NP-MRD: Showing NP-Card for (1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol (NP0168359)

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Record Information

Version

2.0

Created at

2022-09-03 04:08:48 UTC

Updated at

2022-09-03 04:08:48 UTC

NP-MRD ID

NP0168359

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol

Description

Sachaconitine 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. (1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol is found in Aconitum variegatum and Aconitum vilmorinianum. (1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol was first documented in 2005 (PMID: 15797610). Based on a literature review a small amount of articles have been published on Sachaconitine (PMID: 34581046) (PMID: 21417277) (PMID: 19894538) (PMID: 17432903).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032206082D          

 28 33  0  0  1  0            999 V2000
   -0.3274   -2.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962   -2.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -1.6043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197   -0.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7821   -0.0895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0090    0.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0155    0.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202    0.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3453    0.3251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1498    0.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937    1.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346   -0.5353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9178   -0.1091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6456    0.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4646   -0.2533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7393   -1.0995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5387   -1.3033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7618   -2.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1200   -1.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3060   -1.4797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3073   -2.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3984   -1.7119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3902   -1.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4816   -0.4669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8221   -1.5122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3899   -0.6478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0354    0.0925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9630    0.9143    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  1  0  0  0
  5  7  1  0  0  0  0
  7  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 13  1  1  0  0  0
 13 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 23  1  6  0  0  0
 12 24  1  0  0  0  0
  5 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25  3  1  1  0  0  0
 12 25  1  0  0  0  0
 20 26  1  0  0  0  0
 26 13  1  6  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END

     RDKit          3D

 65 70  0  0  0  0  0  0  0  0999 V2000
   -1.6533    3.4738    1.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    1.9829    1.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6637    1.2313    0.7730 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539    1.2407   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7510    0.1620   -1.1252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4155    0.6441   -2.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5787   -1.0028   -0.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7593   -2.1580   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5914   -1.6168    0.6394 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0819   -0.9385    1.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7134   -1.5975    2.9381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6830   -0.7654   -0.1837 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5758   -1.4744   -0.4972 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4578   -1.7945    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956   -1.5986    0.2014 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4481   -0.2534    0.5924 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6474   -0.0919   -0.1002 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7440    0.0382    0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5458    0.8747    0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6544    0.6866   -0.9158 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1772    1.4279   -2.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185    1.2979   -0.6267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5783    0.9922   -1.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331   -0.2720   -1.4806 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4584    0.6065    0.4665 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4915   -0.7074   -1.4233 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7566   -1.5467   -1.3173 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8337   -0.9634   -1.9323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320    3.7698    1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6900    3.7943    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984    3.9141    2.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5912    1.7008    2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8244    1.7167    2.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6897    1.0907    0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9507    2.2606   -0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7381   -0.3009   -2.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7293    1.1453   -3.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3422    1.1981   -2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813   -0.7009    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2425   -1.4134   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3908   -2.7259    0.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3785   -2.7874   -0.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0376   -2.5011    1.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1118   -2.6226    2.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720   -1.0420    3.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5948   -1.7084    3.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -2.4092   -1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325   -2.8815    0.9196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086   -1.2284    1.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5320   -2.4031    0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060   -0.2331    1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9051   -0.8272    1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6347    0.1238    0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7120    0.9961    1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2099    1.7772    0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9952    1.1518    1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021    2.3647   -1.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3900    2.3825   -0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075    0.9268   -2.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425    1.8780   -1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3243   -1.0234   -2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1111    0.4123    1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1929   -0.7434   -2.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -2.5527   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5569   -0.3765   -2.6861 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12  9  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 27  1  0
 27 28  1  0
 27 26  1  0
 26 20  1  0
 20 21  1  6
 20 19  1  0
 19 16  1  0
 16 17  1  0
 17 18  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25  3  1  0
 24  5  1  0
 24 12  1  0
 25 12  1  0
 26 13  1  0
 16 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  4 34  1  0
  4 35  1  0
  6 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  1
 11 44  1  0
 11 45  1  0
 11 46  1  0
 13 47  1  6
 14 48  1  0
 14 49  1  0
 15 50  1  6
 27 64  1  6
 28 65  1  0
 26 63  1  6
 21 57  1  0
 19 55  1  0
 19 56  1  0
 16 51  1  1
 18 52  1  0
 18 53  1  0
 18 54  1  0
 22 58  1  1
 23 59  1  0
 23 60  1  0
 24 61  1  6
 25 62  1  1
M  END


  Mrv1652309032206082D          

 28 33  0  0  1  0            999 V2000
   -0.3274   -2.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962   -2.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -1.6043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197   -0.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7821   -0.0895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0090    0.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0155    0.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202    0.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3453    0.3251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1498    0.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937    1.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346   -0.5353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9178   -0.1091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6456    0.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4646   -0.2533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7393   -1.0995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5387   -1.3033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7618   -2.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1200   -1.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3060   -1.4797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3073   -2.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3984   -1.7119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3902   -1.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4816   -0.4669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8221   -1.5122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3899   -0.6478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0354    0.0925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9630    0.9143    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  1  0  0  0
  5  7  1  0  0  0  0
  7  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 13  1  1  0  0  0
 13 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 23  1  6  0  0  0
 12 24  1  0  0  0  0
  5 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25  3  1  1  0  0  0
 12 25  1  0  0  0  0
 20 26  1  0  0  0  0
 26 13  1  6  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0168359

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(C)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@H](C[C@H]23)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C23H37NO4/c1-5-24-11-21(2)7-6-17(28-4)23-13-8-12-15(27-3)10-22(26,18(13)19(12)25)14(20(23)24)9-16(21)23/h12-20,25-26H,5-11H2,1-4H3/t12-,13-,14+,15+,16-,17+,18-,19+,20-,21+,22+,23-/m1/s1

> <INCHI_KEY>
NGWMZXLZSGJSRI-VHNKBEDGSA-N

> <FORMULA>
C23H37NO4

> <MOLECULAR_WEIGHT>
391.552

> <EXACT_MASS>
391.272258675

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
44.28738731911537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,3R,4S,5S,6S,8S,9S,10R,13R,16S,17R)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8-diol

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
0.3675457453333324

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.759992337051827

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.976863595642094

> <JCHEM_PKA_STRONGEST_BASIC>
10.20044732153014

> <JCHEM_POLAR_SURFACE_AREA>
62.16000000000001

> <JCHEM_REFRACTIVITY>
106.5115

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4S,5S,6S,8S,9S,10R,13R,16S,17R)-11-ethyl-6,16-dimethoxy-13-methyl-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                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.611  -4.460   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.926  -4.371   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.618  -2.995   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.783  -1.614   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.460  -0.167   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.017   0.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.896   1.372   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.398   1.802   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.378   0.607   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.880   0.948   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.335   2.419   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.985  -0.999   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.447  -0.204   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.805   0.849   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.334  -0.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.847  -2.052   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.339  -2.433   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.755  -3.915   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.691  -3.146   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.171  -2.762   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.174  -4.302   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.477  -3.195   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.595  -2.558   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.766  -0.872   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.401  -2.823   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.328  -1.209   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.533   0.173   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.398   1.707   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   24                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   24   25                                             
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   22   26                                             
CONECT   21   20                                                            
CONECT   22   20   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   12    5                                                  
CONECT   25   22    3   12                                                  
CONECT   26   20   13   27                                                  
CONECT   27   26   15   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₇NO₄

Average Mass

391.5520 Da

Monoisotopic Mass

391.27226 Da

IUPAC Name

(1S,2R,3R,4S,5S,6S,8S,9S,10R,13R,16S,17R)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8-diol

Traditional Name

(1S,2R,3R,4S,5S,6S,8S,9S,10R,13R,16S,17R)-11-ethyl-6,16-dimethoxy-13-methyl-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(C)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@H](C[C@H]23)[C@@H]14

InChI Identifier

InChI=1S/C23H37NO4/c1-5-24-11-21(2)7-6-17(28-4)23-13-8-12-15(27-3)10-22(26,18(13)19(12)25)14(20(23)24)9-16(21)23/h12-20,25-26H,5-11H2,1-4H3/t12-,13-,14+,15+,16-,17+,18-,19+,20-,21+,22+,23-/m1/s1

InChI Key

NGWMZXLZSGJSRI-VHNKBEDGSA-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 variegatum	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
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
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	1.33	ALOGPS
logP	0.37	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.98	ChemAxon
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.51 m³·mol⁻¹	ChemAxon
Polarizability	44.29 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

C00028951

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

101297639

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Diaz JG, Ruiza JG, Herz W: Norditerpene and diterpene alkaloids from Aconitum variegatum. Phytochemistry. 2005 Apr;66(7):837-46. doi: 10.1016/j.phytochem.2005.01.019. [PubMed:15797610 ]
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 ]
Liu ZL, Cao J, Zhang HM, Lin LL, Liu HJ, Du SS, Zhou L, Deng ZW: Feeding deterrents from Aconitum episcopale roots against the red flour beetle, Tribolium castaneum. J Agric Food Chem. 2011 Apr 27;59(8):3701-6. doi: 10.1021/jf104879h. Epub 2011 Mar 18. [PubMed:21417277 ]
Ge Y, Mu S, Zhang J, Wang Y, Sun Q, Hao X: [Diterpenoid alkaloids from roots of Aconitum recemulosum and their inhibitory effects on PAF-induced platelet aggregation]. Zhongguo Zhong Yao Za Zhi. 2009 Aug;34(15):1935-7. [PubMed:19894538 ]
Gao F, Chen QH, Wang FP: C19-diterpenoid alkaloids from Aconitum hemsleyanum var. circinatum. J Nat Prod. 2007 May;70(5):876-9. doi: 10.1021/np0700117. Epub 2007 Apr 14. [PubMed:17432903 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol (NP0168359)

MOL for NP0168359 ((1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

3D MOL for NP0168359 ((1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

3D SDF for NP0168359 ((1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

3D-SDF for NP0168359 ((1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

PDB for NP0168359 ((1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

3D PDB for NP0168359 ((1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

SMILES for NP0168359 ((1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

INCHI for NP0168359 ((1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

Structure for NP0168359 ((1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)

3D Structure for NP0168359 ((1s,2r,3r,4s,5s,6s,8s,9s,10r,13r,16s,17r)-11-ethyl-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecane-4,8-diol)