NP-MRD: Showing NP-Card for Canthaxanthin (NP0000007)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2006-05-22 15:12:37 UTC

Updated at

2021-08-19 20:22:27 UTC

NP-MRD ID

NP0000007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Canthaxanthin

Description

Canthaxanthin, also known as Cantaxanthin, Cantaxanthine, or Canthaxanthine is a keto-carotenoid, a pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. Canthaxanin is also classified as a xanthophyll. Xanthophylls are yellow pigments and form one of two major divisions of the carotenoid group; the other division is formed by the carotenes. Both are carotenoids. Xanthophylls and carotenes are similar in structure, but xanthophylls contain oxygen atoms while carotenes are purely hydrocarbons, which do not contain oxygen. Their content of oxygen causes xanthophylls to be more polar (in molecular structure) than carotenes and causes their separation from carotenes in many types of chromatography. (Carotenes are usually more orange in color than xanthophylls. Canthaxanthin is naturally found in bacteria, algae and some fungi. Canthaxanthin is associated with E number E161g and is approved for use as a food coloring agent in different countries, including the United States and the EU. Canthaxanthin is used as poultry feed additive to yield red color in skin and yolks. The European Union permits the use of canthaxanthin in feedstuff at a maximum content of 25 mg/kg of final feedstuff while the United States allows the use of this pigment in broiler chicken and salmonid fish feeds. Canthoxanthin was first isolated in edible chanterelle mushroom (Cantharellus cinnabarinus), from which it derived its name. It has also been found in green algae, bacteria, archea (a halophilic archaeon called Haloferax alexandrines), fungi and bioaccumulates in tissues and egg yolk from wild birds and at low levels in crustaceans and fish such as carp, golden grey mullet, and seabream. Canthaxanthin is not found in wild Atlantic Salmon, but is a minor carotenoid in Pacific Salmon. Canthaxanthin is used in farm-raised trout to give a red/orange color to their flesh similar to wild trout. Canthaxanthin has been used as a food additive for egg yolk, in cosmetics and as a pigmenting agent for human skin applications. It has also been used as a feed additive in fish and crustacean farms. Canthaxanthin is a potent lipid-soluble antioxidant (PMID: 2505240 ). Canthaxanthin increases resistance to lipid peroxidation primarily by enhancing membrane alpha-tocopherol levels and secondarily by providing weak direct antioxidant activity. Canthaxanthin biosynthesis in bacteria and algae proceeds from beta-carotene via the action of an enzyme known as a beta-carotene ketolase, that is able to add a carbonyl group to carbon 4 and 4' of the beta carotene molecule.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311122120252D          

 94 95  0  0  0  0            999 V2000
   10.7171   -6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.9000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -11.1375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -12.7875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6066  -13.6605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769  -14.3018    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769  -12.0982    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6066  -12.7395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7574  -11.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2595  -10.9919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5435  -10.8498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950  -11.3314    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5320  -11.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7569  -12.4403    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2439  -12.0636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3344  -11.4546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1612  -14.7395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -14.4375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862  -13.3105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5901  -12.2645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -11.9625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151  -10.8355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0190   -9.7895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8440   -8.3605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -3.7125    0.0000 H   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   -4.1250    0.0000 H   0  0  0  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
   14.2894   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -2.8875    0.0000 H   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
   13.5749   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2564   -0.3645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8862    0.2768    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8862   -1.9268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2564   -1.2855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1057   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6036   -3.0331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.3196   -3.1752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8681   -2.6936    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3310   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1062   -1.5847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6192   -1.9614    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5287   -2.5704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7019    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8769   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2730   -1.7605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4480   -3.1895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8440   -4.2355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0190   -5.6645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
 20 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 41  1  0  0  0  0
 14 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 42 45  1  0  0  0  0
  7 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 46 49  1  0  0  0  0
  2 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  2  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  2  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
 64 65  2  0  0  0  0
 65 66  1  0  0  0  0
 66 67  2  0  0  0  0
 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
 68 70  1  0  0  0  0
 68 71  1  0  0  0  0
 71 72  1  0  0  0  0
 71 73  1  0  0  0  0
 71 74  1  0  0  0  0
 64 74  1  0  0  0  0
 74 75  1  0  0  0  0
 75 76  1  0  0  0  0
 75 77  1  0  0  0  0
 75 78  1  0  0  0  0
 74 79  1  0  0  0  0
 79 80  1  0  0  0  0
 79 81  1  0  0  0  0
 79 82  1  0  0  0  0
 65 83  1  0  0  0  0
 83 84  1  0  0  0  0
 83 85  1  0  0  0  0
 83 86  1  0  0  0  0
 59 87  1  0  0  0  0
 87 88  1  0  0  0  0
 87 89  1  0  0  0  0
 87 90  1  0  0  0  0
 52 91  1  0  0  0  0
 91 92  1  0  0  0  0
 91 93  1  0  0  0  0
 91 94  1  0  0  0  0
M  END

     RDKit          3D

 94 95  0  0  0  0  0  0  0  0999 V2000
    9.7069    2.8773   -0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8154    1.9776    0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5283    0.6726    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1299    0.3851    0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5739   -0.7998    0.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1364   -0.9461    0.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2194    0.1733    0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5633   -2.1974    0.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1770   -2.1643    0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3039   -3.2553    0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576   -2.7750    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -4.5031    0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8402   -2.4310    0.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5379   -2.0197    0.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5785   -2.7154    0.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7874   -1.9379    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9856   -2.2887    0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2035   -3.7109   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0283   -1.3067    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2408   -1.3198   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1960   -0.2055    0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3636   -0.1440   -0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7722   -1.2571   -1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3412    0.9382   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4383    0.9629   -1.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5978    1.7292   -1.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4963    1.1973   -2.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2046   -0.0158   -2.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7608    1.9531   -2.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2730    2.1084   -3.3372 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3058    2.4919   -0.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2851    3.4611   -0.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8759    3.0636   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1189    3.4058    0.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2778    3.9834   -1.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7192   -0.0874    0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6083   -1.5531    0.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2612    0.5252    2.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7845    0.1054   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2730    1.5479   -0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1886    2.4376    0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4553    3.6647    0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0814    3.8478   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0661    3.0211    0.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1568    2.3600   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3749    1.1739    0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2134   -1.6668    0.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5751   -0.0911   -0.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6822    1.1222    0.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4567    0.2829    1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2928   -2.9431    1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5714   -1.2515    0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7198   -4.1861    0.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6564   -4.4206    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2438   -4.9306    0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9425   -4.3324   -0.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -1.0798    0.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.9120    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -3.7372    0.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7528   -0.8869    0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263   -4.0142   -0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323   -4.3229    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048   -3.9635   -1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397   -0.3988    0.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4714   -2.0697   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8775    0.5745    0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1259   -2.1572   -1.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8562   -0.8921   -2.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8018   -1.6171   -1.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2044    1.6549    0.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3363    0.1004   -1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3111    0.1091   -3.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0569   -0.2929   -3.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9567   -0.9117   -2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2816    2.9803   -1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4681    1.7013   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4615    4.3915   -1.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4775    3.7744    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1086    3.7063    0.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6277    4.3234    1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1378    2.5798    1.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2286    3.7414   -1.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4861    5.0122   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7699    3.6638   -2.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1925   -1.8456    1.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7090   -1.9095    1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2578   -2.1443    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4632   -0.2616    2.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2143    1.0788    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5902    1.2871    2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2817   -0.1496   -1.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6322   -0.5499   -0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2129    1.6845    0.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4994    1.7397   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 27 28  1  0
 22 23  1  0
 17 18  1  0
 14 13  1  0
 13 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2 41  1  0
 41 42  2  0
 41 40  1  0
 40 39  1  0
 39 36  1  0
 36 37  1  0
 36 38  1  0
  2  1  1  0
  6  7  1  0
 11 12  1  0
 33 26  1  0
 36  3  1  0
 14 58  1  0
 15 59  1  0
 16 60  1  0
 19 64  1  0
 20 65  1  0
 21 66  1  0
 24 70  1  0
 25 71  1  0
 31 75  1  0
 31 76  1  0
 32 77  1  0
 32 78  1  0
 34 79  1  0
 34 80  1  0
 34 81  1  0
 35 82  1  0
 35 83  1  0
 35 84  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
 23 67  1  0
 23 68  1  0
 23 69  1  0
 18 61  1  0
 18 62  1  0
 18 63  1  0
 13 57  1  0
 10 53  1  0
  9 52  1  0
  8 51  1  0
  5 47  1  0
  4 46  1  0
 40 93  1  0
 40 94  1  0
 39 91  1  0
 39 92  1  0
 37 85  1  0
 37 86  1  0
 37 87  1  0
 38 88  1  0
 38 89  1  0
 38 90  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  7 48  1  0
  7 49  1  0
  7 50  1  0
 12 54  1  0
 12 55  1  0
 12 56  1  0
M  END


  Mrv1652311122120252D          

 94 95  0  0  0  0            999 V2000
   10.7171   -6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.9000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -11.1375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -12.7875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6066  -13.6605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769  -14.3018    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769  -12.0982    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6066  -12.7395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7574  -11.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2595  -10.9919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5435  -10.8498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950  -11.3314    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5320  -11.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7569  -12.4403    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2439  -12.0636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3344  -11.4546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1612  -14.7395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -14.4375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862  -13.3105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5901  -12.2645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -11.9625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151  -10.8355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0190   -9.7895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -9.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8440   -8.3605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -3.7125    0.0000 H   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   -4.1250    0.0000 H   0  0  0  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
   14.2894   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -2.8875    0.0000 H   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
   13.5749   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2564   -0.3645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8862    0.2768    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8862   -1.9268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2564   -1.2855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1057   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6036   -3.0331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.3196   -3.1752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8681   -2.6936    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3310   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1062   -1.5847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6192   -1.9614    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5287   -2.5704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7019    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8769   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2730   -1.7605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4480   -3.1895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8440   -4.2355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0190   -5.6645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
 20 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 41  1  0  0  0  0
 14 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 42 45  1  0  0  0  0
  7 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 46 49  1  0  0  0  0
  2 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  2  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  2  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
 64 65  2  0  0  0  0
 65 66  1  0  0  0  0
 66 67  2  0  0  0  0
 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
 68 70  1  0  0  0  0
 68 71  1  0  0  0  0
 71 72  1  0  0  0  0
 71 73  1  0  0  0  0
 71 74  1  0  0  0  0
 64 74  1  0  0  0  0
 74 75  1  0  0  0  0
 75 76  1  0  0  0  0
 75 77  1  0  0  0  0
 75 78  1  0  0  0  0
 74 79  1  0  0  0  0
 79 80  1  0  0  0  0
 79 81  1  0  0  0  0
 79 82  1  0  0  0  0
 65 83  1  0  0  0  0
 83 84  1  0  0  0  0
 83 85  1  0  0  0  0
 83 86  1  0  0  0  0
 59 87  1  0  0  0  0
 87 88  1  0  0  0  0
 87 89  1  0  0  0  0
 87 90  1  0  0  0  0
 52 91  1  0  0  0  0
 91 92  1  0  0  0  0
 91 93  1  0  0  0  0
 91 94  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000007

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+

> <INCHI_KEY>
FDSDTBUPSURDBL-DKLMTRRASA-N

> <FORMULA>
C40H52O2

> <MOLECULAR_WEIGHT>
564.854

> <EXACT_MASS>
564.396730914

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
72.15685238575475

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one

> <ALOGPS_LOGP>
8.71

> <JCHEM_LOGP>
9.789514377333333

> <ALOGPS_LOGS>
-6.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.58928982426813

> <JCHEM_PKA_STRONGEST_BASIC>
-4.450363810038525

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
192.9982

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.61e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
canthaxanthin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-NOV-21         0                                  
HETATM    1  H   UNK     0      20.005 -11.550   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      22.673 -14.630   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0      18.672 -13.860   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      17.338 -16.170   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0      20.005 -19.250   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0      17.338 -19.250   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      16.004 -18.480   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      17.338 -20.790   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004 -21.560   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      14.670 -20.790   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      17.338 -23.870   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      14.670 -23.870   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.670 -25.410   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337 -26.180   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337 -27.720   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003 -25.410   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      10.466 -25.500   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      11.157 -26.697   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      12.003 -23.870   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      11.157 -22.583   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      10.466 -23.780   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0      13.337 -23.100   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.614 -21.740   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      13.551 -20.518   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      12.214 -20.253   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      11.191 -21.152   0.000  0.00  0.00           H+0
HETATM   34  C   UNK     0      14.060 -21.740   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0      14.480 -23.222   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      15.389 -22.519   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      15.558 -21.382   0.000  0.00  0.00           H+0
HETATM   38  C   UNK     0      16.004 -26.180   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0      15.234 -27.514   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      17.338 -26.950   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0      16.774 -24.846   0.000  0.00  0.00           H+0
HETATM   42  C   UNK     0      18.672 -21.560   0.000  0.00  0.00           C+0
HETATM   43  H   UNK     0      17.902 -22.894   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      20.005 -22.330   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      19.442 -20.226   0.000  0.00  0.00           H+0
HETATM   46  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   47  H   UNK     0      20.569 -18.274   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      22.673 -17.710   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      22.109 -15.606   0.000  0.00  0.00           H+0
HETATM   50  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   51  H   UNK     0      24.006 -12.320   0.000  0.00  0.00           H+0
HETATM   52  C   UNK     0      22.673 -10.010   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      24.006  -9.240   0.000  0.00  0.00           C+0
HETATM   54  H   UNK     0      25.340 -10.010   0.000  0.00  0.00           H+0
HETATM   55  C   UNK     0      24.006  -7.700   0.000  0.00  0.00           C+0
HETATM   56  H   UNK     0      22.673  -6.930   0.000  0.00  0.00           H+0
HETATM   57  C   UNK     0      25.340  -6.930   0.000  0.00  0.00           C+0
HETATM   58  H   UNK     0      26.674  -7.700   0.000  0.00  0.00           H+0
HETATM   59  C   UNK     0      25.340  -5.390   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      26.674  -4.620   0.000  0.00  0.00           C+0
HETATM   61  H   UNK     0      28.007  -5.390   0.000  0.00  0.00           H+0
HETATM   62  C   UNK     0      26.674  -3.080   0.000  0.00  0.00           C+0
HETATM   63  H   UNK     0      25.340  -2.310   0.000  0.00  0.00           H+0
HETATM   64  C   UNK     0      28.007  -2.310   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      28.007  -0.770   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      29.341   0.000   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      29.341   1.540   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      30.675  -0.770   0.000  0.00  0.00           C+0
HETATM   69  H   UNK     0      32.212  -0.680   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0      31.521   0.517   0.000  0.00  0.00           H+0
HETATM   71  C   UNK     0      30.675  -2.310   0.000  0.00  0.00           C+0
HETATM   72  H   UNK     0      31.521  -3.597   0.000  0.00  0.00           H+0
HETATM   73  H   UNK     0      32.212  -2.400   0.000  0.00  0.00           H+0
HETATM   74  C   UNK     0      29.341  -3.080   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      30.064  -4.440   0.000  0.00  0.00           C+0
HETATM   76  H   UNK     0      29.127  -5.662   0.000  0.00  0.00           H+0
HETATM   77  H   UNK     0      30.463  -5.927   0.000  0.00  0.00           H+0
HETATM   78  H   UNK     0      31.487  -5.028   0.000  0.00  0.00           H+0
HETATM   79  C   UNK     0      28.618  -4.440   0.000  0.00  0.00           C+0
HETATM   80  H   UNK     0      28.198  -2.958   0.000  0.00  0.00           H+0
HETATM   81  H   UNK     0      27.289  -3.661   0.000  0.00  0.00           H+0
HETATM   82  H   UNK     0      27.120  -4.798   0.000  0.00  0.00           H+0
HETATM   83  C   UNK     0      26.674   0.000   0.000  0.00  0.00           C+0
HETATM   84  H   UNK     0      27.444   1.334   0.000  0.00  0.00           H+0
HETATM   85  H   UNK     0      25.340   0.770   0.000  0.00  0.00           H+0
HETATM   86  H   UNK     0      25.904  -1.334   0.000  0.00  0.00           H+0
HETATM   87  C   UNK     0      24.006  -4.620   0.000  0.00  0.00           C+0
HETATM   88  H   UNK     0      24.776  -3.286   0.000  0.00  0.00           H+0
HETATM   89  H   UNK     0      22.673  -3.850   0.000  0.00  0.00           H+0
HETATM   90  H   UNK     0      23.236  -5.954   0.000  0.00  0.00           H+0
HETATM   91  C   UNK     0      21.339  -9.240   0.000  0.00  0.00           C+0
HETATM   92  H   UNK     0      22.109  -7.906   0.000  0.00  0.00           H+0
HETATM   93  H   UNK     0      20.005  -8.470   0.000  0.00  0.00           H+0
HETATM   94  H   UNK     0      20.569 -10.574   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   50                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   46                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   42                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   29                                                  
CONECT   20   19   21   38                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   19   30   34                                             
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   29   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34                                                            
CONECT   38   20   39   40   41                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   38                                                            
CONECT   42   14   43   44   45                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   42                                                            
CONECT   46    7   47   48   49                                             
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   46                                                            
CONECT   50    2   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   91                                                  
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60   87                                                  
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   65   74                                                  
CONECT   65   64   66   83                                                  
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   69   70   71                                             
CONECT   69   68                                                            
CONECT   70   68                                                            
CONECT   71   68   72   73   74                                             
CONECT   72   71                                                            
CONECT   73   71                                                            
CONECT   74   71   64   75   79                                             
CONECT   75   74   76   77   78                                             
CONECT   76   75                                                            
CONECT   77   75                                                            
CONECT   78   75                                                            
CONECT   79   74   80   81   82                                             
CONECT   80   79                                                            
CONECT   81   79                                                            
CONECT   82   79                                                            
CONECT   83   65   84   85   86                                             
CONECT   84   83                                                            
CONECT   85   83                                                            
CONECT   86   83                                                            
CONECT   87   59   88   89   90                                             
CONECT   88   87                                                            
CONECT   89   87                                                            
CONECT   90   87                                                            
CONECT   91   52   92   93   94                                             
CONECT   92   91                                                            
CONECT   93   91                                                            
CONECT   94   91                                                            
MASTER        0    0    0    0    0    0    0    0   94    0  190    0
END

View in JSmol

Synonyms

Value	Source
4,4'-Dioxo-beta-carotene	ChEBI
all-trans-beta-Carotene-4,4'-dione	ChEBI
Carophyll red	ChEBI
e 161g	ChEBI
FOOD Orange 8	ChEBI
Orobronze	ChEBI
4,4'-Dioxo-b-carotene	Generator
4,4'-Dioxo-β-carotene	Generator
all-trans-b-Carotene-4,4'-dione	Generator
all-trans-Β-carotene-4,4'-dione	Generator
4,4'-Diketo-b-carotene	HMDB
4,4'-Diketo-beta-carotene	HMDB
all-trans,beta-Carotene-4,4'-dione	HMDB
beta,beta-Carotene-4,4'-dione	HMDB
Cantaxanthin	HMDB
Cantaxanthine	HMDB
Canthaxanthine	HMDB
L-Orange 7	HMDB
Roxanthin red 10	HMDB

Chemical Formula

C₄₀H₅₂O₂

Average Mass

564.8540 Da

Monoisotopic Mass

564.39673 Da

IUPAC Name

2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one

Traditional Name

canthaxanthin

CAS Registry Number

514-78-3

SMILES

[H]/C(=C(/[H])\C(\[H])=C(\C(\[H])=C(/[H])\C(\[H])=C(\C(\[H])=C(/[H])C1=C(C(=O)C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])/C([H])([H])[H])/C([H])([H])[H])/C(/[H])=C(/C(/[H])=C(\[H])/C(/[H])=C(/C(/[H])=C(\[H])C1=C(C(=O)C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])\C([H])([H])[H])\C([H])([H])[H]

InChI Identifier

InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+

InChI Key

FDSDTBUPSURDBL-DKLMTRRASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acanthochitona defilippii	LOTUS Database	35616633
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Anabaena flos-aquae	KNApSAcK Database	22123792
Aphanizomenon flos-aquae	LOTUS Database	35616633
Arabidopsis thaliana	KNApSAcK Database	22123792
Artemia salina	LOTUS Database	35616633
Asterina pectinifera	LOTUS Database	35616633
Brassica rapa	LOTUS Database	35616633
Cladonia furcata	LOTUS Database	35616633
Corbicula japonica	KNApSAcK Database	22123792
Corbicula sandai	KNApSAcK Database	22123792
Ctenopharyngodon idella	LOTUS Database	35616633
Cucumaria frondosa	LOTUS Database	35616633
Diacronema lutheri	LOTUS Database	35616633
Euglena gracilis	LOTUS Database	35616633
Gelliodes callista	LOTUS Database	35616633
Graesiella emersonii	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Kocuria rosea	LOTUS Database	35616633
Ligia exotica	LOTUS Database	35616633
Lobaria pulmonaria	LOTUS Database	35616633
Metasequoia glyptostroboides	LOTUS Database	35616633
Muriella decolor	LOTUS Database	35616633
Nannochloropsis oculata	LOTUS Database	35616633
Oriolus cruentus	LOTUS Database	35616633
Oscillatoria limosa	LOTUS Database	35616633
Paraeuchaeta russelli	LOTUS Database	35616633
Paralithodes brevipes	LOTUS Database	35616633
Penaeus japonicus	LOTUS Database	35616633
Phoenicoparrus jamesi	LOTUS Database	35616633
Phormidium lucidum	LOTUS Database	35616633
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Protula tubularia	LOTUS Database	35616633
Rhinogobius brunneus	LOTUS Database	35616633
Scenedesmus quadricauda	LOTUS Database	35616633
Skeletonema costatum	LOTUS Database	35616633
Solanum tuberosum	KNApSAcK Database	22123792
Stereocaulon vesuvianum	LOTUS Database	35616633
Thoracosphaera heimii	LOTUS Database	35616633
Tolypothrix tenuis	-	KNApSAcK
Valeriana officinalis	LOTUS Database	35616633
Xipholena punicea	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Agrobacterium aurantiacum	KNApSAcK Database	22123792
Alcaligenes PC1	KNApSAcK Database	22123792
Cantharellus cinnabarinus	KNApSAcK Database	22123792

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
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carotenone (CHEBI:3362 )
C40 isoprenoids (tetraterpenes) (C08583 )
Carotenoids (C08583 )
C40 isoprenoids (tetraterpenes) (LMPR01070264 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	211 - 212 °C	https://en.wikipedia.org/wiki/Canthaxanthin
Boiling Point	717.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2.5e-10 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	9.526 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	0.00046 g/L	ALOGPS
logP	8.71	ALOGPS
logP	9.79	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	19.59	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	193 m³·mol⁻¹	ChemAxon
Polarizability	72.16 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003154

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Canthaxanthin

METLIN ID

3597

PubChem Compound

5281227

PDB ID

Not Available

ChEBI ID

3362

Good Scents ID

rw1365301

References

General References

Paetau I, Chen H, Goh NM, White WS: Interactions in the postprandial appearance of beta-carotene and canthaxanthin in plasma triacylglycerol-rich lipoproteins in humans. Am J Clin Nutr. 1997 Nov;66(5):1133-43. [PubMed:9356530 ]
Meyer JC, Grundmann HP, Seeger B, Schnyder UW: Plasma concentrations of beta-carotene and canthaxanthin during and after stopping intake of a combined preparation. Dermatologica. 1985;171(2):76-81. [PubMed:3930305 ]
Rollman O, Vahlquist A: Psoriasis and vitamin A. Plasma transport and skin content of retinol, dehydroretinol and carotenoids in adult patients versus healthy controls. Arch Dermatol Res. 1985;278(1):17-24. [PubMed:4096526 ]
Bluhm R, Branch R, Johnston P, Stein R: Aplastic anemia associated with canthaxanthin ingested for 'tanning' purposes. JAMA. 1990 Sep 5;264(9):1141-2. [PubMed:2117075 ]
Rosa AP, Scher A, Sorbara JO, Boemo LS, Forgiarini J, Londero A: Effects of canthaxanthin on the productive and reproductive performance of broiler breeders. Poult Sci. 2012 Mar;91(3):660-6. doi: 10.3382/ps.2011-01582. [PubMed:22334741 ]
Mayne ST, Parker RS: Antioxidant activity of dietary canthaxanthin. Nutr Cancer. 1989;12(3):225-36. doi: 10.1080/01635588909514022. [PubMed:2505240 ]

Showing NP-Card for Canthaxanthin (NP0000007)

MOL for NP0000007 (Canthaxanthin)

3D MOL for NP0000007 (Canthaxanthin)

3D SDF for NP0000007 (Canthaxanthin)

3D-SDF for NP0000007 (Canthaxanthin)

PDB for NP0000007 (Canthaxanthin)

3D PDB for NP0000007 (Canthaxanthin)

SMILES for NP0000007 (Canthaxanthin)

INCHI for NP0000007 (Canthaxanthin)

Structure for NP0000007 (Canthaxanthin)

3D Structure for NP0000007 (Canthaxanthin)