NP-MRD: Showing NP-Card for methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate (NP0314379)

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Record Information

Version

2.0

Created at

2022-09-11 12:27:03 UTC

Updated at

2022-09-11 12:27:03 UTC

NP-MRD ID

NP0314379

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate

Description

Elegantin B belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate is found in Trichilia elegans. Based on a literature review very few articles have been published on Elegantin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112214272D          

 41 45  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2432   -0.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611   -2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4382   -3.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2763   -3.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146   -4.3057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0443   -3.1816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2874   -2.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019   -2.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486   -1.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227   -1.7117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2352   -0.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0602   -0.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4727   -1.7117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4727   -0.2827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2977   -0.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605    2.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3099    1.0550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 41 40  1  1  0  0  0
  2 41  1  0  0  0  0
 39 41  1  0  0  0  0
 26 41  1  0  0  0  0
M  END

     RDKit          3D

 75 79  0  0  0  0  0  0  0  0999 V2000
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    2.2430   -1.9918   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824   -2.0225   -2.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -0.9284   -3.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7475   -1.2588   -4.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042    0.3939   -3.2008 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5139    0.8447   -2.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198    2.3786   -2.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843    0.4956   -2.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9311    0.4334   -0.7079 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8611    1.1839    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6026    1.1614    1.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3959   -2.6903    3.1011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120    0.1003    0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -0.0619   -0.4431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2530   -1.2370   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034    1.2265   -0.7706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6283    1.9095    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3014    3.1220    0.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0822    3.5297    1.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236    4.6226    2.5070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9259    2.5019    2.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004    1.4523    1.2647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9055    1.2496    0.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9428    0.9482   -1.8155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4045    0.4098   -2.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0682    0.4025   -4.0581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349   -0.1590   -2.9266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0325    0.7164   -2.4326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4226   -0.3585   -1.6627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2353   -2.5471   -3.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6363   -2.5646    0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1005   -1.1877    1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6112   -2.9532   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093   -2.9402   -3.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219    2.7120   -3.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3717    2.8683   -1.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370   -0.4088   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6496    1.3488   -1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9378    0.9252   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594    2.2939   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4659    0.5916    4.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2193    1.8667    4.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465   -1.9317    0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0729   -2.2501    4.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827   -2.2147    5.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -0.6652    4.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0821    0.1285    1.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396    1.0718    0.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7179   -1.3611    0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0698   -1.1247   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7743   -0.7663   -3.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 14  1  0
 14 11  1  0
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 11 13  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  1
  4  3  1  0
  3 20  1  0
 20 25  1  0
 25 26  1  0
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 28 36  1  0
 36 37  1  0
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 39 40  1  0
 41 40  1  6
 41  2  1  0
  2  1  2  3
 28 29  1  0
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 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
  4 14  1  0
  2  3  1  0
 34 29  1  0
 41 26  1  0
 41 39  1  0
 19 59  1  0
 19 60  1  0
 19 61  1  0
 15 57  1  0
 15 58  1  0
 14 56  1  6
 12 50  1  0
 12 51  1  0
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 13 54  1  0
 13 55  1  0
  7 49  1  0
  6 48  1  0
  5 45  1  0
  5 46  1  0
  5 47  1  0
  3 44  1  1
 20 62  1  1
 25 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  6
 39 75  1  6
  1 42  1  0
  1 43  1  0
 30 72  1  0
 34 73  1  1
 35 74  1  0
 23 63  1  0
 23 64  1  0
 23 65  1  0
M  END


  Mrv1652309112214272D          

 41 45  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2432   -0.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4382   -3.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2763   -3.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605    2.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3099    1.0550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 41 40  1  1  0  0  0
  2 41  1  0  0  0  0
 39 41  1  0  0  0  0
 26 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314379

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1C(C)(C)OC(=O)C=C[C@]1(C)[C@H]1[C@H](C[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]23C1=C)C1=CC(=O)OC1O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O12/c1-13-21(27(5)9-8-18(31)40-26(3,4)17(27)11-19(32)36-7)16(37-14(2)30)12-28(6)22(15-10-20(33)38-24(15)34)39-25(35)23-29(13,28)41-23/h8-10,16-17,21-24,34H,1,11-12H2,2-7H3/t16-,17-,21+,22-,23+,24?,27-,28-,29+/m0/s1

> <INCHI_KEY>
MNZBJKLHQWXTFB-GWQLWQJZSA-N

> <FORMULA>
C29H34O12

> <MOLECULAR_WEIGHT>
574.579

> <EXACT_MASS>
574.205026535

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.515533900177616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(3R,4R)-4-[(1S,3S,6R,7S,9S,10R)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecan-10-yl]-2,2,4-trimethyl-7-oxo-2,3,4,7-tetrahydrooxepin-3-yl]acetate

> <JCHEM_LOGP>
1.5570572506666656

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.730204541674683

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.298263244798638

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3037779642786775

> <JCHEM_POLAR_SURFACE_AREA>
164.26

> <JCHEM_REFRACTIVITY>
137.32399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(3R,4R)-4-[(1S,3S,6R,7S,9S,10R)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2H-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3H-oxepin-3-yl]acetate

> <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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.454  -1.608   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.047  -4.209   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.818  -5.732   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.516  -6.502   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.401  -8.037   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.949  -5.939   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.403  -4.467   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.737  -5.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.451  -3.339   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.536  -3.195   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.306  -1.861   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.846  -1.861   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.616  -3.195   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.616  -0.528   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.156  -0.528   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.089   2.445   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.565   3.910   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.660   5.156   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.105   3.910   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.581   2.445   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.045   1.969   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   41                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5    6   14                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11    4   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20    3   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27   28   41                                             
CONECT   27   26                                                            
CONECT   28   26   29   36                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   29   35                                                  
CONECT   35   34                                                            
CONECT   36   28   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39   41                                                       
CONECT   41   40    2   39   26                                             
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₁₂

Average Mass

574.5790 Da

Monoisotopic Mass

574.20503 Da

IUPAC Name

methyl 2-[(3R,4R)-4-[(1S,3S,6R,7S,9S,10R)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecan-10-yl]-2,2,4-trimethyl-7-oxo-2,3,4,7-tetrahydrooxepin-3-yl]acetate

Traditional Name

methyl [(3R,4R)-4-[(1S,3S,6R,7S,9S,10R)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2H-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3H-oxepin-3-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1C(C)(C)OC(=O)C=C[C@]1(C)[C@H]1[C@H](C[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]23C1=C)C1=CC(=O)OC1O)OC(C)=O

InChI Identifier

InChI=1S/C29H34O12/c1-13-21(27(5)9-8-18(31)40-26(3,4)17(27)11-19(32)36-7)16(37-14(2)30)12-28(6)22(15-10-20(33)38-24(15)34)39-25(35)23-29(13,28)41-23/h8-10,16-17,21-24,34H,1,11-12H2,2-7H3/t16-,17-,21+,22-,23+,24?,27-,28-,29+/m0/s1

InChI Key

MNZBJKLHQWXTFB-GWQLWQJZSA-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
Trichilia elegans	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
Delta_valerolactone
Dioxepane
Delta valerolactone
1,4-dioxepane
Oxane
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Dihydrofuran
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	1.56	ChemAxon
pKa (Strongest Acidic)	5.3	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	164.26 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.32 m³·mol⁻¹	ChemAxon
Polarizability	56.52 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

101701625

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-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate (NP0314379)

MOL for NP0314379 (methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate)

3D MOL for NP0314379 (methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate)

3D SDF for NP0314379 (methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate)

3D-SDF for NP0314379 (methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate)

PDB for NP0314379 (methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate)

3D PDB for NP0314379 (methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate)

SMILES for NP0314379 (methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate)

INCHI for NP0314379 (methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate)

Structure for NP0314379 (methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate)

3D Structure for NP0314379 (methyl 2-[(3r,4r)-4-[(1s,3s,6r,7s,9s,10r)-9-(acetyloxy)-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-7-methyl-11-methylidene-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecan-10-yl]-2,2,4-trimethyl-7-oxo-3h-oxepin-3-yl]acetate)