NP-MRD: Showing NP-Card for acutissimatriterpene D (NP0033676)

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Record Information

Version

2.0

Created at

2021-06-20 17:37:42 UTC

Updated at

2021-06-30 00:03:36 UTC

NP-MRD ID

NP0033676

Secondary Accession Numbers

None

Natural Product Identification

Common Name

acutissimatriterpene D

Provided By

JEOL Database JEOL Logo

Description

(5R,8R)-3-[(1S,2R,3R,5R,6R,9S,14S,15R,18R,19R)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]Docos-11-en-19-yl]-8-methoxy-8-methyl-1,6-dioxaspiro[4.4]Non-3-en-2-one belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. acutissimatriterpene D is found in Phyllanthus acutissima and Phyllanthus acutissimus. acutissimatriterpene D was first documented in 2008 (Tuchinda, P., et al.). Based on a literature review very few articles have been published on (5R,8R)-3-[(1S,2R,3R,5R,6R,9S,14S,15R,18R,19R)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]Docos-11-en-19-yl]-8-methoxy-8-methyl-1,6-dioxaspiro[4.4]Non-3-en-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119373D          

 95103  0  0  0  0            999 V2000
    9.8685   -0.8142   -5.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3529   -0.1887   -4.1335 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2485   -0.8448   -3.5069 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0117   -0.8376   -4.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5700   -2.2440   -2.9869 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6663   -2.4794   -1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4287   -1.2185   -1.2724 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9940   -1.1197   -0.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8133   -0.9955    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.8534    1.2040 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3101   -2.1264    2.0399 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8074   -2.0828    2.3629 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1690   -1.3002    1.2174 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5365   -1.7742   -0.1796 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2735   -0.6077    0.4568 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0821    0.7442   -0.1895 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7964    1.4743    0.2110 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5869    0.5214    0.3281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8353    1.2276    0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9815    2.3496    1.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344    1.8882   -1.1097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4491    2.3168   -1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5140    1.7916   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966    2.3929   -0.8870 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4684    2.7100    0.5089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8932    3.2197    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1421    4.5993    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4464    5.0810    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5167    4.1910    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2845    2.8189    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9811    2.3360    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4426    1.5434    1.3523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019    1.0696    1.5657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4255    0.6204    0.2434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2503   -0.5647   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395    0.1198    0.4220 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7127   -0.7802    1.6586 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3583   -1.5015    1.5999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4119   -2.3858    0.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -0.5148    1.4967 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9995    0.1993    2.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1561   -0.9954    0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3976   -0.8676    2.1540 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0856   -1.1436   -0.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9564   -0.1215   -2.1949 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7607   -0.2632   -5.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1462   -0.7707   -6.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1596   -1.8492   -5.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1657   -1.4648   -5.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8063    0.1759   -4.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1172   -1.2111   -3.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4379   -3.0243   -3.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5976   -2.3120   -2.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2022   -1.1634   -1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214   -0.0112    1.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9172   -2.1642    2.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5354   -3.0339    1.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6905   -1.5954    3.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873   -3.0909    2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719   -1.5913   -1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542   -2.7212   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9339    1.3992    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0859    0.6095   -1.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671    2.0007    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156    2.2550   -0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -0.0603   -0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7662    3.0681    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0657    2.9389    1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2524    1.9724    2.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310    1.2075   -1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3986    2.7777   -1.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785    3.1403   -2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8720    3.3065   -1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5393    1.6831   -1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605    3.4822    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3193    5.3093    0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6275    6.1514    0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5318    4.5661    0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1173    2.1224    0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8131    1.2618    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5411    1.8542    2.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848    0.2274    2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1999   -1.4454    0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3133   -0.3267   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -0.8587   -1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7666   -0.5340   -0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4960   -1.5455    1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7927   -0.2030    2.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560   -2.1367    2.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766   -2.9533    0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9466   -0.5176    3.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9628    0.7136    2.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2231    0.9251    3.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8748    0.3200   -1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2563    0.7131   -2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 32  1  0  0  0  0
 18 17  1  0  0  0  0
 40 13  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 13  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 23 34  1  0  0  0  0
  3  5  1  0  0  0  0
  3  4  1  0  0  0  0
 13 12  1  1  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10 15  1  0  0  0  0
  6  5  1  0  0  0  0
 25 26  1  0  0  0  0
 45  7  1  0  0  0  0
 34 35  1  6  0  0  0
 23 22  2  0  0  0  0
 36 86  1  6  0  0  0
 34 36  1  0  0  0  0
 38 39  1  0  0  0  0
 19 21  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
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 18 66  1  6  0  0  0
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 26 31  2  0  0  0  0
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  3  2  1  6  0  0  0
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 37 38  1  0  0  0  0
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  7 44  1  1  0  0  0
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  5 52  1  0  0  0  0
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  1 46  1  0  0  0  0
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M  END

     RDKit          3D

 95103  0  0  0  0  0  0  0  0999 V2000
    9.8685   -0.8142   -5.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3529   -0.1887   -4.1335 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2485   -0.8448   -3.5069 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0117   -0.8376   -4.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5700   -2.2440   -2.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6663   -2.4794   -1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4287   -1.2185   -1.2724 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9940   -1.1197   -0.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8133   -0.9955    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.8534    1.2040 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3101   -2.1264    2.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8074   -2.0828    2.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690   -1.3002    1.2174 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5365   -1.7742   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2735   -0.6077    0.4568 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0821    0.7442   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7964    1.4743    0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5869    0.5214    0.3281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8353    1.2276    0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9815    2.3496    1.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344    1.8882   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4491    2.3168   -1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5140    1.7916   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966    2.3929   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4684    2.7100    0.5089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8932    3.2197    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1421    4.5993    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4464    5.0810    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5167    4.1910    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2845    2.8189    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9811    2.3360    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4426    1.5434    1.3523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019    1.0696    1.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4255    0.6204    0.2434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2503   -0.5647   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395    0.1198    0.4220 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7127   -0.7802    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -1.5015    1.5999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4119   -2.3858    0.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -0.5148    1.4967 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9995    0.1993    2.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202119373D          

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  5 52  1  0  0  0  0
  5 53  1  0  0  0  0
  1 46  1  0  0  0  0
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  4 49  1  0  0  0  0
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 41 91  1  0  0  0  0
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 41 93  1  0  0  0  0
  8 54  1  0  0  0  0
 29 78  1  0  0  0  0
 30 79  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033676

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@@]2([H])[C@@]3(C(=C([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@]45C([H])([H])[C@]4(C([H])([H])C([H])([H])[C@@]5([H])C4=C([H])[C@@]5(OC4=O)OC([H])([H])[C@@](OC([H])([H])[H])(C([H])([H])[H])C5([H])[H])[C@]12C([H])([H])[H])C([H])([H])[C@]([H])(OC3([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C39H50O6/c1-33(42-5)20-39(44-22-33)19-26(32(41)45-39)27-12-16-38-21-37(27,38)15-13-29-34(2)14-11-25-17-28(24-9-7-6-8-10-24)43-23-35(25,3)30(34)18-31(40)36(29,38)4/h6-11,19,27-31,40H,12-18,20-23H2,1-5H3/t27-,28-,29+,30+,31+,33+,34+,35-,36-,37+,38+,39-/m0/s1

> <INCHI_KEY>
DUBRTGHCJCCRAJ-WJRFPTRPSA-N

> <FORMULA>
C39H50O6

> <MOLECULAR_WEIGHT>
614.823

> <EXACT_MASS>
614.36073933

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
71.44443000092642

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,8R)-3-[(1S,2R,3R,5R,6R,9S,14S,15R,18R,19R)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0^{1,18}.0^{2,15}.0^{5,14}.0^{6,11}]docos-11-en-19-yl]-8-methoxy-8-methyl-1,6-dioxaspiro[4.4]non-3-en-2-one

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
6.195521394333333

> <ALOGPS_LOGS>
-6.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.19133732196787723

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
171.88040000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,8R)-3-[(1S,2R,3R,5R,6R,9S,14S,15R,18R,19R)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0^{1,18}.0^{2,15}.0^{5,14}.0^{6,11}]docos-11-en-19-yl]-8-methoxy-8-methyl-1,6-dioxaspiro[4.4]non-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 95103  0  0  0  0  0  0  0  0999 V2000
    9.8685   -0.8142   -5.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
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 24 25  1  0
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  3  2  1  6
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  7 44  1  1
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  5 53  1  0
  1 46  1  0
  1 47  1  0
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 16 62  1  0
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 29 78  1  0
 30 79  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       9.868  -0.814  -5.301  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.353  -0.189  -4.133  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.248  -0.845  -3.507  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.012  -0.838  -4.416  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.570  -2.244  -2.987  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.666  -2.479  -1.902  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.429  -1.218  -1.272  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.994  -1.120  -0.939  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.813  -0.996   0.375  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.585  -0.853   1.204  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.310  -2.126   2.040  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.807  -2.083   2.363  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.169  -1.300   1.217  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.537  -1.774  -0.180  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.273  -0.608   0.457  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.082   0.744  -0.190  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.796   1.474   0.211  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.587   0.521   0.328  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.835   1.228   0.296  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.982   2.350   1.352  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.034   1.888  -1.110  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.449   2.317  -1.373  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.514   1.792  -0.744  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.897   2.393  -0.887  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.468   2.710   0.509  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.893   3.220   0.401  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.142   4.599   0.329  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.446   5.081   0.200  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.517   4.191   0.139  0.00  0.00           C+0
HETATM   30  C   UNK     0      -9.284   2.819   0.204  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.981   2.336   0.332  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.443   1.543   1.352  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.102   1.070   1.566  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.426   0.620   0.243  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.250  -0.565  -0.338  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.940   0.120   0.422  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.713  -0.780   1.659  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.358  -1.502   1.600  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.412  -2.386   0.476  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.842  -0.515   1.497  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.000   0.199   2.870  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.156  -0.995   0.967  0.00  0.00           C+0
HETATM   43  O   UNK     0       7.398  -0.868   2.154  0.00  0.00           O+0
HETATM   44  O   UNK     0       8.086  -1.144  -0.012  0.00  0.00           O+0
HETATM   45  C   UNK     0       7.956  -0.122  -2.195  0.00  0.00           C+0
HETATM   46  H   UNK     0      10.761  -0.263  -5.612  0.00  0.00           H+0
HETATM   47  H   UNK     0       9.146  -0.771  -6.120  0.00  0.00           H+0
HETATM   48  H   UNK     0      10.160  -1.849  -5.103  0.00  0.00           H+0
HETATM   49  H   UNK     0       7.166  -1.465  -5.300  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.806   0.176  -4.778  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.117  -1.211  -3.909  0.00  0.00           H+0
HETATM   52  H   UNK     0       8.438  -3.024  -3.743  0.00  0.00           H+0
HETATM   53  H   UNK     0       9.598  -2.312  -2.610  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.202  -1.163  -1.671  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.721  -0.011   1.897  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.917  -2.164   2.951  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.535  -3.034   1.465  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.691  -1.595   3.332  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.387  -3.091   2.437  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.872  -1.591  -1.016  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.054  -2.721  -0.302  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.934   1.399   0.030  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.086   0.610  -1.279  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.967   2.001   1.156  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.616   2.255  -0.535  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.585  -0.060  -0.603  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.766   3.068   1.093  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.066   2.939   1.451  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.252   1.972   2.338  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.731   1.208  -1.915  0.00  0.00           H+0
HETATM   71  H   UNK     0      -0.399   2.778  -1.192  0.00  0.00           H+0
HETATM   72  H   UNK     0      -2.579   3.140  -2.072  0.00  0.00           H+0
HETATM   73  H   UNK     0      -4.872   3.307  -1.494  0.00  0.00           H+0
HETATM   74  H   UNK     0      -5.539   1.683  -1.421  0.00  0.00           H+0
HETATM   75  H   UNK     0      -4.861   3.482   1.001  0.00  0.00           H+0
HETATM   76  H   UNK     0      -6.319   5.309   0.373  0.00  0.00           H+0
HETATM   77  H   UNK     0      -8.627   6.151   0.149  0.00  0.00           H+0
HETATM   78  H   UNK     0     -10.532   4.566   0.040  0.00  0.00           H+0
HETATM   79  H   UNK     0     -10.117   2.122   0.158  0.00  0.00           H+0
HETATM   80  H   UNK     0      -7.813   1.262   0.384  0.00  0.00           H+0
HETATM   81  H   UNK     0      -3.541   1.854   2.081  0.00  0.00           H+0
HETATM   82  H   UNK     0      -4.185   0.227   2.261  0.00  0.00           H+0
HETATM   83  H   UNK     0      -4.200  -1.445   0.310  0.00  0.00           H+0
HETATM   84  H   UNK     0      -5.313  -0.327  -0.450  0.00  0.00           H+0
HETATM   85  H   UNK     0      -3.878  -0.859  -1.327  0.00  0.00           H+0
HETATM   86  H   UNK     0      -1.767  -0.534  -0.449  0.00  0.00           H+0
HETATM   87  H   UNK     0      -2.496  -1.546   1.698  0.00  0.00           H+0
HETATM   88  H   UNK     0      -1.793  -0.203   2.585  0.00  0.00           H+0
HETATM   89  H   UNK     0      -0.256  -2.137   2.488  0.00  0.00           H+0
HETATM   90  H   UNK     0       0.377  -2.953   0.521  0.00  0.00           H+0
HETATM   91  H   UNK     0       0.947  -0.518   3.698  0.00  0.00           H+0
HETATM   92  H   UNK     0       1.963   0.714   2.955  0.00  0.00           H+0
HETATM   93  H   UNK     0       0.223   0.925   3.083  0.00  0.00           H+0
HETATM   94  H   UNK     0       8.875   0.320  -1.785  0.00  0.00           H+0
HETATM   95  H   UNK     0       7.256   0.713  -2.322  0.00  0.00           H+0
CONECT    1    2   46   47   48                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2   45                                             
CONECT    4    3   49   50   51                                             
CONECT    5    3    6   52   53                                             
CONECT    6    5    7                                                       
CONECT    7   45   44    6    8                                             
CONECT    8    9    7   54                                                  
CONECT    9   10    8   42                                                  
CONECT   10   11   15   55    9                                             
CONECT   11   12   10   56   57                                             
CONECT   12   13   11   58   59                                             
CONECT   13   40   15   12   14                                             
CONECT   14   13   15   60   61                                             
CONECT   15   16   13   10   14                                             
CONECT   16   15   17   62   63                                             
CONECT   17   18   16   64   65                                             
CONECT   18   17   66   19   40                                             
CONECT   19   21   36   20   18                                             
CONECT   20   19   67   68   69                                             
CONECT   21   19   22   70   71                                             
CONECT   22   23   21   72                                                  
CONECT   23   34   22   24                                                  
CONECT   24   25   23   73   74                                             
CONECT   25   32   26   24   75                                             
CONECT   26   25   31   27                                                  
CONECT   27   28   26   76                                                  
CONECT   28   29   27   77                                                  
CONECT   29   28   30   78                                                  
CONECT   30   31   29   79                                                  
CONECT   31   26   30   80                                                  
CONECT   32   25   33                                                       
CONECT   33   32   34   81   82                                             
CONECT   34   33   23   35   36                                             
CONECT   35   34   83   84   85                                             
CONECT   36   86   34   19   37                                             
CONECT   37   36   38   87   88                                             
CONECT   38   39   37   40   89                                             
CONECT   39   38   90                                                       
CONECT   40   13   41   38   18                                             
CONECT   41   40   91   92   93                                             
CONECT   42   44    9   43                                                  
CONECT   43   42                                                            
CONECT   44    7   42                                                       
CONECT   45    7    3   94   95                                             
CONECT   46    1                                                            
CONECT   47    1                                                            
CONECT   48    1                                                            
CONECT   49    4                                                            
CONECT   50    4                                                            
CONECT   51    4                                                            
CONECT   52    5                                                            
CONECT   53    5                                                            
CONECT   54    8                                                            
CONECT   55   10                                                            
CONECT   56   11                                                            
CONECT   57   11                                                            
CONECT   58   12                                                            
CONECT   59   12                                                            
CONECT   60   14                                                            
CONECT   61   14                                                            
CONECT   62   16                                                            
CONECT   63   16                                                            
CONECT   64   17                                                            
CONECT   65   17                                                            
CONECT   66   18                                                            
CONECT   67   20                                                            
CONECT   68   20                                                            
CONECT   69   20                                                            
CONECT   70   21                                                            
CONECT   71   21                                                            
CONECT   72   22                                                            
CONECT   73   24                                                            
CONECT   74   24                                                            
CONECT   75   25                                                            
CONECT   76   27                                                            
CONECT   77   28                                                            
CONECT   78   29                                                            
CONECT   79   30                                                            
CONECT   80   31                                                            
CONECT   81   33                                                            
CONECT   82   33                                                            
CONECT   83   35                                                            
CONECT   84   35                                                            
CONECT   85   35                                                            
CONECT   86   36                                                            
CONECT   87   37                                                            
CONECT   88   37                                                            
CONECT   89   38                                                            
CONECT   90   39                                                            
CONECT   91   41                                                            
CONECT   92   41                                                            
CONECT   93   41                                                            
CONECT   94   45                                                            
CONECT   95   45                                                            
MASTER        0    0    0    0    0    0    0    0   95    0  206    0
END

RDKit          3D

95103  0  0  0  0  0  0  0  0999 V2000
    9.8685   -0.8142   -5.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3529   -0.1887   -4.1335 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2485   -0.8448   -3.5069 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0117   -0.8376   -4.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5700   -2.2440   -2.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6663   -2.4794   -1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4287   -1.2185   -1.2724 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9940   -1.1197   -0.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8133   -0.9955    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.8534    1.2040 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3101   -2.1264    2.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8074   -2.0828    2.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690   -1.3002    1.2174 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5365   -1.7742   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2735   -0.6077    0.4568 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0821    0.7442   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7964    1.4743    0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5869    0.5214    0.3281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8353    1.2276    0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9815    2.3496    1.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344    1.8882   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4491    2.3168   -1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5140    1.7916   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966    2.3929   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4684    2.7100    0.5089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8932    3.2197    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1421    4.5993    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4464    5.0810    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5167    4.1910    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2845    2.8189    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9811    2.3360    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4426    1.5434    1.3523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019    1.0696    1.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4255    0.6204    0.2434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2503   -0.5647   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395    0.1198    0.4220 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7127   -0.7802    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -1.5015    1.5999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4119   -2.3858    0.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -0.5148    1.4967 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9995    0.1993    2.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1561   -0.9954    0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3976   -0.8676    2.1540 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0856   -1.1436   -0.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9564   -0.1215   -2.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7607   -0.2632   -5.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1462   -0.7707   -6.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1596   -1.8492   -5.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1657   -1.4648   -5.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8063    0.1759   -4.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1172   -1.2111   -3.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4379   -3.0243   -3.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5976   -2.3120   -2.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2022   -1.1634   -1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214   -0.0112    1.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9172   -2.1642    2.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5354   -3.0339    1.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6905   -1.5954    3.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873   -3.0909    2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719   -1.5913   -1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542   -2.7212   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9339    1.3992    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0859    0.6095   -1.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671    2.0007    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156    2.2550   -0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -0.0603   -0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7662    3.0681    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0657    2.9389    1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2524    1.9724    2.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310    1.2075   -1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3986    2.7777   -1.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785    3.1403   -2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8720    3.3065   -1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5393    1.6831   -1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605    3.4822    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3193    5.3093    0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6275    6.1514    0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5318    4.5661    0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1173    2.1224    0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8131    1.2618    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5411    1.8542    2.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848    0.2274    2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1999   -1.4454    0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3133   -0.3267   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -0.8587   -1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7666   -0.5340   -0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4960   -1.5455    1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7927   -0.2030    2.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560   -2.1367    2.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766   -2.9533    0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9466   -0.5176    3.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9628    0.7136    2.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2231    0.9251    3.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8748    0.3200   -1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2563    0.7131   -2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 32  1  0
 18 17  1  0
 40 13  1  0
 15 16  1  6
 16 17  1  0
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 32 33  1  0
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  3  5  1  0
  3  4  1  0
 13 12  1  1
 12 11  1  0
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  6  5  1  0
 25 26  1  0
 45  7  1  0
 34 35  1  6
 23 22  2  0
 36 86  1  6
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 13 14  1  0
 15 14  1  0
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 30 79  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₅₀O₆

Average Mass

614.8230 Da

Monoisotopic Mass

614.36074 Da

IUPAC Name

(5R,8R)-3-[(1S,2R,3R,5R,6R,9S,14S,15R,18R,19R)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0^{1,18}.0^{2,15}.0^{5,14}.0^{6,11}]docos-11-en-19-yl]-8-methoxy-8-methyl-1,6-dioxaspiro[4.4]non-3-en-2-one

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])[C@@]2([H])[C@@]3(C(=C([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@]45C([H])([H])[C@]4(C([H])([H])C([H])([H])[C@@]5([H])C4=C([H])[C@@]5(OC4=O)OC([H])([H])[C@@](OC([H])([H])[H])(C([H])([H])[H])C5([H])[H])[C@]12C([H])([H])[H])C([H])([H])[C@]([H])(OC3([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C39H50O6/c1-33(42-5)20-39(44-22-33)19-26(32(41)45-39)27-12-16-38-21-37(27,38)15-13-29-34(2)14-11-25-17-28(24-9-7-6-8-10-24)43-23-35(25,3)30(34)18-31(40)36(29,38)4/h6-11,19,27-31,40H,12-18,20-23H2,1-5H3/t27-,28-,29+,30+,31+,33+,34+,35-,36-,37+,38+,39-/m0/s1

InChI Key

DUBRTGHCJCCRAJ-WJRFPTRPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Phyllanthus acutissima	JEOL database	Tuchinda, P., et al, J. Nat. Prod. 71, 655 (2008)
Phyllanthus acutissimus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Naphthopyran
Naphthalene
Ketal
Benzenoid
Pyran
Oxane
2-furanone
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.19	ALOGPS
logP	6.2	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Basic)	-0.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	171.88 m³·mol⁻¹	ChemAxon
Polarizability	71.44 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24862531

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tuchinda, P., et al. (2008). Tuchinda, P., et al, J. Nat. Prod. 71, 655 (2008) . J. Nat. Prod..

Showing NP-Card for acutissimatriterpene D (NP0033676)

MOL for NP0033676 (acutissimatriterpene D)

3D MOL for NP0033676 (acutissimatriterpene D)

3D SDF for NP0033676 (acutissimatriterpene D)

3D-SDF for NP0033676 (acutissimatriterpene D)

PDB for NP0033676 (acutissimatriterpene D)

3D PDB for NP0033676 (acutissimatriterpene D)

SMILES for NP0033676 (acutissimatriterpene D)

INCHI for NP0033676 (acutissimatriterpene D)

Structure for NP0033676 (acutissimatriterpene D)

3D Structure for NP0033676 (acutissimatriterpene D)