NP-MRD: Showing NP-Card for 4,22-dimethyl (1r,4s,6s,7r,8s,10r,12s,14r,16r,18s,19r,22s,23r,25s,26r)-7,12,14,25-tetrahydroxy-6,16-dimethyl-23-{[(2e)-2-methylbut-2-enoyl]oxy}-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacosane-4,22-dicarboxylate (NP0164075)

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Record Information

Version

2.0

Created at

2022-09-02 22:53:21 UTC

Updated at

2022-09-02 22:53:22 UTC

NP-MRD ID

NP0164075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,22-dimethyl (1r,4s,6s,7r,8s,10r,12s,14r,16r,18s,19r,22s,23r,25s,26r)-7,12,14,25-tetrahydroxy-6,16-dimethyl-23-{[(2e)-2-methylbut-2-enoyl]oxy}-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacosane-4,22-dicarboxylate

Description

Azadirachtin N belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 4,22-dimethyl (1r,4s,6s,7r,8s,10r,12s,14r,16r,18s,19r,22s,23r,25s,26r)-7,12,14,25-tetrahydroxy-6,16-dimethyl-23-{[(2e)-2-methylbut-2-enoyl]oxy}-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacosane-4,22-dicarboxylate is found in Azadirachta indica. Based on a literature review very few articles have been published on Azadirachtin N.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032200532D          

 48 55  0  0  1  0            999 V2000
   -2.8697   -0.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0863   -0.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4707   -1.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385   -1.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6872   -0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -0.0104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0716   -1.3674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7118   -1.1088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8796   -0.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301   -0.0558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8309    0.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787   -0.5917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7907    0.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2726    0.7431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0584    0.4918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7235    0.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4788    0.6477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335    1.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    2.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0621   -0.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6778   -0.8824    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9291   -0.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5100   -1.6901    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2263   -2.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369   -1.5445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0362   -2.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6363   -1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666   -0.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8745   -0.0584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6832    0.1048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3150   -0.4258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1058   -0.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5737   -0.8703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3984   -0.8911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0720   -1.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2941   -1.2505    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4208   -2.0657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4979   -0.7924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2629   -0.0016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7265   -1.9487    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3944   -2.7039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5736   -2.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3275   -1.6580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6225   -2.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011   -1.6904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412   -2.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638   -3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109   -1.3995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 27 36  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  6  0  0  0
 29 38  1  0  0  0  0
 21 38  1  0  0  0  0
 25 38  1  0  0  0  0
 38 39  1  6  0  0  0
 23 40  1  0  0  0  0
 40 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
  8 43  1  0  0  0  0
 43 44  1  1  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 48 43  1  1  0  0  0
 40 48  1  0  0  0  0
 12 48  1  0  0  0  0
M  END

     RDKit          3D

 92 99  0  0  0  0  0  0  0  0999 V2000
    5.8129   -0.4441   -4.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2798   -0.2590   -3.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0087    0.2528   -2.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3921    0.6614   -2.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4501    0.4086   -0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673    0.9003    0.0756 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    0.0507   -0.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120    0.1989    0.8026 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3313   -1.1083    1.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8817   -1.5182    1.6741 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9699   -2.9323    1.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1257   -1.0872    0.5086 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6283   -2.0697   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430   -3.2142   -0.0417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006   -2.8766    0.5256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1106   -3.8050   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7437   -4.5857   -1.1266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734   -3.9185    0.1182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3452   -4.7942   -0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2930   -1.4454    0.2395 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4025   -0.5896    0.6149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0612   -1.1863    1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0872    0.8606    0.8105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7958    1.6524   -0.0638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4324    0.9545   -0.9873 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6335    1.0387   -2.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394    1.3201   -1.3419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4608   -0.1007   -1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8554   -0.6339   -0.1125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4008    0.0096    0.9572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6247    1.3005    0.9402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7858    1.8519    1.4425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4840    3.2343    1.3009 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6223    3.9955    1.1715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6403    3.3506    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7063    1.9799   -0.4374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0494    1.7352   -0.8470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -0.4587   -0.4493 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1853   -1.2992   -1.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3204    1.1982    0.9915 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7793    2.4081    0.5367 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    2.2646    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4787    1.0438    0.9490 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4107    1.5596    2.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9789    2.6964    2.6689 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267    0.8441    3.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8020    1.2476    4.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243    0.3002    0.3264 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3954    0.3664   -5.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646   -1.4082   -4.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9109   -0.3577   -4.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2638   -0.5498   -2.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0525   -0.1979   -2.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4494    1.4489   -3.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8276    1.1121   -1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9361   -1.9437    1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396   -1.1142    2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -1.1971    2.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1613   -4.9060   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4051   -0.3029    2.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974    1.1133    1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0793    1.8368   -2.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9536    1.6995   -2.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1885   -0.6064   -2.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5633   -0.0651   -1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8628    3.4949    2.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3411    4.8590    0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1266    4.0509   -0.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093    3.6911    0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2193    2.2842   -1.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3071    0.5329    5.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260    2.2452    4.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8589    1.3402    5.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2570    0.5137   -0.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
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 23 71  1  1
 26 72  1  0
 26 73  1  0
 26 74  1  0
 27 75  1  6
 28 76  1  0
 28 77  1  0
 29 78  1  1
 31 79  1  1
 33 80  1  1
 34 81  1  0
 35 82  1  0
 35 83  1  0
 37 84  1  0
 39 85  1  0
 40 86  1  1
 42 87  1  0
 42 88  1  0
 48 92  1  6
  8 56  1  1
  9 57  1  0
  9 58  1  0
 10 59  1  1
 11 60  1  0
  4 53  1  0
  4 54  1  0
  4 55  1  0
  2 52  1  0
  1 49  1  0
  1 50  1  0
  1 51  1  0
 47 89  1  0
 47 90  1  0
 47 91  1  0
M  END


  Mrv1652309032200532D          

 48 55  0  0  1  0            999 V2000
   -2.8697   -0.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0863   -0.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4707   -1.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385   -1.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6872   -0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -0.0104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0716   -1.3674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7118   -1.1088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8796   -0.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301   -0.0558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8309    0.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787   -0.5917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7907    0.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2726    0.7431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0584    0.4918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7235    0.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4788    0.6477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335    1.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    2.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0621   -0.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6778   -0.8824    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9291   -0.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5100   -1.6901    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2263   -2.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369   -1.5445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0362   -2.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6363   -1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666   -0.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8745   -0.0584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6832    0.1048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3150   -0.4258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1058   -0.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5737   -0.8703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3984   -0.8911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0720   -1.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2941   -1.2505    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4208   -2.0657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4979   -0.7924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2629   -0.0016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7265   -1.9487    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3944   -2.7039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5736   -2.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3275   -1.6580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6225   -2.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011   -1.6904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412   -2.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638   -3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109   -1.3995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 27 36  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  6  0  0  0
 29 38  1  0  0  0  0
 21 38  1  0  0  0  0
 25 38  1  0  0  0  0
 38 39  1  6  0  0  0
 23 40  1  0  0  0  0
 40 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
  8 43  1  0  0  0  0
 43 44  1  1  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 48 43  1  1  0  0  0
 40 48  1  0  0  0  0
 12 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1OC[C@]23C1[C@@]1(C)[C@H](O[C@]4(C)C5C[C@H](O[C@@H]6O[C@H](O)C[C@@]56O)[C@]14O)[C@@H]1OC[C@@]([C@@H]21)([C@@H](C[C@@H]3O)OC(=O)C(\C)=C\C)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C33H44O15/c1-7-13(2)24(36)45-16-9-15(34)30-11-44-20(25(37)41-5)21(30)28(3)23(19-22(30)31(16,12-43-19)26(38)42-6)48-29(4)14-8-17(33(28,29)40)46-27-32(14,39)10-18(35)47-27/h7,14-23,27,34-35,39-40H,8-12H2,1-6H3/b13-7+/t14?,15-,16+,17-,18-,19+,20-,21?,22+,23+,27+,28-,29+,30-,31-,32+,33-/m0/s1

> <INCHI_KEY>
IXRAKNFCTKZAEY-AZVDHALPSA-N

> <FORMULA>
C33H44O15

> <MOLECULAR_WEIGHT>
680.7

> <EXACT_MASS>
680.268020717

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
68.20651154931318

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,22-dimethyl (1R,4S,6S,7R,8S,10R,12S,14R,16R,18S,19R,22S,23R,25S,26R)-7,12,14,25-tetrahydroxy-6,16-dimethyl-23-{[(2E)-2-methylbut-2-enoyl]oxy}-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1^{8,15}.0^{1,5}.0^{6,18}.0^{7,16}.0^{10,14}.0^{22,26}]heptacosane-4,22-dicarboxylate

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
-0.8160018096666669

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.469647499921813

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.944929053260998

> <JCHEM_PKA_STRONGEST_BASIC>
-3.010790093017082

> <JCHEM_POLAR_SURFACE_AREA>
205.96999999999997

> <JCHEM_REFRACTIVITY>
156.12340000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,22-dimethyl (1R,4S,6S,7R,8S,10R,12S,14R,16R,18S,19R,22S,23R,25S,26R)-7,12,14,25-tetrahydroxy-6,16-dimethyl-23-{[(2E)-2-methylbut-2-enoyl]oxy}-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1^{8,15}.0^{1,5}.0^{6,18}.0^{7,16}.0^{10,14}.0^{22,26}]heptacosane-4,22-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.357  -1.467   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.894  -0.985   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.745  -2.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.059  -3.518   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.283  -1.527   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.970  -0.019   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.134  -2.552   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.329  -2.070   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.642  -0.562   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.670  -0.104   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.418   1.428   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.254  -1.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.343   0.137   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.242   1.387   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.709   0.918   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.951   1.829   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.360   1.209   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.783   3.360   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.024   4.271   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.716  -0.622   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.865  -1.647   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.334  -0.180   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.552  -3.155   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.889  -3.919   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.029  -2.883   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.401  -4.377   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.521  -3.264   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.204  -1.509   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.099  -0.109   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.609   0.196   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.788  -0.795   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.264  -0.356   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.138  -1.624   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      15.677  -1.663   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.201  -2.847   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.749  -2.334   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.986  -3.856   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.396  -1.479   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.957  -0.003   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.090  -3.638   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.470  -5.047   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.937  -4.893   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.478  -3.095   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.162  -3.895   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -0.189  -3.155   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       1.197  -5.435   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -0.119  -6.235   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       3.940  -2.612   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   43                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20   48                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15   12   21                                                  
CONECT   21   20   22   23   38                                             
CONECT   22   21                                                            
CONECT   23   21   24   40                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   38                                             
CONECT   26   25                                                            
CONECT   27   25   28   36                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   38                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   27   31   37                                             
CONECT   37   36                                                            
CONECT   38   29   21   25   39                                             
CONECT   39   38                                                            
CONECT   40   23   41   48                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42    8   44   48                                             
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46                                                            
CONECT   48   43   40   12                                                  
MASTER        0    0    0    0    0    0    0    0   48    0  110    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₄O₁₅

Average Mass

680.7000 Da

Monoisotopic Mass

680.26802 Da

IUPAC Name

4,22-dimethyl (1R,4S,6S,7R,8S,10R,12S,14R,16R,18S,19R,22S,23R,25S,26R)-7,12,14,25-tetrahydroxy-6,16-dimethyl-23-{[(2E)-2-methylbut-2-enoyl]oxy}-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1^{8,15}.0^{1,5}.0^{6,18}.0^{7,16}.0^{10,14}.0^{22,26}]heptacosane-4,22-dicarboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1OC[C@]23C1[C@@]1(C)[C@H](O[C@]4(C)C5C[C@H](O[C@@H]6O[C@H](O)C[C@@]56O)[C@]14O)[C@@H]1OC[C@@]([C@@H]21)([C@@H](C[C@@H]3O)OC(=O)C(\C)=C\C)C(=O)OC

InChI Identifier

InChI=1S/C33H44O15/c1-7-13(2)24(36)45-16-9-15(34)30-11-44-20(25(37)41-5)21(30)28(3)23(19-22(30)31(16,12-43-19)26(38)42-6)48-29(4)14-8-17(33(28,29)40)46-27-32(14,39)10-18(35)47-27/h7,14-23,27,34-35,39-40H,8-12H2,1-6H3/b13-7+/t14?,15-,16+,17-,18-,19+,20-,21?,22+,23+,27+,28-,29+,30-,31-,32+,33-/m0/s1

InChI Key

IXRAKNFCTKZAEY-AZVDHALPSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Azadirachta indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Tricarboxylic acid or derivatives
Furopyran
Oxepane
Fatty acid ester
Fatty acyl
Pyran
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Polyol
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.47	ALOGPS
logP	-0.82	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	205.97 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	156.12 m³·mol⁻¹	ChemAxon
Polarizability	68.21 Å³	ChemAxon
Number of Rings	8	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

C00049545

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

100976320

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

MOL for NP0164075 (4,22-dimethyl (1r,4s,6s,7r,8s,10r,12s,14r,16r,18s,19r,22s,23r,25s,26r)-7,12,14,25-tetrahydroxy-6,16-dimethyl-23-{[(2e)-2-methylbut-2-enoyl]oxy}-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacosane-4,22-dicarboxylate)

PDB for NP0164075 (4,22-dimethyl (1r,4s,6s,7r,8s,10r,12s,14r,16r,18s,19r,22s,23r,25s,26r)-7,12,14,25-tetrahydroxy-6,16-dimethyl-23-{[(2e)-2-methylbut-2-enoyl]oxy}-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacosane-4,22-dicarboxylate)