NP-MRD: Showing NP-Card for 5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+ (NP0040294)

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Record Information

Version

1.0

Created at

2021-06-20 22:29:40 UTC

Updated at

2021-06-30 00:14:07 UTC

NP-MRD ID

NP0040294

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+

Provided By

JEOL Database JEOL Logo

Description

(E)-2-Methyl-2-butenoic acid (3R)-6,7-(carbonyloxy)-9beta-[(S)-[(3R)-2,7-dioxo-3alpha,9-dimethyl-4alpha-(tigloyloxy)-2,3,3abeta,4,5,7,9abeta,9balpha-octahydroazuleno[4,5-b]furan-6-yl]hydroxymethyl]-2-oxo-3alpha,9-dimethyl-2,3,3abeta,4,5,9,9abeta,9balpha-octahydroazuleno[4,5-b]furan-4alpha-yl ester belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. 5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+ is found in Eupatorium perfoliatum. It was first documented in 2011 (Maas, M., et al.). Based on a literature review very few articles have been published on (E)-2-Methyl-2-butenoic acid (3R)-6,7-(carbonyloxy)-9beta-[(S)-[(3R)-2,7-dioxo-3alpha,9-dimethyl-4alpha-(tigloyloxy)-2,3,3abeta,4,5,7,9abeta,9balpha-octahydroazuleno[4,5-b]furan-6-yl]hydroxymethyl]-2-oxo-3alpha,9-dimethyl-2,3,3abeta,4,5,9,9abeta,9balpha-octahydroazuleno[4,5-b]furan-4alpha-yl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100293D          

 96102  0  0  0  0            999 V2000
    5.0832    3.3063    6.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3047    2.1640    6.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1624    2.2167    5.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417    3.4626    5.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5880    0.9060    5.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761   -0.1641    5.1377 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3044    1.0836    4.6816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -0.0740    4.1323 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0209   -0.2204    2.6399 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9257    1.0443    1.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2220    1.4587    1.0830 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2600    1.3924    2.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    0.6454   -0.2005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0418   -0.8079    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665    1.2995   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6235    1.5350   -2.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875    1.9402   -3.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5346    1.7484   -4.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316    1.9630   -5.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114    1.2416   -3.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    1.1760   -2.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5338    0.7617   -1.3506 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6457   -0.4492   -1.6493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2120   -0.6907   -0.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -1.1364   -0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3298   -1.4585   -0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4597   -1.1862   -2.4636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3249   -2.6303   -2.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210   -0.2212   -2.8187 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2768   -0.3759   -4.2344 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1277   -1.5417   -4.2624 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2594   -2.1699   -5.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -1.8464   -6.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -3.3347   -5.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2517   -4.1403   -6.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9033   -3.5861   -4.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -4.6873   -4.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0874    0.8512   -4.7236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2356    1.7368    1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550    3.0014    0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517    3.6101    0.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8529    3.4166    1.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4832    2.5274    1.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9486    2.5542    2.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5831    1.4142    2.3296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5038    1.3141    3.8664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8090    1.2373    4.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7437    0.5139    5.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6674    0.4010    6.4073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -0.0959    5.7715 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6109    0.6317    6.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    0.0216    4.3367 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5844    4.2717    6.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0598    3.3693    6.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2223    3.4383    4.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    4.3719    5.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975    3.5598    5.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859   -0.9798    4.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475   -0.6004    2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4156   -1.0111    2.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1858    2.5163    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9783    1.9743    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2033   -1.4077    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349   -0.8525    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291   -1.3111   -0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8231    1.4398   -0.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8773    1.6027   -1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -1.3512   -1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105   -0.7680   -2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394   -3.2389   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3876   -3.0832   -2.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756   -2.7065   -4.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485    0.7902   -2.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -0.5126   -4.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2453   -4.4637   -6.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683   -3.5382   -7.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -5.0438   -6.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7899   -2.9330   -3.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5242   -5.3419   -3.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0864   -5.3023   -4.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8431   -4.2589   -3.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4873    0.6314   -5.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139    1.7094   -4.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2574    4.2806    0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861    1.5622    1.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1474    2.8806    3.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4698    3.2463    1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700    0.4767    1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0132    2.2061    4.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851   -1.1547    6.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4812    1.6953    6.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1532    0.5719    7.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741    0.1829    7.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -0.8151    3.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
 48 49  2  0  0  0  0
  3  2  2  0  0  0  0
 11 13  1  0  0  0  0
  7  5  1  0  0  0  0
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M  END

     RDKit          3D

 96102  0  0  0  0  0  0  0  0999 V2000
    5.0832    3.3063    6.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3047    2.1640    6.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1624    2.2167    5.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417    3.4626    5.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5880    0.9060    5.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761   -0.1641    5.1377 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3044    1.0836    4.6816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -0.0740    4.1323 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0209   -0.2204    2.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9257    1.0443    1.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2220    1.4587    1.0830 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2600    1.3924    2.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    0.6454   -0.2005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0418   -0.8079    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665    1.2995   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6235    1.5350   -2.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875    1.9402   -3.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5346    1.7484   -4.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316    1.9630   -5.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114    1.2416   -3.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    1.1760   -2.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5338    0.7617   -1.3506 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6457   -0.4492   -1.6493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2120   -0.6907   -0.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -1.1364   -0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3298   -1.4585   -0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4597   -1.1862   -2.4636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3249   -2.6303   -2.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210   -0.2212   -2.8187 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2768   -0.3759   -4.2344 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1277   -1.5417   -4.2624 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2594   -2.1699   -5.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -1.8464   -6.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -3.3347   -5.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2517   -4.1403   -6.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9033   -3.5861   -4.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -4.6873   -4.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0874    0.8512   -4.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2356    1.7368    1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306212100293D          

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 45 90  1  6  0  0  0
 34 36  2  0  0  0  0
 45 46  1  0  0  0  0
 36 37  1  0  0  0  0
 10 11  1  0  0  0  0
 32 33  2  0  0  0  0
  5  3  1  0  0  0  0
 18 19  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  1  0  0  0
 10  9  1  0  0  0  0
 11 63  1  6  0  0  0
  4 57  1  0  0  0  0
  4 58  1  0  0  0  0
  4 59  1  0  0  0  0
  2 56  1  0  0  0  0
  1 53  1  0  0  0  0
  1 54  1  0  0  0  0
  1 55  1  0  0  0  0
 42 86  1  0  0  0  0
  9 61  1  0  0  0  0
  9 62  1  0  0  0  0
  8 60  1  1  0  0  0
 52 96  1  6  0  0  0
 46 91  1  1  0  0  0
 50 92  1  1  0  0  0
 51 93  1  0  0  0  0
 51 94  1  0  0  0  0
 51 95  1  0  0  0  0
 44 87  1  0  0  0  0
 44 88  1  0  0  0  0
 44 89  1  0  0  0  0
 12 64  1  0  0  0  0
 15 68  1  0  0  0  0
 38 84  1  0  0  0  0
 38 85  1  0  0  0  0
 30 76  1  6  0  0  0
 29 75  1  6  0  0  0
 23 70  1  6  0  0  0
 27 71  1  6  0  0  0
 28 72  1  0  0  0  0
 28 73  1  0  0  0  0
 28 74  1  0  0  0  0
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 35 78  1  0  0  0  0
 35 79  1  0  0  0  0
 36 80  1  0  0  0  0
 37 81  1  0  0  0  0
 37 82  1  0  0  0  0
 37 83  1  0  0  0  0
 14 65  1  0  0  0  0
 14 66  1  0  0  0  0
 14 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C1=C2C(=O)C([H])=C(C([H])([H])[H])[C@]2([H])[C@@]2([H])OC(=O)[C@]([H])(C([H])([H])[H])[C@]2([H])[C@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C1([H])[H])[C@@]1(C([H])=C2OC(=O)C3=C2[C@@]1([H])[C@@]1([H])OC(=O)[C@]([H])(C([H])([H])[H])[C@]1([H])[C@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C3([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C40H44O12/c1-9-15(3)35(43)48-23-12-20(29-22(41)11-17(5)26(29)32-27(23)18(6)37(45)51-32)34(42)40(8)14-25-30-21(39(47)50-25)13-24(49-36(44)16(4)10-2)28-19(7)38(46)52-33(28)31(30)40/h9-11,14,18-19,23-24,26-28,31-34,42H,12-13H2,1-8H3/b15-9+,16-10+/t18-,19-,23-,24-,26+,27-,28-,31+,32-,33+,34-,40-/m1/s1

> <INCHI_KEY>
RKYYJTTWXWMMIE-NPCVJFMNSA-N

> <FORMULA>
C40H44O12

> <MOLECULAR_WEIGHT>
716.78

> <EXACT_MASS>
716.283276857

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
74.28977813701698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,6R,7R,14S)-14-[(S)-[(3R,3aR,4R,9aS,9bR)-3,9-dimethyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-6-yl](hydroxy)methyl]-5,14-dimethyl-4,10-dioxo-3,11-dioxatetracyclo[7.5.1.0^{2,6}.0^{12,15}]pentadeca-9(15),12-dien-7-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
4.2250211633333326

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.08913108631463

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.900364254292946

> <JCHEM_PKA_STRONGEST_BASIC>
-3.236271671369507

> <JCHEM_POLAR_SURFACE_AREA>
168.8

> <JCHEM_REFRACTIVITY>
187.38100000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,6R,7R,14S)-14-[(S)-[(3R,3aR,4R,9aS,9bR)-3,9-dimethyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-6-yl](hydroxy)methyl]-5,14-dimethyl-4,10-dioxo-3,11-dioxatetracyclo[7.5.1.0^{2,6}.0^{12,15}]pentadeca-9(15),12-dien-7-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 96102  0  0  0  0  0  0  0  0999 V2000
    5.0832    3.3063    6.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3047    2.1640    6.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1624    2.2167    5.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417    3.4626    5.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5880    0.9060    5.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761   -0.1641    5.1377 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3044    1.0836    4.6816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -0.0740    4.1323 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0209   -0.2204    2.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9257    1.0443    1.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2220    1.4587    1.0830 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2600    1.3924    2.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    0.6454   -0.2005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0418   -0.8079    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665    1.2995   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6235    1.5350   -2.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875    1.9402   -3.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5346    1.7484   -4.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316    1.9630   -5.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114    1.2416   -3.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    1.1760   -2.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5338    0.7617   -1.3506 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6457   -0.4492   -1.6493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2120   -0.6907   -0.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -1.1364   -0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3298   -1.4585   -0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4597   -1.1862   -2.4636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3249   -2.6303   -2.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210   -0.2212   -2.8187 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2768   -0.3759   -4.2344 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1277   -1.5417   -4.2624 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2594   -2.1699   -5.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -1.8464   -6.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -3.3347   -5.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2517   -4.1403   -6.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9033   -3.5861   -4.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -4.6873   -4.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0874    0.8512   -4.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2356    1.7368    1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550    3.0014    0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517    3.6101    0.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8529    3.4166    1.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4832    2.5274    1.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9486    2.5542    2.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5831    1.4142    2.3296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5038    1.3141    3.8664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8090    1.2373    4.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7437    0.5139    5.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6674    0.4010    6.4073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -0.0959    5.7715 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6109    0.6317    6.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    0.0216    4.3367 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5844    4.2717    6.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0598    3.3693    6.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2495    3.1380    7.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7415    1.1878    6.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223    3.4383    4.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    4.3719    5.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975    3.5598    5.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859   -0.9798    4.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475   -0.6004    2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4156   -1.0111    2.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1858    2.5163    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9783    1.9743    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2033   -1.4077    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349   -0.8525    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291   -1.3111   -0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8231    1.4398   -0.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8773    1.6027   -1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -1.3512   -1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105   -0.7680   -2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394   -3.2389   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3876   -3.0832   -2.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756   -2.7065   -4.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485    0.7902   -2.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -0.5126   -4.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2453   -4.4637   -6.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683   -3.5382   -7.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -5.0438   -6.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7899   -2.9330   -3.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5242   -5.3419   -3.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0864   -5.3023   -4.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8431   -4.2589   -3.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4873    0.6314   -5.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139    1.7094   -4.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2574    4.2806    0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861    1.5622    1.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1474    2.8806    3.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4698    3.2463    1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700    0.4767    1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0132    2.2061    4.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851   -1.1547    6.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4812    1.6953    6.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3741    0.1829    7.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -0.8151    3.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  2  2  0
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  2  1  1  0
 27 28  1  0
 50 51  1  0
 30 31  1  0
 16 17  1  0
  3  4  1  0
 22 69  1  1
  8  7  1  0
 20 18  1  0
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 18 17  1  0
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 25 26  2  0
  5  6  2  0
 31 32  1  0
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 32 34  1  0
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 34 35  1  0
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 10 11  1  0
 32 33  2  0
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 18 19  2  0
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 13 14  1  1
 10  9  1  0
 11 63  1  6
  4 57  1  0
  4 58  1  0
  4 59  1  0
  2 56  1  0
  1 53  1  0
  1 54  1  0
  1 55  1  0
 42 86  1  0
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  8 60  1  1
 52 96  1  6
 46 91  1  1
 50 92  1  1
 51 93  1  0
 51 94  1  0
 51 95  1  0
 44 87  1  0
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 44 89  1  0
 12 64  1  0
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 38 84  1  0
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 30 76  1  6
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 23 70  1  6
 27 71  1  6
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 35 78  1  0
 35 79  1  0
 36 80  1  0
 37 81  1  0
 37 82  1  0
 37 83  1  0
 14 65  1  0
 14 66  1  0
 14 67  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       5.083   3.306   6.816  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.305   2.164   6.247  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.162   2.217   5.533  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.442   3.463   5.113  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.588   0.906   5.094  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.176  -0.164   5.138  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.304   1.084   4.682  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.654  -0.074   4.132  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.021  -0.220   2.640  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.926   1.044   1.787  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.222   1.459   1.083  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.260   1.392   2.071  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.630   0.645  -0.201  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.042  -0.808   0.101  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.866   1.300  -0.864  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.624   1.535  -2.151  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.388   1.940  -3.195  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.535   1.748  -4.274  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.832   1.963  -5.438  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.211   1.242  -3.841  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.329   1.176  -2.531  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.534   0.762  -1.351  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.646  -0.449  -1.649  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.212  -0.691  -0.528  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.425  -1.136  -0.959  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.330  -1.458  -0.207  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.460  -1.186  -2.464  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.325  -2.630  -2.922  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.321  -0.221  -2.819  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.277  -0.376  -4.234  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.128  -1.542  -4.262  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.259  -2.170  -5.460  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.678  -1.846  -6.485  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.198  -3.335  -5.376  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.252  -4.140  -6.643  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.903  -3.586  -4.253  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.889  -4.687  -4.017  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.087   0.851  -4.724  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.236   1.737   1.701  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.455   3.001   0.925  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.352   3.610   0.248  0.00  0.00           O+0
HETATM   42  C   UNK     0      -1.853   3.417   1.057  0.00  0.00           C+0
HETATM   43  C   UNK     0      -2.483   2.527   1.831  0.00  0.00           C+0
HETATM   44  C   UNK     0      -3.949   2.554   2.111  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.583   1.414   2.330  0.00  0.00           C+0
HETATM   46  C   UNK     0      -1.504   1.314   3.866  0.00  0.00           C+0
HETATM   47  O   UNK     0      -2.809   1.237   4.464  0.00  0.00           O+0
HETATM   48  C   UNK     0      -2.744   0.514   5.619  0.00  0.00           C+0
HETATM   49  O   UNK     0      -3.667   0.401   6.407  0.00  0.00           O+0
HETATM   50  C   UNK     0      -1.375  -0.096   5.771  0.00  0.00           C+0
HETATM   51  C   UNK     0      -0.611   0.632   6.866  0.00  0.00           C+0
HETATM   52  C   UNK     0      -0.855   0.022   4.337  0.00  0.00           C+0
HETATM   53  H   UNK     0       4.584   4.272   6.712  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.060   3.369   6.326  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.250   3.138   7.885  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.742   1.188   6.465  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.222   3.438   4.040  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.021   4.372   5.288  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.498   3.560   5.659  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.986  -0.980   4.658  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.047  -0.600   2.617  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.416  -1.011   2.179  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.186   2.516   0.818  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.978   1.974   1.769  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.203  -1.408   0.463  0.00  0.00           H+0
HETATM   66  H   UNK     0       3.835  -0.853   0.856  0.00  0.00           H+0
HETATM   67  H   UNK     0       3.429  -1.311  -0.794  0.00  0.00           H+0
HETATM   68  H   UNK     0       4.823   1.440  -0.381  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.877   1.603  -1.106  0.00  0.00           H+0
HETATM   70  H   UNK     0       1.249  -1.351  -1.800  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.410  -0.768  -2.813  0.00  0.00           H+0
HETATM   72  H   UNK     0      -2.139  -3.239  -2.513  0.00  0.00           H+0
HETATM   73  H   UNK     0      -0.388  -3.083  -2.582  0.00  0.00           H+0
HETATM   74  H   UNK     0      -1.376  -2.707  -4.012  0.00  0.00           H+0
HETATM   75  H   UNK     0      -0.749   0.790  -2.737  0.00  0.00           H+0
HETATM   76  H   UNK     0      -0.564  -0.513  -4.928  0.00  0.00           H+0
HETATM   77  H   UNK     0       1.245  -4.464  -6.932  0.00  0.00           H+0
HETATM   78  H   UNK     0       2.668  -3.538  -7.458  0.00  0.00           H+0
HETATM   79  H   UNK     0       2.859  -5.044  -6.559  0.00  0.00           H+0
HETATM   80  H   UNK     0       2.790  -2.933  -3.390  0.00  0.00           H+0
HETATM   81  H   UNK     0       3.524  -5.342  -3.219  0.00  0.00           H+0
HETATM   82  H   UNK     0       4.086  -5.302  -4.896  0.00  0.00           H+0
HETATM   83  H   UNK     0       4.843  -4.259  -3.694  0.00  0.00           H+0
HETATM   84  H   UNK     0       1.487   0.631  -5.721  0.00  0.00           H+0
HETATM   85  H   UNK     0       0.414   1.709  -4.835  0.00  0.00           H+0
HETATM   86  H   UNK     0      -2.257   4.281   0.558  0.00  0.00           H+0
HETATM   87  H   UNK     0      -4.386   1.562   1.962  0.00  0.00           H+0
HETATM   88  H   UNK     0      -4.147   2.881   3.136  0.00  0.00           H+0
HETATM   89  H   UNK     0      -4.470   3.246   1.441  0.00  0.00           H+0
HETATM   90  H   UNK     0      -1.970   0.477   1.909  0.00  0.00           H+0
HETATM   91  H   UNK     0      -1.013   2.206   4.279  0.00  0.00           H+0
HETATM   92  H   UNK     0      -1.485  -1.155   6.032  0.00  0.00           H+0
HETATM   93  H   UNK     0      -0.481   1.695   6.640  0.00  0.00           H+0
HETATM   94  H   UNK     0      -1.153   0.572   7.816  0.00  0.00           H+0
HETATM   95  H   UNK     0       0.374   0.183   7.024  0.00  0.00           H+0
HETATM   96  H   UNK     0      -1.318  -0.815   3.789  0.00  0.00           H+0
CONECT    1    2   53   54   55                                             
CONECT    2    3    1   56                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3   57   58   59                                             
CONECT    5    7    6    3                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    9   52    7   60                                             
CONECT    9    8   10   61   62                                             
CONECT   10   39   11    9                                                  
CONECT   11   13   10   12   63                                             
CONECT   12   11   64                                                       
CONECT   13   11   15   22   14                                             
CONECT   14   13   65   66   67                                             
CONECT   15   16   13   68                                                  
CONECT   16   21   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   20   17   19                                                  
CONECT   19   18                                                            
CONECT   20   21   38   18                                                  
CONECT   21   16   22   20                                                  
CONECT   22   13   21   23   69                                             
CONECT   23   22   29   24   70                                             
CONECT   24   23   25                                                       
CONECT   25   24   27   26                                                  
CONECT   26   25                                                            
CONECT   27   25   29   28   71                                             
CONECT   28   27   72   73   74                                             
CONECT   29   30   23   27   75                                             
CONECT   30   38   29   31   76                                             
CONECT   31   30   32                                                       
CONECT   32   31   34   33                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34   77   78   79                                             
CONECT   36   34   37   80                                                  
CONECT   37   36   81   82   83                                             
CONECT   38   20   30   84   85                                             
CONECT   39   40   45   10                                                  
CONECT   40   39   42   41                                                  
CONECT   41   40                                                            
CONECT   42   40   43   86                                                  
CONECT   43   42   45   44                                                  
CONECT   44   43   87   88   89                                             
CONECT   45   43   39   90   46                                             
CONECT   46   52   47   45   91                                             
CONECT   47   46   48                                                       
CONECT   48   49   47   50                                                  
CONECT   49   48                                                            
CONECT   50   48   52   51   92                                             
CONECT   51   50   93   94   95                                             
CONECT   52    8   46   50   96                                             
CONECT   53    1                                                            
CONECT   54    1                                                            
CONECT   55    1                                                            
CONECT   56    2                                                            
CONECT   57    4                                                            
CONECT   58    4                                                            
CONECT   59    4                                                            
CONECT   60    8                                                            
CONECT   61    9                                                            
CONECT   62    9                                                            
CONECT   63   11                                                            
CONECT   64   12                                                            
CONECT   65   14                                                            
CONECT   66   14                                                            
CONECT   67   14                                                            
CONECT   68   15                                                            
CONECT   69   22                                                            
CONECT   70   23                                                            
CONECT   71   27                                                            
CONECT   72   28                                                            
CONECT   73   28                                                            
CONECT   74   28                                                            
CONECT   75   29                                                            
CONECT   76   30                                                            
CONECT   77   35                                                            
CONECT   78   35                                                            
CONECT   79   35                                                            
CONECT   80   36                                                            
CONECT   81   37                                                            
CONECT   82   37                                                            
CONECT   83   37                                                            
CONECT   84   38                                                            
CONECT   85   38                                                            
CONECT   86   42                                                            
CONECT   87   44                                                            
CONECT   88   44                                                            
CONECT   89   44                                                            
CONECT   90   45                                                            
CONECT   91   46                                                            
CONECT   92   50                                                            
CONECT   93   51                                                            
CONECT   94   51                                                            
CONECT   95   51                                                            
CONECT   96   52                                                            
MASTER        0    0    0    0    0    0    0    0   96    0  204    0
END

RDKit          3D

96102  0  0  0  0  0  0  0  0999 V2000
    5.0832    3.3063    6.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3047    2.1640    6.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1624    2.2167    5.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417    3.4626    5.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5880    0.9060    5.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761   -0.1641    5.1377 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3044    1.0836    4.6816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -0.0740    4.1323 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0209   -0.2204    2.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9257    1.0443    1.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2220    1.4587    1.0830 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2600    1.3924    2.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    0.6454   -0.2005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0418   -0.8079    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665    1.2995   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6235    1.5350   -2.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875    1.9402   -3.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5346    1.7484   -4.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316    1.9630   -5.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114    1.2416   -3.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    1.1760   -2.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5338    0.7617   -1.3506 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6457   -0.4492   -1.6493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2120   -0.6907   -0.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -1.1364   -0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3298   -1.4585   -0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4597   -1.1862   -2.4636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3249   -2.6303   -2.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210   -0.2212   -2.8187 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2768   -0.3759   -4.2344 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1277   -1.5417   -4.2624 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2594   -2.1699   -5.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -1.8464   -6.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -3.3347   -5.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2517   -4.1403   -6.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9033   -3.5861   -4.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -4.6873   -4.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0874    0.8512   -4.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2356    1.7368    1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550    3.0014    0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517    3.6101    0.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8529    3.4166    1.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4832    2.5274    1.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9486    2.5542    2.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5831    1.4142    2.3296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5038    1.3141    3.8664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8090    1.2373    4.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7437    0.5139    5.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6674    0.4010    6.4073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -0.0959    5.7715 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6109    0.6317    6.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    0.0216    4.3367 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5844    4.2717    6.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0598    3.3693    6.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2495    3.1380    7.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7415    1.1878    6.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223    3.4383    4.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    4.3719    5.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975    3.5598    5.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859   -0.9798    4.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475   -0.6004    2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4156   -1.0111    2.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1858    2.5163    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9783    1.9743    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2033   -1.4077    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349   -0.8525    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291   -1.3111   -0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8231    1.4398   -0.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8773    1.6027   -1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -1.3512   -1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105   -0.7680   -2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394   -3.2389   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3876   -3.0832   -2.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756   -2.7065   -4.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485    0.7902   -2.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -0.5126   -4.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2453   -4.4637   -6.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683   -3.5382   -7.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -5.0438   -6.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7899   -2.9330   -3.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5242   -5.3419   -3.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0864   -5.3023   -4.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8431   -4.2589   -3.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4873    0.6314   -5.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139    1.7094   -4.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2574    4.2806    0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861    1.5622    1.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1474    2.8806    3.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4698    3.2463    1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700    0.4767    1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0132    2.2061    4.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851   -1.1547    6.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4812    1.6953    6.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1532    0.5719    7.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741    0.1829    7.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -0.8151    3.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
 48 49  2  0
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 11 13  1  0
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 14 67  1  0
M  END

View in JSmol

Synonyms

Value	Source
(e)-2-Methyl-2-butenoate (3R)-6,7-(carbonyloxy)-9b-[(S)-[(3R)-2,7-dioxo-3a,9-dimethyl-4a-(tigloyloxy)-2,3,3abeta,4,5,7,9abeta,9balpha-octahydroazuleno[4,5-b]furan-6-yl]hydroxymethyl]-2-oxo-3a,9-dimethyl-2,3,3abeta,4,5,9,9abeta,9balpha-octahydroazuleno[4,5-b]furan-4a-yl ester	Generator
(e)-2-Methyl-2-butenoate (3R)-6,7-(carbonyloxy)-9beta-[(S)-[(3R)-2,7-dioxo-3alpha,9-dimethyl-4alpha-(tigloyloxy)-2,3,3abeta,4,5,7,9abeta,9balpha-octahydroazuleno[4,5-b]furan-6-yl]hydroxymethyl]-2-oxo-3alpha,9-dimethyl-2,3,3abeta,4,5,9,9abeta,9balpha-octahydroazuleno[4,5-b]furan-4alpha-yl ester	Generator
(e)-2-Methyl-2-butenoate (3R)-6,7-(carbonyloxy)-9β-[(S)-[(3R)-2,7-dioxo-3α,9-dimethyl-4α-(tigloyloxy)-2,3,3abeta,4,5,7,9abeta,9balpha-octahydroazuleno[4,5-b]furan-6-yl]hydroxymethyl]-2-oxo-3α,9-dimethyl-2,3,3abeta,4,5,9,9abeta,9balpha-octahydroazuleno[4,5-b]furan-4α-yl ester	Generator
(e)-2-Methyl-2-butenoic acid (3R)-6,7-(carbonyloxy)-9b-[(S)-[(3R)-2,7-dioxo-3a,9-dimethyl-4a-(tigloyloxy)-2,3,3abeta,4,5,7,9abeta,9balpha-octahydroazuleno[4,5-b]furan-6-yl]hydroxymethyl]-2-oxo-3a,9-dimethyl-2,3,3abeta,4,5,9,9abeta,9balpha-octahydroazuleno[4,5-b]furan-4a-yl ester	Generator
(e)-2-Methyl-2-butenoic acid (3R)-6,7-(carbonyloxy)-9β-[(S)-[(3R)-2,7-dioxo-3α,9-dimethyl-4α-(tigloyloxy)-2,3,3abeta,4,5,7,9abeta,9balpha-octahydroazuleno[4,5-b]furan-6-yl]hydroxymethyl]-2-oxo-3α,9-dimethyl-2,3,3abeta,4,5,9,9abeta,9balpha-octahydroazuleno[4,5-b]furan-4α-yl ester	Generator

Chemical Formula

C₄₀H₄₄O₁₂

Average Mass

716.7800 Da

Monoisotopic Mass

716.28328 Da

IUPAC Name

(1S,2R,5R,6R,7R,14S)-14-[(S)-[(3R,3aR,4R,9aS,9bR)-3,9-dimethyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-6-yl](hydroxy)methyl]-5,14-dimethyl-4,10-dioxo-3,11-dioxatetracyclo[7.5.1.0^{2,6}.0^{12,15}]pentadeca-9(15),12-dien-7-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1S,2R,5R,6R,7R,14S)-14-[(S)-[(3R,3aR,4R,9aS,9bR)-3,9-dimethyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-6-yl](hydroxy)methyl]-5,14-dimethyl-4,10-dioxo-3,11-dioxatetracyclo[7.5.1.0^{2,6}.0^{12,15}]pentadeca-9(15),12-dien-7-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O[C@]([H])(C1=C2C(=O)C([H])=C(C([H])([H])[H])[C@]2([H])[C@@]2([H])OC(=O)[C@]([H])(C([H])([H])[H])[C@]2([H])[C@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C1([H])[H])[C@@]1(C([H])=C2OC(=O)C3=C2[C@@]1([H])[C@@]1([H])OC(=O)[C@]([H])(C([H])([H])[H])[C@]1([H])[C@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C3([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C40H44O12/c1-9-15(3)35(43)48-23-12-20(29-22(41)11-17(5)26(29)32-27(23)18(6)37(45)51-32)34(42)40(8)14-25-30-21(39(47)50-25)13-24(49-36(44)16(4)10-2)28-19(7)38(46)52-33(28)31(30)40/h9-11,14,18-19,23-24,26-28,31-34,42H,12-13H2,1-8H3/b15-9+,16-10+/t18-,19-,23-,24-,26+,27-,28-,31+,32-,33+,34-,40-/m1/s1

InChI Key

RKYYJTTWXWMMIE-NPCVJFMNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eupatorium perfoliatum	JEOL database	Maas, M., et al, Phytochem. 72, 635 (2011)

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
Fatty acid ester
2-furanone
Gamma butyrolactone
Fatty acyl
Dihydrofuran
Enol ester
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
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	2.9	ALOGPS
logP	4.23	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	168.8 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	187.38 m³·mol⁻¹	ChemAxon
Polarizability	74.29 Å³	ChemAxon
Number of Rings	7	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

34535929

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53231631

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Maas, M., et al. (2011). Maas, M., et al, Phytochem. 72, 635 (2011). Phytochem..

Showing NP-Card for 5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+ (NP0040294)

MOL for NP0040294 (5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+)

3D MOL for NP0040294 (5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+)

3D SDF for NP0040294 (5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+)

3D-SDF for NP0040294 (5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+)

PDB for NP0040294 (5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+)

3D PDB for NP0040294 (5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+)

SMILES for NP0040294 (5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+)

INCHI for NP0040294 (5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+)

Structure for NP0040294 (5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+)

3D Structure for NP0040294 (5S,6R,7R,8R,11R,14S-14-hydroxy-2-oxo-14(4S,5S,6R,7R,8R,11R-8-tigloyloxygu+)