MiMeDB: Showing metabocard for Lutein (MMDBc0033531)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:52:27 UTC

Update Date

2024-04-30 20:11:58 UTC

Metabolite ID

MMDBc0033531

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 SDF PDB SMILES InChI


  Mrv1652311192105522D          

 42 43  0  0  1  0            999 V2000
   -2.8579  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -13.6125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.5749   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0039   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4233   -0.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0360   -1.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8171  -11.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565  -11.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 20  1  4  0  0  0
 22 23  2  0  0  0  0
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 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 25  1  4  0  0  0
 27 28  2  0  0  0  0
 29 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
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 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
  6 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
  2 42  1  0  0  0  0
M  END


  Mrv1652311192105522D          

 42 43  0  0  1  0            999 V2000
   -2.8579  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -13.6125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.5749   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0039   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4233   -0.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0360   -1.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8171  -11.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565  -11.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 20  1  4  0  0  0
 22 23  2  0  0  0  0
 24 23  1  4  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 25  1  4  0  0  0
 27 28  2  0  0  0  0
 29 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
  6 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
  2 42  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033531

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C=CC=C(C)C=C[C@H]1C(C)=CC(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+/m1/s1

> <INCHI_KEY>
KBPHJBAIARWVSC-JZBIMEDVSA-N

> <FORMULA>
C40H56O2

> <MOLECULAR_WEIGHT>
568.886

> <EXACT_MASS>
568.428031043

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
73.06422770518282

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-4-[(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>
195.06340000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.32e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-NOV-21         0                                  
HETATM    1  O   UNK     0      -5.335 -26.180   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.668 -25.410   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002 -26.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336 -25.410   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.669 -26.180   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336 -23.870   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.669 -23.100   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669 -21.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.003 -20.790   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -13.337 -21.560   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -20.005  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -21.339  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -22.673  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -24.006  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -25.340  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -25.340  -6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -26.674  -4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -26.674  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -28.007  -2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -25.340  -2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -24.006  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -23.190  -1.774   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -22.467  -3.026   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -8.992 -21.920   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -7.012 -21.920   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -6.668 -23.870   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   39                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   29   37   38                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39    6   40   41   42                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   39    2                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

Synonyms

Not Available

Molecular Formula

C₄₀H₅₆O₂

Average Mass

568.886

Monoisotopic Mass

568.428031043

IUPAC Name

(4R)-4-[(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

(4R)-4-[(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

CAS Registry Number

127-40-2

SMILES

CC(C=CC=C(C)C=C[C@H]1C(C)=CC(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+/m1/s1

InChI Key

KBPHJBAIARWVSC-JZBIMEDVSA-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

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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	73.06 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

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

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Diabetes mellitus type 1		Association	Human Blood	HMDB	16452910
Obesity		Association	Human Blood	HMDB	18997681

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.210	0.0900			uM	Adult (>18 years old)	Both	Type I diabetes	HMDB	16452910
Human Blood	Detected and Quantified	0.310	0.110			uM	Children (1 - 13 years old)	Not Specified	Obese	HMDB	18997681
Human Blood	Detected and Quantified	0.156				uM	Adult (>18 years old)	Both	Normal	HMDB	21272408
Human Blood	Detected and Quantified	0.163				uM	Adult (>18 years old)	Both	Normal	HMDB	21272408
Human Blood	Detected and Quantified	0.198				uM	Adult (>18 years old)	Both	Normal	HMDB	19022967
Human Blood	Detected and Quantified	0.38				uM	Adult (>18 years old)	Male	Normal	HMDB	16160701
Human Blood	Detected and Quantified	0.44				uM	Adult (>18 years old)	Female	Normal	HMDB	16160701
Human Blood	Detected and Quantified	0.140	0.0500			uM	Adult (>18 years old)	Male	Normal	HMDB	8922299
Human Blood	Detected and Quantified	0.174	0.0640			uM	Adult (>18 years old)	Male	Normal	HMDB	15946415
Human Blood	Detected and Quantified	0.180	0.0700			uM	Adult (>18 years old)	Female	Normal	HMDB	8922299
Human Blood	Detected and Quantified	0.180	0.0800			uM	Adult (>18 years old)	Female	Normal	HMDB	8922299
Human Blood	Detected and Quantified	0.180	0.0900			uM	Adult (>18 years old)	Both	Normal	HMDB	8922299
Human Blood	Detected and Quantified	0.200	0.100			uM	Adult (>18 years old)	Male	Normal	HMDB	8922299
Human Blood	Detected and Quantified	0.251	0.0980			uM	Adult (>18 years old)	Male	Normal	HMDB	15054421
Human Blood	Detected and Quantified	0.270	0.110			uM	Adult (>18 years old)	Female	Normal	HMDB	1512628
Human Blood	Detected and Quantified	0.280	0.100			uM	Adult (>18 years old)	Male	Normal	HMDB	1512628
Human Blood	Detected and Quantified	0.304	0.111			uM	Adult (>18 years old)	Female	Normal	HMDB	15054421
Human Blood	Detected and Quantified	0.310	0.160			uM	Adult (>18 years old)	Both	Normal	HMDB	16465196
Human Blood	Detected and Quantified	0.320	0.160			uM	Adult (>18 years old)	Female	Normal	HMDB	18813024
Human Blood	Detected and Quantified	0.320	0.230			uM	Children (1 - 13 years old)	Not Specified	Normal	HMDB	18997681
Human Blood	Detected and Quantified	0.329	0.123			uM	Adult (>18 years old)	Female	Normal	HMDB	10427874
Human Blood	Detected and Quantified	0.350	0.200			uM	Adult (>18 years old)	Both	Normal	HMDB	16465196
Human Blood	Detected and Quantified	0.49	0.23			uM	Adult (>18 years old)	Both	Normal	HMDB	15705230
Human Blood	Detected and Quantified	0.52		0.24	0.79	uM	Adult (>18 years old)	Both	Normal	HMDB	16046287
Human Blood	Detected and Quantified	0.53	0.26			uM	Adult (>18 years old)	Both	Normal	HMDB	15705230
Human Blood	Detected and Quantified	270.360	108.636			uM	Adult (>18 years old)	Female	Normal	HMDB	9568782
Human Blood	Detected and Quantified	275.633	98.792			uM	Adult (>18 years old)	Male	Normal	HMDB	9568782
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Eye lens	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Ovary	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Retina	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1097/00006324-199707000-00017. [PubMed:9293517 ]
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. doi: 10.1093/jn/128.10.1802. [PubMed:9772152 ]
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. doi: 10.1093/ajcn.70.2.247. [PubMed:10426702 ]
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 ]
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. doi: 10.1093/ajcn/71.6.1555. [PubMed:10837298 ]
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. doi: 10.1080/07315724.2000.10718975. [PubMed:11023002 ]
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. doi: 10.1046/j.1523-1747.2001.00228-2.x. [PubMed:11168818 ]
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. doi: 10.1093/jn/132.3.518S. [PubMed:11880585 ]
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. doi: 10.1562/0031-8655(2002)075<0503:dololc>2.0.co;2. [PubMed:12017476 ]
Granado F, Olmedilla B, Blanco I: Nutritional and clinical relevance of lutein in human health. Br J Nutr. 2003 Sep;90(3):487-502. doi: 10.1079/bjn2003927. [PubMed:14513828 ]
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. doi: 10.1093/jn/134.9.2280. [PubMed:15333717 ]
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. doi: 10.1042/BJ20040554. [PubMed:15554873 ]
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. doi: 10.1007/s00417-005-1176-z. Epub 2005 Oct 20. [PubMed:15909159 ]
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. doi: 10.1007/s11745-005-1464-3. [PubMed:16382573 ]
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. doi: 10.1093/jn/136.10.2519. [PubMed:16988120 ]
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. doi: 10.1093/jn/136.10.2568. [PubMed:16988128 ]
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 (MMDBc0033531)

MOL for #<Metabolite:0x00007fd0fd056fb0>

3D MOL for #<Metabolite:0x00007fd0fd056fb0>

3D SDF for #<Metabolite:0x00007fd0fd056fb0>

3D-SDF for #<Metabolite:0x00007fd0fd056fb0>

PDB for #<Metabolite:0x00007fd0fd056fb0>

3D PDB for #<Metabolite:0x00007fd0fd056fb0>

SMILES for #<Metabolite:0x00007fd0fd056fb0>

INCHI for #<Metabolite:0x00007fd0fd056fb0>

Structure for #<Metabolite:0x00007fd0fd056fb0>

3D Structure for #<Metabolite:0x00007fd0fd056fb0>