NP-MRD: Showing NP-Card for (1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate (NP0295180)

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Record Information

Version

2.0

Created at

2022-09-10 04:02:38 UTC

Updated at

2022-09-10 04:02:38 UTC

NP-MRD ID

NP0295180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate

Description

Bryostatin 9 belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. (1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate is found in Bugula neritina. Based on a literature review very few articles have been published on bryostatin 9.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102206022D          

 60 63  0  0  1  0            999 V2000
   13.8388    5.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4020    4.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5774    4.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1406    3.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5284    3.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3161    3.9482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8793    3.2483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2671    2.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0916    2.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4793    1.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0425    1.0637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3038    1.7352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6915    1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8303    1.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0057    1.8486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5993    0.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9962    0.3632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4579   -0.3205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2809   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967   -1.0622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2487    0.0141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4299   -0.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4016   -0.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6200    0.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8982    0.4697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3906   -0.1807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3352    1.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9861    1.8202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1616    1.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739    2.5768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9494    2.6051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5126    1.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003    1.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881    1.9336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2107    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    3.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3818    4.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    3.2483    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8339    4.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417    4.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0448    4.7337    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8169    5.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3897    6.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618    6.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7346    7.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5352    7.3080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5068    8.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0795    8.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1903    5.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4181    5.1283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4210    5.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1428    4.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7058    4.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0277    4.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5306    4.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0548    3.2767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7002    3.7906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6180    2.5768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8454    4.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4229    2.5201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  1  1  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 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  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 43 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 53 56  1  0  0  0  0
  7 56  1  0  0  0  0
 56 57  1  6  0  0  0
 56 58  1  0  0  0  0
 15 58  1  1  0  0  0
 50 59  1  6  0  0  0
 41 59  1  6  0  0  0
 38 60  1  0  0  0  0
 28 60  1  6  0  0  0
M  END

     RDKit          3D

124127  0  0  0  0  0  0  0  0999 V2000
    4.9271    1.7629    5.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1486    1.8569    4.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012    0.8811    3.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5679    1.0220    2.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4152    1.9014    1.6615 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9494    0.2505    1.0623 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2950    0.4840   -0.2733 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1138   -0.7562   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3989   -0.7369   -0.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2790   -1.8417   -1.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9705   -3.0083   -1.3461 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6683   -1.5759   -1.1538 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5912   -2.5956   -1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3222   -1.9792   -0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4337   -1.6094   -2.0674 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5900   -2.7836   -2.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9872   -3.5352   -1.3123 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6121   -4.9262   -1.8169 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9286   -5.5524   -2.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2174   -5.6510   -0.6864 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9477   -2.8652   -0.6794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719   -3.3520   -0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6282   -3.5079    0.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2593   -3.7283   -1.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6751   -3.3921   -0.8893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6081   -4.2173   -1.5378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0448   -1.9618   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0639   -1.7422    0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5574   -1.0012    1.4916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8814   -1.3338    1.8354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2726   -1.8919    3.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7208   -2.1985    3.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3833   -2.1129    3.8846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4089    0.4799    1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1780    0.7576   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0210    1.2498    2.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264    0.7486    1.0309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1974    0.1118    2.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6295    2.2045    0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355    2.7007    1.6359 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3556    4.2198    1.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947    4.2419   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158    5.2082   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389    5.3339   -2.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4957    4.5315   -2.8309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7845    6.3555   -3.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5395    6.5137   -4.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2846    2.0781    1.5375 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2411    2.7196    6.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2346    1.6255    4.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9711    2.9036    3.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2436    0.9556    3.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -0.1462    3.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8717    0.2489   -0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0640   -2.3083   -2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3687   -2.7342   -0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0579   -3.5588   -1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8461   -2.8937   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9830   -6.5980   -1.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9844   -6.0758   -0.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7781   -1.8970   -2.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1519   -1.4060   -1.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9565   -2.8468    0.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309102206022D          

 60 63  0  0  1  0            999 V2000
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    4.3818    4.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0448    4.7337    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8169    5.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3897    6.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618    6.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7346    7.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
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 10 11  2  0  0  0  0
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 24 25  1  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
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 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
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 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
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 47 48  1  0  0  0  0
 43 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 53 56  1  0  0  0  0
  7 56  1  0  0  0  0
 56 57  1  6  0  0  0
 56 58  1  0  0  0  0
 15 58  1  1  0  0  0
 50 59  1  6  0  0  0
 41 59  1  6  0  0  0
 38 60  1  0  0  0  0
 28 60  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0295180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@H]1\C(C[C@H]2C[C@@H](OC(=O)C[C@H](O)C[C@@H]3C[C@H](OC(C)=O)C(C)(C)[C@](O)(C[C@@H]4C\C(C[C@@H](O4)\C=C/C(C)(C)[C@]1(O)O2)=C\C(=O)OC)O3)[C@@H](C)O)=C\C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C43H64O17/c1-10-11-35(47)58-39-27(18-37(49)54-9)17-30-21-33(24(2)44)57-38(50)20-28(46)19-31-22-34(55-25(3)45)41(6,7)42(51,59-31)23-32-15-26(16-36(48)53-8)14-29(56-32)12-13-40(4,5)43(39,52)60-30/h12-13,16,18,24,28-34,39,44,46,51-52H,10-11,14-15,17,19-23H2,1-9H3/b13-12-,26-16+,27-18+/t24-,28-,29+,30+,31-,32+,33-,34+,39+,42+,43-/m1/s1

> <INCHI_KEY>
LJHLORJKOHOIPQ-DQPHZCCOSA-N

> <FORMULA>
C43H64O17

> <MOLECULAR_WEIGHT>
852.968

> <EXACT_MASS>
852.414350601

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
124

> <JCHEM_AVERAGE_POLARIZABILITY>
88.80984833838127

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,5Z,7R,8Z,11S,12S,13E,15S,17R,21R,23R,25S)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1^{3,7}.1^{11,15}]nonacos-8-en-12-yl butanoate

> <JCHEM_LOGP>
3.3924804919999993

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.57573121633118

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.585695874559695

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8358312834899717

> <JCHEM_POLAR_SURFACE_AREA>
240.10999999999996

> <JCHEM_REFRACTIVITY>
212.43670000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5Z,7R,8Z,11S,12S,13E,15S,17R,21R,23R,25S)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1^{3,7}.1^{11,15}]nonacos-8-en-12-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      25.832   9.877   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.017   8.571   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.478   8.624   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.663   7.317   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      23.386   5.958   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      21.123   7.370   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      20.308   6.064   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.032   4.704   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.571   4.651   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.295   3.292   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.479   1.986   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      24.834   3.239   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      25.557   1.880   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.216   3.398   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.677   3.451   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.919   1.729   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.793   0.678   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.655  -0.598   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.191  -0.490   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.980  -1.983   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      15.398   0.026   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.869  -0.162   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.816  -1.701   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.357   0.131   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.010   0.877   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.063  -0.337   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.959   2.002   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.307   3.398   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.768   3.451   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.045   4.810   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.506   4.863   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.690   3.556   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.414   2.197   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.151   3.609   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.860   6.116   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.432   6.693   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.179   7.623   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.399   6.064   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.023   7.557   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      10.158   7.785   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.284   8.836   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.858  10.316   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.927  11.425   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.502  12.905   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.571  14.013   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      14.066  13.642   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      12.146  15.493   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      13.215  16.602   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      13.422  11.053   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      13.847   9.573   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      15.719   9.383   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      17.067   8.638   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      18.117   7.512   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      18.718   8.930   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      19.657   7.540   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      18.769   6.116   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      19.974   7.076   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      17.954   4.810   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      12.778   8.465   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      10.123   4.704   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   56                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16   58                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   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                                                       
CONECT   28   27   29   60                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35   39   40   60                                             
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42   59                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   49                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47                                                            
CONECT   49   43   50                                                       
CONECT   50   49   51   59                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   55   56                                             
CONECT   54   53                                                            
CONECT   55   53                                                            
CONECT   56   53    7   57   58                                             
CONECT   57   56                                                            
CONECT   58   56   15                                                       
CONECT   59   50   41                                                       
CONECT   60   38   28                                                       
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₆₄O₁₇

Average Mass

852.9680 Da

Monoisotopic Mass

852.41435 Da

IUPAC Name

(1S,3S,5Z,7R,8Z,11S,12S,13E,15S,17R,21R,23R,25S)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1^{3,7}.1^{11,15}]nonacos-8-en-12-yl butanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H]1\C(C[C@H]2C[C@@H](OC(=O)C[C@H](O)C[C@@H]3C[C@H](OC(C)=O)C(C)(C)[C@](O)(C[C@@H]4C\C(C[C@@H](O4)\C=C/C(C)(C)[C@]1(O)O2)=C\C(=O)OC)O3)[C@@H](C)O)=C\C(=O)OC

InChI Identifier

InChI=1S/C43H64O17/c1-10-11-35(47)58-39-27(18-37(49)54-9)17-30-21-33(24(2)44)57-38(50)20-28(46)19-31-22-34(55-25(3)45)41(6,7)42(51,59-31)23-32-15-26(16-36(48)53-8)14-29(56-32)12-13-40(4,5)43(39,52)60-30/h12-13,16,18,24,28-34,39,44,46,51-52H,10-11,14-15,17,19-23H2,1-9H3/b13-12-,26-16+,27-18+/t24-,28-,29+,30+,31-,32+,33-,34+,39+,42+,43-/m1/s1

InChI Key

LJHLORJKOHOIPQ-DQPHZCCOSA-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
Bugula neritina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Macrolide
Fatty acid ester
Fatty acyl
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Secondary alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.39	ChemAxon
pKa (Strongest Acidic)	10.59	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	240.11 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	212.44 m³·mol⁻¹	ChemAxon
Polarizability	88.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8593546

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23230685

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate (NP0295180)

MOL for NP0295180 ((1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate)

3D MOL for NP0295180 ((1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate)

3D SDF for NP0295180 ((1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate)

3D-SDF for NP0295180 ((1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate)

PDB for NP0295180 ((1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate)

3D PDB for NP0295180 ((1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate)

SMILES for NP0295180 ((1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate)

INCHI for NP0295180 ((1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate)

Structure for NP0295180 ((1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate)

3D Structure for NP0295180 ((1s,3s,5z,7r,8z,11s,12s,13e,15s,17r,21r,23r,25s)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1r)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl butanoate)