NP-MRD: Showing NP-Card for (3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol (NP0065721)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 09:55:14 UTC

Updated at

2022-04-28 09:55:14 UTC

NP-MRD ID

NP0065721

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol

Description

Loroxanthin 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, loroxanthin is considered to be an isoprenoid. (3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol is found in Chlamydomonas reinhardtii, Chlorella vulgaris, Cladophora glomerata, Corbicula japonica , Corbicula sandai , Euglena sanguinea, Scenedesmus obliquus, Tetraselmis suecica and Ulva rigida. (3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol was first documented in 2017 (PMID: 28117410). Based on a literature review a small amount of articles have been published on Loroxanthin (PMID: 35251077) (PMID: 29982094) (PMID: 29037686) (PMID: 28551868).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282211552D          

 43 44  0  0  1  0            999 V2000
    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  1  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
    6.4302  -13.6125    0.0000 C   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
    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
    7.5320  -11.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447  -12.3750    0.0000 C   0  0  2  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
   -8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737  -11.5500    0.0000 C   0  0  2  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  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4719  -13.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2465  -13.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 30 34  1  1  0  0  0
 28 35  1  0  0  0  0
 28 36  1  0  0  0  0
 24 37  1  0  0  0  0
 20 38  1  0  0  0  0
 15 39  1  0  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
  4 42  1  0  0  0  0
  2 43  1  6  0  0  0
M  END

     RDKit          3D

 99100  0  0  0  0  0  0  0  0999 V2000
  -11.0452   -2.0429   -2.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3961   -1.2204   -1.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2805   -1.6756   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6874   -0.7787    0.9789 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.8585   -1.2847    1.5099 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9815    0.5632    0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7563    1.1666   -0.3446 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.2416    2.1615   -1.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9924    1.9265    0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8524    0.0905   -0.8741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.5594    0.0435   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4168    0.0360   -0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1126    0.0114   -0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0395    0.2616    1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9906   -0.0997   -0.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6265   -0.0162   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6054   -0.0848   -1.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130   -0.0189   -0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7767    0.1266    0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -0.0996   -1.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0498   -0.0491   -1.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766   -0.0113   -2.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3022    0.0146   -2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3546    0.1523   -3.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5623    0.2238   -4.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4861    0.1536   -2.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4579    0.1653   -1.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2372    0.1129   -0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5597    0.2777   -0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2120   -0.0165    0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4766    0.0925    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3922   -0.1313    1.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6810    0.1116    1.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1067    0.6229    0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7472   -0.1611    2.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2027   -0.4536    4.1280 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1332    0.6923    4.9275 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9020   -1.1479    4.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8318   -0.7378    3.2131 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8092    0.1584    3.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1140   -2.0426    2.7829 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4243    0.5575   -1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9559    0.6955   -2.9483 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0184   -3.0826   -1.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0717   -1.7721   -2.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8583   -1.9689   -2.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7291   -2.6602   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9484   -0.7200    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8009   -2.2763    1.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8172    0.4074   -0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3317    1.3012    1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5580    3.1072   -0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1965    1.8274   -1.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5543    2.4780   -2.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3663    2.9568    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1246    1.4593    1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9146    1.9807    0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5315    0.4149   -1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5470    0.0261    0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4173    0.0524   -1.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0921    0.8508    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9572   -0.6502    1.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9123    0.8728    1.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0621   -0.5963   -1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3950    0.0725    0.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8841   -0.1876   -2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5385    0.7291    1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8585    0.7940    0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -0.7769    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6760   -0.1943   -2.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4433   -0.0535   -0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111   -0.0147   -3.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206   -0.0597   -1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540   -0.6601   -4.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8248    1.1195   -4.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0453    0.3605   -5.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1047    1.0117   -3.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3115   -0.2389   -2.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7225   -0.0791    0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6297   -0.3169    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9892    0.3865   -0.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1945    0.7980    0.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8616   -0.1860   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5390    1.5270    0.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3473   -1.0308    2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4582    0.6960    2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9348   -1.1831    4.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8967    1.4827    4.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0724   -2.2666    4.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4888   -1.0589    5.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8069   -0.3070    4.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6255    1.0893    3.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1510    0.4645    4.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7099   -2.9003    3.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1201   -2.1129    3.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0222   -2.1277    1.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2274   -0.2755   -1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0973    1.4782   -1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7023    1.6670   -3.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 42  1  0
 42 43  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 39 40  1  1
 39 41  1  0
  7 10  1  0
 39 32  1  0
 19 67  1  0
 19 68  1  0
 19 69  1  0
 17 66  1  0
 16 65  1  0
 15 64  1  0
 14 61  1  0
 14 62  1  0
 14 63  1  0
 12 60  1  0
 11 59  1  0
 10 58  1  6
  1 44  1  0
  1 45  1  0
  1 46  1  0
  3 47  1  0
  4 48  1  1
  5 49  1  0
  6 50  1  0
  6 51  1  0
  8 52  1  0
  8 53  1  0
  8 54  1  0
  9 55  1  0
  9 56  1  0
  9 57  1  0
 20 70  1  0
 21 71  1  0
 22 72  1  0
 23 73  1  0
 25 74  1  0
 25 75  1  0
 25 76  1  0
 26 77  1  0
 27 78  1  0
 28 79  1  0
 42 97  1  0
 42 98  1  0
 43 99  1  0
 30 80  1  0
 31 81  1  0
 34 82  1  0
 34 83  1  0
 34 84  1  0
 35 85  1  0
 35 86  1  0
 36 87  1  1
 37 88  1  0
 38 89  1  0
 38 90  1  0
 40 91  1  0
 40 92  1  0
 40 93  1  0
 41 94  1  0
 41 95  1  0
 41 96  1  0
M  END


  Mrv1652304282211552D          

 43 44  0  0  1  0            999 V2000
    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  1  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
    6.4302  -13.6125    0.0000 C   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
    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
    7.5320  -11.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447  -12.3750    0.0000 C   0  0  2  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
   -8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737  -11.5500    0.0000 C   0  0  2  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  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4719  -13.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2465  -13.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 30 34  1  1  0  0  0
 28 35  1  0  0  0  0
 28 36  1  0  0  0  0
 24 37  1  0  0  0  0
 20 38  1  0  0  0  0
 15 39  1  0  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
  4 42  1  0  0  0  0
  2 43  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0065721

> <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(\CO)/C=C/C1=C(C)C[C@@H](O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H56O3/c1-29(16-12-17-31(3)20-22-37-32(4)24-35(42)26-39(37,6)7)14-10-11-15-30(2)18-13-19-34(28-41)21-23-38-33(5)25-36(43)27-40(38,8)9/h10-24,35-37,41-43H,25-28H2,1-9H3/b11-10+,16-12+,18-13+,22-20+,23-21+,29-14+,30-15+,31-17+,34-19-/t35-,36+,37-/m0/s1

> <INCHI_KEY>
ODGGKCNQKSEQNL-CWBMHJDKSA-N

> <FORMULA>
C40H56O3

> <MOLECULAR_WEIGHT>
584.885

> <EXACT_MASS>
584.422945663

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
74.11970069434244

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-4-[(1E,3Z)-4-hydroxy-3-[(2E,4E,6E,8E,10E,12E,14E)-15-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaen-1-ylidene]but-1-en-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

> <ALOGPS_LOGP>
7.60

> <JCHEM_LOGP>
7.269438174000001

> <ALOGPS_LOGS>
-5.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.21727233987641

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.95381347964502

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8752161350326849

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
196.8381000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-4-[(1E,3Z)-4-hydroxy-3-[(2E,4E,6E,8E,10E,12E,14E)-15-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaen-1-ylidene]but-1-en-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

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      14.670 -23.870   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.670 -25.410   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337 -26.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003 -25.410   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003 -23.870   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337 -23.100   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.614 -21.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.060 -21.740   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000 -23.100   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.003 -23.870   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.337 -23.100   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -14.670 -23.870   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -16.004 -21.560   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -14.670 -20.790   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -13.337 -21.560   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  O   UNK     0     -17.338 -20.790   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -13.947 -25.230   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -15.393 -25.230   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.336 -25.410   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.668 -20.790   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      10.669 -26.180   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      16.004 -26.180   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   43                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   42                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   40                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   39                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   38                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   37                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   35   36                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27   33                                                  
CONECT   33   32                                                            
CONECT   34   30                                                            
CONECT   35   28                                                            
CONECT   36   28                                                            
CONECT   37   24                                                            
CONECT   38   20                                                            
CONECT   39   15                                                            
CONECT   40   11   41                                                       
CONECT   41   40                                                            
CONECT   42    4                                                            
CONECT   43    2                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₅₆O₃

Average Mass

584.8850 Da

Monoisotopic Mass

584.42295 Da

IUPAC Name

(1R)-4-[(1E,3Z)-4-hydroxy-3-[(2E,4E,6E,8E,10E,12E,14E)-15-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaen-1-ylidene]but-1-en-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

Traditional Name

CAS Registry Number

Not Available

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(\CO)/C=C/C1=C(C)C[C@@H](O)CC1(C)C

InChI Identifier

InChI=1S/C40H56O3/c1-29(16-12-17-31(3)20-22-37-32(4)24-35(42)26-39(37,6)7)14-10-11-15-30(2)18-13-19-34(28-41)21-23-38-33(5)25-36(43)27-40(38,8)9/h10-24,35-37,41-43H,25-28H2,1-9H3/b11-10+,16-12+,18-13+,22-20+,23-21+,29-14+,30-15+,31-17+,34-19-/t35-,36+,37-/m0/s1

InChI Key

ODGGKCNQKSEQNL-CWBMHJDKSA-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
Chlamydomonas reinhardtii	LOTUS Database	35616633
Chlorella vulgaris	Plant	KNApSAcK
Cladophora glomerata	LOTUS Database	35616633
Corbicula japonica	Plant	KNApSAcK
Corbicula sandai	Plant	KNApSAcK
Euglena sanguinea	LOTUS Database	35616633
Scenedesmus obliquus	Plant	KNApSAcK
Tetraselmis suecica	LOTUS Database	35616633
Ulva rigida	-	KNApSAcK

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
Long chain fatty alcohol
Fatty alcohol
Fatty acyl
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

C40 isoprenoids (tetraterpenes) (LMPR01070156 )

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	7.6	ALOGPS
logP	7.27	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	16.95	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	196.84 m³·mol⁻¹	ChemAxon
Polarizability	74.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000927

Chemspider ID

10380806

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16061271

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

van den Berg TE, Croce R: The Loroxanthin Cycle: A New Type of Xanthophyll Cycle in Green Algae (Chlorophyta). Front Plant Sci. 2022 Feb 17;13:797294. doi: 10.3389/fpls.2022.797294. eCollection 2022. [PubMed:35251077 ]
Naik SM, Anil AC: Influence of darkness on pigments of Tetraselmis indica (Chlorodendrophyceae, Chlorophyta). J Photochem Photobiol B. 2018 Sep;186:17-22. doi: 10.1016/j.jphotobiol.2018.06.010. Epub 2018 Jun 28. [PubMed:29982094 ]
Wang N, Manabe Y, Sugawara T, Paul NA, Zhao J: Identification and biological activities of carotenoids from the freshwater alga Oedogonium intermedium. Food Chem. 2018 Mar 1;242:247-255. doi: 10.1016/j.foodchem.2017.09.075. Epub 2017 Sep 15. [PubMed:29037686 ]
van den Berg TE, van Oort B, Croce R: Light-harvesting complexes of Botryococcus braunii. Photosynth Res. 2018 Mar;135(1-3):191-201. doi: 10.1007/s11120-017-0405-8. Epub 2017 May 27. [PubMed:28551868 ]
Sansone C, Galasso C, Orefice I, Nuzzo G, Luongo E, Cutignano A, Romano G, Brunet C, Fontana A, Esposito F, Ianora A: The green microalga Tetraselmis suecica reduces oxidative stress and induces repairing mechanisms in human cells. Sci Rep. 2017 Jan 24;7:41215. doi: 10.1038/srep41215. [PubMed:28117410 ]

Showing NP-Card for (3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol (NP0065721)

MOL for NP0065721 ((3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol)

3D MOL for NP0065721 ((3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol)

3D SDF for NP0065721 ((3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol)

3D-SDF for NP0065721 ((3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol)

PDB for NP0065721 ((3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol)

3D PDB for NP0065721 ((3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol)

SMILES for NP0065721 ((3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol)

INCHI for NP0065721 ((3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol)

Structure for NP0065721 ((3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol)

3D Structure for NP0065721 ((3R,3'R,6'R)-beta,epsilon-Carotene-3,3',19-triol)