NP-MRD: Showing NP-Card for [(1r,2r,5s,13s,16e,17r,18r,19s,25s,26r,28r)-16-ethylidene-5,11,30,39-tetramethyl-4,6-dioxa-11,14,30,39-tetraazaundecacyclo[26.10.1.1¹³,¹⁷.0²,²⁶.0⁵,²⁵.0⁷,²³.0¹⁰,²².0¹²,²¹.0¹⁴,¹⁹.0²⁹,³⁷.0³¹,³⁶]tetraconta-7,9,12(21),22,29(37),31,33,35-octaen-18-yl]methanol (NP0283330)

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Record Information

Version

2.0

Created at

2022-09-09 10:32:50 UTC

Updated at

2022-09-09 10:32:50 UTC

NP-MRD ID

NP0283330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2r,5s,13s,16e,17r,18r,19s,25s,26r,28r)-16-ethylidene-5,11,30,39-tetramethyl-4,6-dioxa-11,14,30,39-tetraazaundecacyclo[26.10.1.1¹³,¹⁷.0²,²⁶.0⁵,²⁵.0⁷,²³.0¹⁰,²².0¹²,²¹.0¹⁴,¹⁹.0²⁹,³⁷.0³¹,³⁶]tetraconta-7,9,12(21),22,29(37),31,33,35-octaen-18-yl]methanol

Description

[(1R,2R,5S,13S,16E,17R,18R,19S,25S,26R,28R)-16-ethylidene-5,11,30,39-tetramethyl-4,6-dioxa-11,14,30,39-tetraazaundecacyclo[26.10.1.1¹³,¹⁷.0²,²⁶.0⁵,²⁵.0⁷,²³.0¹⁰,²².0¹²,²¹.0¹⁴,¹⁹.0²⁹,³⁷.0³¹,³⁶]Tetraconta-7(23),8,10(22),12(21),29(37),31,33,35-octaen-18-yl]methanol belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. Based on a literature review very few articles have been published on [(1R,2R,5S,13S,16E,17R,18R,19S,25S,26R,28R)-16-ethylidene-5,11,30,39-tetramethyl-4,6-dioxa-11,14,30,39-tetraazaundecacyclo[26.10.1.1¹³,¹⁷.0²,²⁶.0⁵,²⁵.0⁷,²³.0¹⁰,²².0¹²,²¹.0¹⁴,¹⁹.0²⁹,³⁷.0³¹,³⁶]Tetraconta-7(23),8,10(22),12(21),29(37),31,33,35-octaen-18-yl]methanol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092212322D          

 48 58  0  0  1  0            999 V2000
    0.8423   -1.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2269   -1.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0624    0.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750    0.7974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6697    1.5862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9812    0.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -0.1124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9022    0.1135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6603   -0.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577   -1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4973    0.8808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9466    1.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7642    2.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404    2.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433    3.1676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1540    3.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2835    3.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251    4.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595    4.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7522    4.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106    3.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9762    3.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4033    3.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1377    3.5438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8305    3.0957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5770    2.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529    1.5763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7380    1.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0568    1.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3312    0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1343   -0.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2863   -0.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7258    2.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3499    3.2182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.1794    4.3677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.4866    4.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2521    3.3737    0.0000 C   0  0  0  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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  8  7  1  6  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12  5  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 15  1  6  0  0  0
 15 16  1  0  0  0  0
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 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
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 14 23  1  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  0  0  0  0
 30 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 26 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 25 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 21 46  1  0  0  0  0
 40 47  1  6  0  0  0
 28 47  1  6  0  0  0
 47 48  1  0  0  0  0
M  END

     RDKit          3D

 96106  0  0  0  0  0  0  0  0999 V2000
    8.7163   -2.8542   -0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7497   -2.9187    0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7908   -2.0270    0.8132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8031   -2.0717    1.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1600    3.9499    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9531    4.0237   -0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460    2.8674   -0.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9590    1.6621   -0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1860    1.5656   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3963    0.4007   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0942    0.5248   -1.4692 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.8346   -1.1744    0.5460 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 46  1  0
 46 44  1  0
 44 45  1  6
 44 43  1  0
 43 42  1  0
 42 41  1  0
 41 26  1  0
 26 27  1  0
 27 28  1  0
 28 47  1  0
 47 48  1  0
 47 40  1  0
 40 39  1  0
 39 30  1  0
 30 29  2  0
 29 37  1  0
 37 38  1  0
 37 36  1  0
 36 35  2  0
 35 34  1  0
 34 33  2  0
 33 32  1  0
 32 31  2  0
 26 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
  8  3  1  0
 23 18  1  0
  6  5  1  0
 22 21  1  0
  9 12  1  0
 25 44  1  0
 23 14  1  0
 40 41  1  0
 31 30  1  0
 29 28  1  0
 31 36  1  0
  1 49  1  0
  1 50  1  0
  1 51  1  0
  2 52  1  0
  4 53  1  0
  4 54  1  0
 12 63  1  1
 13 64  1  0
 13 65  1  0
  6 55  1  1
  7 56  1  0
  7 57  1  0
  8 58  1  6
  9 59  1  6
 10 60  1  0
 10 61  1  0
 11 62  1  0
 17 66  1  0
 17 67  1  0
 17 68  1  0
 19 69  1  0
 20 70  1  0
 45 91  1  0
 45 92  1  0
 45 93  1  0
 42 89  1  0
 42 90  1  0
 41 88  1  1
 26 74  1  1
 27 75  1  0
 27 76  1  0
 28 77  1  1
 48 94  1  0
 48 95  1  0
 48 96  1  0
 40 87  1  1
 39 85  1  0
 39 86  1  0
 38 82  1  0
 38 83  1  0
 38 84  1  0
 35 81  1  0
 34 80  1  0
 33 79  1  0
 32 78  1  0
 25 73  1  6
 24 71  1  0
 24 72  1  0
M  END


  Mrv1652309092212322D          

 48 58  0  0  1  0            999 V2000
    0.8423   -1.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2269   -1.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0624    0.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750    0.7974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6697    1.5862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9812    0.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -0.1124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9022    0.1135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6603   -0.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577   -1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4973    0.8808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9466    1.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7642    2.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404    2.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433    3.1676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1540    3.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2835    3.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251    4.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595    4.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7522    4.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106    3.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9762    3.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4033    3.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1377    3.5438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8305    3.0957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5770    2.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529    1.5763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7380    1.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4724    1.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0568    1.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8806    1.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3312    0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9581   -0.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1343   -0.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6836    0.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8686    0.5082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863   -0.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7258    2.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3499    3.2182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5648    3.4717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6065    4.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9137    4.7436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1794    4.3677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2210    5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4866    4.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462    2.5719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2521    3.3737    0.0000 C   0  0  0  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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12  5  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  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
 14 23  1  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  0  0  0  0
 30 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 26 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 25 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 21 46  1  0  0  0  0
 40 47  1  6  0  0  0
 28 47  1  6  0  0  0
 47 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\CN2[C@H]3CC4=C([C@@H]2C[C@@H]1[C@H]3CO)N(C)C1=CC=C2O[C@]3(C)OC[C@@H]5[C@@H](C[C@H]6N(C)[C@@H]5CC5=C6N(C)C6=CC=CC=C56)[C@@H]3CC2=C41

> <INCHI_IDENTIFIER>
InChI=1S/C41H48N4O3/c1-6-21-18-45-34-17-27-38-26-13-30-24-15-35-39-25(22-9-7-8-10-31(22)43(39)4)16-33(42(35)3)29(24)20-47-41(30,2)48-37(26)12-11-32(38)44(5)40(27)36(45)14-23(21)28(34)19-46/h6-12,23-24,28-30,33-36,46H,13-20H2,1-5H3/b21-6-/t23-,24+,28+,29+,30-,33+,34-,35+,36-,41-/m0/s1

> <INCHI_KEY>
ZUIDZDKAJCEORF-AYLOMWFQSA-N

> <FORMULA>
C41H48N4O3

> <MOLECULAR_WEIGHT>
644.86

> <EXACT_MASS>
644.372641422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
74.08026284738563

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2R,5S,13S,16E,17R,18R,19S,25S,26R,28R)-16-ethylidene-5,11,30,39-tetramethyl-4,6-dioxa-11,14,30,39-tetraazaundecacyclo[26.10.1.1^{13,17}.0^{2,26}.0^{5,25}.0^{7,23}.0^{10,22}.0^{12,21}.0^{14,19}.0^{29,37}.0^{31,36}]tetraconta-7,9,12(21),22,29(37),31,33,35-octaen-18-yl]methanol

> <JCHEM_LOGP>
5.125951132333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.40235437273207

> <JCHEM_PKA_STRONGEST_BASIC>
7.454242610504719

> <JCHEM_POLAR_SURFACE_AREA>
55.03000000000001

> <JCHEM_REFRACTIVITY>
190.7589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R,5S,13S,16E,17R,18R,19S,25S,26R,28R)-16-ethylidene-5,11,30,39-tetramethyl-4,6-dioxa-11,14,30,39-tetraazaundecacyclo[26.10.1.1^{13,17}.0^{2,26}.0^{5,25}.0^{7,23}.0^{10,22}.0^{12,21}.0^{14,19}.0^{29,37}.0^{31,36}]tetraconta-7,9,12(21),22,29(37),31,33,35-octaen-18-yl]methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.572  -3.617   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.424  -2.592   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.738  -1.084   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.117   0.236   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.887   1.488   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.250   2.961   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.832   1.372   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.054  -0.210   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.551   0.212   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.966  -0.395   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.148  -1.925   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.795   1.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.634   3.019   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.293   4.560   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.755   4.476   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.201   5.913   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.287   6.309   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.396   6.884   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.474   8.422   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.844   9.124   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.138   8.288   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.060   6.750   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.689   6.048   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.353   5.913   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.724   6.615   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.017   5.779   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.544   4.313   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.245   2.942   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.711   2.469   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.082   3.171   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.173   2.084   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.710   2.167   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.552   0.877   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.855  -0.496   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.317  -0.579   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.476   0.711   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      10.955   0.949   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       9.868  -0.142   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.555   4.636   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.853   6.007   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.388   6.480   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.465   8.018   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       9.172   8.855   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       7.801   8.153   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.879   9.691   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       6.508   8.989   0.000  0.00  0.00           O+0
HETATM   47  N   UNK     0      10.166   4.801   0.000  0.00  0.00           N+0
HETATM   48  C   UNK     0       9.804   6.298   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14    6   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   46                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   14   18                                                  
CONECT   24   22   25                                                       
CONECT   25   24   26   44                                                  
CONECT   26   25   27   41                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   47                                                  
CONECT   29   28   30   37                                                  
CONECT   30   29   31   39                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31   37                                                  
CONECT   37   36   29   38                                                  
CONECT   38   37                                                            
CONECT   39   30   40                                                       
CONECT   40   39   41   47                                                  
CONECT   41   40   26   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   25   45   46                                             
CONECT   45   44                                                            
CONECT   46   44   21                                                       
CONECT   47   40   28   48                                                  
CONECT   48   47                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₄₈N₄O₃

Average Mass

644.8600 Da

Monoisotopic Mass

644.37264 Da

IUPAC Name

[(1R,2R,5S,13S,16E,17R,18R,19S,25S,26R,28R)-16-ethylidene-5,11,30,39-tetramethyl-4,6-dioxa-11,14,30,39-tetraazaundecacyclo[26.10.1.1^{13,17}.0^{2,26}.0^{5,25}.0^{7,23}.0^{10,22}.0^{12,21}.0^{14,19}.0^{29,37}.0^{31,36}]tetraconta-7,9,12(21),22,29(37),31,33,35-octaen-18-yl]methanol

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C1\CN2[C@H]3CC4=C([C@@H]2C[C@@H]1[C@H]3CO)N(C)C1=CC=C2O[C@]3(C)OC[C@@H]5[C@@H](C[C@H]6N(C)[C@@H]5CC5=C6N(C)C6=CC=CC=C56)[C@@H]3CC2=C41

InChI Identifier

InChI=1S/C41H48N4O3/c1-6-21-18-45-34-17-27-38-26-13-30-24-15-35-39-25(22-9-7-8-10-31(22)43(39)4)16-33(42(35)3)29(24)20-47-41(30,2)48-37(26)12-11-32(38)44(5)40(27)36(45)14-23(21)28(34)19-46/h6-12,23-24,28-30,33-36,46H,13-20H2,1-5H3/b21-6-/t23-,24+,28+,29+,30-,33+,34-,35+,36-,41-/m0/s1

InChI Key

ZUIDZDKAJCEORF-AYLOMWFQSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Sarpagine-skeleton
Vobasan skeleton
Beta-carboline
Pyridoindole
Chromane
Benzopyran
N-alkylindole
1-benzopyran
3-alkylindole
Indole
Indole or derivatives
Quinuclidine
Aralkylamine
Ketal
Substituted pyrrole
Benzenoid
Piperidine
Oxane
N-methylpyrrole
1,3-aminoalcohol
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Acetal
Primary alcohol
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Organic nitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	5.13	ChemAxon
pKa (Strongest Acidic)	15.4	ChemAxon
pKa (Strongest Basic)	7.45	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.03 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	190.76 m³·mol⁻¹	ChemAxon
Polarizability	74.08 Å³	ChemAxon
Number of Rings	11	ChemAxon
Bioavailability	No	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

163041143

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]