NP-MRD: Showing NP-Card for methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate (NP0282401)

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Record Information

Version

2.0

Created at

2022-09-09 09:12:38 UTC

Updated at

2022-09-09 09:12:38 UTC

NP-MRD ID

NP0282401

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate

Description

Methyl 2-[(1S,2S,4R,5R,10S,12S,14R)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]Nonadeca-6,8-dien-4-yl]prop-2-enoate 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. methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate is found in Antillogorgia bipinnata. Based on a literature review very few articles have been published on methyl 2-[(1S,2S,4R,5R,10S,12S,14R)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]Nonadeca-6,8-dien-4-yl]prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092211122D          

 36 40  0  0  1  0            999 V2000
    1.4054   -3.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2089   -3.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727   -3.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5331   -4.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762   -3.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401   -4.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485   -2.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8846   -1.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812   -1.9633    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8415   -2.7527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -2.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -3.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5258   -2.3377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5173   -1.3611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0722   -0.7839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224   -0.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3916    0.2604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9938    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    0.4257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4223    1.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9898    1.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270    0.5779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1674   -0.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9894   -0.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1766   -0.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9523   -1.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277   -0.7995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520   -2.1911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8158   -2.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6193   -2.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8589   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1832   -3.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3485   -0.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847   -1.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.7026    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 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  1  1  0  0  0
 19 21  1  0  0  0  0
 22 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 17 34  1  6  0  0  0
 34 35  1  0  0  0  0
 14 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    2.8930    0.4744    1.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687    0.3140    0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4400    0.3622   -0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0665    0.2235   -1.9340 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7798    0.5608   -0.4922 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7821    0.6198   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0126    0.1094    0.1171 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4640    1.1584   -0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1883    2.3498   -0.1152 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6355    2.9431    0.8597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1306    4.2408    0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992    4.8692    1.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8142    4.8803   -0.2821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5705    2.0262    0.4042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7860    0.7543    0.8942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3878    1.2814   -0.3927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8606    1.4975    0.0300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2746    0.1311    0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5243   -0.8823   -0.5136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4871   -0.4817   -1.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0182   -2.1033    0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8612   -2.1018   -0.6115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5345   -2.3306    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -3.0343    1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6303   -2.7852    1.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3717   -3.3252    2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3824   -1.9361    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5306   -1.7246   -0.5519 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.2747   -0.5324 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9153   -2.1389   -0.2746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271   -2.8561   -1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596   -3.7638   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2908   -2.7215   -2.4228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6777    2.3597    1.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4334    3.0525    1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983    4.2310    1.3487 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1763    0.4392    2.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9253    0.6383    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6039   -0.0678   -1.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2325    1.6233   -1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4314    0.2116   -2.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5482    0.0964    1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177    1.5891   -1.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282    0.7700   -1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3308    3.1004   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7810    5.4438    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3758    5.6595    2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4385    4.1574    2.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1902    0.6985   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4731    1.9046   -0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1891    0.2019    1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4438   -0.2398    1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2884    0.5258   -2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5015   -0.5188   -1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3270   -1.1793   -2.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9305   -2.6524   -1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5341   -3.6484    1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047   -3.6508    1.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0441   -4.2777    2.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6881   -1.2080   -1.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8954   -4.4832   -1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5416   -4.2938    0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
 14 15  1  1
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 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
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 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 17 34  1  0
 34 35  1  0
 35 36  2  0
 29  7  1  0
 16 14  1  0
 22 19  1  0
 28 23  1  0
 35 14  1  0
  6 39  1  0
  6 40  1  0
  6 41  1  0
  1 37  1  0
  1 38  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  9 45  1  6
 12 46  1  0
 12 47  1  0
 12 48  1  0
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 26 60  1  0
 29 61  1  6
 32 62  1  0
 32 63  1  0
 32 64  1  0
M  END


  Mrv1652309092211122D          

 36 40  0  0  1  0            999 V2000
    1.4054   -3.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2089   -3.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727   -3.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5331   -4.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762   -3.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401   -4.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485   -2.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8846   -1.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812   -1.9633    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8415   -2.7527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -2.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -3.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5258   -2.3377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5173   -1.3611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0722   -0.7839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224   -0.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3916    0.2604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9938    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    0.4257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4223    1.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9898    1.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270    0.5779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1674   -0.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9894   -0.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1766   -0.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9523   -1.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277   -0.7995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520   -2.1911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8158   -2.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6193   -2.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8589   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1832   -3.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3485   -0.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847   -1.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.7026    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 22 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 17 34  1  6  0  0  0
 34 35  1  0  0  0  0
 14 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0282401

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C)[C@H]1C[C@H](OC(C)=O)[C@]23OC2[C@@H](C[C@]2(C)O[C@@H]2C2=CC(C)=C(O2)[C@@H]1OC(C)=O)OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O11/c1-10-7-15-20-24(5,35-20)9-16-21-25(36-21,23(29)34-16)17(31-12(3)26)8-14(11(2)22(28)30-6)19(18(10)33-15)32-13(4)27/h7,14,16-17,19-21H,2,8-9H2,1,3-6H3/t14-,16-,17+,19-,20-,21?,24+,25+/m1/s1

> <INCHI_KEY>
SETTUTVEWZFWRZ-JELJFLFASA-N

> <FORMULA>
C25H28O11

> <MOLECULAR_WEIGHT>
504.488

> <EXACT_MASS>
504.163161722

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.56601430962442

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1S,2S,4R,5R,10S,12S,14R)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-dien-4-yl]prop-2-enoate

> <JCHEM_LOGP>
1.5425030546666663

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8658984753516643

> <JCHEM_POLAR_SURFACE_AREA>
143.4

> <JCHEM_REFRACTIVITY>
116.9969

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(1S,2S,4R,5R,10S,12S,14R)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-dien-4-yl]prop-2-enoate

> <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       2.623  -6.263   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.123  -5.913   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.176  -7.037   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.728  -8.511   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.676  -6.688   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.728  -7.812   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.571  -4.440   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.518  -3.315   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.018  -3.665   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.571  -5.138   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.071  -5.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.376  -6.961   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.982  -4.364   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.966  -2.541   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.135  -1.463   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.349  -1.049   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.731   0.486   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.855   1.539   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.204   0.795   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.655   2.234   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.714   2.247   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.717   1.079   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.912  -0.019   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.447  -0.150   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.796  -1.650   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.244  -2.174   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.518  -2.616   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.465  -1.492   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.070  -4.090   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.123  -5.214   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.623  -4.865   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.070  -3.391   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.675  -5.989   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -0.650  -0.644   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.531  -2.179   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.704  -3.178   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16   35                                             
CONECT   15   14   16                                                       
CONECT   16   15   14   17                                                  
CONECT   17   16   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   19   23                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27    7   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   17   35                                                       
CONECT   35   34   14   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(1S,2S,4R,5R,10S,12S,14R)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1,.0,.0,]nonadeca-6,8-dien-4-yl]prop-2-enoic acid	Generator

Chemical Formula

C₂₅H₂₈O₁₁

Average Mass

504.4880 Da

Monoisotopic Mass

504.16316 Da

IUPAC Name

methyl 2-[(1S,2S,4R,5R,10S,12S,14R)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-dien-4-yl]prop-2-enoate

Traditional Name

methyl 2-[(1S,2S,4R,5R,10S,12S,14R)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-dien-4-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C)[C@H]1C[C@H](OC(C)=O)[C@]23OC2[C@@H](C[C@]2(C)O[C@@H]2C2=CC(C)=C(O2)[C@@H]1OC(C)=O)OC3=O

InChI Identifier

InChI=1S/C25H28O11/c1-10-7-15-20-24(5,35-20)9-16-21-25(36-21,23(29)34-16)17(31-12(3)26)8-14(11(2)22(28)30-6)19(18(10)33-15)32-13(4)27/h7,14,16-17,19-21H,2,8-9H2,1,3-6H3/t14-,16-,17+,19-,20-,21?,24+,25+/m1/s1

InChI Key

SETTUTVEWZFWRZ-JELJFLFASA-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
Antillogorgia bipinnata	LOTUS Database	35616633

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

Tetracarboxylic acid or derivatives
Macrolide
Gamma butyrolactone
Para-dioxane
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Furan
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.54	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	143.4 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117 m³·mol⁻¹	ChemAxon
Polarizability	49.57 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

163187182

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate (NP0282401)

MOL for NP0282401 (methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate)

3D MOL for NP0282401 (methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate)

3D SDF for NP0282401 (methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate)

3D-SDF for NP0282401 (methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate)

PDB for NP0282401 (methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate)

3D PDB for NP0282401 (methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate)

SMILES for NP0282401 (methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate)

INCHI for NP0282401 (methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate)

Structure for NP0282401 (methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate)

3D Structure for NP0282401 (methyl 2-[(1s,2s,4r,5r,10s,12s,14r)-2,5-bis(acetyloxy)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.1⁶,⁹.0¹,¹⁵.0¹⁰,¹²]nonadeca-6,8-dien-4-yl]prop-2-enoate)