NP-MRD: Showing NP-Card for 12-dehydroneoazedarachin D (NP0042088)

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Record Information

Version

2.0

Created at

2021-06-20 23:50:12 UTC

Updated at

2021-06-30 00:16:58 UTC

NP-MRD ID

NP0042088

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-dehydroneoazedarachin D

Provided By

JEOL Database JEOL Logo

Description

(1S,2S,5S,6R,9R,10S,11R,13R,14R,15S,18S,20R)-6-(furan-3-yl)-11,18-dihydroxy-15-methoxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]Icosan-20-yl acetate 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. 12-dehydroneoazedarachin D is found in Melia azedarach. 12-dehydroneoazedarachin D was first documented in 2013 (Akihisa, T., et al.). Based on a literature review very few articles have been published on (1S,2S,5S,6R,9R,10S,11R,13R,14R,15S,18S,20R)-6-(furan-3-yl)-11,18-dihydroxy-15-methoxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]Icosan-20-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101503D          

 76 81  0  0  0  0            999 V2000
   -1.6118   -1.2301    4.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -0.5996    3.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891    0.6707    3.2964 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2275    0.5296    3.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664   -0.0789    2.1327 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4220    0.6981    0.8338 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0375    2.1433    0.9671 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9212    2.8417   -0.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    3.0227    2.0647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1119    2.9300    2.1428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6856    3.7063    1.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7973    5.0470    1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    5.6866    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4540    5.6531    2.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    1.4678    2.0503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2153    1.5369    2.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    0.8258    0.7311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8019   -0.5098    0.3231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2617   -1.0729   -1.0013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6271   -0.1525   -2.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851   -1.2800   -1.0032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6113   -2.4951   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446    0.0382   -0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4514   -0.1389   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -0.2321    0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939   -0.2229   -1.9884 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3097   -1.3239   -2.8184 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -0.9045   -4.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8910   -2.7460   -2.5686 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2885   -2.9934   -3.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382   -3.3676   -4.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1066   -3.4783   -4.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380   -3.2038   -3.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4394   -2.9160   -2.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8472   -3.7044   -3.1576 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5601   -2.9445   -2.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457   -3.4403   -3.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7844   -1.5124   -2.4957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5479   -1.4323    4.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -2.1835    4.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021   -0.6135    5.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    1.2445    4.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -1.1098    2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457   -0.1159    2.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133    2.0638    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702    3.6997   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154    4.0651    1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8513    2.7541    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    3.3666    3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004    6.7628    0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979    5.2713   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    5.5259   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    2.0145    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    0.5468    2.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5794    2.1152    2.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3579    1.5217   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763   -0.3351    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7053   -1.2647    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7656   -2.0208   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966   -0.1855   -2.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3898   -3.4504   -0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057   -2.5203    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -2.5189    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190    0.7764   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8285    0.7666   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0790   -0.3608   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -1.6513   -4.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9192    0.0338   -4.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.7333   -4.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154   -2.9219   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438   -3.5346   -5.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8769   -3.7311   -5.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6309   -2.6753   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -3.8961   -4.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8223   -4.6507   -2.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2293   -0.8608   -3.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0  0  0  0
 23 21  1  0  0  0  0
 30 29  1  0  0  0  0
 30 34  2  0  0  0  0
 17 15  1  0  0  0  0
 10 11  1  0  0  0  0
 15 10  1  0  0  0  0
  6 17  1  0  0  0  0
 34 33  1  0  0  0  0
 33 32  1  0  0  0  0
 32 31  2  0  0  0  0
 31 30  1  0  0  0  0
  6  5  1  1  0  0  0
 17 56  1  6  0  0  0
  9 10  1  0  0  0  0
 21 22  1  1  0  0  0
  6 23  1  0  0  0  0
 38 76  1  6  0  0  0
 17 18  1  0  0  0  0
 23 64  1  6  0  0  0
 23 24  1  0  0  0  0
  7  8  1  0  0  0  0
 21 38  1  0  0  0  0
 15 16  1  6  0  0  0
 27 38  1  0  0  0  0
 19 20  1  0  0  0  0
 24 25  2  0  0  0  0
 27 26  1  0  0  0  0
  5  4  1  0  0  0  0
 26 24  1  0  0  0  0
 15  3  1  0  0  0  0
  4  3  1  0  0  0  0
 38 36  1  0  0  0  0
 11 12  1  0  0  0  0
 36 35  1  0  0  0  0
 12 13  1  0  0  0  0
 29 27  1  0  0  0  0
 12 14  2  0  0  0  0
 18 19  1  0  0  0  0
  3  2  1  0  0  0  0
 27 28  1  6  0  0  0
  2  1  1  0  0  0  0
  6  7  1  0  0  0  0
 36 37  2  0  0  0  0
 29 35  1  0  0  0  0
 29 70  1  1  0  0  0
 19 21  1  0  0  0  0
  3 42  1  1  0  0  0
 18 57  1  0  0  0  0
 18 58  1  0  0  0  0
 19 59  1  6  0  0  0
 26 65  1  0  0  0  0
 26 66  1  0  0  0  0
  7 45  1  1  0  0  0
  9 47  1  0  0  0  0
  9 48  1  0  0  0  0
 10 49  1  1  0  0  0
  5 43  1  0  0  0  0
  5 44  1  0  0  0  0
 28 67  1  0  0  0  0
 28 68  1  0  0  0  0
 28 69  1  0  0  0  0
 35 74  1  0  0  0  0
 35 75  1  0  0  0  0
 34 73  1  0  0  0  0
 32 72  1  0  0  0  0
 31 71  1  0  0  0  0
 22 61  1  0  0  0  0
 22 62  1  0  0  0  0
 22 63  1  0  0  0  0
  8 46  1  0  0  0  0
 16 53  1  0  0  0  0
 16 54  1  0  0  0  0
 16 55  1  0  0  0  0
 20 60  1  0  0  0  0
 13 50  1  0  0  0  0
 13 51  1  0  0  0  0
 13 52  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
M  END

     RDKit          3D

 76 81  0  0  0  0  0  0  0  0999 V2000
   -1.6118   -1.2301    4.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -0.5996    3.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891    0.6707    3.2964 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2275    0.5296    3.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664   -0.0789    2.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4220    0.6981    0.8338 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0375    2.1433    0.9671 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9212    2.8417   -0.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    3.0227    2.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1119    2.9300    2.1428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6856    3.7063    1.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7973    5.0470    1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    5.6866    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4540    5.6531    2.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    1.4678    2.0503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2153    1.5369    2.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    0.8258    0.7311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8019   -0.5098    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617   -1.0729   -1.0013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6271   -0.1525   -2.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851   -1.2800   -1.0032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6113   -2.4951   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446    0.0382   -0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4514   -0.1389   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -0.2321    0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939   -0.2229   -1.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3097   -1.3239   -2.8184 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -0.9045   -4.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8910   -2.7460   -2.5686 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2885   -2.9934   -3.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382   -3.3676   -4.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1066   -3.4783   -4.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380   -3.2038   -3.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4394   -2.9160   -2.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8472   -3.7044   -3.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5601   -2.9445   -2.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457   -3.4403   -3.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7844   -1.5124   -2.4957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5479   -1.4323    4.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -2.1835    4.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021   -0.6135    5.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    1.2445    4.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -1.1098    2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457   -0.1159    2.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133    2.0638    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702    3.6997   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154    4.0651    1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8513    2.7541    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    3.3666    3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004    6.7628    0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979    5.2713   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    5.5259   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    2.0145    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    0.5468    2.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5794    2.1152    2.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3579    1.5217   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763   -0.3351    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7053   -1.2647    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7656   -2.0208   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966   -0.1855   -2.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3898   -3.4504   -0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057   -2.5203    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -2.5189    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190    0.7764   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8285    0.7666   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0790   -0.3608   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -1.6513   -4.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9192    0.0338   -4.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.7333   -4.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154   -2.9219   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438   -3.5346   -5.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8769   -3.7311   -5.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6309   -2.6753   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -3.8961   -4.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8223   -4.6507   -2.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2293   -0.8608   -3.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0
 23 21  1  0
 30 29  1  0
 30 34  2  0
 17 15  1  0
 10 11  1  0
 15 10  1  0
  6 17  1  0
 34 33  1  0
 33 32  1  0
 32 31  2  0
 31 30  1  0
  6  5  1  1
 17 56  1  6
  9 10  1  0
 21 22  1  1
  6 23  1  0
 38 76  1  6
 17 18  1  0
 23 64  1  6
 23 24  1  0
  7  8  1  0
 21 38  1  0
 15 16  1  6
 27 38  1  0
 19 20  1  0
 24 25  2  0
 27 26  1  0
  5  4  1  0
 26 24  1  0
 15  3  1  0
  4  3  1  0
 38 36  1  0
 11 12  1  0
 36 35  1  0
 12 13  1  0
 29 27  1  0
 12 14  2  0
 18 19  1  0
  3  2  1  0
 27 28  1  6
  2  1  1  0
  6  7  1  0
 36 37  2  0
 29 35  1  0
 29 70  1  1
 19 21  1  0
  3 42  1  1
 18 57  1  0
 18 58  1  0
 19 59  1  6
 26 65  1  0
 26 66  1  0
  7 45  1  1
  9 47  1  0
  9 48  1  0
 10 49  1  1
  5 43  1  0
  5 44  1  0
 28 67  1  0
 28 68  1  0
 28 69  1  0
 35 74  1  0
 35 75  1  0
 34 73  1  0
 32 72  1  0
 31 71  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
  8 46  1  0
 16 53  1  0
 16 54  1  0
 16 55  1  0
 20 60  1  0
 13 50  1  0
 13 51  1  0
 13 52  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
M  END


  Mrv1652306212101503D          

 76 81  0  0  0  0            999 V2000
   -1.6118   -1.2301    4.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -0.5996    3.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891    0.6707    3.2964 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2275    0.5296    3.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664   -0.0789    2.1327 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4220    0.6981    0.8338 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0375    2.1433    0.9671 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9212    2.8417   -0.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    3.0227    2.0647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1119    2.9300    2.1428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6856    3.7063    1.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7973    5.0470    1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    5.6866    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4540    5.6531    2.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    1.4678    2.0503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2153    1.5369    2.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    0.8258    0.7311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8019   -0.5098    0.3231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2617   -1.0729   -1.0013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6271   -0.1525   -2.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851   -1.2800   -1.0032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6113   -2.4951   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446    0.0382   -0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4514   -0.1389   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -0.2321    0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939   -0.2229   -1.9884 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3097   -1.3239   -2.8184 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -0.9045   -4.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8910   -2.7460   -2.5686 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2885   -2.9934   -3.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382   -3.3676   -4.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1066   -3.4783   -4.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380   -3.2038   -3.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4394   -2.9160   -2.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8472   -3.7044   -3.1576 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5601   -2.9445   -2.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457   -3.4403   -3.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7844   -1.5124   -2.4957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5479   -1.4323    4.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -2.1835    4.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021   -0.6135    5.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    1.2445    4.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -1.1098    2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457   -0.1159    2.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133    2.0638    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702    3.6997   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154    4.0651    1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8513    2.7541    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    3.3666    3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004    6.7628    0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979    5.2713   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    5.5259   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    2.0145    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    0.5468    2.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5794    2.1152    2.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3579    1.5217   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763   -0.3351    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7053   -1.2647    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7656   -2.0208   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966   -0.1855   -2.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3898   -3.4504   -0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057   -2.5203    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -2.5189    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190    0.7764   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8285    0.7666   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0790   -0.3608   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -1.6513   -4.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9192    0.0338   -4.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.7333   -4.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154   -2.9219   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438   -3.5346   -5.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8769   -3.7311   -5.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6309   -2.6753   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -3.8961   -4.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8223   -4.6507   -2.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2293   -0.8608   -3.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0  0  0  0
 23 21  1  0  0  0  0
 30 29  1  0  0  0  0
 30 34  2  0  0  0  0
 17 15  1  0  0  0  0
 10 11  1  0  0  0  0
 15 10  1  0  0  0  0
  6 17  1  0  0  0  0
 34 33  1  0  0  0  0
 33 32  1  0  0  0  0
 32 31  2  0  0  0  0
 31 30  1  0  0  0  0
  6  5  1  1  0  0  0
 17 56  1  6  0  0  0
  9 10  1  0  0  0  0
 21 22  1  1  0  0  0
  6 23  1  0  0  0  0
 38 76  1  6  0  0  0
 17 18  1  0  0  0  0
 23 64  1  6  0  0  0
 23 24  1  0  0  0  0
  7  8  1  0  0  0  0
 21 38  1  0  0  0  0
 15 16  1  6  0  0  0
 27 38  1  0  0  0  0
 19 20  1  0  0  0  0
 24 25  2  0  0  0  0
 27 26  1  0  0  0  0
  5  4  1  0  0  0  0
 26 24  1  0  0  0  0
 15  3  1  0  0  0  0
  4  3  1  0  0  0  0
 38 36  1  0  0  0  0
 11 12  1  0  0  0  0
 36 35  1  0  0  0  0
 12 13  1  0  0  0  0
 29 27  1  0  0  0  0
 12 14  2  0  0  0  0
 18 19  1  0  0  0  0
  3  2  1  0  0  0  0
 27 28  1  6  0  0  0
  2  1  1  0  0  0  0
  6  7  1  0  0  0  0
 36 37  2  0  0  0  0
 29 35  1  0  0  0  0
 29 70  1  1  0  0  0
 19 21  1  0  0  0  0
  3 42  1  1  0  0  0
 18 57  1  0  0  0  0
 18 58  1  0  0  0  0
 19 59  1  6  0  0  0
 26 65  1  0  0  0  0
 26 66  1  0  0  0  0
  7 45  1  1  0  0  0
  9 47  1  0  0  0  0
  9 48  1  0  0  0  0
 10 49  1  1  0  0  0
  5 43  1  0  0  0  0
  5 44  1  0  0  0  0
 28 67  1  0  0  0  0
 28 68  1  0  0  0  0
 28 69  1  0  0  0  0
 35 74  1  0  0  0  0
 35 75  1  0  0  0  0
 34 73  1  0  0  0  0
 32 72  1  0  0  0  0
 31 71  1  0  0  0  0
 22 61  1  0  0  0  0
 22 62  1  0  0  0  0
 22 63  1  0  0  0  0
  8 46  1  0  0  0  0
 16 53  1  0  0  0  0
 16 54  1  0  0  0  0
 16 55  1  0  0  0  0
 20 60  1  0  0  0  0
 13 50  1  0  0  0  0
 13 51  1  0  0  0  0
 13 52  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042088

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@@]2([H])[C@@]3(C([H])([H])[H])[C@@]([H])(OC([H])([H])[H])OC([H])([H])[C@@]2([C@@]([H])(O[H])C([H])([H])[C@@]3([H])OC(=O)C([H])([H])[H])[C@@]2([H])C(=O)C([H])([H])[C@@]3(C([H])([H])[H])[C@]([H])(C4=C([H])OC([H])=C4[H])C([H])([H])C(=O)[C@@]3([H])[C@]12C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C29H38O9/c1-14(30)38-22-10-21(34)29-13-37-25(35-5)27(22,3)19(29)9-20(33)28(4)23-17(31)8-16(15-6-7-36-12-15)26(23,2)11-18(32)24(28)29/h6-7,12,16,19-25,33-34H,8-11,13H2,1-5H3/t16-,19-,20+,21-,22+,23+,24-,25-,26-,27+,28-,29+/m0/s1

> <INCHI_KEY>
DWLRLNPCQNWYLX-CONKGLMSSA-N

> <FORMULA>
C29H38O9

> <MOLECULAR_WEIGHT>
530.614

> <EXACT_MASS>
530.251582804

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.33722650075337

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,6R,9R,10S,11R,13R,14R,15S,18S,20R)-6-(furan-3-yl)-11,18-dihydroxy-15-methoxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.0^{1,13}.0^{2,10}.0^{5,9}]icosan-20-yl acetate

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
0.9779292883333323

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.906334364407183

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.205867465691927

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8614349100852685

> <JCHEM_POLAR_SURFACE_AREA>
132.50000000000003

> <JCHEM_REFRACTIVITY>
132.9114

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,6R,9R,10S,11R,13R,14R,15S,18S,20R)-6-(furan-3-yl)-11,18-dihydroxy-15-methoxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.0^{1,13}.0^{2,10}.0^{5,9}]icosan-20-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 76 81  0  0  0  0  0  0  0  0999 V2000
   -1.6118   -1.2301    4.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -0.5996    3.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891    0.6707    3.2964 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2275    0.5296    3.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664   -0.0789    2.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4220    0.6981    0.8338 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0375    2.1433    0.9671 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9212    2.8417   -0.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    3.0227    2.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1119    2.9300    2.1428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6856    3.7063    1.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7973    5.0470    1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    5.6866    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4540    5.6531    2.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    1.4678    2.0503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2153    1.5369    2.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    0.8258    0.7311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8019   -0.5098    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617   -1.0729   -1.0013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6271   -0.1525   -2.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851   -1.2800   -1.0032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6113   -2.4951   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446    0.0382   -0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4514   -0.1389   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -0.2321    0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939   -0.2229   -1.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3097   -1.3239   -2.8184 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -0.9045   -4.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8910   -2.7460   -2.5686 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2885   -2.9934   -3.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382   -3.3676   -4.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1066   -3.4783   -4.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8472   -3.7044   -3.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5457   -3.4403   -3.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5479   -1.4323    4.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0021   -0.6135    5.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    1.2445    4.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8457   -0.1159    2.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133    2.0638    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702    3.6997   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154    4.0651    1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8513    2.7541    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    3.3666    3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004    6.7628    0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979    5.2713   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    5.5259   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    2.0145    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    0.5468    2.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5794    2.1152    2.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3579    1.5217   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763   -0.3351    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7053   -1.2647    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7656   -2.0208   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966   -0.1855   -2.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3898   -3.4504   -0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057   -2.5203    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -2.5189    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190    0.7764   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8285    0.7666   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0790   -0.3608   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -1.6513   -4.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9192    0.0338   -4.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.7333   -4.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154   -2.9219   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438   -3.5346   -5.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8769   -3.7311   -5.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6309   -2.6753   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -3.8961   -4.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8223   -4.6507   -2.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2293   -0.8608   -3.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0
 23 21  1  0
 30 29  1  0
 30 34  2  0
 17 15  1  0
 10 11  1  0
 15 10  1  0
  6 17  1  0
 34 33  1  0
 33 32  1  0
 32 31  2  0
 31 30  1  0
  6  5  1  1
 17 56  1  6
  9 10  1  0
 21 22  1  1
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 38 76  1  6
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  7  8  1  0
 21 38  1  0
 15 16  1  6
 27 38  1  0
 19 20  1  0
 24 25  2  0
 27 26  1  0
  5  4  1  0
 26 24  1  0
 15  3  1  0
  4  3  1  0
 38 36  1  0
 11 12  1  0
 36 35  1  0
 12 13  1  0
 29 27  1  0
 12 14  2  0
 18 19  1  0
  3  2  1  0
 27 28  1  6
  2  1  1  0
  6  7  1  0
 36 37  2  0
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 29 70  1  1
 19 21  1  0
  3 42  1  1
 18 57  1  0
 18 58  1  0
 19 59  1  6
 26 65  1  0
 26 66  1  0
  7 45  1  1
  9 47  1  0
  9 48  1  0
 10 49  1  1
  5 43  1  0
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 28 67  1  0
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 31 71  1  0
 22 61  1  0
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 16 53  1  0
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 13 50  1  0
 13 51  1  0
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  1 39  1  0
  1 40  1  0
  1 41  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      -1.612  -1.230   4.638  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.833  -0.600   3.383  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.189   0.671   3.296  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.228   0.530   3.309  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.766  -0.079   2.133  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.422   0.698   0.834  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.038   2.143   0.967  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.921   2.842  -0.279  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.421   3.023   2.065  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.112   2.930   2.143  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.686   3.706   1.061  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.797   5.047   1.254  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.403   5.687   0.042  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.454   5.653   2.258  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.671   1.468   2.050  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.215   1.537   2.047  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.129   0.826   0.731  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.802  -0.510   0.323  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.262  -1.073  -1.001  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.627  -0.153  -2.032  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.285  -1.280  -1.003  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.611  -2.495  -0.093  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.945   0.038  -0.495  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.451  -0.139  -0.587  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.192  -0.232   0.388  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.994  -0.223  -1.988  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.310  -1.324  -2.818  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.454  -0.905  -4.309  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.891  -2.746  -2.569  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.289  -2.993  -3.055  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.738  -3.368  -4.356  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.107  -3.478  -4.286  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.538  -3.204  -3.031  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.439  -2.916  -2.291  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.847  -3.704  -3.158  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.560  -2.945  -2.960  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.546  -3.440  -3.140  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.784  -1.512  -2.496  0.00  0.00           C+0
HETATM   39  H   UNK     0      -0.548  -1.432   4.792  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.147  -2.184   4.639  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.002  -0.614   5.453  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.459   1.244   4.193  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.424  -1.110   2.123  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.846  -0.116   2.295  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.113   2.064   1.163  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.370   3.700  -0.177  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.715   4.065   1.892  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.851   2.754   3.035  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.443   3.367   3.095  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.500   6.763   0.211  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.398   5.271  -0.138  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.756   5.526  -0.824  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.595   2.014   1.137  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.677   0.547   2.111  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.579   2.115   2.904  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.358   1.522  -0.089  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.876  -0.335   0.192  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.705  -1.265   1.104  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.766  -2.021  -1.223  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.597  -0.186  -2.119  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.390  -3.450  -0.577  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.006  -2.520   0.813  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.658  -2.519   0.219  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.719   0.776  -1.280  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.829   0.767  -2.434  0.00  0.00           H+0
HETATM   66  H   UNK     0       4.079  -0.361  -1.947  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.046  -1.651  -4.998  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.919   0.034  -4.501  0.00  0.00           H+0
HETATM   69  H   UNK     0       3.502  -0.733  -4.577  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.915  -2.922  -1.486  0.00  0.00           H+0
HETATM   71  H   UNK     0       4.144  -3.535  -5.244  0.00  0.00           H+0
HETATM   72  H   UNK     0       6.877  -3.731  -5.001  0.00  0.00           H+0
HETATM   73  H   UNK     0       5.631  -2.675  -1.254  0.00  0.00           H+0
HETATM   74  H   UNK     0       1.978  -3.896  -4.226  0.00  0.00           H+0
HETATM   75  H   UNK     0       1.822  -4.651  -2.610  0.00  0.00           H+0
HETATM   76  H   UNK     0       0.229  -0.861  -3.180  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    3    1                                                       
CONECT    3   15    4    2   42                                             
CONECT    4    5    3                                                       
CONECT    5    6    4   43   44                                             
CONECT    6   17    5   23    7                                             
CONECT    7    9    8    6   45                                             
CONECT    8    7   46                                                       
CONECT    9    7   10   47   48                                             
CONECT   10   11   15    9   49                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   50   51   52                                             
CONECT   14   12                                                            
CONECT   15   17   10   16    3                                             
CONECT   16   15   53   54   55                                             
CONECT   17   15    6   56   18                                             
CONECT   18   17   19   57   58                                             
CONECT   19   20   18   21   59                                             
CONECT   20   19   60                                                       
CONECT   21   23   22   38   19                                             
CONECT   22   21   61   62   63                                             
CONECT   23   21    6   64   24                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   27   24   65   66                                             
CONECT   27   38   26   29   28                                             
CONECT   28   27   67   68   69                                             
CONECT   29   30   27   35   70                                             
CONECT   30   29   34   31                                                  
CONECT   31   32   30   71                                                  
CONECT   32   33   31   72                                                  
CONECT   33   34   32                                                       
CONECT   34   30   33   73                                                  
CONECT   35   36   29   74   75                                             
CONECT   36   38   35   37                                                  
CONECT   37   36                                                            
CONECT   38   76   21   27   36                                             
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    3                                                            
CONECT   43    5                                                            
CONECT   44    5                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48    9                                                            
CONECT   49   10                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   16                                                            
CONECT   54   16                                                            
CONECT   55   16                                                            
CONECT   56   17                                                            
CONECT   57   18                                                            
CONECT   58   18                                                            
CONECT   59   19                                                            
CONECT   60   20                                                            
CONECT   61   22                                                            
CONECT   62   22                                                            
CONECT   63   22                                                            
CONECT   64   23                                                            
CONECT   65   26                                                            
CONECT   66   26                                                            
CONECT   67   28                                                            
CONECT   68   28                                                            
CONECT   69   28                                                            
CONECT   70   29                                                            
CONECT   71   31                                                            
CONECT   72   32                                                            
CONECT   73   34                                                            
CONECT   74   35                                                            
CONECT   75   35                                                            
CONECT   76   38                                                            
MASTER        0    0    0    0    0    0    0    0   76    0  162    0
END

RDKit          3D

76 81  0  0  0  0  0  0  0  0999 V2000
   -1.6118   -1.2301    4.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -0.5996    3.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891    0.6707    3.2964 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2275    0.5296    3.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664   -0.0789    2.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4220    0.6981    0.8338 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0375    2.1433    0.9671 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9212    2.8417   -0.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    3.0227    2.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1119    2.9300    2.1428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6856    3.7063    1.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7973    5.0470    1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    5.6866    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4540    5.6531    2.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    1.4678    2.0503 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2153    1.5369    2.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    0.8258    0.7311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8019   -0.5098    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617   -1.0729   -1.0013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6271   -0.1525   -2.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851   -1.2800   -1.0032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6113   -2.4951   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446    0.0382   -0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4514   -0.1389   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -0.2321    0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939   -0.2229   -1.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3097   -1.3239   -2.8184 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4536   -0.9045   -4.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8910   -2.7460   -2.5686 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.3979    5.2713   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    5.5259   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    2.0145    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    0.5468    2.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5794    2.1152    2.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3579    1.5217   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763   -0.3351    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7053   -1.2647    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7656   -2.0208   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966   -0.1855   -2.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3898   -3.4504   -0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057   -2.5203    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -2.5189    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190    0.7764   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8285    0.7666   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0790   -0.3608   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -1.6513   -4.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9192    0.0338   -4.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.7333   -4.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154   -2.9219   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438   -3.5346   -5.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8769   -3.7311   -5.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6309   -2.6753   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -3.8961   -4.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8223   -4.6507   -2.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2293   -0.8608   -3.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0
 23 21  1  0
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 15 10  1  0
  6 17  1  0
 34 33  1  0
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M  END

View in JSmol

Synonyms

Value	Source
(1S,2S,5S,6R,9R,10S,11R,13R,14R,15S,18S,20R)-6-(Furan-3-yl)-11,18-dihydroxy-15-methoxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.0,.0,.0,]icosan-20-yl acetic acid	Generator

Chemical Formula

C₂₉H₃₈O₉

Average Mass

530.6140 Da

Monoisotopic Mass

530.25158 Da

IUPAC Name

(1S,2S,5S,6R,9R,10S,11R,13R,14R,15S,18S,20R)-6-(furan-3-yl)-11,18-dihydroxy-15-methoxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.0^{1,13}.0^{2,10}.0^{5,9}]icosan-20-yl acetate

Traditional Name

(1S,2S,5S,6R,9R,10S,11R,13R,14R,15S,18S,20R)-6-(furan-3-yl)-11,18-dihydroxy-15-methoxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.0^{1,13}.0^{2,10}.0^{5,9}]icosan-20-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])[C@@]2([H])[C@@]3(C([H])([H])[H])[C@@]([H])(OC([H])([H])[H])OC([H])([H])[C@@]2([C@@]([H])(O[H])C([H])([H])[C@@]3([H])OC(=O)C([H])([H])[H])[C@@]2([H])C(=O)C([H])([H])[C@@]3(C([H])([H])[H])[C@]([H])(C4=C([H])OC([H])=C4[H])C([H])([H])C(=O)[C@@]3([H])[C@]12C([H])([H])[H]

InChI Identifier

InChI=1S/C29H38O9/c1-14(30)38-22-10-21(34)29-13-37-25(35-5)27(22,3)19(29)9-20(33)28(4)23-17(31)8-16(15-6-7-36-12-15)26(23,2)11-18(32)24(28)29/h6-7,12,16,19-25,33-34H,8-11,13H2,1-5H3/t16-,19-,20+,21-,22+,23+,24-,25-,26-,27+,28-,29+/m0/s1

InChI Key

DWLRLNPCQNWYLX-CONKGLMSSA-N

Experimental Spectra

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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melia azedarach	JEOL database	Akihisa, T., et al, Phytochemistry 89, 59 (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
17-furanylsteroid skeleton
Steroid ester
Hydroxysteroid
1-hydroxysteroid
Steroid
Naphthopyran
Naphthalene
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Ketone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	2.05	ALOGPS
logP	0.98	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	14.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	132.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.91 m³·mol⁻¹	ChemAxon
Polarizability	55.34 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

71681431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Akihisa, T., et al. (2013). Akihisa, T., et al, Phytochemistry 89, 59 (2013) . Phytochem..

Showing NP-Card for 12-dehydroneoazedarachin D (NP0042088)

MOL for NP0042088 (12-dehydroneoazedarachin D)

3D MOL for NP0042088 (12-dehydroneoazedarachin D)

3D SDF for NP0042088 (12-dehydroneoazedarachin D)

3D-SDF for NP0042088 (12-dehydroneoazedarachin D)

PDB for NP0042088 (12-dehydroneoazedarachin D)

3D PDB for NP0042088 (12-dehydroneoazedarachin D)

SMILES for NP0042088 (12-dehydroneoazedarachin D)

INCHI for NP0042088 (12-dehydroneoazedarachin D)

Structure for NP0042088 (12-dehydroneoazedarachin D)

3D Structure for NP0042088 (12-dehydroneoazedarachin D)