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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:43 UTC

Update Date

2022-03-07 02:49:18 UTC

HMDB ID

HMDB0003233

Secondary Accession Numbers

HMDB03233

Metabolite Identification

Common Name

Lutein

Description

Lutein is a common carotenoid xanthophyll found in nature. Carotenoids are among the most common pigments in nature and are natural lipid-soluble antioxidants. Lutein is one of the two carotenoids (the other is zeaxanthin) that accumulate in the eye lens and macular region of the retina with concentrations in the macula greater than those found in plasma and other tissues. Lutein and zeaxanthin have identical chemical formulas and are isomers, but they are not stereoisomers. The main difference between them is in the location of a double bond in one of the end rings. This difference gives lutein three chiral centers whereas zeaxanthin has two. A relationship between macular pigment optical density, a marker of lutein and zeaxanthin concentration in the macula, and lens optical density, an antecedent of cataractous changes, has been suggested. The xanthophylls may act to protect the eye from ultraviolet phototoxicity via quenching reactive oxygen species and/or other mechanisms. Some observational studies have shown that generous intakes of lutein and zeaxanthin, particularly from certain xanthophyll-rich foods like spinach, broccoli, and eggs, are associated with a significant reduction in the risk for cataracts (up to 20%) and age-related macular degeneration (up to 40%). While the pathophysiology of cataract and age-related macular degeneration is complex and contains both environmental and genetic components, research studies suggest dietary factors including antioxidant vitamins and xanthophylls may contribute to a reduction in the risk of these degenerative eye diseases. Further research is necessary to confirm these observations (PMID: 11023002 ).

Structure

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

  Mrv1652304242019082D          

 42 43  0  0  0  0            999 V2000
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  1  2  2  0  0  0  0
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 42 30  1  1  0  0  0
M  END

HMDB0003233
     RDKit          3D
Lutein
 98 99  0  0  0  0  0  0  0  0999 V2000
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M  END

  Mrv1652304242019082D          

 42 43  0  0  0  0            999 V2000
 9993.907910000.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6221 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.338210000.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10001.051010000.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0003233

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37-/m0/s1

> <INCHI_KEY>
KBPHJBAIARWVSC-RGZFRNHPSA-N

> <FORMULA>
C40H56O2

> <MOLECULAR_WEIGHT>
568.886

> <EXACT_MASS>
568.428031043

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
74.25844985738175

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol

> <ALOGPS_LOGP>
8.29

> <JCHEM_LOGP>
8.550209330666668

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.907213404525137

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.21727233987641

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9139435291721482

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
195.0634

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.32e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carotenoid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003233
     RDKit          3D
Lutein
 98 99  0  0  0  0  0  0  0  0999 V2000
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   12.7604    2.2919   -1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
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 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
 37 89  1  6
 38 90  1  0
 39 91  1  0
 39 92  1  0
 41 93  1  0
 41 94  1  0
 41 95  1  0
 42 96  1  0
 42 97  1  0
 42 98  1  0
M  END

HEADER    PROTEIN                                 24-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-20         0                                  
HETATM    1  C   UNK     0    8655.2958667.024   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8656.6288666.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8657.9658667.024   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8659.2988666.253   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8657.9658668.565   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8651.6588668.222   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8653.6188668.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8655.2958663.946   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8660.6318667.024   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.9648666.253   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8649.9628663.946   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8663.2978667.024   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.6308666.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.2978668.565   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.9638667.024   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8667.2968666.253   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8668.6298667.024   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.9618666.253   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8671.2978667.024   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.9618664.714   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.6308666.253   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8673.9628667.024   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8675.2948666.253   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8676.6278667.024   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8675.2948664.714   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8677.9638666.253   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8681.6028665.058   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8679.6428665.077   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8677.9638669.331   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8683.2968669.331   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0    8652.6298667.024   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8651.2958666.254   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8651.2958664.714   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8652.6298663.944   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8653.9628664.714   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8653.9628666.254   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8680.6308669.334   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8679.2978668.564   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0    8679.2978667.024   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0    8680.6308666.254   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0    8681.9648667.024   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0    8681.9648668.564   0.000  0.00  0.00           C+0
CONECT    1    2   36                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3    9                                                       
CONECT    5    3                                                            
CONECT    6   31                                                            
CONECT    7   31                                                            
CONECT    8   35                                                            
CONECT    9    4   10                                                       
CONECT   10    9   12                                                       
CONECT   11   33                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   21                                                       
CONECT   20   18                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   26                                                       
CONECT   25   23                                                            
CONECT   26   24   39                                                       
CONECT   27   40                                                            
CONECT   28   40                                                            
CONECT   29   38                                                            
CONECT   30   42                                                            
CONECT   31   32   36    6    7                                             
CONECT   32   31   33                                                       
CONECT   33   32   34   11                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36    8                                                  
CONECT   36   31   35    1                                                  
CONECT   37   38   42                                                       
CONECT   38   37   39   29                                                  
CONECT   39   38   40   26                                                  
CONECT   40   39   41   27   28                                             
CONECT   41   40   42                                                       
CONECT   42   37   41   30                                                  
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

COMPND    HMDB0003233
HETATM    1  C1  UNL     1      11.019   3.345   0.225  1.00  0.00           C  
HETATM    2  C2  UNL     1      11.592   2.145  -0.401  1.00  0.00           C  
HETATM    3  C3  UNL     1      12.760   2.292  -1.096  1.00  0.00           C  
HETATM    4  C4  UNL     1      13.281   1.063  -1.694  1.00  0.00           C  
HETATM    5  O1  UNL     1      12.580   0.761  -2.889  1.00  0.00           O  
HETATM    6  C5  UNL     1      13.248  -0.128  -0.774  1.00  0.00           C  
HETATM    7  C6  UNL     1      12.161  -0.075   0.238  1.00  0.00           C  
HETATM    8  C7  UNL     1      11.506  -1.370   0.558  1.00  0.00           C  
HETATM    9  C8  UNL     1      12.550   0.636   1.530  1.00  0.00           C  
HETATM   10  C9  UNL     1      11.032   0.811  -0.392  1.00  0.00           C  
HETATM   11  C10 UNL     1       9.869   0.551   0.488  1.00  0.00           C  
HETATM   12  C11 UNL     1       8.710   0.231  -0.080  1.00  0.00           C  
HETATM   13  C12 UNL     1       7.477  -0.064   0.585  1.00  0.00           C  
HETATM   14  C13 UNL     1       7.290  -0.060   2.021  1.00  0.00           C  
HETATM   15  C14 UNL     1       6.410  -0.307  -0.172  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.092  -0.635   0.308  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.077  -0.752  -0.568  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.746  -1.103  -0.021  1.00  0.00           C  
HETATM   19  C18 UNL     1       2.139  -1.499  -1.762  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.870  -1.331   0.322  1.00  0.00           C  
HETATM   21  C20 UNL     1       0.527  -1.742   1.105  1.00  0.00           C  
HETATM   22  C21 UNL     1      -0.475  -1.563   0.214  1.00  0.00           C  
HETATM   23  C22 UNL     1      -1.833  -1.662   0.387  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.886  -1.351  -0.186  1.00  0.00           C  
HETATM   25  C24 UNL     1      -1.674  -0.590  -1.508  1.00  0.00           C  
HETATM   26  C25 UNL     1      -3.926  -0.891  -1.063  1.00  0.00           C  
HETATM   27  C26 UNL     1      -5.162  -1.014  -0.531  1.00  0.00           C  
HETATM   28  C27 UNL     1      -6.383  -0.632  -1.140  1.00  0.00           C  
HETATM   29  C28 UNL     1      -7.505  -0.800  -0.394  1.00  0.00           C  
HETATM   30  C29 UNL     1      -7.242  -1.422   0.939  1.00  0.00           C  
HETATM   31  C30 UNL     1      -8.794  -0.194  -0.758  1.00  0.00           C  
HETATM   32  C31 UNL     1      -9.819  -0.370   0.058  1.00  0.00           C  
HETATM   33  C32 UNL     1     -11.161   0.087   0.012  1.00  0.00           C  
HETATM   34  C33 UNL     1     -11.913  -0.308   1.092  1.00  0.00           C  
HETATM   35  C34 UNL     1     -11.315  -1.150   2.165  1.00  0.00           C  
HETATM   36  C35 UNL     1     -13.286   0.252   1.277  1.00  0.00           C  
HETATM   37  C36 UNL     1     -13.256   1.741   1.005  1.00  0.00           C  
HETATM   38  O2  UNL     1     -12.612   2.348   2.131  1.00  0.00           O  
HETATM   39  C37 UNL     1     -12.529   2.128  -0.240  1.00  0.00           C  
HETATM   40  C38 UNL     1     -11.863   0.906  -0.929  1.00  0.00           C  
HETATM   41  C39 UNL     1     -13.065   0.136  -1.526  1.00  0.00           C  
HETATM   42  C40 UNL     1     -11.139   1.455  -2.110  1.00  0.00           C  
HETATM   43  H1  UNL     1      10.481   3.956  -0.566  1.00  0.00           H  
HETATM   44  H2  UNL     1      10.367   3.143   1.076  1.00  0.00           H  
HETATM   45  H3  UNL     1      11.831   4.014   0.597  1.00  0.00           H  
HETATM   46  H4  UNL     1      13.241   3.206  -1.214  1.00  0.00           H  
HETATM   47  H5  UNL     1      14.361   1.180  -2.020  1.00  0.00           H  
HETATM   48  H6  UNL     1      12.504  -0.250  -2.972  1.00  0.00           H  
HETATM   49  H7  UNL     1      13.062  -1.041  -1.407  1.00  0.00           H  
HETATM   50  H8  UNL     1      14.220  -0.319  -0.270  1.00  0.00           H  
HETATM   51  H9  UNL     1      11.042  -1.392   1.582  1.00  0.00           H  
HETATM   52  H10 UNL     1      12.188  -2.218   0.533  1.00  0.00           H  
HETATM   53  H11 UNL     1      10.677  -1.612  -0.157  1.00  0.00           H  
HETATM   54  H12 UNL     1      12.499  -0.128   2.346  1.00  0.00           H  
HETATM   55  H13 UNL     1      11.858   1.456   1.750  1.00  0.00           H  
HETATM   56  H14 UNL     1      13.543   1.065   1.380  1.00  0.00           H  
HETATM   57  H15 UNL     1      10.900   0.433  -1.406  1.00  0.00           H  
HETATM   58  H16 UNL     1       9.886   0.622   1.549  1.00  0.00           H  
HETATM   59  H17 UNL     1       8.781   0.225  -1.193  1.00  0.00           H  
HETATM   60  H18 UNL     1       8.159   0.367   2.596  1.00  0.00           H  
HETATM   61  H19 UNL     1       6.390   0.573   2.294  1.00  0.00           H  
HETATM   62  H20 UNL     1       7.054  -1.046   2.491  1.00  0.00           H  
HETATM   63  H21 UNL     1       6.544  -0.260  -1.273  1.00  0.00           H  
HETATM   64  H22 UNL     1       4.840  -0.809   1.348  1.00  0.00           H  
HETATM   65  H23 UNL     1       4.303  -0.574  -1.577  1.00  0.00           H  
HETATM   66  H24 UNL     1       3.106  -1.743  -2.102  1.00  0.00           H  
HETATM   67  H25 UNL     1       1.789  -0.532  -1.874  1.00  0.00           H  
HETATM   68  H26 UNL     1       1.580  -2.338  -1.488  1.00  0.00           H  
HETATM   69  H27 UNL     1       2.482  -1.465   1.677  1.00  0.00           H  
HETATM   70  H28 UNL     1       0.387  -2.057   2.009  1.00  0.00           H  
HETATM   71  H29 UNL     1      -0.076  -1.381  -0.813  1.00  0.00           H  
HETATM   72  H30 UNL     1      -2.185  -2.228   1.390  1.00  0.00           H  
HETATM   73  H31 UNL     1      -1.247   0.048  -0.783  1.00  0.00           H  
HETATM   74  H32 UNL     1      -2.505  -0.044  -1.951  1.00  0.00           H  
HETATM   75  H33 UNL     1      -1.511  -1.530  -1.884  1.00  0.00           H  
HETATM   76  H34 UNL     1      -3.888  -0.508  -2.015  1.00  0.00           H  
HETATM   77  H35 UNL     1      -5.137  -1.450   0.512  1.00  0.00           H  
HETATM   78  H36 UNL     1      -6.493  -0.226  -2.122  1.00  0.00           H  
HETATM   79  H37 UNL     1      -8.136  -1.659   1.491  1.00  0.00           H  
HETATM   80  H38 UNL     1      -6.654  -0.710   1.556  1.00  0.00           H  
HETATM   81  H39 UNL     1      -6.717  -2.421   0.800  1.00  0.00           H  
HETATM   82  H40 UNL     1      -8.962   0.389  -1.632  1.00  0.00           H  
HETATM   83  H41 UNL     1      -9.510  -1.028   0.919  1.00  0.00           H  
HETATM   84  H42 UNL     1     -12.135  -1.312   2.934  1.00  0.00           H  
HETATM   85  H43 UNL     1     -10.461  -0.546   2.570  1.00  0.00           H  
HETATM   86  H44 UNL     1     -10.944  -2.112   1.809  1.00  0.00           H  
HETATM   87  H45 UNL     1     -14.091  -0.288   0.809  1.00  0.00           H  
HETATM   88  H46 UNL     1     -13.459   0.171   2.380  1.00  0.00           H  
HETATM   89  H47 UNL     1     -14.282   2.077   0.986  1.00  0.00           H  
HETATM   90  H48 UNL     1     -11.645   2.270   1.950  1.00  0.00           H  
HETATM   91  H49 UNL     1     -11.769   2.872   0.015  1.00  0.00           H  
HETATM   92  H50 UNL     1     -13.171   2.551  -1.016  1.00  0.00           H  
HETATM   93  H51 UNL     1     -13.085  -0.911  -1.175  1.00  0.00           H  
HETATM   94  H52 UNL     1     -14.021   0.615  -1.285  1.00  0.00           H  
HETATM   95  H53 UNL     1     -13.009   0.097  -2.643  1.00  0.00           H  
HETATM   96  H54 UNL     1     -10.797   0.696  -2.823  1.00  0.00           H  
HETATM   97  H55 UNL     1     -10.337   2.124  -1.830  1.00  0.00           H  
HETATM   98  H56 UNL     1     -11.944   2.114  -2.647  1.00  0.00           H  
CONECT    1    2   43   44   45
CONECT    2    3    3   10
CONECT    3    4   46
CONECT    4    5    6   47
CONECT    5   48
CONECT    6    7   49   50
CONECT    7    8    9   10
CONECT    8   51   52   53
CONECT    9   54   55   56
CONECT   10   11   57
CONECT   11   12   12   58
CONECT   12   13   59
CONECT   13   14   15   15
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   32   82
CONECT   32   33   83
CONECT   33   34   34   40
CONECT   34   35   36
CONECT   35   84   85   86
CONECT   36   37   87   88
CONECT   37   38   39   89
CONECT   38   90
CONECT   39   40   91   92
CONECT   40   41   42
CONECT   41   93   94   95
CONECT   42   96   97   98
END

HMDB0003233
     RDKit          3D
Lutein
 98 99  0  0  0  0  0  0  0  0999 V2000
   11.0187    3.3449    0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5925    2.1445   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7604    2.2919   -1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809    1.0629   -1.6938 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5795    0.7607   -2.8888 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2476   -0.1284   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1612   -0.0751    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5060   -1.3699    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5499    0.6358    1.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0322    0.8110   -0.3921 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8694    0.5514    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7103    0.2312   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4770   -0.0636    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2901   -0.0598    2.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4098   -0.3070   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0919   -0.6354    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771   -0.7518   -0.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7465   -1.1032   -0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1386   -1.4988   -1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8699   -1.3311    0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5267   -1.7424    1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747   -1.5633    0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8331   -1.6623    0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8863   -1.3506   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739   -0.5904   -1.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1852   -2.2279    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2469    0.0481   -0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6541   -0.7096    1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7166   -2.4209    0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9623    0.3889   -1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5100   -1.0281    0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol	ChEBI
Bo-xan	ChEBI
e 161b	ChEBI
Xanthophyll	ChEBI
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol	Generator
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol	Generator
Lutein F	MeSH
Lutein g	MeSH
Lutein, gamma	MeSH
gamma Lutein	MeSH
(3R,3'R,6'R)-Lutein	HMDB
(3R,3'R,6'R)-beta,epsilon-Carotene-3,3'-diol	HMDB
(3R,3'R,6'R)-β,ε-Carotene-3,3'-diol	HMDB
(3R,3’R,6’R)-Lutein	HMDB
(3R,3’R,6’R)-β,ε-Carotene-3,3’-diol	HMDB
(all-E)-Lutein	HMDB
6'-Hydro-4',5'-dehydro-beta-carotene-3,3'-diol	HMDB
6'-Hydro-4',5'-dehydro-β-carotene-3,3'-diol	HMDB
6’-Hydro-4’,5’-dehydro-β-carotene-3,3’-diol	HMDB
Lutein	HMDB
Luteine	HMDB
all-trans-(+)-Xanthophyll	HMDB
all-trans-Lutein	HMDB
all-trans-Xanthophyll	HMDB
trans-Lutein	HMDB

Chemical Formula

C₄₀H₅₆O₂

Average Molecular Weight

568.886

Monoisotopic Molecular Weight

568.428031043

IUPAC Name

(1R,4R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol

Traditional Name

carotenoid

CAS Registry Number

127-40-2

SMILES

C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C

InChI Identifier

InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37-/m0/s1

InChI Key

KBPHJBAIARWVSC-RGZFRNHPSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carotenol (CHEBI:28838 )
C40 isoprenoids (tetraterpenes) (C08601 )
Carotenoids (C08601 )
C40 isoprenoids (tetraterpenes) (LMPR01070274 )

Ontology

Not Available

Adipose tissue (HMDB: HMDB0003233)

Eye Lens (HMDB: HMDB0003233)

Epithelium

Epidermis (HMDB: HMDB0003233)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16046287)

Organ

Gland

Adrenal Gland (HMDB: HMDB0003233)

Cell

Fibroblasts (HMDB: HMDB0003233)
Neuron (HMDB: HMDB0003233)

Organ substructure

Retina (HMDB: HMDB0003233)

Cellular substructure

Membrane (HMDB: HMDB0003233)
Extracellular (HMDB: HMDB0003233)

Source

Exogenous

Exogenous (HMDB: HMDB0003233)

Food

Vegetable

Fruit vegetable

Garden tomato (FooDB: FOOD00171)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Egg

Eggs (FooDB: FOOD00619)
Egg yolk (FooDB: FOOD00919)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0003233)
Antioxidant (HMDB: HMDB0003233)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0003233)

Biomarker

Diabetes mellitus type 2 (MarkerDB: MDB00000416)

Agriculture

Pesticide (HMDB: HMDB0003233)

Biological role

Anti atherosclerotic (HMDB: HMDB0003233)
Anti cancer (HMDB: HMDB0003233)
Anti maculitic (HMDB: HMDB0003233)
Anti nyctalopic (HMDB: HMDB0003233)
Anti proliferant (HMDB: HMDB0003233)
Anti radicular (HMDB: HMDB0003233)
Anti retinitic (HMDB: HMDB0003233)
Bruchifuge (HMDB: HMDB0003233)
Colorant (HMDB: HMDB0003233)
Insectifuge (HMDB: HMDB0003233)
Prooxidant (HMDB: HMDB0003233)
Quinone-reductase inducer (HMDB: HMDB0003233)
Retinoprotectant (HMDB: HMDB0003233)
Ubiquiot (HMDB: HMDB0003233)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	196 °C	Not Available
Boiling Point	702.27 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	5.6e-11 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	11.524 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00073 g/L	ALOGPS
logP	8.29	ALOGPS
logP	8.55	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	18.22	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	195.06 m³·mol⁻¹	ChemAxon
Polarizability	74.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	259.911	30932474
DeepCCS	[M-H]-	258.016	30932474
DeepCCS	[M-2H]-	291.976	30932474
DeepCCS	[M+Na]+	265.935	30932474
AllCCS	[M+H]+	259.3	32859911
AllCCS	[M+H-H2O]+	257.6	32859911
AllCCS	[M+NH4]+	260.9	32859911
AllCCS	[M+Na]+	261.3	32859911
AllCCS	[M-H]-	231.0	32859911
AllCCS	[M+Na-2H]-	234.6	32859911
AllCCS	[M+HCOO]-	238.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lutein	C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C	6137.6	Standard polar	33892256
Lutein	C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C	4714.4	Standard non polar	33892256
Lutein	C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C	4370.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lutein,1TMS,isomer #1	CC1=C[C@H](O[Si](C)(C)C)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C	4765.9	Semi standard non polar	33892256
Lutein,1TMS,isomer #2	CC1=C[C@H](O)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C	4758.6	Semi standard non polar	33892256
Lutein,2TMS,isomer #1	CC1=C[C@H](O[Si](C)(C)C)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C	4721.6	Semi standard non polar	33892256
Lutein,1TBDMS,isomer #1	CC1=C[C@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C	4963.0	Semi standard non polar	33892256
Lutein,1TBDMS,isomer #2	CC1=C[C@H](O)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C	4955.0	Semi standard non polar	33892256
Lutein,2TBDMS,isomer #1	CC1=C[C@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C	5160.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lutein GC-MS ("Lutein,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lutein GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lutein GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lutein GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lutein GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lutein GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lutein GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lutein 20V, Positive-QTOF	splash10-00kr-0942120000-1ea7d21108843411033c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lutein 20V, Positive-QTOF	splash10-0170-0942220000-6f1a6499f3edad61c0e8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lutein 20V, Positive-QTOF	splash10-0170-0942220000-35ebb4c0d96329a15eb9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lutein 20V, Positive-QTOF	splash10-00n0-0942120000-6f0f9e5c558e5fc6fc39	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 10V, Positive-QTOF	splash10-0gb9-0111190000-56a7b3ad9850d88a093a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 20V, Positive-QTOF	splash10-0frt-0729640000-fa9f79f8a73fa60b8abf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 40V, Positive-QTOF	splash10-0002-2439510000-8c70ee5c9af7440a4672	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 10V, Negative-QTOF	splash10-014i-0000090000-e64043a148b331ba05a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 20V, Negative-QTOF	splash10-014i-0000090000-a48901fc52e8e64be250	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 40V, Negative-QTOF	splash10-0udr-0522590000-ed879e2e3d350ac0e502	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 10V, Positive-QTOF	splash10-014r-0121930000-b93c4284d63c87f0039c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 20V, Positive-QTOF	splash10-0uel-0113920000-f619218ed5b32e075e70	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 40V, Positive-QTOF	splash10-0wmi-0059500000-ba48ee62bc6ea7e22dbf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 10V, Negative-QTOF	splash10-014i-0202090000-e7ff503087b047287234	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 20V, Negative-QTOF	splash10-014i-0405490000-4908259aa27c690d5b58	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein 40V, Negative-QTOF	splash10-0201-0519300000-3ec7b022b5aedb2ab3d0	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Adipose Tissue
Adrenal Gland
Epidermis
Eye Lens
Fibroblasts
Intestine
Neuron
Ovary
Placenta
Retina
Spleen
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.180 +/- 0.0800 uM	Adult (>18 years old)	Female	Normal	8922299	details
Blood	Detected and Quantified	0.200 +/- 0.100 uM	Adult (>18 years old)	Male	Normal	8922299	details
Blood	Detected and Quantified	0.180 +/- 0.0700 uM	Adult (>18 years old)	Female	Normal	8922299	details
Blood	Detected and Quantified	0.140 +/- 0.0500 uM	Adult (>18 years old)	Male	Normal	8922299	details
Blood	Detected and Quantified	0.156 uM	Adult (>18 years old)	Both	Normal	21272408	details
Blood	Detected and Quantified	0.163 uM	Adult (>18 years old)	Both	Normal	21272408	details
Blood	Detected and Quantified	0.198 uM	Adult (>18 years old)	Both	Normal	19022967	details
Blood	Detected and Quantified	0.180 +/- 0.0900 uM	Adult (>18 years old)	Both	Normal	8922299	details
Blood	Detected and Quantified	0.310 +/- 0.160 uM	Adult (>18 years old)	Both	Normal	16465196	details
Blood	Detected and Quantified	0.350 +/- 0.200 uM	Adult (>18 years old)	Both	Normal	16465196	details
Blood	Detected and Quantified	0.44 uM	Adult (>18 years old)	Female	Normal	16160701	details
Blood	Detected and Quantified	0.270 +/- 0.110 uM	Adult (>18 years old)	Female	Normal	1512628	details
Blood	Detected and Quantified	0.304 +/- 0.111 uM	Adult (>18 years old)	Female	Normal	15054421	details
Blood	Detected and Quantified	0.320 +/- 0.160 uM	Adult (>18 years old)	Female	Normal	18813024	details
Blood	Detected and Quantified	0.329 +/- 0.123 uM	Adult (>18 years old)	Female	Normal	10427874	details
Blood	Detected and Quantified	270.360 +/- 108.636 uM	Adult (>18 years old)	Female	Normal	9568782	details
Blood	Detected and Quantified	0.38 uM	Adult (>18 years old)	Male	Normal	16160701	details
Blood	Detected and Quantified	0.174 +/- 0.0640 uM	Adult (>18 years old)	Male	Normal	15946415	details
Blood	Detected and Quantified	0.251 +/- 0.0980 uM	Adult (>18 years old)	Male	Normal	15054421	details
Blood	Detected and Quantified	0.280 +/- 0.100 uM	Adult (>18 years old)	Male	Normal	1512628	details
Blood	Detected and Quantified	275.633 +/- 98.792 uM	Adult (>18 years old)	Male	Normal	9568782	details
Blood	Detected and Quantified	0.320 +/- 0.230 uM	Children (1 - 13 years old)	Not Specified	Normal	18997681	details
Blood	Detected and Quantified	0.52 (0.24-0.79) uM	Adult (>18 years old)	Both	Normal	16046287	details
Blood	Detected and Quantified	0.53 +/- 0.26 uM	Adult (>18 years old)	Both	Normal	15705230	details
Blood	Detected and Quantified	0.49 +/- 0.23 uM	Adult (>18 years old)	Both	Normal	15705230	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.210 +/- 0.0900 uM	Adult (>18 years old)	Both	Type I diabetes	16452910	details
Blood	Detected and Quantified	0.310 +/- 0.110 uM	Children (1 - 13 years old)	Not Specified	Obese	18997681	details
Blood	Detected and Quantified	0.390 +/- 0.150 uM	Children (1 - 13 years old)	Not Specified	Overweight	18997681	details

Associated Disorders and Diseases

Disease References

Diabetes mellitus type 1
Granado-Lorencio F, Olmedilla-Alonso B, Blanco-Navarro I, Botella-Romero F, Simal-Anton A: Assessment of carotenoid status and the relation to glycaemic control in type I diabetics: a follow-up study. Eur J Clin Nutr. 2006 Aug;60(8):1000-8. Epub 2006 Feb 1. [PubMed:16452910 ]
Obesity
Burrows TL, Warren JM, Colyvas K, Garg ML, Collins CE: Validation of overweight children's fruit and vegetable intake using plasma carotenoids. Obesity (Silver Spring). 2009 Jan;17(1):162-8. doi: 10.1038/oby.2008.495. Epub 2008 Nov 6. [PubMed:18997681 ]

Associated OMIM IDs

222100 (Diabetes mellitus type 1)
601665 (Obesity)

External Links

DrugBank ID

DB00137

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Lutein

METLIN ID

Not Available

PubChem Compound

5281243

PDB ID

Not Available

ChEBI ID

28838

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000416

Good Scents ID

rw1373101

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Wenzel AJ, Gerweck C, Barbato D, Nicolosi RJ, Handelman GJ, Curran-Celentano J: A 12-wk egg intervention increases serum zeaxanthin and macular pigment optical density in women. J Nutr. 2006 Oct;136(10):2568-73. [PubMed:16988128 ]
Rapp LM, Maple SS, Choi JH: Lutein and zeaxanthin concentrations in rod outer segment membranes from perifoveal and peripheral human retina. Invest Ophthalmol Vis Sci. 2000 Apr;41(5):1200-9. [PubMed:10752961 ]
Khachik F, Bernstein PS, Garland DL: Identification of lutein and zeaxanthin oxidation products in human and monkey retinas. Invest Ophthalmol Vis Sci. 1997 Aug;38(9):1802-11. [PubMed:9286269 ]
Handelman GJ, Nightingale ZD, Lichtenstein AH, Schaefer EJ, Blumberg JB: Lutein and zeaxanthin concentrations in plasma after dietary supplementation with egg yolk. Am J Clin Nutr. 1999 Aug;70(2):247-51. [PubMed:10426702 ]
Dasch B, Fuhs A, Schmidt J, Behrens T, Meister A, Wellmann J, Fobker M, Pauleikhoff D, Hense HW: Serum levels of macular carotenoids in relation to age-related maculopathy: the Muenster Aging and Retina Study (MARS). Graefes Arch Clin Exp Ophthalmol. 2005 Oct;243(10):1028-35. Epub 2005 Oct 20. [PubMed:15909159 ]
Hammond BR Jr, Wooten BR, Snodderly DM: Density of the human crystalline lens is related to the macular pigment carotenoids, lutein and zeaxanthin. Optom Vis Sci. 1997 Jul;74(7):499-504. [PubMed:9293517 ]
Johnson EJ, Hammond BR, Yeum KJ, Qin J, Wang XD, Castaneda C, Snodderly DM, Russell RM: Relation among serum and tissue concentrations of lutein and zeaxanthin and macular pigment density. Am J Clin Nutr. 2000 Jun;71(6):1555-62. [PubMed:10837298 ]
Mares-Perlman JA, Millen AE, Ficek TL, Hankinson SE: The body of evidence to support a protective role for lutein and zeaxanthin in delaying chronic disease. Overview. J Nutr. 2002 Mar;132(3):518S-524S. [PubMed:11880585 ]
Reboul E, Abou L, Mikail C, Ghiringhelli O, Andre M, Portugal H, Jourdheuil-Rahmani D, Amiot MJ, Lairon D, Borel P: Lutein transport by Caco-2 TC-7 cells occurs partly by a facilitated process involving the scavenger receptor class B type I (SR-BI). Biochem J. 2005 Apr 15;387(Pt 2):455-61. [PubMed:15554873 ]
Park JS, Chew BP, Wong TS: Dietary lutein absorption from marigold extract is rapid in BALB/c mice. J Nutr. 1998 Oct;128(10):1802-6. [PubMed:9772152 ]
Chitchumroonchokchai C, Schwartz SJ, Failla ML: Assessment of lutein bioavailability from meals and a supplement using simulated digestion and caco-2 human intestinal cells. J Nutr. 2004 Sep;134(9):2280-6. [PubMed:15333717 ]
Eichler O, Sies H, Stahl W: Divergent optimum levels of lycopene, beta-carotene and lutein protecting against UVB irradiation in human fibroblastst. Photochem Photobiol. 2002 May;75(5):503-6. [PubMed:12017476 ]
Chen L, Collins XH, Tabatabai LB, White WS: Use of a 13C tracer to investigate lutein as a ligand for plasma transthyretin in humans. Lipids. 2005 Oct;40(10):1013-22. [PubMed:16382573 ]
Granado F, Olmedilla B, Blanco I: Nutritional and clinical relevance of lutein in human health. Br J Nutr. 2003 Sep;90(3):487-502. [PubMed:14513828 ]
Bruch-Gerharz D, Stahl W, Gerharz CD, Megahed M, Wingerath T, Sies H, Ruzicka T: Accumulation of the xanthophyll lutein in skin amyloid deposits of systemic amyloidosis (al type). J Invest Dermatol. 2001 Jan;116(1):196-7. [PubMed:11168818 ]
Goodrow EF, Wilson TA, Houde SC, Vishwanathan R, Scollin PA, Handelman G, Nicolosi RJ: Consumption of one egg per day increases serum lutein and zeaxanthin concentrations in older adults without altering serum lipid and lipoprotein cholesterol concentrations. J Nutr. 2006 Oct;136(10):2519-24. [PubMed:16988120 ]
Moeller SM, Jacques PF, Blumberg JB: The potential role of dietary xanthophylls in cataract and age-related macular degeneration. J Am Coll Nutr. 2000 Oct;19(5 Suppl):522S-527S. [PubMed:11023002 ]
Ma L, Lin XM: Effects of lutein and zeaxanthin on aspects of eye health. J Sci Food Agric. 2010 Jan 15;90(1):2-12. doi: 10.1002/jsfa.3785. [PubMed:20355006 ]
Namitha KK, Negi PS: Chemistry and biotechnology of carotenoids. Crit Rev Food Sci Nutr. 2010 Sep;50(8):728-60. doi: 10.1080/10408398.2010.499811. [PubMed:20830634 ]

Showing metabocard for Lutein (HMDB0003233)

MOL for HMDB0003233 (Lutein)

3D MOL for HMDB0003233 (Lutein)

3D SDF for HMDB0003233 (Lutein)

3D-SDF for HMDB0003233 (Lutein)

PDB for HMDB0003233 (Lutein)

3D PDB for HMDB0003233 (Lutein)

SMILES for HMDB0003233 (Lutein)

INCHI for HMDB0003233 (Lutein)

Structure for HMDB0003233 (Lutein)

3D Structure for HMDB0003233 (Lutein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra