NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol (NP0323242)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 02:32:21 UTC

Updated at

2022-09-12 02:32:21 UTC

NP-MRD ID

NP0323242

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol

Description

Talatisamine 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. (2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol is found in Aconitum carmichaelii, Aconitum columbianum, Aconitum episcopale, Aconitum forrestii, Aconitum hemsleyanum, Aconitum jaluense, Aconitum japonicum, Aconitum kongboense, Aconitum legendrei, Aconitum nasutum, Aconitum nemorum, Aconitum racemulosum, Aconitum sanyoense, Aconitum sczukinii, Aconitum talassicum, Aconitum transsectum and Aconitum vilmorinianum. (2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol was first documented in 2021 (PMID: 34581046). Based on a literature review a small amount of articles have been published on Talatisamine (PMID: 35913407) (PMID: 34471676) (PMID: 33418305) (PMID: 33160222).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122204322D          

 30 35  0  0  1  0            999 V2000
   -1.4010    0.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774    0.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069   -0.0868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -1.6016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0643   -1.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2015   -2.7030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746   -2.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0580   -2.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7469   -2.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2722   -2.0163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0767   -2.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -2.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612   -1.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -0.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250    0.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169   -0.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081   -1.2240    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2326   -0.2113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2339    0.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465   -0.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656   -0.5916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4651   -0.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6885    0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3907   -1.4376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5718   -2.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -1.5820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3162   -1.0433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9615   -1.7836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8892   -2.6054    0.0000 O   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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 14 18  1  0  0  0  0
  5 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
 14 27  1  0  0  0  0
 28 27  1  1  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END

     RDKit          3D

 69 74  0  0  0  0  0  0  0  0999 V2000
   -0.9243    3.5315    1.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997    2.0937    1.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2560    1.2083    0.8109 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3182    1.3076   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987   -0.0263   -0.7760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3654    0.2108   -2.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5152    0.8783   -2.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5693    0.4668   -1.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2497   -0.9428    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4159   -2.1222    0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0056   -1.6959    1.0015 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0855   -1.1344    2.2709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -1.9944    3.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3658   -0.8571   -0.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9209   -1.5278   -0.4634 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9202   -1.6049    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2875   -1.2914    0.0705 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6803    0.1487    0.2904 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0471    0.2298    0.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    0.5012    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8942    1.1279   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7906    0.6501   -1.3345 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9608    1.1904   -2.6386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275    1.1392   -0.9031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5559    0.5866   -1.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2296   -0.5768   -1.2524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0530    0.5677    0.3954 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6753   -0.8289   -1.5468 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0589   -1.4464   -1.4142 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0116   -0.6765   -2.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849    4.2194    2.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0348    3.8023    2.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634    3.7664    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874    2.0584    2.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4701    1.6704    2.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176    2.1623   -0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2558    1.4798    0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6051   -0.8776   -2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7411    0.5472   -2.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3616    0.4749   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9265   -0.5580   -1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4092    1.2017   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286   -1.4294   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6756   -0.4382    1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4051   -2.9151   -0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8808   -2.5369    1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4802   -2.6742    1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4839   -2.2697    3.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -1.6413    4.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280   -2.9767    3.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228   -2.5319   -0.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991   -1.0228    1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9751   -2.6826    0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0551   -1.9659    0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    0.3335    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8726    0.5642    0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6607   -0.3666    1.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4030    1.3890    1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4577    1.8887    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6272    1.7498   -1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8126    2.1709   -2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652    2.2433   -0.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334    1.4022   -2.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0346    0.2893   -2.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3914   -1.4452   -1.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6754    0.6491    1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3154   -1.1386   -2.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0834   -2.5032   -1.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8522   -1.2016   -2.0534 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  6
  6  7  1  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 11  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 29  1  0
 29 30  1  0
 29 28  1  0
 28 22  1  0
 22 23  1  6
 22 21  1  0
 21 18  1  0
 18 19  1  0
 19 20  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27  3  1  0
 26  5  1  0
 26 14  1  0
 27 14  1  0
 28 15  1  0
 18 17  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  1
 13 48  1  0
 13 49  1  0
 13 50  1  0
 15 51  1  6
 16 52  1  0
 16 53  1  0
 17 54  1  1
 29 68  1  6
 30 69  1  0
 28 67  1  6
 23 61  1  0
 21 59  1  0
 21 60  1  0
 18 55  1  1
 20 56  1  0
 20 57  1  0
 20 58  1  0
 24 62  1  1
 25 63  1  0
 25 64  1  0
 26 65  1  6
 27 66  1  1
M  END


  Mrv1652309122204322D          

 30 35  0  0  1  0            999 V2000
   -1.4010    0.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774    0.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069   -0.0868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -1.6016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0643   -1.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2015   -2.7030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746   -2.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0580   -2.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7469   -2.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2722   -2.0163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0767   -2.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -2.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612   -1.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -0.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250    0.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169   -0.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081   -1.2240    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2326   -0.2113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2339    0.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465   -0.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656   -0.5916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4651   -0.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6885    0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3907   -1.4376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5718   -2.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -1.5820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3162   -1.0433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9615   -1.7836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8892   -2.6054    0.0000 O   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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 14 18  1  0  0  0  0
  5 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
 14 27  1  0  0  0  0
 28 27  1  1  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0323242

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(COC)CC[C@H](OC)C34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)C(C[C@H]23)C14

> <INCHI_IDENTIFIER>
InChI=1S/C24H39NO5/c1-5-25-11-22(12-28-2)7-6-18(30-4)24-14-8-13-16(29-3)10-23(27,19(14)20(13)26)15(21(24)25)9-17(22)24/h13-21,26-27H,5-12H2,1-4H3/t13-,14-,15?,16+,17-,18+,19-,20+,21?,22+,23+,24?/m1/s1

> <INCHI_KEY>
BDCURAWBZJMFIK-FIIQKEKKSA-N

> <FORMULA>
C24H39NO5

> <MOLECULAR_WEIGHT>
421.578

> <EXACT_MASS>
421.28282336

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
47.686194723529

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6S,8S,13S,16S,17R)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8-diol

> <JCHEM_LOGP>
-0.27009890766666655

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.759992242477043

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.976864404427808

> <JCHEM_PKA_STRONGEST_BASIC>
10.212672834576093

> <JCHEM_POLAR_SURFACE_AREA>
71.39000000000001

> <JCHEM_REFRACTIVITY>
113.03739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6S,8S,13S,16S,17R)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8-diol

> <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      -2.615   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.078   1.214   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.386  -0.162   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.220  -1.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.543  -2.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.987  -3.527   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.243  -5.046   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.686  -5.583   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.108  -4.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.394  -4.958   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.375  -3.764   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.877  -4.105   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.332  -5.576   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.981  -2.157   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.398  -0.333   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.473   0.039   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.591  -0.598   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.762  -2.285   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.167  -0.394   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.170   1.146   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.687  -0.011   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.842  -1.104   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.335  -0.724   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.752   0.758   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.329  -2.683   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.801  -4.005   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.442  -2.953   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.324  -1.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.528  -3.329   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.393  -4.863   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   18                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   18   27                                             
CONECT   15   14    3   16                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14    5                                                  
CONECT   19   16   20   21   28                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   14   28                                                  
CONECT   28   27   19   29                                                  
CONECT   29   28   25   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₉NO₅

Average Mass

421.5780 Da

Monoisotopic Mass

421.28282 Da

IUPAC Name

(2R,3R,4S,5S,6S,8S,13S,16S,17R)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8-diol

Traditional Name

(2R,3R,4S,5S,6S,8S,13S,16S,17R)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8-diol

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(COC)CC[C@H](OC)C34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)C(C[C@H]23)C14

InChI Identifier

InChI=1S/C24H39NO5/c1-5-25-11-22(12-28-2)7-6-18(30-4)24-14-8-13-16(29-3)10-23(27,19(14)20(13)26)15(21(24)25)9-17(22)24/h13-21,26-27H,5-12H2,1-4H3/t13-,14-,15?,16+,17-,18+,19-,20+,21?,22+,23+,24?/m1/s1

InChI Key

BDCURAWBZJMFIK-FIIQKEKKSA-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 carmichaelii	LOTUS Database	35616633
Aconitum columbianum	LOTUS Database	35616633
Aconitum episcopale	LOTUS Database	35616633
Aconitum forrestii	LOTUS Database	35616633
Aconitum hemsleyanum	LOTUS Database	35616633
Aconitum jaluense	LOTUS Database	35616633
Aconitum japonicum	LOTUS Database	35616633
Aconitum kongboense	LOTUS Database	35616633
Aconitum legendrei	LOTUS Database	35616633
Aconitum nasutum	LOTUS Database	35616633
Aconitum nemorum	LOTUS Database	35616633
Aconitum racemulosum	LOTUS Database	35616633
Aconitum sanyoense	LOTUS Database	35616633
Aconitum sczukinii	LOTUS Database	35616633
Aconitum talassicum	LOTUS Database	35616633
Aconitum transsectum	LOTUS Database	35616633
Aconitum vilmorinianum	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
Quinolidine
Alkaloid or derivatives
Azepane
Piperidine
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.27	ChemAxon
pKa (Strongest Acidic)	13.98	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.04 m³·mol⁻¹	ChemAxon
Polarizability	47.69 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00001669

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

146014457

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xie CY, Huang S, Chen L, Gao F, Zhou XL: [Diterpenoid alkaloids from roots of Aconitum kongboense]. Zhongguo Zhong Yao Za Zhi. 2021 Sep;46(17):4424-4432. doi: 10.19540/j.cnki.cjcmm.20210622.201. [PubMed:34581046 ]
Yao LL, Zhang SQ, Guo C, Li BX, Yang HJ, Yin TP, Cai L: A new C(19)-diterpenoid alkaloid in Aconitum georgei Comber. Nat Prod Res. 2022 Aug 1:1-6. doi: 10.1080/14786419.2022.2104276. [PubMed:35913407 ]
Wong AR, Fastuca NJ, Mak VW, Kerkovius JK, Stevenson SM, Reisman SE: Total Syntheses of the C(19) Diterpenoid Alkaloids (-)-Talatisamine, (-)-Liljestrandisine, and (-)-Liljestrandinine by a Fragment Coupling Approach. ACS Cent Sci. 2021 Aug 25;7(8):1311-1316. doi: 10.1021/acscentsci.1c00540. Epub 2021 Jul 27. [PubMed:34471676 ]
Xu X, Xie X, Zhang H, Wang P, Li G, Chen J, Chen G, Cao X, Xiong L, Peng F, Peng C: Water-soluble alkaloids extracted from Aconiti Radix lateralis praeparata protect against chronic heart failure in rats via a calcium signaling pathway. Biomed Pharmacother. 2021 Mar;135:111184. doi: 10.1016/j.biopha.2020.111184. Epub 2021 Jan 5. [PubMed:33418305 ]
Chen LL, Lai CJ, Mao LY, Yin BW, Tian M, Jin BL, Wei XY, Chen JL, Ge H, Zhao X, Li WY, Guo J, Cui GH, Huang LQ: Chemical constituents in different parts of seven species of Aconitum based on UHPLC-Q-TOF/MS. J Pharm Biomed Anal. 2021 Jan 30;193:113713. doi: 10.1016/j.jpba.2020.113713. Epub 2020 Oct 20. [PubMed:33160222 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol (NP0323242)

MOL for NP0323242 ((2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

3D MOL for NP0323242 ((2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

3D SDF for NP0323242 ((2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

3D-SDF for NP0323242 ((2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

PDB for NP0323242 ((2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

3D PDB for NP0323242 ((2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

SMILES for NP0323242 ((2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

INCHI for NP0323242 ((2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

Structure for NP0323242 ((2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

3D Structure for NP0323242 ((2r,3r,4s,5s,6s,8s,13s,16s,17r)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)