NP-MRD: Showing NP-Card for methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate (NP0288972)

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Record Information

Version

2.0

Created at

2022-09-09 18:55:48 UTC

Updated at

2022-09-09 18:55:48 UTC

NP-MRD ID

NP0288972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate

Description

Methyl (5Z,8S,9E,11S,12S)-11-{[(4Z,7R,8S,11R)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2R,3R,4S,5R,6R)-6-[(2R)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate belongs to the class of organic compounds known as other hydroxyeicosapolyenoic acids. These are hydroxyeicosapolyenoic acids which do not belong to the Hydroxyeicosapentaenoic acids, the Hydroxyeicosatetraenoic acids, or the Hydroxyeicosatrienoic acids. methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate is found in Avrainvillea nigricans. Based on a literature review very few articles have been published on methyl (5Z,8S,9E,11S,12S)-11-{[(4Z,7R,8S,11R)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2R,3R,4S,5R,6R)-6-[(2R)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092220552D          

 63 63  0  0  1  0            999 V2000
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    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
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  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
   -1.4289   -4.9500    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  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 C   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 O   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
   10.7171   -6.1875    0.0000 C   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
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 23  1  6  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 25 38  1  0  0  0  0
 38 39  1  1  0  0  0
  9 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
  7 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  1  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 60 62  1  0  0  0  0
 62 63  1  0  0  0  0
M  END

     RDKit          3D

143143  0  0  0  0  0  0  0  0999 V2000
   -1.6386   -6.6785    3.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1128   -6.2606    3.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441   -4.8184    4.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065   -4.2470    4.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8154   -3.1796    3.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072   -2.4404    2.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6875   -0.9580    3.1363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7867   -0.4070    2.2182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4842   -0.3812    2.7521 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6399   -1.2863    1.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2235   -0.9765    0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6186   -1.9173   -0.1505 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9825   -2.0839    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8891   -2.9798   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0615   -2.6531   -0.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935   -1.3368   -0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0066   -0.6594   -2.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9010   -1.3482   -2.9941 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3150   -2.5430   -3.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0943   -2.8107   -3.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1798   -3.4585   -4.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -4.6435   -4.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -1.4919   -1.4583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1313   -2.3780   -2.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3497   -1.9609   -3.6737 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0882   -0.7903   -3.8013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123   -0.1653   -5.0287 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0042    0.8821   -4.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161    2.1110   -5.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3596    3.2457   -5.2447 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3420    3.0865   -6.2261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0261    3.2255   -3.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9461    4.2514   -3.7489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5966   -1.1351   -6.1499 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6232   -2.0682   -6.2768 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313   -1.8269   -5.9216 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7655   -1.0523   -6.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9331   -1.9314   -4.4251 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7446   -0.8876   -4.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8979    0.9892    2.8860 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7638    1.8056    3.6682 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720    0.9784    3.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4902    0.2300    3.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    0.8046    2.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    2.2155    3.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651    2.8379    1.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819    2.6800    0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5398    3.3362   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7438    2.6981   -1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9753   -0.2533    3.0520 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9229   -0.6803    3.9984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8226    1.2096    3.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9940    2.0155    2.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8676    3.4885    2.1453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1297    4.1075    1.9874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204    3.9685    1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8326    5.4945    1.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9018    6.0099    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878    5.5506    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8541    5.9823    1.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769    6.6371    2.2660 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798    5.6490    1.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0584    6.0800    2.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0189   -5.8247    3.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433   -6.8670    4.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4277   -7.5267    3.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -6.3222    2.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6670   -6.9534    4.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815   -4.9364    5.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3716   -4.2790    3.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2561   -4.7557    4.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8667   -2.8730    3.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4205   -2.3439    1.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -2.9605    2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2975   -1.0750    4.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -0.8302    3.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -2.2414    2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4695   -0.0254    0.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226   -2.9396   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913   -2.5375    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4686   -1.1171    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -4.0317   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309092220552D          

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M  END
> <DATABASE_ID>
NP0288972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C[C@H](O)[C@@H](O[C@H](C\C=C/CCC)[C@@H](O)\C=C\[C@H](O)CCCCC(=O)OC)\C=C\[C@H](C\C=C/CCCC(=O)OC)OC[C@H]1O[C@@H](OC[C@H](O)CO)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C47H80O16/c1-5-7-9-11-12-16-23-37(51)40(62-39(24-17-10-8-6-2)38(52)29-27-34(49)21-19-20-26-43(54)59-4)30-28-36(22-15-13-14-18-25-42(53)58-3)60-33-41-44(55)45(56)46(57)47(63-41)61-32-35(50)31-48/h10,12-13,15-17,27-30,34-41,44-52,55-57H,5-9,11,14,18-26,31-33H2,1-4H3/b15-13-,16-12-,17-10-,29-27+,30-28+/t34-,35-,36+,37+,38+,39-,40+,41-,44+,45+,46-,47-/m1/s1

> <INCHI_KEY>
HHLAUZKHZJILSH-OVUIPQBESA-N

> <FORMULA>
C47H80O16

> <MOLECULAR_WEIGHT>
901.141

> <EXACT_MASS>
900.544636496

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
143

> <JCHEM_AVERAGE_POLARIZABILITY>
100.221911084645

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (5Z,8S,9E,11S,12S,14Z)-11-{[(4Z,7R,8S,9E,11R)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2R,3R,4S,5R,6R)-6-[(2R)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate

> <JCHEM_LOGP>
4.414126038333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.99038461688668

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.179736409412287

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8472041933751964

> <JCHEM_POLAR_SURFACE_AREA>
251.35999999999996

> <JCHEM_REFRACTIVITY>
242.38660000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
38

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (5Z,8S,9E,11S,12S,14Z)-11-{[(4Z,7R,8S,9E,11R)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2R,3R,4S,5R,6R)-6-[(2R)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      17.338 -10.010   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   50                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   40                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   12   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   38                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   27   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   25   39                                                  
CONECT   39   38                                                            
CONECT   40    9   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48                                                            
CONECT   50    7   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   63                                                       
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  126    0
END

View in JSmol

Synonyms

Value	Source
Methyl (5Z,8S,9E,11S,12S)-11-{[(4Z,7R,8S,11R)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2R,3R,4S,5R,6R)-6-[(2R)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoic acid	Generator

Chemical Formula

C₄₇H₈₀O₁₆

Average Mass

901.1410 Da

Monoisotopic Mass

900.54464 Da

IUPAC Name

methyl (5Z,8S,9E,11S,12S,14Z)-11-{[(4Z,7R,8S,9E,11R)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2R,3R,4S,5R,6R)-6-[(2R)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C[C@H](O)[C@@H](O[C@H](C\C=C/CCC)[C@@H](O)\C=C\[C@H](O)CCCCC(=O)OC)\C=C\[C@H](C\C=C/CCCC(=O)OC)OC[C@H]1O[C@@H](OC[C@H](O)CO)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C47H80O16/c1-5-7-9-11-12-16-23-37(51)40(62-39(24-17-10-8-6-2)38(52)29-27-34(49)21-19-20-26-43(54)59-4)30-28-36(22-15-13-14-18-25-42(53)58-3)60-33-41-44(55)45(56)46(57)47(63-41)61-32-35(50)31-48/h10,12-13,15-17,27-30,34-41,44-52,55-57H,5-9,11,14,18-26,31-33H2,1-4H3/b15-13-,16-12-,17-10-,29-27+,30-28+/t34-,35-,36+,37+,38+,39-,40+,41-,44+,45+,46-,47-/m1/s1

InChI Key

HHLAUZKHZJILSH-OVUIPQBESA-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
Avrainvillea nigricans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as other hydroxyeicosapolyenoic acids. These are hydroxyeicosapolyenoic acids which do not belong to the Hydroxyeicosapentaenoic acids, the Hydroxyeicosatetraenoic acids, or the Hydroxyeicosatrienoic acids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Other hydroxyeicosapolyenoic acids

Alternative Parents

Substituents

Hydroxyeicosapolyenoic acid
Glycosylglycerol
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Fatty acid ester
Glycerolipid
Fatty acid methyl ester
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Methyl ester
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Dialkyl ether
Acetal
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
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	4.41	ChemAxon
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	251.36 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	242.39 m³·mol⁻¹	ChemAxon
Polarizability	100.22 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

162949238

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate (NP0288972)

MOL for NP0288972 (methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate)

3D MOL for NP0288972 (methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate)

3D SDF for NP0288972 (methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate)

3D-SDF for NP0288972 (methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate)

PDB for NP0288972 (methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate)

3D PDB for NP0288972 (methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate)

SMILES for NP0288972 (methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate)

INCHI for NP0288972 (methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate)

Structure for NP0288972 (methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate)

3D Structure for NP0288972 (methyl (5z,8s,9e,11s,12s,14z)-11-{[(4z,7r,8s,9e,11r)-8,11-dihydroxy-16-methoxy-16-oxohexadeca-4,9-dien-7-yl]oxy}-8-{[(2r,3r,4s,5r,6r)-6-[(2r)-2,3-dihydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-12-hydroxyicosa-5,9,14-trienoate)