NP-MRD: Showing NP-Card for Rhodoxanthin (NP0052230)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 23:22:00 UTC

Updated at

2022-04-27 23:22:00 UTC

NP-MRD ID

NP0052230

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rhodoxanthin

Description

Rhodoxanthin 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, rhodoxanthin is considered to be an isoprenoid. Rhodoxanthin is found in Adiantum spp., Cladonia gracilis, Cladonia rangiferina, Ctenopharyngodon idella, Cyrtomium falcatum, Epicoccum nigrum, Epicoccum spp., Equisetum arvense , Ilicura militaris, Lonicera ruprechtiana, Metasequoia glyptostroboides, Micrococcus tetragenus, Potamogeton natans, Taxus baccata and Taxus cuspidata. Rhodoxanthin was first documented in 2013 (PMID: 24055537). Based on a literature review a significant number of articles have been published on Rhodoxanthin (PMID: 34957624) (PMID: 33845183) (PMID: 35344590) (PMID: 33373476) (PMID: 32645673) (PMID: 32426461).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201222D          

 42 43  0  0  0  0            999 V2000
    8.5737   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   13.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   13.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6754   11.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9008   11.2341    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 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
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 21 29  1  0  0  0  0
 17 30  1  0  0  0  0
 13 31  1  0  0  0  0
  8 32  1  0  0  0  0
  4 33  1  0  0  0  0
  1 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
  1 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 34 42  1  0  0  0  0
M  END

     RDKit          3D

 92 93  0  0  0  0  0  0  0  0999 V2000
   11.5483   -0.2216   -2.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7978    0.5467   -1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0440    0.9164   -1.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3452    1.6396    0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4062    1.5525    0.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2423    2.4903    0.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9215    1.7732    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7583    1.2531    1.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8837    2.9243    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7262    0.8425   -0.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5640    0.2516   -0.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4282    0.4079    0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2342   -0.1136   -0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -0.8700   -1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058    0.0814    0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9176   -0.3928    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7598   -0.2644    1.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5618   -0.6908    0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5969   -1.2876   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3704   -0.6398    1.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3516   -0.6177    2.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8792   -0.5802    2.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9970   -0.7818    2.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3607   -0.8414    2.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7932   -1.0902    4.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3086   -0.9069    1.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7147   -1.1808    1.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4900   -1.0336    0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9034   -1.2888    0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6511   -1.8516    1.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4959   -0.9359   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8435   -1.1036   -0.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3496   -0.5114   -1.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7427   -0.7934   -2.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3010   -2.1910   -2.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5898    0.1594   -2.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9753    1.4765   -2.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5256    2.5597   -2.3369 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6229    1.5048   -3.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6329    0.5815   -2.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1775    1.5220   -1.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4810    0.3860   -3.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4300   -0.2835   -3.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6917    0.1721   -3.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2087   -1.2626   -2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8421    0.6968   -1.9196 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1511    3.4404   -0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4859    2.8375    1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9745    1.8389    2.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6370    0.1590    2.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7055    1.4531    2.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2972    3.0731    1.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3924    3.8962    0.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2768    2.7182   -0.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4996   -0.3576   -1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4874    0.9829    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -0.5508   -2.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1801   -1.9550   -1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0387   -0.7015   -1.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2969    0.6331    1.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772   -0.9589   -0.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230    0.1603    2.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5513   -1.6392   -0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842   -0.5283   -1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2128   -2.1886   -0.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5840   -1.1040    0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0999   -0.1532    3.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9993   -0.4013    4.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -0.9789    1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2113   -0.5393    4.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8694   -0.8976    4.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6590   -2.2006    4.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9616   -0.7308    0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2001   -1.5042    2.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9695   -0.6736   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2782   -2.8531    2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7372   -1.8881    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5576   -1.2021    2.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8373   -0.5284   -1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5215   -1.6675   -0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8890   -2.7520   -1.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0147   -2.6862   -2.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3873   -2.1724   -1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6146    0.0310   -2.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2038    2.5601   -3.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5792    1.2559   -4.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6652    2.5024   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1138    1.6622   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6367    1.1782   -0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4756    0.6171   -2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5025    1.2854   -4.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4443   -0.4751   -4.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  2  0
 20 18  1  0
 18 19  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 36 37  1  0
 37 38  2  0
 37 39  1  0
 39 40  1  0
 40 41  1  0
 40 42  1  0
  7 10  1  0
 40 33  1  0
 25 70  1  0
 25 71  1  0
 25 72  1  0
 23 69  1  0
 22 68  1  0
 21 67  1  0
 20 66  1  0
 19 63  1  0
 19 64  1  0
 19 65  1  0
 17 62  1  0
 16 61  1  0
 15 60  1  0
 14 57  1  0
 14 58  1  0
 14 59  1  0
 12 56  1  0
 11 55  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  3 46  1  0
  6 47  1  0
  6 48  1  0
  8 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
  9 54  1  0
 26 73  1  0
 27 74  1  0
 28 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 32 80  1  0
 35 81  1  0
 35 82  1  0
 35 83  1  0
 36 84  1  0
 39 85  1  0
 39 86  1  0
 41 87  1  0
 41 88  1  0
 41 89  1  0
 42 90  1  0
 42 91  1  0
 42 92  1  0
M  END


  Mrv1652304282201222D          

 42 43  0  0  0  0            999 V2000
    8.5737   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   13.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   13.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6754   11.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9008   11.2341    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 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
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 21 29  1  0  0  0  0
 17 30  1  0  0  0  0
 13 31  1  0  0  0  0
  8 32  1  0  0  0  0
  4 33  1  0  0  0  0
  1 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
  1 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 34 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052230

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C1\C(C)=CC(=O)CC1(C)C)=C/C=C/C(/C)=C/C=C1/C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H50O2/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/h11-26H,27-28H2,1-10H3/b15-11+,16-12+,19-13+,20-14+,29-17+,30-18+,31-21+,32-22+,37-23-,38-24-

> <INCHI_KEY>
VWXMLZQUDPCJPL-ZDHAIZATSA-N

> <FORMULA>
C40H50O2

> <MOLECULAR_WEIGHT>
562.838

> <EXACT_MASS>
562.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
70.70112400346176

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4E)-3,5,5-trimethyl-4-[(2E,4E,6E,8E,10E,12E,14E,16E)-3,7,12,16-tetramethyl-18-[(1E)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-ylidene]octadeca-2,4,6,8,10,12,14,16-octaen-1-ylidene]cyclohex-2-en-1-one

> <ALOGPS_LOGP>
8.64

> <JCHEM_LOGP>
9.123214285333333

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.363883497492284

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
193.9646000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.38e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rhodoxanthin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      16.004  23.100   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.670  22.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.670  20.790   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337  20.020   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337  18.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  17.710   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  15.400   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  16.170   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.003  20.790   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.004  24.640   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.338  25.410   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      18.672  24.640   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      20.005  25.410   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      18.672  23.100   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      17.338  22.330   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      18.061  20.970   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      16.615  20.970   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.670  25.410   0.000  0.00  0.00           C+0
CONECT    1    2   34   39                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   31                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   21                                                            
CONECT   30   17                                                            
CONECT   31   13                                                            
CONECT   32    8                                                            
CONECT   33    4                                                            
CONECT   34    1   35   42                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38    1   40   41                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   34                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₅₀O₂

Average Mass

562.8380 Da

Monoisotopic Mass

562.38108 Da

IUPAC Name

(4E)-3,5,5-trimethyl-4-[(2E,4E,6E,8E,10E,12E,14E,16E)-3,7,12,16-tetramethyl-18-[(1E)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-ylidene]octadeca-2,4,6,8,10,12,14,16-octaen-1-ylidene]cyclohex-2-en-1-one

Traditional Name

rhodoxanthin

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C1\C(C)=CC(=O)CC1(C)C)=C/C=C/C(/C)=C/C=C1/C(C)=CC(=O)CC1(C)C

InChI Identifier

InChI=1S/C40H50O2/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/h11-26H,27-28H2,1-10H3/b15-11+,16-12+,19-13+,20-14+,29-17+,30-18+,31-21+,32-22+,37-23-,38-24-

InChI Key

VWXMLZQUDPCJPL-ZDHAIZATSA-N

Experimental Spectra

Not Available

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
Adiantum spp.	Plant	KNApSAcK
Cladonia gracilis	LOTUS Database	35616633
Cladonia rangiferina	LOTUS Database	35616633
Ctenopharyngodon idella	LOTUS Database	35616633
Cyrtomium falcatum	LOTUS Database	35616633
Epicoccum nigrum	LOTUS Database	35616633
Epicoccum spp.	Fungi	KNApSAcK
Equisetum arvense	Plant	KNApSAcK
Ilicura militaris	LOTUS Database	35616633
Lonicera ruprechtiana	Plant	KNApSAcK
Metasequoia glyptostroboides	LOTUS Database	35616633
Micrococcus tetragenus	Bacteria	KNApSAcK
Potamogeton natans	Plant	KNApSAcK
Taxus baccata	Plant	KNApSAcK
Taxus cuspidata	LOTUS Database	35616633

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

xanthophyll (CHEBI:8835 )
C40 isoprenoids (tetraterpenes) (C08610 )
Carotenoids (C08610 )
C40 isoprenoids (tetraterpenes) (LMPR01070280 )

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	8.64	ALOGPS
logP	9.12	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-4.4	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	9	ChemAxon
Refractivity	193.96 m³·mol⁻¹	ChemAxon
Polarizability	70.7 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003784

Chemspider ID

4444663

KEGG Compound ID

C08610

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rhodoxanthin

METLIN ID

Not Available

PubChem Compound

5281251

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Schex R, Schweiggert R, Steingass CB: Atmospheric pressure chemical ionization mass spectrometry of retro-carotenoids. Rapid Commun Mass Spectrom. 2022 Apr 15;36(7):e9250. doi: 10.1002/rcm.9250. [PubMed:34957624 ]
Schex R, Lieb VM, Schafer C, Schweiggert R, Steingass CB: Carotenoid profiles of red- and yellow-colored arils of cultivars of Taxus baccata L. and Taxus x media Rehder. Phytochemistry. 2021 Jun;186:112741. doi: 10.1016/j.phytochem.2021.112741. Epub 2021 Apr 10. [PubMed:33845183 ]
Furubayashi M, Maoka T, Mitani Y: Promiscuous activity of beta-carotene hydroxylase CrtZ on epoxycarotenoids leads to the formation of rare carotenoids with 6-hydroxy-3-keto-epsilon-ends. FEBS Lett. 2022 Mar 28. doi: 10.1002/1873-3468.14342. [PubMed:35344590 ]
Khan T, Litvin R, Sebelik V, Polivka T: Excited-State Evolution of Keto-Carotenoids after Excess Energy Excitation in the UV Region. Chemphyschem. 2021 Mar 3;22(5):471-480. doi: 10.1002/cphc.202000982. Epub 2021 Feb 2. [PubMed:33373476 ]
Schex R, Bonrath W, Schafer C, Schweiggert R: The impact of (E/Z)-isomerization and aggregation on the color of rhodoxanthin formulations for food and beverages. Food Chem. 2020 Dec 1;332:127370. doi: 10.1016/j.foodchem.2020.127370. Epub 2020 Jun 23. [PubMed:32645673 ]
Royer J, Shanklin J, Balch-Kenney N, Mayorga M, Houston P, de Jong RM, McMahon J, Laprade L, Blomquist P, Berry T, Cai Y, LoBuglio K, Trueheart J, Chevreux B: Rhodoxanthin synthase from honeysuckle; a membrane diiron enzyme catalyzes the multistep conversation of beta-carotene to rhodoxanthin. Sci Adv. 2020 Apr 22;6(17):eaay9226. doi: 10.1126/sciadv.aay9226. eCollection 2020 Apr. [PubMed:32426461 ]
Schex R, Schweiggert F, Wustenberg B, Bonrath W, Schafer C, Schweiggert R: Kinetic and Thermodynamic Study of the Thermally Induced (E/Z)-Isomerization of the retro-Carotenoid Rhodoxanthin. J Agric Food Chem. 2020 May 6;68(18):5259-5269. doi: 10.1021/acs.jafc.0c00933. Epub 2020 Apr 21. [PubMed:32314916 ]
Poliak P, Skorna P, Klein E, Lukes V: Thermodynamics of radical scavenging of symmetric carotenoids and their charged species. Food Chem. 2018 Dec 1;268:542-549. doi: 10.1016/j.foodchem.2018.06.063. Epub 2018 Jun 14. [PubMed:30064795 ]
Berg CJ, LaFountain AM, Prum RO, Frank HA, Tauber MJ: Vibrational and electronic spectroscopy of the retro-carotenoid rhodoxanthin in avian plumage, solid-state films, and solution. Arch Biochem Biophys. 2013 Nov 15;539(2):142-55. doi: 10.1016/j.abb.2013.09.009. Epub 2013 Sep 19. [PubMed:24055537 ]
Subhash Y, Tushar L, Sasikala C, Ramana CV: Mongoliicoccus alkaliphilus sp. nov. and Litoribacter alkaliphilus sp. nov., isolated from salt pans. Int J Syst Evol Microbiol. 2013 Sep;63(Pt 9):3457-3462. doi: 10.1099/ijs.0.049924-0. Epub 2013 Mar 29. [PubMed:23543498 ]

Showing NP-Card for Rhodoxanthin (NP0052230)

MOL for NP0052230 (Rhodoxanthin)

3D MOL for NP0052230 (Rhodoxanthin)

3D SDF for NP0052230 (Rhodoxanthin)

3D-SDF for NP0052230 (Rhodoxanthin)

PDB for NP0052230 (Rhodoxanthin)

3D PDB for NP0052230 (Rhodoxanthin)

SMILES for NP0052230 (Rhodoxanthin)

INCHI for NP0052230 (Rhodoxanthin)

Structure for NP0052230 (Rhodoxanthin)

3D Structure for NP0052230 (Rhodoxanthin)