NP-MRD: Showing NP-Card for turrapubin A (NP0043470)

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Record Information

Version

2.0

Created at

2021-06-21 00:52:23 UTC

Updated at

2021-06-30 00:19:10 UTC

NP-MRD ID

NP0043470

Secondary Accession Numbers

None

Natural Product Identification

Common Name

turrapubin A

Provided By

JEOL Database JEOL Logo

Description

TURRAPUBIN A 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. turrapubin A is found in Turraea pubescens. turrapubin A was first documented in 2013 (Yuan, C. -M., et al.). Based on a literature review very few articles have been published on TURRAPUBIN A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102523D          

 86 90  0  0  0  0            999 V2000
   -3.0557    0.3307   -1.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7385    0.3269   -1.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1814   -0.1871    0.0913 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6242   -1.7309    0.0668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5443   -2.5361   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683   -1.8092   -0.4338 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0276   -2.8989   -1.3776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9908   -2.7499   -2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9928   -3.9404   -3.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -1.7977   -2.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081   -1.9980    0.6677 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6491   -3.2648    1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5898   -3.9878    1.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2006   -3.6130    1.8062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1500   -4.9006    1.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1960   -3.9501    3.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371   -2.3725    1.5302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2076   -2.6035    1.9955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4520   -2.1597    3.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9086   -1.2029    3.9593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3895   -2.9567    4.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6950   -2.6055    5.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3108    0.9723    0.7306 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3661    0.4838    1.9026 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4407    0.7373   -2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6066   -2.3922   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9355   -4.7216    3.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3330   -1.6105    2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4424   -3.3113    5.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8432    1.0708    5.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7364    4.0459    2.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  6  0  0  0
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M  END

     RDKit          3D

 86 90  0  0  0  0  0  0  0  0999 V2000
   -3.0557    0.3307   -1.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7385    0.3269   -1.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1814   -0.1871    0.0913 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6242   -1.7309    0.0668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5443   -2.5361   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9355   -4.7216    3.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3330   -1.6105    2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9286   -2.0328    1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869   -3.6556    1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4424   -3.3113    5.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -2.6829    5.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1167   -1.5966    5.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330    1.7357    1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010   -0.4670    4.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432    1.0708    5.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1569    0.6757    3.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485    1.0215   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364    4.0459    2.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0180    4.3970    2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7949    4.8712    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4804    4.1804   -0.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7558    3.0193   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911    3.5600   -2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8435    1.7189   -2.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063    5.2999   -3.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2610    7.0644   -3.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7768    3.4412   -1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    1.9203   -4.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253    3.0246   -4.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    0.7658   -4.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  6
 23 24  1  0
  3 23  1  0
 44 43  1  6
 42 43  1  0
  2 44  1  0
 28 29  1  0
 33 28  1  0
 33 34  1  1
 28 23  1  0
 35 36  1  0
 33 44  1  0
  3 47  1  1
 11 12  1  0
 17 63  1  1
 11  6  1  0
 18 19  1  0
 12 14  1  0
 19 20  2  0
  4  3  1  0
 19 21  1  0
 17 18  1  0
 21 22  1  0
 36 40  2  0
 44 42  1  0
 42 41  1  0
 41 35  1  0
 35 33  1  0
 40 39  1  0
 39 38  1  0
 38 37  2  0
 37 36  1  0
  1  2  2  3
 24 25  1  0
 12 13  2  0
 25 27  2  0
  3  2  1  0
  7  8  1  0
 14 15  1  6
  8 10  2  0
 14 17  1  0
  8  9  1  0
 14 16  1  0
 29 30  1  0
  4  6  1  0
 30 31  1  0
  6  7  1  0
 30 32  2  0
  4 17  1  0
 25 26  1  0
 11 55  1  0
 11 56  1  0
  6 51  1  6
 18 64  1  0
 18 65  1  0
  1 45  1  0
  1 46  1  0
 28 73  1  6
 23 69  1  1
 42 86  1  6
 41 84  1  0
 41 85  1  0
 35 80  1  1
 15 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 16 62  1  0
  5 48  1  0
  5 49  1  0
  5 50  1  0
 34 77  1  0
 34 78  1  0
 34 79  1  0
 22 66  1  0
 22 67  1  0
 22 68  1  0
 40 83  1  0
 38 82  1  0
 37 81  1  0
  9 52  1  0
  9 53  1  0
  9 54  1  0
 31 74  1  0
 31 75  1  0
 31 76  1  0
 26 70  1  0
 26 71  1  0
 26 72  1  0
M  END


  Mrv1652306212102523D          

 86 90  0  0  0  0            999 V2000
   -3.0557    0.3307   -1.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7385    0.3269   -1.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1814   -0.1871    0.0913 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6242   -1.7309    0.0668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5443   -2.5361   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683   -1.8092   -0.4338 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0276   -2.8989   -1.3776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9908   -2.7499   -2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9928   -3.9404   -3.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -1.7977   -2.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081   -1.9980    0.6677 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6491   -3.2648    1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5898   -3.9878    1.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2006   -3.6130    1.8062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1500   -4.9006    1.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1960   -3.9501    3.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371   -2.3725    1.5302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2076   -2.6035    1.9955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4520   -2.1597    3.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9086   -1.2029    3.9593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3895   -2.9567    4.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6950   -2.6055    5.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3108    0.9723    0.7306 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3661    0.4838    1.9026 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3200    1.2493    3.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0849    0.5852    4.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2190    2.3426    3.1243 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7085    1.6883   -0.2274 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2168    2.8856    0.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    2.7864    1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7498    4.1152    1.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0385    1.7631    1.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0338    2.1185   -1.5552 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9727    3.2838   -1.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0341    2.4666   -2.7174 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6926    3.8092   -2.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    5.0762   -3.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1790    5.9959   -2.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761    5.3861   -2.3561 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823    4.0664   -2.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014    2.1768   -4.0031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6714    1.0147   -3.6033 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0588   -0.0046   -2.9396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7115    0.9082   -2.1188 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4407    0.7373   -2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7850   -0.0712   -0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -0.2329    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6066   -2.3922   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3694   -3.6110   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3850   -2.2371   -1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2073   -5.1641    1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145   -4.8429   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7755   -4.3327    3.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4466   -3.0705    3.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355   -4.7216    3.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3330   -1.6105    2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9286   -2.0328    1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869   -3.6556    1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4424   -3.3113    5.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -2.6829    5.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1167   -1.5966    5.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330    1.7357    1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010   -0.4670    4.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432    1.0708    5.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1569    0.6757    3.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485    1.0215   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364    4.0459    2.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0180    4.3970    2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7949    4.8712    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4804    4.1804   -0.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7558    3.0193   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911    3.5600   -2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8435    1.7189   -2.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063    5.2999   -3.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2610    7.0644   -3.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7768    3.4412   -1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    1.9203   -4.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253    3.0246   -4.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    0.7658   -4.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  6  0  0  0
 23 24  1  0  0  0  0
  3 23  1  0  0  0  0
 44 43  1  6  0  0  0
 42 43  1  0  0  0  0
  2 44  1  0  0  0  0
 28 29  1  0  0  0  0
 33 28  1  0  0  0  0
 33 34  1  1  0  0  0
 28 23  1  0  0  0  0
 35 36  1  0  0  0  0
 33 44  1  0  0  0  0
  3 47  1  1  0  0  0
 11 12  1  0  0  0  0
 17 63  1  1  0  0  0
 11  6  1  0  0  0  0
 18 19  1  0  0  0  0
 12 14  1  0  0  0  0
 19 20  2  0  0  0  0
  4  3  1  0  0  0  0
 19 21  1  0  0  0  0
 17 18  1  0  0  0  0
 21 22  1  0  0  0  0
 36 40  2  0  0  0  0
 44 42  1  0  0  0  0
 42 41  1  0  0  0  0
 41 35  1  0  0  0  0
 35 33  1  0  0  0  0
 40 39  1  0  0  0  0
 39 38  1  0  0  0  0
 38 37  2  0  0  0  0
 37 36  1  0  0  0  0
  1  2  2  3  0  0  0
 24 25  1  0  0  0  0
 12 13  2  0  0  0  0
 25 27  2  0  0  0  0
  3  2  1  0  0  0  0
  7  8  1  0  0  0  0
 14 15  1  6  0  0  0
  8 10  2  0  0  0  0
 14 17  1  0  0  0  0
  8  9  1  0  0  0  0
 14 16  1  0  0  0  0
 29 30  1  0  0  0  0
  4  6  1  0  0  0  0
 30 31  1  0  0  0  0
  6  7  1  0  0  0  0
 30 32  2  0  0  0  0
  4 17  1  0  0  0  0
 25 26  1  0  0  0  0
 11 55  1  0  0  0  0
 11 56  1  0  0  0  0
  6 51  1  6  0  0  0
 18 64  1  0  0  0  0
 18 65  1  0  0  0  0
  1 45  1  0  0  0  0
  1 46  1  0  0  0  0
 28 73  1  6  0  0  0
 23 69  1  1  0  0  0
 42 86  1  6  0  0  0
 41 84  1  0  0  0  0
 41 85  1  0  0  0  0
 35 80  1  1  0  0  0
 15 57  1  0  0  0  0
 15 58  1  0  0  0  0
 15 59  1  0  0  0  0
 16 60  1  0  0  0  0
 16 61  1  0  0  0  0
 16 62  1  0  0  0  0
  5 48  1  0  0  0  0
  5 49  1  0  0  0  0
  5 50  1  0  0  0  0
 34 77  1  0  0  0  0
 34 78  1  0  0  0  0
 34 79  1  0  0  0  0
 22 66  1  0  0  0  0
 22 67  1  0  0  0  0
 22 68  1  0  0  0  0
 40 83  1  0  0  0  0
 38 82  1  0  0  0  0
 37 81  1  0  0  0  0
  9 52  1  0  0  0  0
  9 53  1  0  0  0  0
  9 54  1  0  0  0  0
 31 74  1  0  0  0  0
 31 75  1  0  0  0  0
 31 76  1  0  0  0  0
 26 70  1  0  0  0  0
 26 71  1  0  0  0  0
 26 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043470

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1[C@]([H])([C@@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]2(C([H])([H])[H])[C@]([H])(C3=C([H])OC([H])=C3[H])C([H])([H])[C@@]3([H])O[C@@]123)[C@@]1(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])C([H])([H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O11/c1-16-27(31(7)22(13-26(38)39-9)30(5,6)23(37)14-24(31)41-17(2)34)28(42-18(3)35)29(43-19(4)36)32(8)21(20-10-11-40-15-20)12-25-33(16,32)44-25/h10-11,15,21-22,24-25,27-29H,1,12-14H2,2-9H3/t21-,22-,24+,25+,27+,28+,29-,31+,32+,33+/m0/s1

> <INCHI_KEY>
VXKJLBGAQIDBPO-YILSLSMRSA-N

> <FORMULA>
C33H42O11

> <MOLECULAR_WEIGHT>
614.688

> <EXACT_MASS>
614.272712172

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
63.0023493639786

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R,2S,3R)-2-[(3R,3aR,4R,5R,6R,7aS,7bR)-4,5-bis(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-octahydroindeno[3,3a-b]oxiren-6-yl]-3-(acetyloxy)-2,6,6-trimethyl-5-oxocyclohexyl]acetate

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
2.792558257333335

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.886610862439895

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8598681253288

> <JCHEM_POLAR_SURFACE_AREA>
147.94000000000003

> <JCHEM_REFRACTIVITY>
151.77679999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,2S,3R)-2-[(3R,3aR,4R,5R,6R,7aS,7bR)-4,5-bis(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[3,3a-b]oxiren-6-yl]-3-(acetyloxy)-2,6,6-trimethyl-5-oxocyclohexyl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 86 90  0  0  0  0  0  0  0  0999 V2000
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    1.9928   -3.9404   -3.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -1.7977   -2.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081   -1.9980    0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6491   -3.2648    1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5898   -3.9878    1.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2006   -3.6130    1.8062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1500   -4.9006    1.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3846    2.7864    1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0385    1.7631    1.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0338    2.1185   -1.5552 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9727    3.2838   -1.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0341    2.4666   -2.7174 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6926    3.8092   -2.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    5.0762   -3.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1790    5.9959   -2.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761    5.3861   -2.3561 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823    4.0664   -2.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014    2.1768   -4.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6714    1.0147   -3.6033 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0588   -0.0046   -2.9396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7115    0.9082   -2.1188 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4407    0.7373   -2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7850   -0.0712   -0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -0.2329    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6066   -2.3922   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3694   -3.6110   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3850   -2.2371   -1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0185   -4.0372   -3.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547   -3.8054   -4.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298   -4.8413   -2.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -1.1672    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9093   -2.0852    0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2073   -5.1641    1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145   -4.8429   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4191   -5.7529    1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755   -4.3327    3.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4466   -3.0705    3.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355   -4.7216    3.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3330   -1.6105    2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9286   -2.0328    1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869   -3.6556    1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4424   -3.3113    5.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -2.6829    5.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1167   -1.5966    5.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330    1.7357    1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010   -0.4670    4.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432    1.0708    5.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1569    0.6757    3.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485    1.0215   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364    4.0459    2.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0180    4.3970    2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7949    4.8712    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4804    4.1804   -0.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7558    3.0193   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911    3.5600   -2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8435    1.7189   -2.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063    5.2999   -3.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2610    7.0644   -3.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7768    3.4412   -1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    1.9203   -4.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253    3.0246   -4.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    0.7658   -4.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  6
 23 24  1  0
  3 23  1  0
 44 43  1  6
 42 43  1  0
  2 44  1  0
 28 29  1  0
 33 28  1  0
 33 34  1  1
 28 23  1  0
 35 36  1  0
 33 44  1  0
  3 47  1  1
 11 12  1  0
 17 63  1  1
 11  6  1  0
 18 19  1  0
 12 14  1  0
 19 20  2  0
  4  3  1  0
 19 21  1  0
 17 18  1  0
 21 22  1  0
 36 40  2  0
 44 42  1  0
 42 41  1  0
 41 35  1  0
 35 33  1  0
 40 39  1  0
 39 38  1  0
 38 37  2  0
 37 36  1  0
  1  2  2  3
 24 25  1  0
 12 13  2  0
 25 27  2  0
  3  2  1  0
  7  8  1  0
 14 15  1  6
  8 10  2  0
 14 17  1  0
  8  9  1  0
 14 16  1  0
 29 30  1  0
  4  6  1  0
 30 31  1  0
  6  7  1  0
 30 32  2  0
  4 17  1  0
 25 26  1  0
 11 55  1  0
 11 56  1  0
  6 51  1  6
 18 64  1  0
 18 65  1  0
  1 45  1  0
  1 46  1  0
 28 73  1  6
 23 69  1  1
 42 86  1  6
 41 84  1  0
 41 85  1  0
 35 80  1  1
 15 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 16 62  1  0
  5 48  1  0
  5 49  1  0
  5 50  1  0
 34 77  1  0
 34 78  1  0
 34 79  1  0
 22 66  1  0
 22 67  1  0
 22 68  1  0
 40 83  1  0
 38 82  1  0
 37 81  1  0
  9 52  1  0
  9 53  1  0
  9 54  1  0
 31 74  1  0
 31 75  1  0
 31 76  1  0
 26 70  1  0
 26 71  1  0
 26 72  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      -3.056   0.331  -1.526  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.738   0.327  -1.256  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.181  -0.187   0.091  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.624  -1.731   0.067  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.544  -2.536  -0.908  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.868  -1.809  -0.434  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.028  -2.899  -1.378  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.991  -2.750  -2.332  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.993  -3.940  -3.240  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.750  -1.798  -2.435  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.908  -1.998   0.668  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.649  -3.265   1.439  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.590  -3.988   1.777  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.201  -3.613   1.806  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.150  -4.901   1.041  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.196  -3.950   3.317  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.737  -2.373   1.530  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.208  -2.603   1.996  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.452  -2.160   3.425  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.909  -1.203   3.959  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.389  -2.957   4.006  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.695  -2.606   5.357  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.311   0.972   0.731  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.366   0.484   1.903  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.320   1.249   3.029  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.085   0.585   4.133  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.219   2.343   3.124  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.709   1.688  -0.227  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.217   2.886   0.413  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.385   2.786   1.099  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.750   4.115   1.685  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.038   1.763   1.241  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.034   2.119  -1.555  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.973   3.284  -1.325  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.034   2.467  -2.717  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.693   3.809  -2.688  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.183   5.076  -3.096  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.179   5.996  -2.867  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.276   5.386  -2.356  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.982   4.066  -2.260  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.201   2.177  -4.003  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.671   1.015  -3.603  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.059  -0.005  -2.940  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.712   0.908  -2.119  0.00  0.00           C+0
HETATM   45  H   UNK     0      -3.441   0.737  -2.456  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.785  -0.071  -0.829  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.047  -0.233   0.766  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.607  -2.392  -0.691  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.369  -3.611  -0.867  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.385  -2.237  -1.950  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.105  -0.892  -0.964  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.018  -4.037  -3.725  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.755  -3.805  -4.013  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.230  -4.841  -2.668  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.939  -1.167   1.371  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.909  -2.085   0.230  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.207  -5.164   1.122  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.115  -4.843  -0.017  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.419  -5.753   1.435  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.776  -4.333   3.644  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.447  -3.071   3.920  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.936  -4.722   3.563  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.333  -1.611   2.197  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.929  -2.033   1.404  0.00  0.00           H+0
HETATM   65  H   UNK     0      -2.487  -3.656   1.895  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.442  -3.311   5.730  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.802  -2.683   5.984  0.00  0.00           H+0
HETATM   68  H   UNK     0      -4.117  -1.597   5.404  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.033   1.736   1.050  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.801  -0.467   4.210  0.00  0.00           H+0
HETATM   71  H   UNK     0       0.843   1.071   5.082  0.00  0.00           H+0
HETATM   72  H   UNK     0       2.157   0.676   3.943  0.00  0.00           H+0
HETATM   73  H   UNK     0       1.549   1.022  -0.440  0.00  0.00           H+0
HETATM   74  H   UNK     0       3.736   4.046   2.152  0.00  0.00           H+0
HETATM   75  H   UNK     0       2.018   4.397   2.446  0.00  0.00           H+0
HETATM   76  H   UNK     0       2.795   4.871   0.897  0.00  0.00           H+0
HETATM   77  H   UNK     0      -0.480   4.180  -0.936  0.00  0.00           H+0
HETATM   78  H   UNK     0      -1.756   3.019  -0.608  0.00  0.00           H+0
HETATM   79  H   UNK     0      -1.491   3.560  -2.249  0.00  0.00           H+0
HETATM   80  H   UNK     0       1.843   1.719  -2.695  0.00  0.00           H+0
HETATM   81  H   UNK     0       0.206   5.300  -3.501  0.00  0.00           H+0
HETATM   82  H   UNK     0       2.261   7.064  -3.009  0.00  0.00           H+0
HETATM   83  H   UNK     0       3.777   3.441  -1.874  0.00  0.00           H+0
HETATM   84  H   UNK     0       0.851   1.920  -4.846  0.00  0.00           H+0
HETATM   85  H   UNK     0      -0.425   3.025  -4.298  0.00  0.00           H+0
HETATM   86  H   UNK     0      -1.501   0.766  -4.240  0.00  0.00           H+0
CONECT    1    2   45   46                                                  
CONECT    2   44    1    3                                                  
CONECT    3   23   47    4    2                                             
CONECT    4    5    3    6   17                                             
CONECT    5    4   48   49   50                                             
CONECT    6   11    4    7   51                                             
CONECT    7    8    6                                                       
CONECT    8    7   10    9                                                  
CONECT    9    8   52   53   54                                             
CONECT   10    8                                                            
CONECT   11   12    6   55   56                                             
CONECT   12   11   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17   16                                             
CONECT   15   14   57   58   59                                             
CONECT   16   14   60   61   62                                             
CONECT   17   63   18   14    4                                             
CONECT   18   19   17   64   65                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   66   67   68                                             
CONECT   23   24    3   28   69                                             
CONECT   24   23   25                                                       
CONECT   25   24   27   26                                                  
CONECT   26   25   70   71   72                                             
CONECT   27   25                                                            
CONECT   28   29   33   23   73                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30   74   75   76                                             
CONECT   32   30                                                            
CONECT   33   28   34   44   35                                             
CONECT   34   33   77   78   79                                             
CONECT   35   36   41   33   80                                             
CONECT   36   35   40   37                                                  
CONECT   37   38   36   81                                                  
CONECT   38   39   37   82                                                  
CONECT   39   40   38                                                       
CONECT   40   36   39   83                                                  
CONECT   41   42   35   84   85                                             
CONECT   42   43   44   41   86                                             
CONECT   43   44   42                                                       
CONECT   44   43    2   33   42                                             
CONECT   45    1                                                            
CONECT   46    1                                                            
CONECT   47    3                                                            
CONECT   48    5                                                            
CONECT   49    5                                                            
CONECT   50    5                                                            
CONECT   51    6                                                            
CONECT   52    9                                                            
CONECT   53    9                                                            
CONECT   54    9                                                            
CONECT   55   11                                                            
CONECT   56   11                                                            
CONECT   57   15                                                            
CONECT   58   15                                                            
CONECT   59   15                                                            
CONECT   60   16                                                            
CONECT   61   16                                                            
CONECT   62   16                                                            
CONECT   63   17                                                            
CONECT   64   18                                                            
CONECT   65   18                                                            
CONECT   66   22                                                            
CONECT   67   22                                                            
CONECT   68   22                                                            
CONECT   69   23                                                            
CONECT   70   26                                                            
CONECT   71   26                                                            
CONECT   72   26                                                            
CONECT   73   28                                                            
CONECT   74   31                                                            
CONECT   75   31                                                            
CONECT   76   31                                                            
CONECT   77   34                                                            
CONECT   78   34                                                            
CONECT   79   34                                                            
CONECT   80   35                                                            
CONECT   81   37                                                            
CONECT   82   38                                                            
CONECT   83   40                                                            
CONECT   84   41                                                            
CONECT   85   41                                                            
CONECT   86   42                                                            
MASTER        0    0    0    0    0    0    0    0   86    0  180    0
END

RDKit          3D

86 90  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₂O₁₁

Average Mass

614.6880 Da

Monoisotopic Mass

614.27271 Da

IUPAC Name

methyl 2-[(1R,2S,3R)-2-[(3R,3aR,4R,5R,6R,7aS,7bR)-4,5-bis(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-octahydroindeno[3,3a-b]oxiren-6-yl]-3-(acetyloxy)-2,6,6-trimethyl-5-oxocyclohexyl]acetate

Traditional Name

methyl [(1R,2S,3R)-2-[(3R,3aR,4R,5R,6R,7aS,7bR)-4,5-bis(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[3,3a-b]oxiren-6-yl]-3-(acetyloxy)-2,6,6-trimethyl-5-oxocyclohexyl]acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1[C@]([H])([C@@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]2(C([H])([H])[H])[C@]([H])(C3=C([H])OC([H])=C3[H])C([H])([H])[C@@]3([H])O[C@@]123)[C@@]1(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])C([H])([H])C(=O)OC([H])([H])[H]

InChI Identifier

InChI=1S/C33H42O11/c1-16-27(31(7)22(13-26(38)39-9)30(5,6)23(37)14-24(31)41-17(2)34)28(42-18(3)35)29(43-19(4)36)32(8)21(20-10-11-40-15-20)12-25-33(16,32)44-25/h10-11,15,21-22,24-25,27-29H,1,12-14H2,2-9H3/t21-,22-,24+,25+,27+,28+,29-,31+,32+,33+/m0/s1

InChI Key

VXKJLBGAQIDBPO-YILSLSMRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Turraea pubescens	JEOL database	Yuan, C. -M., et al, J. Nat. Prod. 76, 1166 (2013)

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
Tetracarboxylic acid or derivatives
Oxane
Furan
Heteroaromatic compound
Methyl ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen 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	3.69	ALOGPS
logP	2.79	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	17.89	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	147.94 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	151.78 m³·mol⁻¹	ChemAxon
Polarizability	63 Å³	ChemAxon
Number of Rings	5	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

29784801

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71725783

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yuan, C. -M., et al. (2013). Yuan, C. -M., et al, J. Nat. Prod. 76, 1166 (2013). J. Nat. Prod..

Showing NP-Card for turrapubin A (NP0043470)

MOL for NP0043470 (turrapubin A)

3D MOL for NP0043470 (turrapubin A)

3D SDF for NP0043470 (turrapubin A)

3D-SDF for NP0043470 (turrapubin A)

PDB for NP0043470 (turrapubin A)

3D PDB for NP0043470 (turrapubin A)

SMILES for NP0043470 (turrapubin A)

INCHI for NP0043470 (turrapubin A)

Structure for NP0043470 (turrapubin A)

3D Structure for NP0043470 (turrapubin A)