NP-MRD: Showing NP-Card for 2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate (NP0167653)

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Record Information

Version

2.0

Created at

2022-09-03 03:17:20 UTC

Updated at

2022-09-03 03:17:20 UTC

NP-MRD ID

NP0167653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate

Description

2',10',13'-Tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]Pentadecan]-11'-en-9'-yl pyridine-3-carboxylate belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system. 2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate is found in Prumnopitys andina. 2',10',13'-Tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]Pentadecan]-11'-en-9'-yl pyridine-3-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121517352D          

 56 61  0  0  0  0            999 V2000
    7.4159    3.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2084    3.2002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8033    3.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4060    2.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8111    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0186    2.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8210    2.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4237    1.4855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6312    1.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4337    2.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6412    2.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0463    2.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9397    2.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105    2.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919    3.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216    3.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699    3.5436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029    4.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1326    5.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140    6.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657    6.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6360    5.8656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546    5.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951    2.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9898    2.9739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1724    2.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8603    2.0987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6671    3.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0305    1.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3670    1.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038    1.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376   -0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    0.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7837    0.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2856   -0.0170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9695   -0.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714   -1.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1515   -0.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439    1.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0363    1.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6079    0.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069    0.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5426    1.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    1.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7907   -0.3175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8973   -1.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590   -1.4524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2421   -1.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1984    2.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7933    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5858    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7834    1.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1884    1.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3960    1.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 35 40  1  0  0  0  0
 12 40  1  0  0  0  0
 40 41  1  0  0  0  0
  9 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 41 43  1  0  0  0  0
 34 44  1  0  0  0  0
 29 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 32 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
  4 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 51 56  1  0  0  0  0
M  END

     RDKit          3D

110115  0  0  0  0  0  0  0  0999 V2000
   -6.6788   -5.8806    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4218   -5.1732    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9352   -4.2208   -0.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454   -3.4647    0.0587 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6847   -3.7193   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014   -2.4269   -1.4265 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1725   -2.0064   -0.2321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2869   -3.0921    0.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225   -3.7519    1.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015   -4.8812    1.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9655   -3.3915    2.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692   -0.6808   -0.4067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8536    0.3356    0.5797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2458   -0.1516    1.9204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0050    1.5870    0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641    1.3341    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323    0.3229   -0.4960 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1917    0.0598   -0.4385 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    0.4204   -1.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137    0.9919   -2.4705 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4778    0.1198   -1.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2002    1.1792   -0.5512 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.4843    0.2613   -0.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8691    0.2511   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4314    1.1317   -1.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6446    2.0226   -1.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2966    2.0105   -1.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6068    4.7179    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8177    7.3408   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6351    6.3272   -1.0815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303    5.0491   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776    0.1748    0.4667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2821    1.2335   -0.1112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2858    1.8392    0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1406    2.9322   -0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5202    1.4828    1.7003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5057   -1.0164   -0.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8826   -6.6431    1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839   -3.8742    1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8245   -4.3045   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720   -4.3832   -1.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -2.6743   -2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287   -1.8973    0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6174   -4.7897    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1188   -5.8134    1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859   -4.8693    2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -0.3912   -1.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811   -0.6677    2.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684    0.7563    2.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368   -0.7631    1.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830    1.7850   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249    2.4606    0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0874    2.7332   -2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8533    5.4838    2.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
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 55105  1  0
 55106  1  0
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 34 91  1  0
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 25 80  1  0
 26 81  1  0
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 28 83  1  0
 29 84  1  0
M  END


  Mrv0541 04121517352D          

 56 61  0  0  0  0            999 V2000
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    8.8033    3.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8210    2.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6312    1.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4337    2.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6412    2.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2376   -0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7907   -0.3175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1984    2.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7933    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5858    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7834    1.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1884    1.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3960    1.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 34 35  1  0  0  0  0
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 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 35 40  1  0  0  0  0
 12 40  1  0  0  0  0
 40 41  1  0  0  0  0
  9 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 41 43  1  0  0  0  0
 34 44  1  0  0  0  0
 29 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 32 47  1  0  0  0  0
 47 48  1  0  0  0  0
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 48 50  1  0  0  0  0
  4 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 51 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)C(CC(=O)OC1CCC2(C)C(C(OC(C)=O)C3CC(OC(C)=O)C(C)=C(C(OC(C)=O)C2OC(=O)C2=CC=CN=C2)C3(C)C)C11CO1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C43H54N2O11/c1-24-32(52-25(2)46)20-30-36(53-26(3)47)38-42(7,39(56-40(50)29-16-13-19-44-22-29)37(54-27(4)48)35(24)41(30,5)6)18-17-33(43(38)23-51-43)55-34(49)21-31(45(8)9)28-14-11-10-12-15-28/h10-16,19,22,30-33,36-39H,17-18,20-21,23H2,1-9H3

> <INCHI_KEY>
WECXFEYIUJGNQW-UHFFFAOYSA-N

> <FORMULA>
C43H54N2O11

> <MOLECULAR_WEIGHT>
774.908

> <EXACT_MASS>
774.372760567

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
82.47284591157883

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate

> <ALOGPS_LOGP>
4.81

> <JCHEM_LOGP>
4.154531015666667

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.787937813543047

> <JCHEM_POLAR_SURFACE_AREA>
160.16

> <JCHEM_REFRACTIVITY>
201.87209999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      13.843   6.402   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      15.322   5.974   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      16.433   7.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.691   4.479   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.581   3.412   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.101   3.840   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.733   5.335   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      11.991   2.773   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.512   3.201   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.143   4.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.664   5.125   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.553   4.058   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.354   5.585   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.180   4.819   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.331   6.352   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.080   7.249   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.677   6.615   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.232   8.782   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.981   9.680   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.133  11.212   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.536  11.847   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.787  10.949   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       6.635   9.417   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.658   4.334   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.714   5.551   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.188   5.343   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.606   3.918   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.245   6.560   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.790   2.954   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.552   1.914   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.127   2.499   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.699   0.343   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.177  -0.210   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.504   0.714   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.063   1.190   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.000  -0.032   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.410  -1.454   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.347  -2.676   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.883  -1.655   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.922   2.562   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.401   2.134   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.468   1.024   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       8.973   0.655   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       4.746   1.910   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.232   2.315   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.525   3.238   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       1.476  -0.593   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       1.675  -2.120   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       3.097  -2.711   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       0.452  -3.056   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      17.170   4.050   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      18.281   5.117   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      19.760   4.689   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      20.129   3.194   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      19.018   2.127   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      17.539   2.555   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   51                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   41                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   40                                             
CONECT   13   12                                                            
CONECT   14   12   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   14   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30   44                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   47                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   44                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   35   12   41                                                  
CONECT   41   40    9   42   43                                             
CONECT   42   41   43                                                       
CONECT   43   42   41                                                       
CONECT   44   34   29   45   46                                             
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   32   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51    4   52   56                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   51                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  122    0
END

View in JSmol

Synonyms

Value	Source
2',10',13'-Tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0,]pentadecan]-11'-en-9'-yl pyridine-3-carboxylic acid	Generator
2',10',13'-Tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₄₃H₅₄N₂O₁₁

Average Mass

774.9080 Da

Monoisotopic Mass

774.37276 Da

IUPAC Name

2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate

Traditional Name

2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

CN(C)C(CC(=O)OC1CCC2(C)C(C(OC(C)=O)C3CC(OC(C)=O)C(C)=C(C(OC(C)=O)C2OC(=O)C2=CC=CN=C2)C3(C)C)C11CO1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C43H54N2O11/c1-24-32(52-25(2)46)20-30-36(53-26(3)47)38-42(7,39(56-40(50)29-16-13-19-44-22-29)37(54-27(4)48)35(24)41(30,5)6)18-17-33(43(38)23-51-43)55-34(49)21-31(45(8)9)28-14-11-10-12-15-28/h10-16,19,22,30-33,36-39H,17-18,20-21,23H2,1-9H3

InChI Key

WECXFEYIUJGNQW-UHFFFAOYSA-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
Prumnopitys andina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Taxanes and derivatives

Alternative Parents

Substituents

Taxane diterpenoid
Pentacarboxylic acid or derivatives
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Fatty acid ester
Aralkylamine
Monocyclic benzene moiety
Fatty acyl
Pyridine
Benzenoid
Heteroaromatic compound
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organopnictogen 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	4.81	ALOGPS
logP	4.15	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	8.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	160.16 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	201.87 m³·mol⁻¹	ChemAxon
Polarizability	82.47 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14446211

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate (NP0167653)

MOL for NP0167653 (2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate)

3D MOL for NP0167653 (2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate)

3D SDF for NP0167653 (2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate)

3D-SDF for NP0167653 (2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate)

PDB for NP0167653 (2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate)

3D PDB for NP0167653 (2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate)

SMILES for NP0167653 (2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate)

INCHI for NP0167653 (2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate)

Structure for NP0167653 (2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate)

3D Structure for NP0167653 (2',10',13'-tris(acetyloxy)-5'-{[3-(dimethylamino)-3-phenylpropanoyl]oxy}-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.0³,⁸]pentadecan]-11'-en-9'-yl pyridine-3-carboxylate)