NP-MRD: Showing NP-Card for (1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one (NP0320029)

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Record Information

Version

2.0

Created at

2022-09-11 21:22:41 UTC

Updated at

2022-09-11 21:22:41 UTC

NP-MRD ID

NP0320029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one

Description

Oscillariolide belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one was first documented in 2016 (PMID: 27579900). Based on a literature review a small amount of articles have been published on Oscillariolide (PMID: 31458533) (PMID: 26998826).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223222D          

 53 54  0  0  1  0            999 V2000
    2.5249   11.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249   10.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9538   10.6561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9538   11.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6683   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3828   10.6561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3828   11.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0973   10.2436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0973    9.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8117   10.6561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8117   11.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5262   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2407   10.6561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2407   11.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9551   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3676   10.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5426    9.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6696    9.8311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6696    9.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3841   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0985    9.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8130   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0985    9.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8130    8.5936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5275    9.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8130    7.7686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9925    7.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6335    7.8548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0626    7.1110    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8163    6.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9025    5.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6562    5.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2351    5.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3213    4.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0750    4.3140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6539    4.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9002    4.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9864    3.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2328    4.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4791    4.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8116    3.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3929    5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0603    5.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8140    5.3207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9741    6.4767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6415    6.9616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3952    6.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0960   10.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815   10.2436    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.8104    9.4186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0960    9.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 25  1  1  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 27 47  1  0  0  0  0
 47 48  1  1  0  0  0
 30 48  1  1  0  0  0
  2 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 49 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END

     RDKit          3D

122123  0  0  0  0  0  0  0  0999 V2000
    8.0923    2.3708    2.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7202    2.8413    1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4666    2.5222   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5447    1.2742   -0.2393 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2991    0.2433    0.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4096    0.9658   -1.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5516   -0.1184   -2.1556 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2266    0.2327   -1.7458 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8194   -1.5309   -1.8145 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1995   -2.0327   -2.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3246   -2.1303   -0.5712 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8118   -3.5080   -0.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313   -2.3310   -0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1639   -3.2281   -1.3713 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2345   -2.8555   -2.7104 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -3.5218   -1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162   -4.1264    0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710   -4.6506   -2.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974   -2.3531   -1.3699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0632   -1.2374   -0.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823   -2.8290   -1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6458   -1.7959   -1.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6816   -1.0598   -2.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5861   -1.4388   -0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217   -0.3884   -0.9823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4920    0.7240   -0.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403   -1.0679   -0.8463 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9097   -2.3039   -1.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2043   -1.5209    0.4285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6094   -1.6440    0.5656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9885   -0.8306    1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2574   -1.1523    2.4240 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2498   -1.9445    1.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0089   -0.0052    3.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6345    1.3025    2.4848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8546    1.1649    1.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4316    2.4957    2.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7089    3.7079    2.2518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6106    4.8899    2.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7979    3.4930    1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2784    3.4556   -0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7028    3.7268   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4151    3.1717   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2091    2.3444   -1.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1313    2.9920   -1.5020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1703    1.0404   -0.6947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1387   -0.1993   -1.2394 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1924   -1.1961   -0.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8525    3.7679    1.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5213    4.2804    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9672    5.4663    0.9709 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.1787    4.0718    2.8584 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0925    3.3382    3.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2574    1.6972    2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4478    2.6979    3.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3703    2.2730   -0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8706    3.3523   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6315    1.5199    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0274   -0.0442    1.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0906    1.9704   -2.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4731    0.8986   -2.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4806   -0.0375   -3.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284    0.8152   -0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -2.1459   -2.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7035   -1.3703   -2.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1015   -3.0271   -2.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8496   -2.2059   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7697   -1.8018    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7089   -3.5424   -0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7122   -2.7092    0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3317   -1.3553   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7444   -4.2166   -1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925   -3.6324   -3.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156   -4.8828    0.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -3.3790    0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2902   -4.6555    0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2427   -5.3295   -2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649   -4.2647   -3.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966   -5.2216   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473   -1.9798   -2.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5078   -1.1556    0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081   -3.2353   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -3.6190   -2.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995    0.0173   -2.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8978   -2.7428   -1.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1380   -1.0033    2.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0527   -1.8603    3.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8046   -2.8665    1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8036   -1.3395    0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0360   -2.2987    2.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8326    0.0511    4.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1116   -0.1458    2.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5956    1.5011    2.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8129    1.0460    0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4840    2.4363    2.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5430    2.5542    3.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0363    3.9955    3.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6541    4.6676    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1118    5.5940    1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6780    5.5108    3.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0802    2.6585    1.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0866    4.3920    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9337    4.7839   -0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3955    3.1541    0.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9153    3.2831   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6659    3.6340   -2.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2187   -0.3196   -2.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3530   -2.0139   -1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1275   -0.6269   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2970    4.0689   -0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1033    3.3446    3.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7443    2.3343    3.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2200    3.8798    4.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
 53 52  1  0
 52 49  1  0
 49 50  2  0
 50 51  1  0
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  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
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  9 10  1  0
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 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
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 25 27  1  0
 27 28  1  6
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 29 30  1  0
 30 48  1  0
 48 47  1  0
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 46 44  1  0
 44 45  2  0
 44 43  1  0
 43 41  2  0
 41 42  1  0
 41 40  1  0
 40 38  1  0
 38 39  1  0
 38 37  1  0
 37 35  1  0
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 35 34  1  0
 34 32  1  0
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 31 30  1  0
 53120  1  0
 53121  1  0
 53122  1  0
 50119  1  0
  1 54  1  0
  1 55  1  0
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  3 57  1  0
  4 58  1  1
  5 59  1  0
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  6 61  1  0
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  9 64  1  6
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 30 93  1  1
 48117  1  0
 48118  1  0
 47116  1  6
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 42112  1  0
 42113  1  0
 42114  1  0
 40110  1  0
 40111  1  0
 38106  1  1
 39107  1  0
 39108  1  0
 39109  1  0
 37104  1  0
 37105  1  0
 35102  1  6
 36103  1  0
 34100  1  0
 34101  1  0
 32 96  1  1
 33 97  1  0
 33 98  1  0
 33 99  1  0
 31 94  1  0
 31 95  1  0
M  END


  Mrv1652309112223222D          

 53 54  0  0  1  0            999 V2000
    2.5249   11.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249   10.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9538   10.6561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9538   11.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6683   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3828   10.6561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3828   11.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0973   10.2436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0973    9.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8117   10.6561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8117   11.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5262   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2407   10.6561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2407   11.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9551   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3676   10.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5426    9.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6696    9.8311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6696    9.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3841   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0985    9.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8130   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0985    9.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8130    8.5936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5275    9.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8130    7.7686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9925    7.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6335    7.8548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0626    7.1110    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8163    6.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9025    5.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6562    5.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2351    5.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3213    4.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0750    4.3140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6539    4.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9002    4.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9864    3.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2328    4.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4791    4.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8116    3.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3929    5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0603    5.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8140    5.3207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9741    6.4767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6415    6.9616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3952    6.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   10.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0960   10.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815   10.2436    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.8104    9.4186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0960    9.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 25  1  1  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 27 47  1  0  0  0  0
 47 48  1  1  0  0  0
 30 48  1  1  0  0  0
  2 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 49 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO\C(=C/Br)C(=C)C[C@H](O)C[C@H](O)[C@@H](C)[C@H](O)C[C@H](O)C(C)(C)[C@H](O)C\C(C)=C\[C@H](O)[C@@]1(C)O[C@@H]2C[C@H]1OC(=O)\C=C(C)/CC(C)CC(O)CC(C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C41H69BrO11/c1-23-11-24(2)17-39(50)52-38-20-31(14-25(3)13-29(43)12-23)53-41(38,9)37(49)16-26(4)15-35(47)40(7,8)36(48)21-33(46)28(6)32(45)19-30(44)18-27(5)34(22-42)51-10/h16-17,22-23,25,28-33,35-38,43-49H,5,11-15,18-21H2,1-4,6-10H3/b24-17-,26-16+,34-22-/t23?,25?,28-,29?,30+,31+,32+,33-,35-,36+,37+,38-,41-/m1/s1

> <INCHI_KEY>
PLLOEODSUMNSFG-RBDUAFRVSA-N

> <FORMULA>
C41H69BrO11

> <MOLECULAR_WEIGHT>
817.896

> <EXACT_MASS>
816.402326

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
122

> <JCHEM_AVERAGE_POLARIZABILITY>
83.67615546842508

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4Z,13S,15R)-15-[(1S,2E,5R,7S,9R,10R,11S,13S,16Z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one

> <JCHEM_LOGP>
3.5205119873333364

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.099284123478814

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.414849104768628

> <JCHEM_PKA_STRONGEST_BASIC>
-0.968583896150209

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
211.1216

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4Z,13S,15R)-15-[(1S,2E,5R,7S,9R,10R,11S,13S,16Z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.713  21.431   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.713  19.891   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.047  19.121   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.381  19.891   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.381  21.431   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.714  19.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.048  19.891   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.048  21.431   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.382  19.121   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.382  17.581   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.715  19.891   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.715  21.431   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.049  19.121   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.383  19.891   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.383  21.431   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      16.716  19.121   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.486  20.455   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.946  17.788   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.050  18.351   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.050  16.811   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      19.384  19.121   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.717  18.351   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.051  19.121   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.717  16.811   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.051  16.041   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      23.385  16.811   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      22.051  14.501   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.519  14.662   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      23.583  14.662   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      24.384  13.274   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.790  12.647   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.951  11.116   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      27.358  10.490   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      24.705  10.211   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      24.866   8.679   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      26.273   8.053   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      23.621   7.774   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      22.214   8.400   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      22.375   6.869   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.968   7.495   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      19.561   8.122   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      18.315   7.216   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      19.400   9.653   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      20.646  10.558   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      22.053   9.932   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      20.485  12.090   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      21.731  12.995   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      23.138  12.369   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       3.379  19.121   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       2.046  19.891   0.000  0.00  0.00           C+0
HETATM   51 Br   UNK     0       0.712  19.121   0.000  0.00  0.00          Br+0
HETATM   52  O   UNK     0       3.379  17.581   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       2.046  16.811   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   49                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   47                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   48                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   27   48                                                  
CONECT   48   47   30                                                       
CONECT   49    2   50   52                                                  
CONECT   50   49   51                                                       
CONECT   51   50                                                            
CONECT   52   49   53                                                       
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  108    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₆₉BrO₁₁

Average Mass

817.8960 Da

Monoisotopic Mass

816.40233 Da

IUPAC Name

(1R,4Z,13S,15R)-15-[(1S,2E,5R,7S,9R,10R,11S,13S,16Z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CO\C(=C/Br)C(=C)C[C@H](O)C[C@H](O)[C@@H](C)[C@H](O)C[C@H](O)C(C)(C)[C@H](O)C\C(C)=C\[C@H](O)[C@@]1(C)O[C@@H]2C[C@H]1OC(=O)\C=C(C)/CC(C)CC(O)CC(C)C2

InChI Identifier

InChI=1S/C41H69BrO11/c1-23-11-24(2)17-39(50)52-38-20-31(14-25(3)13-29(43)12-23)53-41(38,9)37(49)16-26(4)15-35(47)40(7,8)36(48)21-33(46)28(6)32(45)19-30(44)18-27(5)34(22-42)51-10/h16-17,22-23,25,28-33,35-38,43-49H,5,11-15,18-21H2,1-4,6-10H3/b24-17-,26-16+,34-22-/t23?,25?,28-,29?,30+,31+,32+,33-,35-,36+,37+,38-,41-/m1/s1

InChI Key

PLLOEODSUMNSFG-RBDUAFRVSA-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 macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Monosaccharide
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Secondary alcohol
Haloalkene
Organoheterocyclic compound
Bromoalkene
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Polyol
Vinyl bromide
Oxacycle
Vinyl halide
Organohalogen compound
Organobromide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	3.52	ChemAxon
pKa (Strongest Acidic)	13.41	ChemAxon
pKa (Strongest Basic)	-0.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	211.12 m³·mol⁻¹	ChemAxon
Polarizability	83.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

101209502

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gil A, Giarrusso M, Lamariano-Merketegi J, Lorente A, Albericio F, Alvarez M: Toward the Synthesis of Phormidolides. ACS Omega. 2018 Feb 27;3(2):2351-2362. doi: 10.1021/acsomega.8b00125. eCollection 2018 Feb 28. [PubMed:31458533 ]
Gil A, Lamariano-Merketegi J, Lorente A, Albericio F, Alvarez M: Enantioselective Synthesis of the Polyhydroxylated Chain of Oscillariolide and Phormidolides A-C. Org Lett. 2016 Sep 16;18(18):4485-7. doi: 10.1021/acs.orglett.6b02014. Epub 2016 Aug 31. [PubMed:27579900 ]
Gil A, Lamariano-Merketegi J, Lorente A, Albericio F, Alvarez M: Synthesis of (E)-4-Bromo-3-methoxybut-3-en-2-one, the Key Fragment in the Polyhydroxylated Chain Common to Oscillariolide and Phormidolides A-C. Chemistry. 2016 May 17;22(21):7033-5. doi: 10.1002/chem.201600770. Epub 2016 Apr 13. [PubMed:26998826 ]
LOTUS database [Link]

Showing NP-Card for (1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one (NP0320029)

MOL for NP0320029 ((1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one)

3D MOL for NP0320029 ((1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one)

3D SDF for NP0320029 ((1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one)

3D-SDF for NP0320029 ((1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one)

PDB for NP0320029 ((1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one)

3D PDB for NP0320029 ((1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one)

SMILES for NP0320029 ((1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one)

INCHI for NP0320029 ((1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one)

Structure for NP0320029 ((1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one)

3D Structure for NP0320029 ((1r,4z,13s,15r)-15-[(1s,2e,5r,7s,9r,10r,11s,13s,16z)-17-bromo-1,5,7,9,11,13-hexahydroxy-16-methoxy-3,6,6,10-tetramethyl-15-methylideneheptadeca-2,16-dien-1-yl]-9-hydroxy-5,7,11,15-tetramethyl-2,14-dioxabicyclo[11.2.1]hexadec-4-en-3-one)