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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 22:35:58 UTC

Update Date

2021-09-23 22:35:59 UTC

HMDB ID

HMDB0303013

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lutein ester

Description

Lutein, also known as all-trans-lutein or 3,3'-dihydroxy-alpha-carotene, is a member of the class of compounds known as xanthophylls. Xanthophylls 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. Lutein is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Lutein can be found in dandelion and ginkgo nuts, which makes lutein a potential biomarker for the consumption of these food products. Lutein can be found primarily in blood, as well as throughout most human tissues. Lutein exists in all eukaryotes, ranging from yeast to humans. Lutein is isomeric with zeaxanthin, differing only in the placement of one double bond. Lutein and zeaxanthin can be interconverted in the body through an intermediate called meso-zeaxanthin. The principal natural stereoisomer of lutein is (3R,3‚Ä≤R,6‚Ä≤R)-beta,epsilon-carotene-3,3‚Ä≤-diol. Lutein is a lipophilic molecule and is generally insoluble in water. The presence of the long chromophore of conjugated double bonds (polyene chain) provides the distinctive light-absorbing properties. The polyene chain is susceptible to oxidative degradation by light or heat and is chemically unstable in acids .

Structure

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


  Mrv0541 02231219402D          

 42 43  0  0  1  0            999 V2000
   32.5681   -7.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1376  -24.3488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5981  -22.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0106  -21.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6950  -10.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1075   -9.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1376  -19.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5666  -16.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1390  -14.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5681  -12.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1390   -9.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5666  -21.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4232  -22.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2825   -9.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5681   -8.2610    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1376  -21.8738    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1376  -23.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2825   -8.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4232  -23.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8535   -8.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8522  -19.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2811  -17.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.8522  -23.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  1  0  0  0
  2 17  1  0  0  0  0
  3 13  1  0  0  0  0
  4 13  1  0  0  0  0
  5 14  1  0  0  0  0
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 38 41  1  0  0  0  0
 39 41  2  0  0  0  0
 40 42  2  0  0  0  0
M  END

HMDB0303013
     RDKit          3D
Lutein ester
 98 99  0  0  0  0  0  0  0  0999 V2000
   10.9436    3.0798   -2.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9586    1.9821   -1.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2173    2.2840   -1.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2668    1.2062   -1.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3494    1.6785   -0.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5943    0.1210   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3998   -0.4366   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3847    0.5971   -1.7918 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2007    0.6512   -0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9887    0.4052   -1.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02231219402D          

 42 43  0  0  1  0            999 V2000
   32.5681   -7.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1376  -24.3488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5981  -22.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0106  -21.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6950  -10.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1075   -9.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1376  -19.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5666  -16.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1390  -14.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5681  -12.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1390   -9.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5666  -21.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4232  -22.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2825   -9.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5681   -8.2610    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1376  -21.8738    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1376  -23.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2825   -8.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4232  -23.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8535   -8.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8522  -19.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2811  -17.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4246  -14.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8535  -11.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1376  -21.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8522  -20.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5666  -19.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1390  -12.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9956  -16.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7101  -14.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2811  -18.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4246  -13.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5666  -18.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1390  -13.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9956  -16.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7101  -15.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8535  -11.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5681  -10.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8535   -9.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8522  -22.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5681   -9.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8522  -23.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  1  0  0  0
  2 17  1  0  0  0  0
  3 13  1  0  0  0  0
  4 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 14  1  0  0  0  0
  7 21  1  0  0  0  0
  8 22  1  0  0  0  0
  9 23  1  0  0  0  0
 10 24  1  0  0  0  0
 11 39  1  0  0  0  0
 12 40  1  0  0  0  0
 13 16  1  0  0  0  0
 13 19  1  0  0  0  0
 14 18  1  0  0  0  0
 14 41  1  0  0  0  0
 15 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 25  1  1  0  0  0
 16 40  1  0  0  0  0
 17 19  1  0  0  0  0
 17 42  1  0  0  0  0
 20 39  1  0  0  0  0
 21 26  1  0  0  0  0
 21 27  2  0  0  0  0
 22 29  2  0  0  0  0
 22 31  1  0  0  0  0
 23 30  2  0  0  0  0
 23 32  1  0  0  0  0
 24 28  2  0  0  0  0
 24 37  1  0  0  0  0
 25 26  2  0  0  0  0
 27 33  1  0  0  0  0
 28 34  1  0  0  0  0
 29 35  1  0  0  0  0
 30 36  1  0  0  0  0
 31 33  2  0  0  0  0
 32 34  2  0  0  0  0
 35 36  2  0  0  0  0
 37 38  2  0  0  0  0
 38 41  1  0  0  0  0
 39 41  2  0  0  0  0
 40 42  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303013

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]2C(C)=CC(O)CC2(C)C)C(C)(C)C1

> <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-RTIVXWJOSA-N

> <FORMULA>
C40H56O2

> <MOLECULAR_WEIGHT>
568.8714

> <EXACT_MASS>
568.428031036

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
73.3787748950564

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303013
     RDKit          3D
Lutein ester
 98 99  0  0  0  0  0  0  0  0999 V2000
   10.9436    3.0798   -2.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9586    1.9821   -1.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2173    2.2840   -1.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2668    1.2062   -1.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3494    1.6785   -0.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5943    0.1210   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3998   -0.4366   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8736   -1.2726   -2.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7110   -1.3825   -0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3847    0.5971   -1.7918 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2007    0.6512   -0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9887    0.4052   -1.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8043    0.4456   -0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9800    0.7215    0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5995    0.2099   -0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3800    0.2332   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2074    0.0132   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9527    0.0188   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    0.2752    1.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932   -0.1823   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441   -0.1721    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047   -0.3345   -0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8366   -0.3315    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -0.4428   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9999   -0.5703   -1.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2473   -0.4348    0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4479   -0.4958   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6097   -0.4820    0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8591   -0.4884    0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0416   -0.5067   -1.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9797   -0.4912    1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2390   -0.4549    0.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4383   -0.4507    1.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6110   -0.3830    0.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5049   -0.3274   -0.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9411   -0.3381    1.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0294    0.1445    2.8322 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.8125   -0.7008    3.6334 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6983    0.4714    3.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6270   -0.5433    2.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1238   -1.9503    3.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4446   -0.2737    3.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0038    2.8389   -1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3908    4.0157   -1.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7886    3.1657   -3.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5722    3.2972   -1.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5460    0.7498   -2.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6781    2.5391   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2746   -0.6888   -0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2616    0.6247    0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5242   -0.8198   -3.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9747   -1.2761   -2.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4944   -2.3128   -2.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3308   -0.8484    0.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4315   -2.1980   -0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8838   -1.9193   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0395    0.3635   -2.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3757    0.9088    0.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8398    0.1547   -2.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1868    0.2909    1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0390    1.8126    1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9348    0.2177    1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454   -0.0078   -2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533    0.4406    0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2415   -0.1848   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151    0.5605    1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559    1.1519    1.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4656   -0.5940    1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8275   -0.3429   -1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5225   -0.0407    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417   -0.4633   -1.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479   -0.2366    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2400   -1.3489   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9299   -0.8731   -2.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5920    0.3686   -2.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111   -0.3747    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5150   -0.5591   -1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4992   -0.4692    1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0423   -0.1238   -1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0416   -1.5746   -1.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2527    0.0822   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7615   -0.5399    2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3755   -0.4162   -0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5265   -0.2807   -1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0095    0.6216   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0474   -1.2271   -1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5626    0.3438    0.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4910   -1.3244    1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6078    1.1199    2.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2472   -0.1446    4.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7886    0.5122    4.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3655    1.4511    3.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4386   -2.6590    2.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1334   -2.1655    3.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9779   -2.0351    4.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8265   -0.0921    4.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8348    0.5966    3.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8252   -1.1794    3.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 40 41  1  0
 40 42  1  0
 10  2  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
  5 48  1  0
  6 49  1  0
  6 50  1  0
  8 51  1  0
  8 52  1  0
  8 53  1  0
  9 54  1  0
  9 55  1  0
  9 56  1  0
 10 57  1  6
 11 58  1  0
 12 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
 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                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      60.794 -13.881   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      48.790 -45.451   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      45.916 -41.601   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      46.686 -40.267   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      62.897 -19.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      63.667 -17.731   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      48.790 -36.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      51.458 -31.591   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      58.126 -27.741   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      60.794 -23.121   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      58.126 -18.501   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      51.458 -40.831   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      47.457 -41.601   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      62.127 -17.731   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      60.794 -15.421   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      48.790 -40.831   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      48.790 -43.911   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      62.127 -16.191   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      47.457 -43.141   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      59.460 -16.191   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      50.124 -36.981   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      52.791 -32.361   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      56.793 -26.971   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      59.460 -22.351   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      48.790 -39.291   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      50.124 -38.521   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      51.458 -36.211   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      58.126 -23.121   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      54.125 -31.591   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      55.459 -27.741   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      52.791 -33.901   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      56.793 -25.431   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      51.458 -34.671   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      58.126 -24.661   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      54.125 -30.051   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      55.459 -29.281   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      59.460 -20.811   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      60.794 -20.041   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      59.460 -17.731   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      50.124 -41.601   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      60.794 -18.501   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      50.124 -43.141   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   17                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6   14                                                            
CONECT    7   21                                                            
CONECT    8   22                                                            
CONECT    9   23                                                            
CONECT   10   24                                                            
CONECT   11   39                                                            
CONECT   12   40                                                            
CONECT   13    3    4   16   19                                             
CONECT   14    5    6   18   41                                             
CONECT   15    1   18   20                                                  
CONECT   16   13   25   40                                                  
CONECT   17    2   19   42                                                  
CONECT   18   14   15                                                       
CONECT   19   13   17                                                       
CONECT   20   15   39                                                       
CONECT   21    7   26   27                                                  
CONECT   22    8   29   31                                                  
CONECT   23    9   30   32                                                  
CONECT   24   10   28   37                                                  
CONECT   25   16   26                                                       
CONECT   26   21   25                                                       
CONECT   27   21   33                                                       
CONECT   28   24   34                                                       
CONECT   29   22   35                                                       
CONECT   30   23   36                                                       
CONECT   31   22   33                                                       
CONECT   32   23   34                                                       
CONECT   33   27   31                                                       
CONECT   34   28   32                                                       
CONECT   35   29   36                                                       
CONECT   36   30   35                                                       
CONECT   37   24   38                                                       
CONECT   38   37   41                                                       
CONECT   39   11   20   41                                                  
CONECT   40   12   16   42                                                  
CONECT   41   14   38   39                                                  
CONECT   42   17   40                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

COMPND    HMDB0303013
HETATM    1  C1  UNL     1      10.944   3.080  -2.023  1.00  0.00           C  
HETATM    2  C2  UNL     1      11.959   1.982  -1.821  1.00  0.00           C  
HETATM    3  C3  UNL     1      13.217   2.284  -1.701  1.00  0.00           C  
HETATM    4  C4  UNL     1      14.267   1.206  -1.493  1.00  0.00           C  
HETATM    5  O1  UNL     1      15.349   1.679  -0.799  1.00  0.00           O  
HETATM    6  C5  UNL     1      13.594   0.121  -0.654  1.00  0.00           C  
HETATM    7  C6  UNL     1      12.400  -0.437  -1.372  1.00  0.00           C  
HETATM    8  C7  UNL     1      12.874  -1.273  -2.533  1.00  0.00           C  
HETATM    9  C8  UNL     1      11.711  -1.382  -0.375  1.00  0.00           C  
HETATM   10  C9  UNL     1      11.385   0.597  -1.792  1.00  0.00           C  
HETATM   11  C10 UNL     1      10.201   0.651  -0.886  1.00  0.00           C  
HETATM   12  C11 UNL     1       8.989   0.405  -1.311  1.00  0.00           C  
HETATM   13  C12 UNL     1       7.804   0.446  -0.455  1.00  0.00           C  
HETATM   14  C13 UNL     1       7.980   0.722   0.981  1.00  0.00           C  
HETATM   15  C14 UNL     1       6.600   0.210  -0.984  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.380   0.233  -0.200  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.207   0.013  -0.771  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.953   0.019  -0.063  1.00  0.00           C  
HETATM   19  C18 UNL     1       2.876   0.275   1.384  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.793  -0.182  -0.693  1.00  0.00           C  
HETATM   21  C20 UNL     1       0.544  -0.172   0.073  1.00  0.00           C  
HETATM   22  C21 UNL     1      -0.605  -0.334  -0.601  1.00  0.00           C  
HETATM   23  C22 UNL     1      -1.837  -0.332   0.113  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.994  -0.443  -0.507  1.00  0.00           C  
HETATM   25  C24 UNL     1      -3.000  -0.570  -1.971  1.00  0.00           C  
HETATM   26  C25 UNL     1      -4.247  -0.435   0.254  1.00  0.00           C  
HETATM   27  C26 UNL     1      -5.448  -0.496  -0.291  1.00  0.00           C  
HETATM   28  C27 UNL     1      -6.610  -0.482   0.573  1.00  0.00           C  
HETATM   29  C28 UNL     1      -7.859  -0.488   0.114  1.00  0.00           C  
HETATM   30  C29 UNL     1      -8.042  -0.507  -1.347  1.00  0.00           C  
HETATM   31  C30 UNL     1      -8.980  -0.491   1.095  1.00  0.00           C  
HETATM   32  C31 UNL     1     -10.239  -0.455   0.752  1.00  0.00           C  
HETATM   33  C32 UNL     1     -11.438  -0.451   1.551  1.00  0.00           C  
HETATM   34  C33 UNL     1     -12.611  -0.383   0.835  1.00  0.00           C  
HETATM   35  C34 UNL     1     -12.505  -0.327  -0.651  1.00  0.00           C  
HETATM   36  C35 UNL     1     -13.941  -0.338   1.426  1.00  0.00           C  
HETATM   37  C36 UNL     1     -14.029   0.145   2.832  1.00  0.00           C  
HETATM   38  O2  UNL     1     -14.813  -0.701   3.633  1.00  0.00           O  
HETATM   39  C37 UNL     1     -12.698   0.471   3.419  1.00  0.00           C  
HETATM   40  C38 UNL     1     -11.627  -0.543   2.997  1.00  0.00           C  
HETATM   41  C39 UNL     1     -12.124  -1.950   3.371  1.00  0.00           C  
HETATM   42  C40 UNL     1     -10.445  -0.274   3.846  1.00  0.00           C  
HETATM   43  H1  UNL     1      10.004   2.839  -1.498  1.00  0.00           H  
HETATM   44  H2  UNL     1      11.391   4.016  -1.684  1.00  0.00           H  
HETATM   45  H3  UNL     1      10.789   3.166  -3.114  1.00  0.00           H  
HETATM   46  H4  UNL     1      13.572   3.297  -1.740  1.00  0.00           H  
HETATM   47  H5  UNL     1      14.546   0.750  -2.456  1.00  0.00           H  
HETATM   48  H6  UNL     1      15.678   2.539  -1.209  1.00  0.00           H  
HETATM   49  H7  UNL     1      14.275  -0.689  -0.410  1.00  0.00           H  
HETATM   50  H8  UNL     1      13.262   0.625   0.291  1.00  0.00           H  
HETATM   51  H9  UNL     1      12.524  -0.820  -3.502  1.00  0.00           H  
HETATM   52  H10 UNL     1      13.975  -1.276  -2.553  1.00  0.00           H  
HETATM   53  H11 UNL     1      12.494  -2.313  -2.425  1.00  0.00           H  
HETATM   54  H12 UNL     1      11.331  -0.848   0.504  1.00  0.00           H  
HETATM   55  H13 UNL     1      12.432  -2.198  -0.095  1.00  0.00           H  
HETATM   56  H14 UNL     1      10.884  -1.919  -0.904  1.00  0.00           H  
HETATM   57  H15 UNL     1      11.039   0.363  -2.818  1.00  0.00           H  
HETATM   58  H16 UNL     1      10.376   0.909   0.155  1.00  0.00           H  
HETATM   59  H17 UNL     1       8.840   0.155  -2.368  1.00  0.00           H  
HETATM   60  H18 UNL     1       7.187   0.291   1.605  1.00  0.00           H  
HETATM   61  H19 UNL     1       8.039   1.813   1.201  1.00  0.00           H  
HETATM   62  H20 UNL     1       8.935   0.218   1.344  1.00  0.00           H  
HETATM   63  H21 UNL     1       6.545  -0.008  -2.064  1.00  0.00           H  
HETATM   64  H22 UNL     1       5.453   0.441   0.846  1.00  0.00           H  
HETATM   65  H23 UNL     1       4.242  -0.185  -1.861  1.00  0.00           H  
HETATM   66  H24 UNL     1       3.815   0.560   1.872  1.00  0.00           H  
HETATM   67  H25 UNL     1       2.156   1.152   1.495  1.00  0.00           H  
HETATM   68  H26 UNL     1       2.466  -0.594   1.968  1.00  0.00           H  
HETATM   69  H27 UNL     1       1.827  -0.343  -1.749  1.00  0.00           H  
HETATM   70  H28 UNL     1       0.522  -0.041   1.142  1.00  0.00           H  
HETATM   71  H29 UNL     1      -0.542  -0.463  -1.671  1.00  0.00           H  
HETATM   72  H30 UNL     1      -1.848  -0.237   1.188  1.00  0.00           H  
HETATM   73  H31 UNL     1      -2.240  -1.349  -2.262  1.00  0.00           H  
HETATM   74  H32 UNL     1      -3.930  -0.873  -2.439  1.00  0.00           H  
HETATM   75  H33 UNL     1      -2.592   0.369  -2.441  1.00  0.00           H  
HETATM   76  H34 UNL     1      -4.211  -0.375   1.356  1.00  0.00           H  
HETATM   77  H35 UNL     1      -5.515  -0.559  -1.367  1.00  0.00           H  
HETATM   78  H36 UNL     1      -6.499  -0.469   1.664  1.00  0.00           H  
HETATM   79  H37 UNL     1      -9.042  -0.124  -1.621  1.00  0.00           H  
HETATM   80  H38 UNL     1      -8.042  -1.575  -1.689  1.00  0.00           H  
HETATM   81  H39 UNL     1      -7.253   0.082  -1.878  1.00  0.00           H  
HETATM   82  H40 UNL     1      -8.761  -0.540   2.135  1.00  0.00           H  
HETATM   83  H41 UNL     1     -10.375  -0.416  -0.353  1.00  0.00           H  
HETATM   84  H42 UNL     1     -13.526  -0.281  -1.064  1.00  0.00           H  
HETATM   85  H43 UNL     1     -12.010   0.622  -0.974  1.00  0.00           H  
HETATM   86  H44 UNL     1     -12.047  -1.227  -1.100  1.00  0.00           H  
HETATM   87  H45 UNL     1     -14.563   0.344   0.753  1.00  0.00           H  
HETATM   88  H46 UNL     1     -14.491  -1.324   1.359  1.00  0.00           H  
HETATM   89  H47 UNL     1     -14.608   1.120   2.825  1.00  0.00           H  
HETATM   90  H48 UNL     1     -15.247  -0.145   4.354  1.00  0.00           H  
HETATM   91  H49 UNL     1     -12.789   0.512   4.525  1.00  0.00           H  
HETATM   92  H50 UNL     1     -12.366   1.451   3.044  1.00  0.00           H  
HETATM   93  H51 UNL     1     -11.439  -2.659   2.868  1.00  0.00           H  
HETATM   94  H52 UNL     1     -13.133  -2.165   3.056  1.00  0.00           H  
HETATM   95  H53 UNL     1     -11.978  -2.035   4.479  1.00  0.00           H  
HETATM   96  H54 UNL     1     -10.826  -0.092   4.942  1.00  0.00           H  
HETATM   97  H55 UNL     1      -9.835   0.597   3.600  1.00  0.00           H  
HETATM   98  H56 UNL     1      -9.825  -1.179   3.943  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

HMDB0303013
     RDKit          3D
Lutein ester
 98 99  0  0  0  0  0  0  0  0999 V2000
   10.9436    3.0798   -2.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9586    1.9821   -1.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2173    2.2840   -1.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2668    1.2062   -1.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3494    1.6785   -0.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5943    0.1210   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3998   -0.4366   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8736   -1.2726   -2.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7110   -1.3825   -0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3847    0.5971   -1.7918 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2007    0.6512   -0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9887    0.4052   -1.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8043    0.4456   -0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9800    0.7215    0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5995    0.2099   -0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3800    0.2332   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2074    0.0132   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9527    0.0188   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    0.2752    1.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932   -0.1823   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441   -0.1721    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047   -0.3345   -0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8366   -0.3315    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -0.4428   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9999   -0.5703   -1.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2473   -0.4348    0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4479   -0.4958   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6097   -0.4820    0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8591   -0.4884    0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0416   -0.5067   -1.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9797   -0.4912    1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2390   -0.4549    0.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4383   -0.4507    1.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -12.6983    0.4714    3.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6270   -0.5433    2.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1238   -1.9503    3.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4446   -0.2737    3.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0038    2.8389   -1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3908    4.0157   -1.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
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   15.6781    2.5391   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2746   -0.6888   -0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2415   -0.1848   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151    0.5605    1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559    1.1519    1.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4656   -0.5940    1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2400   -1.3489   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9299   -0.8731   -2.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5920    0.3686   -2.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111   -0.3747    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5150   -0.5591   -1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4992   -0.4692    1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0423   -0.1238   -1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0416   -1.5746   -1.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2527    0.0822   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7615   -0.5399    2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3755   -0.4162   -0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5265   -0.2807   -1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.8348    0.5966    3.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8252   -1.1794    3.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3'-Dihydroxy-alpha-carotene	HMDB
all-trans-(+)-Xanthophyll	HMDB
all-trans-Lutein	HMDB
beta,epsilon-Carotene-3,3'-diol	HMDB
bo-Xan	HMDB
Lutein ester	HMDB
Luteine	HMDB
trans-Lutein	HMDB
Vegetable lutein	HMDB
Vegetable luteol	HMDB
Lutein F	MeSH, HMDB
Lutein g	MeSH, HMDB
Lutein, gamma	MeSH, HMDB
gamma Lutein	MeSH, HMDB

Chemical Formula

C₄₀H₅₆O₂

Average Molecular Weight

568.8714

Monoisotopic Molecular Weight

568.428031036

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]2C(C)=CC(O)CC2(C)C)C(C)(C)C1

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-RTIVXWJOSA-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

Ontology

Not Available

Blood (HMDB: HMDB0303013)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0303013)

Nerve cell (HMDB: HMDB0303013)

Adrenal gland (HMDB: HMDB0303013)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0303013)

Source

Exogenous

Food

Food (HMDB: HMDB0303013)

Herb and spice

Herb

Dandelion (FooDB: FOOD00181)

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Fruit

Fruits (HMDB: HMDB0303013)

Vegetable

Vegetables (HMDB: HMDB0303013)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0303013)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0303013)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0303013)

Cellular process

Cell signaling (HMDB: HMDB0303013)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0303013)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0303013)

Nutrient

Nutrient (HMDB: HMDB0303013)

Industrial application

Emulsifier (HMDB: HMDB0303013)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0303013)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	73.38 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
AllCCS	[M+H]+	259.284	32859911
AllCCS	[M+H-H2O]+	257.578	32859911
AllCCS	[M+Na]+	261.311	32859911
AllCCS	[M+NH4]+	260.859	32859911
AllCCS	[M-H]-	230.987	32859911
AllCCS	[M+Na-2H]-	234.578	32859911
AllCCS	[M+HCOO]-	238.671	32859911
DeepCCS	[M+H]+	254.591	30932474
DeepCCS	[M-H]-	252.766	30932474
DeepCCS	[M-2H]-	286.008	30932474
DeepCCS	[M+Na]+	260.197	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lutein ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-1000190000-79574985e26da720cbd6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lutein ester GC-MS (1 TMS) - 70eV, Positive	splash10-004i-3100039000-baee6b30a2822c061477	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 10V, Positive-QTOF	splash10-0gb9-0111190000-56a7b3ad9850d88a093a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 20V, Positive-QTOF	splash10-0frt-0729640000-fa9f79f8a73fa60b8abf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 40V, Positive-QTOF	splash10-0002-2439510000-8c70ee5c9af7440a4672	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 10V, Negative-QTOF	splash10-014i-0000090000-e64043a148b331ba05a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 20V, Negative-QTOF	splash10-014i-0000090000-a48901fc52e8e64be250	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 40V, Negative-QTOF	splash10-0udr-0522590000-ed879e2e3d350ac0e502	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 10V, Positive-QTOF	splash10-014i-0043490000-6587386703e49b5ed9a0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 20V, Positive-QTOF	splash10-0gz0-0656890000-78ff1269d16692ec007a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 40V, Positive-QTOF	splash10-1030-0546900000-f40ee2500358463a4322	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 10V, Negative-QTOF	splash10-014i-0000090000-7d1de7a1b619e7f7ad6c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 20V, Negative-QTOF	splash10-014i-0342490000-0b5700b22b94c921a096	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lutein ester 40V, Negative-QTOF	splash10-02a9-0649570000-12d271b2950633507bac	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007276

KNApSAcK ID

C00003774

Chemspider ID

4938343

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6433159

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Lutein ester (HMDB0303013)

MOL for HMDB0303013 (Lutein ester)

3D MOL for HMDB0303013 (Lutein ester)

3D SDF for HMDB0303013 (Lutein ester)

3D-SDF for HMDB0303013 (Lutein ester)

PDB for HMDB0303013 (Lutein ester)

3D PDB for HMDB0303013 (Lutein ester)

SMILES for HMDB0303013 (Lutein ester)

INCHI for HMDB0303013 (Lutein ester)

Structure for HMDB0303013 (Lutein ester)

3D Structure for HMDB0303013 (Lutein ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra