NP-MRD: Showing NP-Card for (2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate (NP0221989)

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Record Information

Version

2.0

Created at

2022-09-05 23:42:31 UTC

Updated at

2022-09-05 23:42:32 UTC

NP-MRD ID

NP0221989

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate

Description

(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl (2E,4S,5R,6E,8S,9R,10E,12S,13S,14S,16S,18S)-13-{[(2R,3S,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. Based on a literature review very few articles have been published on (2S,3R,4R)-2,3,4,5-tetrahydroxypentyl (2E,4S,5R,6E,8S,9R,10E,12S,13S,14S,16S,18S)-13-{[(2R,3S,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062201422D          

 57 57  0  0  1  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    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  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  6  0  0  0
 11 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 52 53  1  1  0  0  0
 52 54  1  0  0  0  0
 54 55  1  6  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END

     RDKit          3D

131131  0  0  0  0  0  0  0  0999 V2000
   -8.0846    2.7628    2.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9018    2.4728    3.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4382    1.0617    3.0252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7075    0.2004    3.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3653    0.5766    3.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0286    1.2024    3.9222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0370    2.6227    4.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0350    0.6794    2.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0602    0.5612    1.5521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3186    1.8320    0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3738   -0.7100    0.8542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4583   -1.4342    0.8599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4322   -1.4261   -0.0505 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6462   -1.2303    0.5296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7927   -1.4943   -0.1049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7923   -2.4011    0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3474   -3.6759    0.9275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3581   -3.9605    1.8225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9619   -5.3965    2.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7533   -3.0387    2.4147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7884   -1.6331   -1.5964 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1509   -0.4354   -2.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5307   -2.0770   -2.1994 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7303   -3.2715   -2.9332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5092   -2.4460   -1.1440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6485   -3.7606   -0.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1804   -1.7088    0.9481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5998   -3.0189    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9040   -1.1718    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0978   -1.6476   -0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828   -2.8393   -1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2257   -0.9179   -0.6837 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3834    0.1409    0.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563   -0.4478   -2.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1923    0.5451   -2.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5908    0.0612   -2.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -0.5884   -3.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7747   -1.9060   -3.8783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6688   -0.2168   -3.8755 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5165   -1.3475   -3.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3081    1.0298   -3.4421 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4633    2.2252   -3.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7546    1.1370   -2.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0494    1.1387   -1.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0062    1.0254   -2.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5429    1.2826   -0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7287    1.4319    0.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8727    1.2655   -0.0714 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4387    1.4097    1.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9475    1.2392    1.0087 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6832    1.3762    2.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4889    2.0313   -0.1230 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.7873    1.5635   -0.3876 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6085    3.5062    0.0964 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1315    4.0374   -1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6735    3.8372    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8904    3.2298    0.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8487    2.4159    1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9887    2.2370    2.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2450    0.9284    1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3949    0.7606    3.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2643    0.0123    2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4002   -0.7646    3.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857   -0.5228    3.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8081    0.4922    4.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516    0.7598    4.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9369    2.8333    4.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9780    3.3779    3.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2262    2.8548    5.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8249   -0.3968    3.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454    1.1472    3.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9088    0.5684    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3855    2.0174    0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8989    1.7656   -0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7722    2.6360    1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3232   -0.3357   -0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2410   -0.4667   -0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2271   -1.9357    1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6939   -2.5646   -0.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8649   -5.3864    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1886   -6.0097    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5175   -5.7911    2.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6011   -2.3442   -1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0359   -0.1482   -1.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0565   -1.3303   -2.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6258   -3.6587   -2.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340   -2.4292   -1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9502   -4.3739   -1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0750   -1.8952    2.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7381   -3.1498   -0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
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 57131  1  0
M  END


  Mrv1652309062201422D          

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  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
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 25 26  1  6  0  0  0
 11 27  1  0  0  0  0
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 29 30  2  0  0  0  0
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 54 55  1  6  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C[C@H](C)C[C@H](C)[C@H](O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@@H]1O)[C@@H](C)\C=C(/C)[C@H](O)[C@@H](C)\C=C(/C)[C@H](O)[C@@H](C)\C=C(/C)C(=O)OC[C@H](O)[C@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C42H74O15/c1-12-21(2)13-22(3)14-27(8)40(57-42-39(52)38(51)37(50)33(56-42)20-54-30(11)44)28(9)16-25(6)34(47)23(4)15-24(5)35(48)26(7)17-29(10)41(53)55-19-32(46)36(49)31(45)18-43/h15-17,21-23,26-28,31-40,42-43,45-52H,12-14,18-20H2,1-11H3/b24-15+,25-16+,29-17+/t21-,22-,23-,26-,27-,28-,31+,32-,33+,34+,35-,36+,37+,38-,39-,40-,42-/m0/s1

> <INCHI_KEY>
NCIXLNTUPVOTSJ-UIYRFPKKSA-N

> <FORMULA>
C42H74O15

> <MOLECULAR_WEIGHT>
819.039

> <EXACT_MASS>
818.502771683

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
131

> <JCHEM_AVERAGE_POLARIZABILITY>
89.34994891140902

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl (2E,4S,5R,6E,8S,9R,10E,12S,13S,14S,16S,18S)-13-{[(2R,3S,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate

> <JCHEM_LOGP>
2.845109799666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.726747626492038

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.10302224608005

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1204343941959332

> <JCHEM_POLAR_SURFACE_AREA>
253.12999999999997

> <JCHEM_REFRACTIVITY>
213.93300000000013

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl (2E,4S,5R,6E,8S,9R,10E,12S,13S,14S,16S,18S)-13-{[(2R,3S,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.670 -14.630   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      18.672   4.620   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      16.004   4.620   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      14.670   8.470   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      16.004   9.240   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      12.003   8.470   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      12.003  11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   15   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   13   26                                                  
CONECT   26   25                                                            
CONECT   27   11   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  114    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4R)-2,3,4,5-Tetrahydroxypentyl (2E,4S,5R,6E,8S,9R,10E,12S,13S,14S,16S,18S)-13-{[(2R,3S,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoic acid	Generator

Chemical Formula

C₄₂H₇₄O₁₅

Average Mass

819.0390 Da

Monoisotopic Mass

818.50277 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C[C@H](C)C[C@H](C)[C@H](O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@@H]1O)[C@@H](C)\C=C(/C)[C@H](O)[C@@H](C)\C=C(/C)[C@H](O)[C@@H](C)\C=C(/C)C(=O)OC[C@H](O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C42H74O15/c1-12-21(2)13-22(3)14-27(8)40(57-42-39(52)38(51)37(50)33(56-42)20-54-30(11)44)28(9)16-25(6)34(47)23(4)15-24(5)35(48)26(7)17-29(10)41(53)55-19-32(46)36(49)31(45)18-43/h15-17,21-23,26-28,31-40,42-43,45-52H,12-14,18-20H2,1-11H3/b24-15+,25-16+,29-17+/t21-,22-,23-,26-,27-,28-,31+,32-,33+,34+,35-,36+,37+,38-,39-,40-,42-/m0/s1

InChI Key

NCIXLNTUPVOTSJ-UIYRFPKKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Hydroxyeicosapolyenoic acid
Eicosanoid
Terpene glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Long chain fatty alcohol
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Fatty acid ester
Sugar acid
Fatty acyl
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Polyol
Oxacycle
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Primary alcohol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	2.85	ChemAxon
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	253.13 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	213.93 m³·mol⁻¹	ChemAxon
Polarizability	89.35 Å³	ChemAxon
Number of Rings	1	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163063079

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate (NP0221989)

MOL for NP0221989 ((2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate)

3D MOL for NP0221989 ((2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate)

3D SDF for NP0221989 ((2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate)

3D-SDF for NP0221989 ((2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate)

PDB for NP0221989 ((2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate)

3D PDB for NP0221989 ((2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate)

SMILES for NP0221989 ((2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate)

INCHI for NP0221989 ((2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate)

Structure for NP0221989 ((2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate)

3D Structure for NP0221989 ((2s,3r,4r)-2,3,4,5-tetrahydroxypentyl (2e,4s,5r,6e,8s,9r,10e,12s,13s,14s,16s,18s)-13-{[(2r,3s,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethylicosa-2,6,10-trienoate)