NP-MRD: Showing NP-Card for (1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol (NP0261231)

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Record Information

Version

2.0

Created at

2022-09-08 03:37:04 UTC

Updated at

2022-09-08 03:37:04 UTC

NP-MRD ID

NP0261231

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

Description

9-Cis-violaxanthin 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, 9-cis-violaxanthin is considered to be an isoprenoid lipid molecule. (1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol is found in Asparagus falcatus, Mangifera indica, Pittosporum tobira and Rosa foetida. (1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol was first documented in 2016 (PMID: 27960276). 9-Cis-violaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 28490141) (PMID: 26945857).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304232017432D          

 44 47  0  0  0  0            999 V2000
   -5.2296    0.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9440   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9439    1.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9438    1.9132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2055    2.3239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2150    1.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6344    2.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1960    3.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4933    1.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6343    3.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4687    2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0593    1.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9149    3.5706    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9054    4.3955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2015   -0.1490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1894    0.7140    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4747    0.3034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9143   -0.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4870   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040    1.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4696    1.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6237   -0.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3299   -1.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5025   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7727   -0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6237    0.7180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0581   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3331    1.1486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3438   -0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582   -1.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149   -0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2004   -0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4859   -0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2003   -1.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284   -0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428   -0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574   -0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3717   -0.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862   -0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3717    0.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5151   -0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2296   -0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  6  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
  5  6  1  0  0  0  0
 10 13  1  0  0  0  0
 44  1  1  0  0  0  0
 44  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  3  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 15 19  1  1  0  0  0
 16 20  1  0  0  0  0
 16 21  1  1  0  0  0
 16 17  1  0  0  0  0
 18 22  1  0  0  0  0
 18 23  1  0  0  0  0
 18 24  1  0  0  0  0
 19 25  2  0  0  0  0
 20 26  1  0  0  0  0
 22 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  1  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 41  1  0  0  0  0
 39 40  1  0  0  0  0
 40 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END

     RDKit          3D

100103  0  0  0  0  0  0  0  0999 V2000
   -7.9313    3.4261   -2.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2919    2.3089   -2.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0978    2.4715   -1.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3590    1.4566   -0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1305    1.7878   -0.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    0.8592    0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6285   -0.5704    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1056    1.2847    0.4901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0220    0.4078    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921    0.9613    1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2710    0.0401    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.6175    1.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6038    2.0849    1.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6139   -0.2503    1.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667    0.2254    1.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9459   -0.7042    1.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1649   -0.6608    1.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0676    1.1770    1.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5383   -0.5898    1.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2711   -1.5534    0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7541   -1.4240    0.9091 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5358   -1.7343   -0.1991 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2613   -0.4028    0.0829 C   0  0  1  0  0  0  0  0  0  0  0  0
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   12.2464    0.5606    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7996    0.2898    1.9559 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9140    1.5496    2.6244 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9542   -0.5611    2.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4434   -1.7675    2.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5800   -2.7269    1.8892 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5198   -2.5368    3.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1780    1.2217   -1.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3598    1.1076   -2.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4450    0.1426   -1.9878 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.4002    0.7198   -1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7090    0.5099   -2.5439 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.7970    1.8215   -3.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7587   -0.4911   -2.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9758    1.2525    2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6121   -1.8297    1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1956    0.0854    2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
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  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 32  1  0
 32 33  2  0
 34 33  1  6
 34 35  1  0
 35 36  1  0
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 39 40  1  0
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 17 18  1  0
 17 19  1  0
 19 20  2  0
 21 20  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 36 34  1  0
 23 21  1  0
 42 34  1  0
 29 21  1  0
  7 51  1  0
  7 52  1  0
  7 53  1  0
  5 50  1  0
  4 49  1  0
  3 48  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
 32 84  1  0
 33 85  1  0
 37 86  1  0
 37 87  1  0
 37 88  1  0
 38 89  1  0
 38 90  1  0
 39 91  1  1
 40 92  1  0
 41 93  1  0
 41 94  1  0
 43 95  1  0
 43 96  1  0
 43 97  1  0
 44 98  1  0
 44 99  1  0
 44100  1  0
  8 54  1  0
  9 55  1  0
 10 56  1  0
 11 57  1  0
 13 58  1  0
 13 59  1  0
 13 60  1  0
 14 61  1  0
 15 62  1  0
 16 63  1  0
 18 64  1  0
 18 65  1  0
 18 66  1  0
 19 67  1  0
 20 68  1  0
 24 69  1  0
 24 70  1  0
 24 71  1  0
 25 72  1  0
 25 73  1  0
 26 74  1  6
 27 75  1  0
 28 76  1  0
 28 77  1  0
 30 78  1  0
 30 79  1  0
 30 80  1  0
 31 81  1  0
 31 82  1  0
 31 83  1  0
M  END


  Mrv1652304232017432D          

 44 47  0  0  0  0            999 V2000
   -5.2296    0.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9440   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9439    1.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9438    1.9132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2055    2.3239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2150    1.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6344    2.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1960    3.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4933    1.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6343    3.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4687    2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0593    1.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9149    3.5706    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9054    4.3955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2015   -0.1490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1894    0.7140    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4747    0.3034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9143   -0.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4870   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040    1.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4696    1.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6237   -0.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3299   -1.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5025   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7727   -0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6237    0.7180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0581   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3331    1.1486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3438   -0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582   -1.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149   -0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2004   -0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4859   -0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2003   -1.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284   -0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428   -0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574   -0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3717   -0.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0862   -0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3717    0.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -0.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5151   -0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2296   -0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  6  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
  5  6  1  0  0  0  0
 10 13  1  0  0  0  0
 44  1  1  0  0  0  0
 44  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  3  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 15 19  1  1  0  0  0
 16 20  1  0  0  0  0
 16 21  1  1  0  0  0
 16 17  1  0  0  0  0
 18 22  1  0  0  0  0
 18 23  1  0  0  0  0
 18 24  1  0  0  0  0
 19 25  2  0  0  0  0
 20 26  1  0  0  0  0
 22 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  1  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 41  1  0  0  0  0
 39 40  1  0  0  0  0
 40 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0261231

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19-,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1

> <INCHI_KEY>
SZCBXWMUOPQSOX-NLNQYMAJSA-N

> <FORMULA>
C40H56O4

> <MOLECULAR_WEIGHT>
600.884

> <EXACT_MASS>
600.417860283

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
73.4757874462924

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,6S)-6-[(1E,3Z,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

> <ALOGPS_LOGP>
8.33

> <JCHEM_LOGP>
7.257461110666667

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.440714029770106

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.838654038442144

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7377022034819802

> <JCHEM_POLAR_SURFACE_AREA>
62.22

> <JCHEM_REFRACTIVITY>
192.32700000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.68e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-cis-violaxanthin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-20         0                                  
HETATM    1  C   UNK     0      -9.762   1.261   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.095  -1.048   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.095   2.032   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.095   3.571   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.717   4.338   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -9.735   2.798   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0     -12.384   4.350   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.699   5.878   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.387   3.554   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.384   5.901   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -13.942   4.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.177   3.037   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.041   6.665   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -11.023   8.205   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.576  -0.278   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.554   1.333   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.220   0.566   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.907  -0.971   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.242  -1.048   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.887   2.109   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.210   2.102   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.231  -0.195   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.682  -2.296   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.138  -2.305   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.909  -0.278   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.231   1.340   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.575  -1.048   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.555   2.144   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.242  -0.278   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.575  -2.588   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.908  -1.048   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.574  -0.278   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.241  -1.048   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.907  -0.278   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.241  -2.589   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.426  -1.048   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.760  -0.278   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.094  -1.048   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.427  -0.279   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.761  -1.048   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -4.427   1.262   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -7.095  -0.278   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -8.428  -1.048   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -9.762  -0.278   0.000  0.00  0.00           C+0
CONECT    1   44    3                                                       
CONECT    2   44                                                            
CONECT    3    1    4                                                       
CONECT    4    5    6    7    3                                             
CONECT    5    4    8    9    6                                             
CONECT    6    4    5                                                       
CONECT    7    4   10   11   12                                             
CONECT    8    5   13                                                       
CONECT    9    5                                                            
CONECT   10    7   13                                                       
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    8   14   10                                                  
CONECT   14   13                                                            
CONECT   15   16   17   18   19                                             
CONECT   16   15   20   21   17                                             
CONECT   17   15   16                                                       
CONECT   18   15   22   23   24                                             
CONECT   19   15   25                                                       
CONECT   20   16   26                                                       
CONECT   21   16                                                            
CONECT   22   18   26                                                       
CONECT   23   18                                                            
CONECT   24   18                                                            
CONECT   25   19   27                                                       
CONECT   26   20   22   28                                                  
CONECT   27   25   29   30                                                  
CONECT   28   26                                                            
CONECT   29   27   31                                                       
CONECT   30   27                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33   36                                                       
CONECT   35   33                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   41   40                                                  
CONECT   40   39   42                                                       
CONECT   41   39                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44                                                       
CONECT   44    1    2   43                                                  
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₅₆O₄

Average Mass

600.8840 Da

Monoisotopic Mass

600.41786 Da

IUPAC Name

(1R,3S,6S)-6-[(1E,3Z,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

Traditional Name

9-cis-violaxanthin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19-,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1

InChI Key

SZCBXWMUOPQSOX-NLNQYMAJSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Asparagus falcatus	LOTUS Database	35616633
Mangifera indica	LOTUS Database	35616633
Pittosporum tobira	LOTUS Database	35616633
Rosa foetida	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
Oxepane
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

violaxanthin (CHEBI:35305 )
C40 isoprenoids (tetraterpenes) (C13433 )
Carotenoids (C13433 )
C40 isoprenoids (tetraterpenes) (LMPR01070284 )

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	8.33	ALOGPS
logP	7.26	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	14.84	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.22 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	192.33 m³·mol⁻¹	ChemAxon
Polarizability	73.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045500

Chemspider ID

4445401

KEGG Compound ID

C13433

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282218

PDB ID

Not Available

ChEBI ID

35305

Good Scents ID

Not Available

References

General References

Lu Q, Huang X, Lv S, Pan S: Carotenoid profiling of red navel orange "Cara Cara" harvested from five regions in China. Food Chem. 2017 Oct 1;232:788-798. doi: 10.1016/j.foodchem.2017.04.064. Epub 2017 Apr 12. [PubMed:28490141 ]
Araki M, Kaku N, Harada M, Ando Y, Yamaguchi R, Shindo K: Production of Auroxanthins from Violaxanthin and 9-cis-Violaxanthin by Acidic Treatment and the Antioxidant Activities of Violaxanthin, 9-cis-Violaxanthin, and Auroxanthins. J Agric Food Chem. 2016 Dec 14;64(49):9352-9355. doi: 10.1021/acs.jafc.6b04506. Epub 2016 Dec 5. [PubMed:27960276 ]
Bruno M, Al-Babili S: On the substrate specificity of the rice strigolactone biosynthesis enzyme DWARF27. Planta. 2016 Jun;243(6):1429-40. doi: 10.1007/s00425-016-2487-5. Epub 2016 Mar 5. [PubMed:26945857 ]
LOTUS database [Link]

Showing NP-Card for (1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol (NP0261231)

MOL for NP0261231 ((1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

3D MOL for NP0261231 ((1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

3D SDF for NP0261231 ((1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

3D-SDF for NP0261231 ((1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

PDB for NP0261231 ((1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

3D PDB for NP0261231 ((1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

SMILES for NP0261231 ((1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

INCHI for NP0261231 ((1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

Structure for NP0261231 ((1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)

3D Structure for NP0261231 ((1r,3s,6s)-6-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol)