NP-MRD: Showing NP-Card for aconifine (NP0216611)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 16:38:55 UTC

Updated at

2022-09-05 16:38:55 UTC

NP-MRD ID

NP0216611

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aconifine

Description

Aconifine, also known as nagarine, belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. aconifine is found in Aconitum karakolicum, Aconitum kusnezoffii, Aconitum nagarum and Aconitum soongaricum. aconifine was first documented in 2004 (PMID: 15548242). Based on a literature review a small amount of articles have been published on aconifine (PMID: 21582830).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052218382D          

 47 53  0  0  1  0            999 V2000
   -0.3892    1.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420    0.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -0.0965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -1.5822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1069   -1.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089   -1.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203   -2.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658   -2.4074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5647   -3.1370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7386   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651   -1.9996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7559   -2.8805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433   -3.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -1.1386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7448   -0.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    0.0376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3127   -0.3021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5752    0.1440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4066    0.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -1.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2286   -0.1963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1386    0.7272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5830    1.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7745    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8450    2.1378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    0.0078    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4271    0.7790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6610   -0.5791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5314   -0.3316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9834    0.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3846   -1.4246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2259   -1.6908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5644   -2.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378   -1.5663    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4542   -2.4723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -1.0284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9548   -1.7699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5255   -2.4371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1241   -3.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291   -2.9067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8780   -3.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4368   -4.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1907   -5.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -5.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268   -4.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730   -4.0552    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
  3 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 21 18  1  1  0  0  0
  5 21  1  0  0  0  0
 15 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  6  0  0  0
 37 35  1  1  0  0  0
 22 37  1  0  0  0  0
 37 38  1  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 42 47  1  0  0  0  0
M  END

     RDKit          3D

 94100  0  0  0  0  0  0  0  0999 V2000
   -3.0669   -2.2301   -2.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7979   -1.3997   -1.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0473   -0.6277   -0.6717 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8300    0.1015    0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1658    1.2750    0.8888 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5821    1.5410    2.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9820    1.7979    2.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3300    2.0383    3.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6113    2.5691    0.1588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9582    2.8207    0.4516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4530    2.3594   -1.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884    2.0727   -1.6154 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0135    1.6114   -2.9307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6666    2.5976   -3.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    1.1367   -0.7272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7038   -0.3156   -0.9412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8544   -1.0103    0.0810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2370   -0.1517    1.3145 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1961   -0.8908    1.9540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -1.3939    3.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6882    1.1830    0.7693 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6229   -0.9047   -0.0637 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2090   -1.5530    1.0609 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -2.8804    1.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296   -3.4325    2.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888   -3.6124    0.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1733   -1.6234   -1.2549 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1476   -2.1640   -2.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0967   -0.8842   -2.1437 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4230   -1.3634   -2.0849 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -1.7936   -3.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767    0.5794   -1.9086 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1434    1.1122   -2.7442 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036    1.2513   -2.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474    1.3577   -0.8044 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3474    2.7064   -0.3803 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980    0.5260    0.0838 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3877    0.8523   -0.4744 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3835    0.1323    0.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4131    0.6763    0.9067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123    1.9331    0.9824 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4455   -0.1140    1.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4944   -1.4873    1.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4897   -2.2158    2.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4703   -1.5682    2.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4407   -0.1912    2.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4375    0.5148    2.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8562   -2.8055   -3.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4423   -3.0022   -2.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5773   -1.5929   -3.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5034   -0.7079   -2.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5210   -2.0308   -0.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7442    0.4714   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2687   -0.6188    0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    2.5301    2.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2823    0.8280    3.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7312    2.9357    4.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0557    1.2232    4.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3836    2.3465    3.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011    3.4205    0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4389    3.2143   -0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736    1.6095   -1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7196    3.3229   -1.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5325    3.0771   -1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630    2.2117   -4.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559    3.4070   -3.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7297    3.1058   -3.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4813   -0.5439   -1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349   -2.0332    0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750   -0.1072    2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6977   -1.9565    3.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0248   -2.1787    3.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -0.6349    3.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1829    2.0331    1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4281   -2.7048    3.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -3.6171    3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2942   -4.3653    2.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486   -2.5565   -0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -2.8519   -2.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075   -1.0055   -3.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9200   -2.1540   -3.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2711   -2.5917   -3.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9129   -0.9685   -4.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966    1.3784   -3.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3062    0.6912   -2.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0894    2.2536   -2.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6023    2.7173    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618    0.9002    1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4859    1.9654   -0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7169   -1.9826    0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5197   -3.3036    2.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2450   -2.1645    3.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2220    0.2949    3.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188    1.6029    2.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  6  7  1  0
  7  8  1  0
  5 21  1  0
 21 18  1  0
 18 19  1  0
 19 20  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  1  0
 12 13  1  0
 13 14  1  0
 15 35  1  1
 35 36  1  1
 35 34  1  0
 34 32  1  0
 32 33  1  6
 32 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  2  0
 40 42  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 38 37  1  0
 37 22  1  0
 22 23  1  1
 23 24  1  0
 24 25  1  0
 24 26  2  0
 22 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 16  3  1  0
 37 35  1  0
  9  5  1  0
 29 32  1  0
 15 21  1  0
 47 42  1  0
 22 17  1  0
  1 48  1  0
  1 49  1  0
  1 50  1  0
  2 51  1  0
  2 52  1  0
  4 53  1  0
  4 54  1  0
  6 55  1  0
  6 56  1  0
  8 57  1  0
  8 58  1  0
  8 59  1  0
 21 74  1  1
 18 70  1  1
 20 71  1  0
 20 72  1  0
 20 73  1  0
 17 69  1  1
 16 68  1  6
 12 64  1  6
 11 62  1  0
 11 63  1  0
  9 60  1  1
 10 61  1  0
 14 65  1  0
 14 66  1  0
 14 67  1  0
 36 87  1  0
 34 85  1  0
 34 86  1  0
 33 84  1  0
 38 89  1  6
 43 90  1  0
 44 91  1  0
 45 92  1  0
 46 93  1  0
 47 94  1  0
 37 88  1  1
 25 75  1  0
 25 76  1  0
 25 77  1  0
 27 78  1  1
 28 79  1  0
 29 80  1  6
 31 81  1  0
 31 82  1  0
 31 83  1  0
M  END


  Mrv1652309052218382D          

 47 53  0  0  1  0            999 V2000
   -0.3892    1.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420    0.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -0.0965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -1.5822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1069   -1.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089   -1.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203   -2.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658   -2.4074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5647   -3.1370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7386   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651   -1.9996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7559   -2.8805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433   -3.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -1.1386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7448   -0.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    0.0376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3127   -0.3021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5752    0.1440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4066    0.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -1.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2286   -0.1963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1386    0.7272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5830    1.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7745    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8450    2.1378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    0.0078    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4271    0.7790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6610   -0.5791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5314   -0.3316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9834    0.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3846   -1.4246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2259   -1.6908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5644   -2.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378   -1.5663    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4542   -2.4723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -1.0284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9548   -1.7699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5255   -2.4371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1241   -3.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291   -2.9067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8780   -3.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4368   -4.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1907   -5.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -5.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268   -4.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730   -4.0552    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
  3 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 21 18  1  1  0  0  0
  5 21  1  0  0  0  0
 15 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  6  0  0  0
 37 35  1  1  0  0  0
 22 37  1  0  0  0  0
 37 38  1  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 42 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216611

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(COC)[C@H]3[C@@H](OC)[C@H]4C1[C@]3([C@H](C[C@H]2O)OC)[C@]1(O)C[C@@]2(O)[C@H](OC(=O)C3=CC=CC=C3)[C@@H]1[C@]4(OC(C)=O)[C@@H](O)[C@@H]2OC

> <INCHI_IDENTIFIER>
InChI=1S/C34H47NO12/c1-7-35-15-30(16-42-3)19(37)13-20(43-4)33-23(30)22(44-5)21(25(33)35)34(47-17(2)36)24-27(46-29(39)18-11-9-8-10-12-18)31(40,14-32(24,33)41)28(45-6)26(34)38/h8-12,19-28,37-38,40-41H,7,13-16H2,1-6H3/t19-,20+,21+,22+,23-,24+,25?,26+,27-,28+,30+,31-,32+,33-,34+/m1/s1

> <INCHI_KEY>
GMSKTJVHWUUOMY-UHBPHNCFSA-N

> <FORMULA>
C34H47NO12

> <MOLECULAR_WEIGHT>
661.745

> <EXACT_MASS>
661.309825957

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
69.08757777179586

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,4R,5R,6S,7S,8S,9R,13R,14R,16S,17R,18R)-8-(acetyloxy)-11-ethyl-2,5,7,14-tetrahydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

> <JCHEM_LOGP>
-1.5142350069999972

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.124154145065763

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.456963798048495

> <JCHEM_PKA_STRONGEST_BASIC>
9.418388556788642

> <JCHEM_POLAR_SURFACE_AREA>
173.68

> <JCHEM_REFRACTIVITY>
162.92839999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4R,5R,6S,7S,8S,9R,13R,14R,16S,17R,18R)-8-(acetyloxy)-11-ethyl-2,5,7,14-tetrahydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.726   3.165   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.012   1.508   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.182  -0.180   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.230  -1.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.555  -2.953   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.066  -3.634   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.750  -3.388   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.705  -4.596   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.123  -4.494   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.054  -5.856   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.379  -4.926   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.361  -3.733   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.278  -5.377   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.441  -7.038   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.970  -2.125   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.390  -0.301   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.467   0.070   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.584  -0.564   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.074   0.269   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.626   0.399   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.751  -2.251   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.160  -0.366   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.992   1.357   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.955   2.530   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.446   2.224   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.444   3.990   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.680   0.015   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.397   1.454   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.834  -1.081   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.459  -0.619   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.302   0.730   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.318  -2.659   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.888  -3.156   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.787  -3.979   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.431  -2.924   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.714  -4.615   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.314  -1.920   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.516  -3.304   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.581  -4.549   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       7.698  -5.763   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       9.201  -5.426   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       7.239  -7.233   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.282  -8.366   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       7.823  -9.835   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.320 -10.172   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.277  -9.040   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.736  -7.570   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   21                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   21   35                                             
CONECT   16   15    3   17                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18    5   15                                                  
CONECT   22   17   23   27   37                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33   34   38                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   15   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   22   38                                                  
CONECT   38   37   32   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   47                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   42                                                       
MASTER        0    0    0    0    0    0    0    0   47    0  106    0
END

View in JSmol

Synonyms

Value	Source
10-Hydroxyaconitine	ChEBI
Nagarine	ChEBI

Chemical Formula

C₃₄H₄₇NO₁₂

Average Mass

661.7450 Da

Monoisotopic Mass

661.30983 Da

IUPAC Name

(1R,2S,3S,4R,5R,6S,7S,8S,9R,13R,14R,16S,17R,18R)-8-(acetyloxy)-11-ethyl-2,5,7,14-tetrahydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(COC)[C@H]3[C@@H](OC)[C@H]4C1[C@]3([C@H](C[C@H]2O)OC)[C@]1(O)C[C@@]2(O)[C@H](OC(=O)C3=CC=CC=C3)[C@@H]1[C@]4(OC(C)=O)[C@@H](O)[C@@H]2OC

InChI Identifier

InChI=1S/C34H47NO12/c1-7-35-15-30(16-42-3)19(37)13-20(43-4)33-23(30)22(44-5)21(25(33)35)34(47-17(2)36)24-27(46-29(39)18-11-9-8-10-12-18)31(40,14-32(24,33)41)28(45-6)26(34)38/h8-12,19-28,37-38,40-41H,7,13-16H2,1-6H3/t19-,20+,21+,22+,23-,24+,25?,26+,27-,28+,30+,31-,32+,33-,34+/m1/s1

InChI Key

GMSKTJVHWUUOMY-UHBPHNCFSA-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
Aconitum karakolicum	LOTUS Database	35616633
Aconitum kusnezoffii	LOTUS Database	35616633
Aconitum nagarum	LOTUS Database	35616633
Aconitum soongaricum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Benzoate ester
Quinolidine
Benzoic acid or derivatives
Alkaloid or derivatives
Benzoyl
Azepane
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Piperidine
Benzenoid
Cyclic alcohol
Tertiary alcohol
Tertiary aliphatic amine
Secondary alcohol
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Dialkyl ether
Ether
Organopnictogen compound
Carbonyl group
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Amine
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

diterpenoid (CHEBI:2429 )

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	-1.5	ChemAxon
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	9.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	173.68 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	162.93 m³·mol⁻¹	ChemAxon
Polarizability	69.09 Å³	ChemAxon
Number of Rings	7	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

C00001610

Chemspider ID

390310

KEGG Compound ID

C08655

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441705

PDB ID

Not Available

ChEBI ID

2429

Good Scents ID

Not Available

References

General References

Bello-Ramirez AM, Nava-Ocampo AA: A QSAR analysis of toxicity of Aconitum alkaloids. Fundam Clin Pharmacol. 2004 Dec;18(6):699-704. doi: 10.1111/j.1472-8206.2004.00280.x. [PubMed:15548242 ]
Tashkhodjaev B, Sultankhodjaev MN: 8beta-Acet-oxy-14alpha-benzo-yloxy-N-ethyl-3alpha,10beta,13beta,15alpha-tetra-hydr-oxy-1alpha,6alpha,16beta-trimeth-oxy-4beta-(methoxy-methyl-ene)aconitane: aconifine from Aconitum karakolicum Rapaics. Acta Crystallogr Sect E Struct Rep Online. 2009 Jun 10;65(Pt 7):o1543-4. doi: 10.1107/S1600536809021436. [PubMed:21582830 ]
LOTUS database [Link]

Showing NP-Card for aconifine (NP0216611)

MOL for NP0216611 (aconifine)

3D MOL for NP0216611 (aconifine)

3D SDF for NP0216611 (aconifine)

3D-SDF for NP0216611 (aconifine)

PDB for NP0216611 (aconifine)

3D PDB for NP0216611 (aconifine)

SMILES for NP0216611 (aconifine)

INCHI for NP0216611 (aconifine)

Structure for NP0216611 (aconifine)

3D Structure for NP0216611 (aconifine)