NP-MRD: Showing NP-Card for (1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate (NP0202304)

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Record Information

Version

2.0

Created at

2022-09-04 21:30:12 UTC

Updated at

2022-09-04 21:30:12 UTC

NP-MRD ID

NP0202304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate

Description

(1S,2R,3R,5R,7R,10S,11R,14R,15S)-3-(acetyloxy)-15-[(2R,3R,5S)-2-(acetyloxy)-5-[(1S)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]Octadecan-7-yl benzoate 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. Based on a literature review very few articles have been published on (1S,2R,3R,5R,7R,10S,11R,14R,15S)-3-(acetyloxy)-15-[(2R,3R,5S)-2-(acetyloxy)-5-[(1S)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]Octadecan-7-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042223302D          

 56 62  0  0  1  0            999 V2000
   -0.9033   -4.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1758   -4.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249   -4.5685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1490   -3.3084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497   -2.8729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8229   -2.0484    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1400   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693   -0.7929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1370   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0923    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7737   -0.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4934   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.1221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3979    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1176   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8343    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3661    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0858   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1782    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4585    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2707    1.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8025    0.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5222   -0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7101   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2063    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1464    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    1.5287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8025    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828    2.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949    3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5510    3.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.7528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5222    1.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -0.7661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6569   -0.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4797   -0.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9427    0.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396   -0.8851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5772   -3.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1881   -3.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9662   -2.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3047   -3.6511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315   -4.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590   -4.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6308   -4.9111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
  9 14  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 18 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 37 42  1  0  0  0  0
 17 42  1  0  0  0  0
 12 42  1  0  0  0  0
 42 43  1  1  0  0  0
  8 44  1  0  0  0  0
 44 45  1  6  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  2  0  0  0  0
 44 49  1  0  0  0  0
  6 49  1  0  0  0  0
  5 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 50 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  2  0  0  0  0
M  END

     RDKit          3D

118124  0  0  0  0  0  0  0  0999 V2000
   -9.4731    1.0450   -2.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7233    0.2420   -1.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0114   -0.9710   -1.5068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7082    0.8046   -0.9332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9992   -0.0174    0.0435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6142   -0.1256   -0.4580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6402   -0.9601    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3530   -0.6476   -0.4961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1623   -0.6336    0.3964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1820    0.3514    1.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402    0.2158    2.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0700    0.0280    0.7432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2615    1.0077   -0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591   -0.3866   -0.2910 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4384   -1.2641   -1.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9887   -1.6724   -1.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8885   -0.8964   -0.5674 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3395   -1.2217   -0.6513 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7567   -2.5822   -0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7458   -1.1007   -2.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1085   -0.5720   -2.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0818   -0.6132   -1.2371 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1218    0.3144   -1.5562 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9778    2.3377   -2.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8536    3.3591   -2.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1847    3.0743   -2.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0478   -0.0832    0.0372 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4167    0.4101    1.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -0.4399    1.8307 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6504    0.1521    2.8929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6878   -0.3064    4.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9618    0.3669    5.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3737   -1.3193    4.3848 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866   -0.8369    0.7906 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8022   -2.2299    1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018    0.6391   -1.1508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9756    0.3690   -2.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486    1.0499   -3.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6208    0.7839   -4.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5090    1.9348   -3.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9143    1.0686   -0.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6506    1.9619    1.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6110    0.6538    1.6272 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.9510   -0.2034    1.9409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0254   -1.5668    1.5263 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.0557    1.8209   -2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6994   -0.6332   -1.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653   -2.0535    0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4658   -0.6663    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593   -1.4746   -1.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -1.6595    0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4447    1.3716    1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8664    0.0469    2.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325   -0.6167    2.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5189    1.2074    2.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2680    1.2941   -1.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222    1.8804    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -0.7014   -2.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1504   -2.1293   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3970   -1.5937   -2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0346   -2.7727   -1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672    0.1671   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6650   -2.9242   -0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9827   -2.8023    0.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1024    0.4774   -2.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5632   -1.1654   -3.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8892    3.8828   -2.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1036   -0.2255   -1.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875    1.8550   -0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1353    1.2577    0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309042223302D          

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M  END
> <DATABASE_ID>
NP0202304

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]([C@@H]1C[C@@H]([C@@H](OC(C)=O)O1)[C@@H]1CC[C@]23C[C@]12CC[C@@H]1[C@@]2(C)CC[C@@H](OC(=O)C4=CC=CC=C4)C(C)(C)[C@@H]2C[C@@H](OC(C)=O)[C@@]31C)C(C)(C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C45H62O11/c1-25(46)51-36-23-34-40(5,6)35(55-38(50)29-14-12-11-13-15-29)18-19-42(34,9)33-17-20-44-24-45(44,43(33,36)10)21-16-31(44)30-22-32(54-39(30)53-27(3)48)37(52-26(2)47)41(7,8)56-28(4)49/h11-15,30-37,39H,16-24H2,1-10H3/t30-,31+,32+,33-,34+,35-,36-,37+,39+,42-,43+,44-,45-/m1/s1

> <INCHI_KEY>
QQPZAQHSZQEXNP-WYQHFDAPSA-N

> <FORMULA>
C45H62O11

> <MOLECULAR_WEIGHT>
778.98

> <EXACT_MASS>
778.429212816

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
85.13925349148096

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,5R,7R,10S,11R,14R,15S)-3-(acetyloxy)-15-[(2R,3R,5S)-2-(acetyloxy)-5-[(1S)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0^{1,14}.0^{2,11}.0^{5,10}]octadecan-7-yl benzoate

> <JCHEM_LOGP>
6.685714395666663

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3588678084725725

> <JCHEM_POLAR_SURFACE_AREA>
140.73000000000002

> <JCHEM_REFRACTIVITY>
203.11250000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,5R,7R,10S,11R,14R,15S)-3-(acetyloxy)-15-[(2R,3R,5S)-2-(acetyloxy)-5-[(1S)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0^{1,14}.0^{2,11}.0^{5,10}]octadecan-7-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.686  -8.441   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.328  -7.715   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.980  -8.528   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.278  -6.176   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.586  -5.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.536  -3.824   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.261  -2.959   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.689  -1.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.256  -0.264   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.172   1.215   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.102   2.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.318   1.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.311  -0.043   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.795  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.788  -1.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.304  -1.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.827   0.228   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.343   0.499   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.820  -0.949   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.336  -0.678   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.852  -0.407   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.375   1.041   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.891   1.312   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.883   0.135   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.360  -1.314   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.399   0.406   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.923   1.854   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.439   2.125   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.431   0.948   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.908  -0.500   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.392  -0.771   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.382   2.218   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.852   3.664   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.714   2.992   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.866   1.947   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.873   3.125   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.357   2.854   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.365   4.031   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.888   5.479   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.404   5.750   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.895   6.657   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.834   1.405   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.841   2.583   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.229  -1.430   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -3.093  -0.155   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -4.629  -0.266   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -5.493   1.008   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -5.301  -1.652   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -2.752  -2.878   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -2.944  -6.089   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -2.218  -7.447   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -3.670  -4.731   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -4.302  -6.815   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -4.352  -8.354   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -5.710  -9.081   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -3.044  -9.167   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   50                                                  
CONECT    6    5    7   49                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   44                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   42                                             
CONECT   13   12   14                                                       
CONECT   14   13    9   12   15                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   42                                                  
CONECT   18   17   19   20   35                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   22   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   18   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   37   17   12   43                                             
CONECT   43   42                                                            
CONECT   44    8   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   44    6                                                       
CONECT   50    5   51   52   53                                             
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   50   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,3R,5R,7R,10S,11R,14R,15S)-3-(Acetyloxy)-15-[(2R,3R,5S)-2-(acetyloxy)-5-[(1S)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0,.0,.0,]octadecan-7-yl benzoic acid	Generator

Chemical Formula

C₄₅H₆₂O₁₁

Average Mass

778.9800 Da

Monoisotopic Mass

778.42921 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]([C@@H]1C[C@@H]([C@@H](OC(C)=O)O1)[C@@H]1CC[C@]23C[C@]12CC[C@@H]1[C@@]2(C)CC[C@@H](OC(=O)C4=CC=CC=C4)C(C)(C)[C@@H]2C[C@@H](OC(C)=O)[C@@]31C)C(C)(C)OC(C)=O

InChI Identifier

InChI=1S/C45H62O11/c1-25(46)51-36-23-34-40(5,6)35(55-38(50)29-14-12-11-13-15-29)18-19-42(34,9)33-17-20-44-24-45(44,43(33,36)10)21-16-31(44)30-22-32(54-39(30)53-27(3)48)37(52-26(2)47)41(7,8)56-28(4)49/h11-15,30-37,39H,16-24H2,1-10H3/t30-,31+,32+,33-,34+,35-,36-,37+,39+,42-,43+,44-,45-/m1/s1

InChI Key

QQPZAQHSZQEXNP-WYQHFDAPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Bile acid, alcohol, or derivatives
Steroid ester
Pentacarboxylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	6.69	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	140.73 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	203.11 m³·mol⁻¹	ChemAxon
Polarizability	85.14 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

162869170

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate (NP0202304)

MOL for NP0202304 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate)

3D MOL for NP0202304 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate)

3D SDF for NP0202304 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate)

3D-SDF for NP0202304 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate)

PDB for NP0202304 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate)

3D PDB for NP0202304 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate)

SMILES for NP0202304 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate)

INCHI for NP0202304 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate)

Structure for NP0202304 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate)

3D Structure for NP0202304 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-3-(acetyloxy)-15-[(2r,3r,5s)-2-(acetyloxy)-5-[(1s)-1,2-bis(acetyloxy)-2-methylpropyl]oxolan-3-yl]-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl benzoate)