NP-MRD: Showing NP-Card for (1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate (NP0323494)

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Record Information

Version

2.0

Created at

2022-09-12 02:57:20 UTC

Updated at

2022-09-12 02:57:20 UTC

NP-MRD ID

NP0323494

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate

Description

Daphnezomine V belongs to the class of organic compounds known as daphniphylline-type alkaloids. These are alkaloids (or derivatives thereof) from the genus Daphniphyllum, possessing 22 carbon polycyclic fused ring systems with or without the C8 side chain. The C8 unit consists of 6-oxabicyclo[3.2.1]Octane or 2,8-dioxabicyclo[3.2.1]Octane. (1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate is found in Daphniphyllum macropodum. Based on a literature review very few articles have been published on Daphnezomine V.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122204572D          

 36 42  0  0  1  0            999 V2000
    4.2430   -1.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4201   -1.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -2.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574   -1.2422    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3162   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8504    0.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027    0.0794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6086    0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2658   -0.7466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0796   -1.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3439   -1.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5891   -1.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2913   -1.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236   -0.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0251    0.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7412   -0.2668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.4839    0.6135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3181    0.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077    1.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428    2.0188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6037    1.5403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5688    0.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6665    3.0256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4778    3.1750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6952    3.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005    2.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0657    1.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995    1.3229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6702    2.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -1.2983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5644   -1.5996    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.5672   -2.4246    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1760   -0.8853    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 23 21  1  1  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  1  0  0  0
 27 32  1  0  0  0  0
 17 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  6  0  0  0
 12 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  9 36  1  0  0  0  0
M  CHG  2  34   1  35  -1
M  END

     RDKit          3D

 83 89  0  0  0  0  0  0  0  0999 V2000
   -2.6321    4.0412    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481    2.7881    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6167   -1.0688    1.0860 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7589   -2.1617    1.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0238   -1.6035    1.1486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1997   -2.9819    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4436   -2.7810   -0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9912   -1.4610   -1.4018 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1565   -1.6290   -2.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0028   -2.6230   -3.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0338   -2.4687   -1.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5018   -1.2563   -1.4313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2285   -0.5079   -0.2119 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.3621   -0.4863   -0.1989 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.3048    0.8758   -0.2029 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.3581   -0.4608    1.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5301   -0.3203    0.2194 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4481   -0.0390   -0.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3301    0.5371   -0.5099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4584   -0.3025   -0.7601 N   0  0  1  0  0  4  0  0  0  0  0  0
   -4.4142    0.2492   -1.5365 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.0677   -0.7662    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8922    4.0571    1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298    3.8969    0.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9197    4.9273    0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0268    3.8312    0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8430    2.2621    1.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3336    2.3765   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547    2.1484    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2198    1.4240    2.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205    2.0851    2.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917   -0.4663    3.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5078    0.1208    2.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163   -1.7976    2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -2.8159    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4527   -2.8660    2.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3111   -1.6666    2.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -3.7328    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1775   -3.3571    1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5148   -2.8881   -1.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9422   -3.6009   -1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9836   -0.6713   -3.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286   -2.0768   -3.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3302   -3.6345   -3.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -2.2518   -4.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9334   -3.3805   -1.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -2.3489   -2.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3110   -0.4769   -2.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1176    0.6020   -1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1050    1.0987    0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449   -1.2546   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -1.9998    0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745    0.3782    2.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    1.9675    2.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1645    1.7570    1.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333    1.9389   -1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    2.9210   -0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6691    2.3072   -0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3508    0.6165   -0.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2510    1.0113   -2.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3860   -0.7097    0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4636   -1.5118    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934   -1.2887   -0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 12 11  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 23 21  1  6
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 17 33  1  0
 33 34  1  0
 34 35  1  6
 34 36  1  0
 33  4  1  0
 17  7  1  0
 31 23  1  0
 36  9  1  0
 16 12  1  0
 32 27  1  0
 34 12  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  6
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  8 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  1
 10 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  6
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 24 70  1  0
 25 71  1  0
 25 72  1  0
 28 73  1  0
 28 74  1  0
 28 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 31 80  1  6
 33 81  1  6
 36 82  1  0
 36 83  1  0
M  CHG  2  34   1  35  -1
M  END


  Mrv1652309122204572D          

 36 42  0  0  1  0            999 V2000
    4.2430   -1.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4201   -1.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2077    1.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428    2.0188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6037    1.5403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5688    0.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774    2.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6665    3.0256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4778    3.1750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6952    3.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005    2.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0657    1.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995    1.3229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6702    2.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -1.2983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5644   -1.5996    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.5672   -2.4246    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1760   -0.8853    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 23 21  1  1  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  1  0  0  0
 27 32  1  0  0  0  0
 17 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  6  0  0  0
 12 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  9 36  1  0  0  0  0
M  CHG  2  34   1  35  -1
M  END
> <DATABASE_ID>
NP0323494

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC[C@@]2(C)[C@@H]3CCC45CCC[C@@H]4[C@@]2(C[C@H](O)C(=O)[C@]2(C)CO[C@@]4(C)CC[C@@H]2O4)[C@H]1[N+]5([O-])C3

> <INCHI_IDENTIFIER>
InChI=1S/C30H47NO5/c1-18(2)20-9-12-27(4)19-8-14-29-11-6-7-22(29)30(27,24(20)31(29,34)16-19)15-21(32)25(33)26(3)17-35-28(5)13-10-23(26)36-28/h18-24,32H,6-17H2,1-5H3/t19-,20-,21+,22+,23+,24+,26-,27+,28-,29?,30+,31?/m1/s1

> <INCHI_KEY>
MYQBCJMRZZUWRE-OEEBOYFXSA-N

> <FORMULA>
C30H47NO5

> <MOLECULAR_WEIGHT>
501.708

> <EXACT_MASS>
501.345423617

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
56.30707852285451

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,10S,13S,14R)-2-[(2S)-3-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-1-methyl-14-(propan-2-yl)-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,12}]hexadecan-12-ium-12-olate

> <JCHEM_LOGP>
3.6357024053333316

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.3519744141458

> <JCHEM_PKA_STRONGEST_BASIC>
3.338697368731216

> <JCHEM_POLAR_SURFACE_AREA>
78.82000000000001

> <JCHEM_REFRACTIVITY>
137.71829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,10S,13S,14R)-2-[(2S)-3-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,12}]hexadecan-12-ium-12-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       7.920  -3.483   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.384  -3.594   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.712  -4.979   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.520  -2.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.190  -0.920   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.321   0.393   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.738   0.148   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.003   1.501   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.363  -1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.015  -3.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.642  -3.405   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.100  -2.011   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.544  -2.018   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.164  -0.600   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.047   0.373   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.384  -0.498   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.934  -0.585   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.418   0.866   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.903   1.145   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.594   0.784   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.388   2.596   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.387   3.768   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.127   2.875   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.062   1.337   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.518   4.290   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.244   5.648   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.759   5.927   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.164   7.412   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.921   4.917   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.856   3.378   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.612   2.469   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.118   4.180   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.955  -2.423   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       2.920  -2.986   0.000  0.00  0.00           N+1
HETATM   35  O   UNK     0       2.925  -4.526   0.000  0.00  0.00           O-1
HETATM   36  C   UNK     0       4.062  -1.653   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   17                                             
CONECT    8    7                                                            
CONECT    9    7   10   36                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16   34                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16    7   18   33                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   31                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   32                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   23   32                                                  
CONECT   32   31   27                                                       
CONECT   33   17    4   34                                                  
CONECT   34   33   12   35   36                                             
CONECT   35   34                                                            
CONECT   36   34    9                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₇NO₅

Average Mass

501.7080 Da

Monoisotopic Mass

501.34542 Da

IUPAC Name

(1S,2R,3R,10S,13S,14R)-2-[(2S)-3-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-1-methyl-14-(propan-2-yl)-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,12}]hexadecan-12-ium-12-olate

Traditional Name

(1S,2R,3R,10S,13S,14R)-2-[(2S)-3-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,12}]hexadecan-12-ium-12-olate

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC[C@@]2(C)[C@@H]3CCC45CCC[C@@H]4[C@@]2(C[C@H](O)C(=O)[C@]2(C)CO[C@@]4(C)CC[C@@H]2O4)[C@H]1[N+]5([O-])C3

InChI Identifier

InChI=1S/C30H47NO5/c1-18(2)20-9-12-27(4)19-8-14-29-11-6-7-22(29)30(27,24(20)31(29,34)16-19)15-21(32)25(33)26(3)17-35-28(5)13-10-23(26)36-28/h18-24,32H,6-17H2,1-5H3/t19-,20-,21+,22+,23+,24+,26-,27+,28-,29?,30+,31?/m1/s1

InChI Key

MYQBCJMRZZUWRE-OEEBOYFXSA-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
Daphniphyllum macropodum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as daphniphylline-type alkaloids. These are alkaloids (or derivatives thereof) from the genus Daphniphyllum, possessing 22 carbon polycyclic fused ring systems with or without the C8 side chain. The C8 unit consists of 6-oxabicyclo[3.2.1]Octane or 2,8-dioxabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Daphniphylline-type alkaloids

Sub Class

Not Available

Direct Parent

Daphniphylline-type alkaloids

Alternative Parents

Substituents

Daphniphylline-type alkaloid
Sesquiterpenoid
Azaspirodecane
Indole or derivatives
Indolizidine
Azepane
Ketal
Oxepane
Meta-dioxane
Acyloin
Piperidine
N-alkylpyrrolidine
Alpha-hydroxy ketone
Trialkyl amine oxide
Oxolane
Pyrrolidine
Ketone
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
N-oxide
Trisubstituted n-oxide
Acetal
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organic salt
Organic zwitterion
Alcohol
Organonitrogen compound
Organooxygen compound
Aldehyde
Hydrocarbon derivative
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	3.64	ChemAxon
pKa (Strongest Acidic)	13.35	ChemAxon
pKa (Strongest Basic)	3.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.72 m³·mol⁻¹	ChemAxon
Polarizability	56.31 Å³	ChemAxon
Number of Rings	7	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

102424835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate (NP0323494)

MOL for NP0323494 ((1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate)

3D MOL for NP0323494 ((1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate)

3D SDF for NP0323494 ((1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate)

3D-SDF for NP0323494 ((1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate)

PDB for NP0323494 ((1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate)

3D PDB for NP0323494 ((1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate)

SMILES for NP0323494 ((1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate)

INCHI for NP0323494 ((1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate)

Structure for NP0323494 ((1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate)

3D Structure for NP0323494 ((1s,2r,3r,10s,13s,14r)-2-[(2s)-3-[(1r,4r,5s)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-oxopropyl]-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0²,¹³.0³,⁷.0⁷,¹²]hexadecan-12-ium-12-olate)