NP-MRD: Showing NP-Card for Lutein 5,6-epoxide (NP0049898)

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Record Information

Version

2.0

Created at

2022-03-17 21:19:53 UTC

Updated at

2022-03-17 21:19:53 UTC

NP-MRD ID

NP0049898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lutein 5,6-epoxide

Description

Lutein 5,6-epoxide, also known as taraxanthin, 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. Thus, lutein 5,6-epoxide is considered to be an isoprenoid lipid molecule. Lutein 5,6-epoxide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Lutein 5,6-epoxide has been detected, but not quantified in, several different foods, such as common grapes, rices, sunflowers, dandelions, and garden tomato (var.). This could make lutein 5,6-epoxide a potential biomarker for the consumption of these foods. Lutein 5,6-epoxide is found in Brassica napus, Brassica oleracea, Caltha palustris, Camellia sasanqua, Citrus junos, Citrus wilsonii, Cladonia firma, Cladonia turgida, Cladophora fracta, Cucurbita maxima, Cuscuta australis , Cytisus scoparius, Diospyros kaki, Equisetum palustre, Eutreptiella gymnastica, Holothuria tubulosa, Impatiens nolitangere, Metasequoia glyptostroboides, Mimosa aculeaticarpa, Sohaghnum palustre, Terminalia catappa, Tussilago farfara , Umbilicaria rigida and Urtica dioica . An epoxycarotenol derivative of lutein.

Structure

MOL SDF PDB SMILES InChI

lutein 5,6-epoxide
  Mrv1572001071617052D          
  Marvin  03020616482D          
 43 45  0  0  0  0            999 V2000
   -6.7893   -0.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0748    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5038   -1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2182   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3603   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6459    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9314   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6459    1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5025   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880    1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3591    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7844   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7844   -1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2133   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6422   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6422   -1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7857    0.1816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5001    1.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2146    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0748   -1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712    1.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7857    1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9163    0.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5038    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0913    0.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0876   -0.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5001   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9126   -0.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2146    1.0066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9291    1.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2182   -1.0559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9327   -1.4684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7893   -1.0559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0748   -0.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 42  1  0  0  0  0
  1 33  1  0  0  0  0
  1  2  1  1  0  0  0
 42  3  1  0  0  0  0
 33  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3 40  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 26 25  1  1  0  0  0
 26 31  1  0  0  0  0
 26 36  1  0  0  0  0
 31 27  2  0  0  0  0
 36 28  1  0  0  0  0
 27 38  1  0  0  0  0
  4 40  1  0  0  0  0
 28 38  1  0  0  0  0
 42 29  1  1  0  0  0
 31 30  1  0  0  0  0
 33 32  1  0  0  0  0
 33 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  1  0  0  0  0
 38 39  1  6  0  0  0
 40 41  1  1  0  0  0
 42 43  1  0  0  0  0
  1 43  1  0  0  0  0
M  END

lutein 5,6-epoxide
  Mrv1572001071617052D          
  Marvin  03020616482D          
 43 45  0  0  0  0            999 V2000
   -6.7893   -0.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0748    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5038   -1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2182   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3603   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6459    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9314   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6459    1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5025   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880    1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3591    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7844   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7844   -1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2133   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6422   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6422   -1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7857    0.1816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5001    1.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2146    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0748   -1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712    1.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7857    1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9163    0.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5038    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0913    0.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0876   -0.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5001   -0.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9126   -0.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2146    1.0066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9291    1.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2182   -1.0559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9327   -1.4684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7893   -1.0559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0748   -0.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 42  1  0  0  0  0
  1 33  1  0  0  0  0
  1  2  1  1  0  0  0
 42  3  1  0  0  0  0
 33  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3 40  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 26 25  1  1  0  0  0
 26 31  1  0  0  0  0
 26 36  1  0  0  0  0
 31 27  2  0  0  0  0
 36 28  1  0  0  0  0
 27 38  1  0  0  0  0
  4 40  1  0  0  0  0
 28 38  1  0  0  0  0
 42 29  1  1  0  0  0
 31 30  1  0  0  0  0
 33 32  1  0  0  0  0
 33 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  1  0  0  0  0
 38 39  1  6  0  0  0
 40 41  1  1  0  0  0
 42 43  1  0  0  0  0
  1 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049898

> <DATABASE_NAME>
NP-MRD

> <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/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-25,34-36,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35-,36-,39+,40-/m0/s1

> <INCHI_KEY>
DYUUPIKEWLHQGQ-FJOIUHRLSA-N

> <FORMULA>
C40H56O3

> <MOLECULAR_WEIGHT>
584.885

> <EXACT_MASS>
584.422945663

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
73.60307485636955

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-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]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

> <ALOGPS_LOGP>
8.39

> <JCHEM_LOGP>
8.003617862999999

> <ALOGPS_LOGS>
-5.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.21727233987641

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.139684034106125

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3910077414822246

> <JCHEM_POLAR_SURFACE_AREA>
52.989999999999995

> <JCHEM_REFRACTIVITY>
193.75150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.24e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lutein 5,6-epoxide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: lutein 5,6-epoxide                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0     -12.673  -0.431   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.340   0.339   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.007  -2.741   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -15.341  -0.431   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.006  -0.431   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.672   0.339   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.339  -0.431   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.672   1.879   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.005   0.339   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.671  -0.431   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.338   0.339   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.004  -0.431   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.338   1.879   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.670   0.339   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.663  -0.431   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.997   0.339   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.331  -0.431   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.664   0.339   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.331  -1.971   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.998  -0.431   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.332   0.339   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.665  -0.431   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.999   0.339   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.665  -1.971   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.333  -0.431   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.667   0.339   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.000   2.649   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.334   0.339   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.340  -2.741   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.333   2.649   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.667   1.879   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -14.777   1.673   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -14.007   0.339   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -13.237   1.673   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.230  -1.765   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.000  -0.431   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.770  -1.765   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      15.334   1.879   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      16.668   2.649   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0     -15.341  -1.971   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -16.674  -2.741   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0     -12.673  -1.971   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0     -11.340  -1.201   0.000  0.00  0.00           O+0
CONECT    1   42   33    2   43                                             
CONECT    2    1    5                                                       
CONECT    3   42   40                                                       
CONECT    4   33   40                                                       
CONECT    5    2    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22                                                            
CONECT   25   23   26                                                       
CONECT   26   25   31   36                                                  
CONECT   27   31   38                                                       
CONECT   28   36   38                                                       
CONECT   29   42                                                            
CONECT   30   31                                                            
CONECT   31   26   27   30                                                  
CONECT   32   33                                                            
CONECT   33    1    4   32   34                                             
CONECT   34   33                                                            
CONECT   35   36                                                            
CONECT   36   26   28   35   37                                             
CONECT   37   36                                                            
CONECT   38   27   28   39                                                  
CONECT   39   38                                                            
CONECT   40    3    4   41                                                  
CONECT   41   40                                                            
CONECT   42    1    3   29   43                                             
CONECT   43   42    1                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Value	Source
Taraxanthin	HMDB

Chemical Formula

C₄₀H₅₆O₃

Average Mass

584.8850 Da

Monoisotopic Mass

584.42295 Da

IUPAC Name

(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-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]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

Traditional Name

lutein 5,6-epoxide

CAS Registry Number

28368-08-3

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/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C

InChI Identifier

InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-25,34-36,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35-,36-,39+,40-/m0/s1

InChI Key

DYUUPIKEWLHQGQ-FJOIUHRLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brassica napus	LOTUS Database	35616633
Brassica oleracea	LOTUS Database	35616633
Caltha palustris	LOTUS Database	35616633
Camellia sasanqua	LOTUS Database	35616633
Citrus junos	LOTUS Database	35616633
Citrus wilsonii	Plant	KNApSAcK
Cladonia firma	LOTUS Database	35616633
Cladonia turgida	LOTUS Database	35616633
Cladophora fracta	LOTUS Database	35616633
Cucurbita maxima	LOTUS Database	35616633
Cuscuta australis	Plant	KNApSAcK
Cytisus scoparius	LOTUS Database	35616633
Diospyros kaki	LOTUS Database	35616633
Equisetum palustre	LOTUS Database	35616633
Eutreptiella gymnastica	LOTUS Database	35616633
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Holothuria tubulosa	LOTUS Database	35616633
Impatiens noli-tangere	Plant	KNApSAcK
Ipomoea aquatica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Metasequoia glyptostroboides	LOTUS Database	35616633
Mimosa aculeaticarpa	LOTUS Database	35616633
Oryza sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sohaghnum palustre	-	KNApSAcK
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Taraxacum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Terminalia catappa	LOTUS Database	35616633
Tussilago farfara	Plant	KNApSAcK
Umbilicaria rigida	LOTUS Database	35616633
Urtica dioica	Plant	KNApSAcK
Vitis	FooDB	PHYTOHUB
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Oxepane
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxycarotenol (CHEBI:27448 )
C40 isoprenoids (tetraterpenes) (C08602 )
Carotenoids (C08602 )
C40 isoprenoids (tetraterpenes) (LMPR01070275 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	8.39	ALOGPS
logP	8	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	193.75 m³·mol⁻¹	ChemAxon
Polarizability	73.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon