9  C8  UNL     1     -11.999   0.499   1.001  1.00  0.00           C  
HETATM   10  C9  UNL     1     -11.768   1.956   1.285  1.00  0.00           C  
HETATM   11  C10 UNL     1     -10.816   2.632   0.331  1.00  0.00           C  
HETATM   12  C11 UNL     1     -10.321   1.704  -0.719  1.00  0.00           C  
HETATM   13  C12 UNL     1     -11.433   1.287  -1.682  1.00  0.00           C  
HETATM   14  C13 UNL     1      -9.273   2.373  -1.576  1.00  0.00           C  
HETATM   15  C14 UNL     1      -5.382   0.266   0.294  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.684  -0.326  -0.800  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.385  -0.551  -0.855  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.472  -1.069  -1.742  1.00  0.00           C  
HETATM   19  C18 UNL     1      -2.879  -1.574  -3.094  1.00  0.00           C  
HETATM   20  C19 UNL     1      -1.155  -1.152  -1.511  1.00  0.00           C  
HETATM   21  C20 UNL     1      -0.176  -1.700  -2.420  1.00  0.00           C  
HETATM   22  C21 UNL     1       1.083  -1.681  -2.063  1.00  0.00           C  
HETATM   23  C22 UNL     1       1.603  -1.155  -0.853  1.00  0.00           C  
HETATM   24  C23 UNL     1       2.926  -1.177  -0.582  1.00  0.00           C  
HETATM   25  C24 UNL     1       3.768  -1.785  -1.610  1.00  0.00           C  
HETATM   26  C25 UNL     1       3.513  -0.561   0.587  1.00  0.00           C  
HETATM   27  C26 UNL     1       4.791  -0.553   0.912  1.00  0.00           C  
HETATM   28  C27 UNL     1       5.297   0.114   2.119  1.00  0.00           C  
HETATM   29  C28 UNL     1       6.595   0.065   2.353  1.00  0.00           C  
HETATM   30  C29 UNL     1       7.179   0.747   3.574  1.00  0.00           C  
HETATM   31  C30 UNL     1       7.458  -0.663   1.413  1.00  0.00           C  
HETATM   32  C31 UNL     1       8.797  -1.005   1.982  1.00  0.00           C  
HETATM   33  C32 UNL     1       9.706  -0.369   1.224  1.00  0.00           C  
HETATM   34  C33 UNL     1      11.201  -0.325   1.288  1.00  0.00           C  
HETATM   35  C34 UNL     1      11.680  -1.266   2.376  1.00  0.00           C  
HETATM   36  C35 UNL     1      11.726   1.039   1.614  1.00  0.00           C  
HETATM   37  C36 UNL     1      11.754  -0.837  -0.037  1.00  0.00           C  
HETATM   38  C37 UNL     1      10.826  -0.767  -1.183  1.00  0.00           C  
HETATM   39  C38 UNL     1       9.649   0.121  -1.163  1.00  0.00           C  
HETATM   40  C39 UNL     1       9.006   0.369   0.183  1.00  0.00           C  
HETATM   41  C40 UNL     1       9.008   1.895   0.355  1.00  0.00           C  
HETATM   42  O2  UNL     1       7.682  -0.077   0.213  1.00  0.00           O  
HETATM   43  H1  UNL     1      -7.905   1.908   1.379  1.00  0.00           H  
HETATM   44  H2  UNL     1      -6.307   1.732   2.036  1.00  0.00           H  
HETATM   45  H3  UNL     1      -7.454   0.446   2.430  1.00  0.00           H  
HETATM   46  H4  UNL     1      -6.897  -0.673  -1.476  1.00  0.00           H  
HETATM   47  H5  UNL     1      -9.114  -0.658  -1.878  1.00  0.00           H  
HETATM   48  H6  UNL     1     -10.543  -2.330  -0.193  1.00  0.00           H  
HETATM   49  H7  UNL     1     -11.961  -2.091   0.867  1.00  0.00           H  
HETATM   50  H8  UNL     1     -10.296  -2.125   1.554  1.00  0.00           H  
HETATM   51  H9  UNL     1     -12.267   0.044   2.023  1.00  0.00           H  
HETATM   52  H10 UNL     1     -12.927   0.332   0.433  1.00  0.00           H  
HETATM   53  H11 UNL     1     -11.385   2.093   2.314  1.00  0.00           H  
HETATM   54  H12 UNL     1     -12.775   2.449   1.239  1.00  0.00           H  
HETATM   55  H13 UNL     1     -11.385   3.462  -0.163  1.00  0.00           H  
HETATM   56  H14 UNL     1      -9.951   3.101   0.834  1.00  0.00           H  
HETATM   57  H15 UNL     1     -11.743   0.241  -1.538  1.00  0.00           H  
HETATM   58  H16 UNL     1     -12.226   2.038  -1.599  1.00  0.00           H  
HETATM   59  H17 UNL     1     -11.096   1.330  -2.756  1.00  0.00           H  
HETATM   60  H18 UNL     1      -8.698   3.150  -1.076  1.00  0.00           H  
HETATM   61  H19 UNL     1      -8.645   1.557  -2.006  1.00  0.00           H  
HETATM   62  H20 UNL     1      -9.780   2.869  -2.444  1.00  0.00           H  
HETATM   63  H21 UNL     1      -4.828   0.628   1.174  1.00  0.00           H  
HETATM   64  H22 UNL     1      -5.174  -0.652  -1.733  1.00  0.00           H  
HETATM   65  H23 UNL     1      -2.944  -0.175   0.168  1.00  0.00           H  
HETATM   66  H24 UNL     1      -3.990  -1.515  -3.127  1.00  0.00           H  
HETATM   67  H25 UNL     1      -2.606  -2.638  -3.192  1.00  0.00           H  
HETATM   68  H26 UNL     1      -2.426  -0.950  -3.894  1.00  0.00           H  
HETATM   69  H27 UNL     1      -0.855  -0.774  -0.551  1.00  0.00           H  
HETATM   70  H28 UNL     1      -0.479  -2.125  -3.406  1.00  0.00           H  
HETATM   71  H29 UNL     1       1.764  -2.142  -2.832  1.00  0.00           H  
HETATM   72  H30 UNL     1       1.011  -0.719  -0.086  1.00  0.00           H  
HETATM   73  H31 UNL     1       4.838  -1.798  -1.413  1.00  0.00           H  
HETATM   74  H32 UNL     1       3.562  -1.207  -2.562  1.00  0.00           H  
HETATM   75  H33 UNL     1       3.385  -2.828  -1.801  1.00  0.00           H  
HETATM   76  H34 UNL     1       2.833  -0.029   1.286  1.00  0.00           H  
HETATM   77  H35 UNL     1       5.450  -1.071   0.238  1.00  0.00           H  
HETATM   78  H36 UNL     1       4.611   0.612   2.758  1.00  0.00           H  
HETATM   79  H37 UNL     1       8.016   1.396   3.311  1.00  0.00           H  
HETATM   80  H38 UNL     1       7.447  -0.063   4.289  1.00  0.00           H  
HETATM   81  H39 UNL     1       6.398   1.349   4.097  1.00  0.00           H  
HETATM   82  H40 UNL     1       7.018  -1.720   1.246  1.00  0.00           H  
HETATM   83  H41 UNL     1       9.001  -1.624   2.825  1.00  0.00           H  
HETATM   84  H42 UNL     1      11.642  -0.656   3.335  1.00  0.00           H  
HETATM   85  H43 UNL     1      10.974  -2.087   2.503  1.00  0.00           H  
HETATM   86  H44 UNL     1      12.719  -1.569   2.202  1.00  0.00           H  
HETATM   87  H45 UNL     1      11.259   1.420   2.535  1.00  0.00           H  
HETATM   88  H46 UNL     1      12.855   1.016   1.714  1.00  0.00           H  
HETATM   89  H47 UNL     1      11.455   1.709   0.774  1.00  0.00           H  
HETATM   90  H48 UNL     1      11.973  -1.957   0.107  1.00  0.00           H  
HETATM   91  H49 UNL     1      12.757  -0.392  -0.201  1.00  0.00           H  
HETATM   92  H50 UNL     1      11.467  -0.400  -2.061  1.00  0.00           H  
HETATM   93  H51 UNL     1      10.518  -1.791  -1.547  1.00  0.00           H  
HETATM   94  H52 UNL     1       9.859   1.101  -1.683  1.00  0.00           H  
HETATM   95  H53 UNL     1       8.847  -0.323  -1.823  1.00  0.00           H  
HETATM   96  H54 UNL     1       9.643   2.406  -0.358  1.00  0.00           H  
HETATM   97  H55 UNL     1       9.228   2.116   1.388  1.00  0.00           H  
HETATM   98  H56 UNL     1       7.926   2.238   0.212  1.00  0.00           H  
CONECT    1    2   43   44   45
CONECT    2    3   15   15
CONECT    3    4    4   46
CONECT    4    5   47
CONECT    5    6    7   12
CONECT    6    7
CONECT    7    8    9
CONECT    8   48   49   50
CONECT    9   10   51   52
CONECT   10   11   53   54
CONECT   11   12   55   56
CONECT   12   13   14
CONECT   13   57   58   59
CONECT   14   60   61   62
CONECT   15   16   63
CONECT   16   17   17   64
CONECT   17   18   65
CONECT   18   19   20   20
CONECT   19   66   67   68
CONECT   20   21   69
CONECT   21   22   22   70
CONECT   22   23   71
CONECT   23   24   24   72
CONECT   24   25   26
CONECT   25   73   74   75
CONECT   26   27   27   76
CONECT   27   28   77
CONECT   28   29   29   78
CONECT   29   30   31
CONECT   30   79   80   81
CONECT   31   32   42   82
CONECT   32   33   33   83
CONECT   33   34   40
CONECT   34   35   36   37
CONECT   35   84   85   86
CONECT   36   87   88   89
CONECT   37   38   90   91
CONECT   38   39   92   93
CONECT   39   40   94   95
CONECT   40   41   42
CONECT   41   96   97   98
END
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SMILES for HMDB0035316 ((5R,5'R,6S,8'R)-Luteochrome)

C/C(/C=C/C=C(/C)\C=C/C12OC1(C)CCCC2(C)C)=C\C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CCCC(C)(C)C2=C1
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INCHI for HMDB0035316 ((5R,5'R,6S,8'R)-Luteochrome)

InChI=1S/C40H56O2/c1-30(19-13-20-32(3)23-28-40-37(7,8)25-16-27-39(40,10)42-40)17-11-12-18-31(2)21-14-22-33(4)34-29-35-36(5,6)24-15-26-38(35,9)41-34/h11-14,17-23,28-29,34H,15-16,24-27H2,1-10H3/b12-11-,19-13+,21-14+,28-23-,30-17+,31-18+,32-20-,33-22-
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC40H56O2
Average Molecular Weight568.8714
Monoisotopic Molecular Weight568.428031036
IUPAC Name4,4,7a-trimethyl-2-[(2Z,4E,6E,8Z,10E,12E,14Z,16Z)-6,11,15-trimethyl-17-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}heptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-2,4,5,6,7,7a-hexahydro-1-benzofuran
Traditional Name4,4,7a-trimethyl-2-[(2Z,4E,6E,8Z,10E,12E,14Z,16Z)-6,11,15-trimethyl-17-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}heptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-2,5,6,7-tetrahydro-1-benzofuran
CAS Registry NumberNot Available
SMILES
C/C(/C=C/C=C(/C)\C=C/C12OC1(C)CCCC2(C)C)=C\C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CCCC(C)(C)C2=C1
InChI Identifier
InChI=1S/C40H56O2/c1-30(19-13-20-32(3)23-28-40-37(7,8)25-16-27-39(40,10)42-40)17-11-12-18-31(2)21-14-22-33(4)34-29-35-36(5,6)24-15-26-38(35,9)41-34/h11-14,17-23,28-29,34H,15-16,24-27H2,1-10H3/b12-11-,19-13+,21-14+,28-23-,30-17+,31-18+,32-20-,33-22-
InChI KeyHSOIPJLINDKQOV-VCAYJPBHSA-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
  • Benzofuran
  • Oxepane
  • Dihydrofuran
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 - 171 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00018 g/LALOGPS
logP9.59ALOGPS
logP9.91ChemAxon
logS-6.5ALOGPS
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area21.76 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity188.95 m³·mol⁻¹ChemAxon
Polarizability72.14 ųChemAxon
Number of Rings4ChemAxon
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]+241.61331661259
DarkChem[M-H]-234.70131661259
DeepCCS[M-2H]-283.55930932474
DeepCCS[M+Na]+257.97630932474
AllCCS[M+H]+258.932859911
AllCCS[M+H-H2O]+257.332859911
AllCCS[M+NH4]+260.432859911
AllCCS[M+Na]+260.932859911
AllCCS[M-H]-232.932859911
AllCCS[M+Na-2H]-236.932859911
AllCCS[M+HCOO]-241.532859911

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. 6.97 minutes32390414
Predicted by Siyang on May 30, 202237.4502 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20220.97 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid5477.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid936.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid399.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid489.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid387.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid1928.1 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 Acid1264.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)119.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid3274.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid1027.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid2129.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid1539.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid742.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate564.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA1098.2 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
(5R,5'R,6S,8'R)-LuteochromeC/C(/C=C/C=C(/C)\C=C/C12OC1(C)CCCC2(C)C)=C\C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CCCC(C)(C)C2=C15537.3Standard polar33892256
(5R,5'R,6S,8'R)-LuteochromeC/C(/C=C/C=C(/C)\C=C/C12OC1(C)CCCC2(C)C)=C\C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CCCC(C)(C)C2=C14420.1Standard non polar33892256
(5R,5'R,6S,8'R)-LuteochromeC/C(/C=C/C=C(/C)\C=C/C12OC1(C)CCCC2(C)C)=C\C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CCCC(C)(C)C2=C14395.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3600290000-0d89f3ab061f00837b0c2017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 10V, Positive-QTOFsplash10-014i-0595580000-da3de18d27b82cb1d09b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 20V, Positive-QTOFsplash10-066s-0296010000-524ab44bfc7e744fe09d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 40V, Positive-QTOFsplash10-06sr-8895100000-0b4914a0ec65ea13ef402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 10V, Negative-QTOFsplash10-014i-0100190000-2fa143c4500a2ba2b1192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 20V, Negative-QTOFsplash10-014i-0310190000-b1ae307cf33b96efccb42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 40V, Negative-QTOFsplash10-0f79-1910250000-f1afbd313656085a83652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 10V, Positive-QTOFsplash10-0uxr-0032090000-6706a10431c36ba6d7bd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 20V, Positive-QTOFsplash10-0udr-0165190000-324b7e0e884dcdfaa1b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 40V, Positive-QTOFsplash10-0019-0934200000-017fbb1202c93dade5a82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 10V, Negative-QTOFsplash10-014i-0200090000-44ba945db36b2df7c2e92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 20V, Negative-QTOFsplash10-014i-0124190000-52f3c445cf7537abb0442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 40V, Negative-QTOFsplash10-01c0-0298050000-53201085297316705a932021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB013985
KNApSAcK IDNot Available
Chemspider ID35013901
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751703
PDB IDNot Available
ChEBI ID176086
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.