NP-MRD: Showing NP-Card for (1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol (NP0243892)

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Record Information

Version

2.0

Created at

2022-09-07 04:32:58 UTC

Updated at

2022-09-07 04:32:59 UTC

NP-MRD ID

NP0243892

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol

Description

(1S,5R,8S,9S,11R,13R,14S,16S,17R,18R,19S)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecane-8,13,19-triol belongs to the class of organic compounds known as hetisine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetisine skeleton, which is a heptacyclic compound with an additional N-C-6 bond as compared with the hetidine-type, and thus, is one of most complex entries in the atisane-class. (1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol is found in Aconitum orientale. Based on a literature review very few articles have been published on (1S,5R,8S,9S,11R,13R,14S,16S,17R,18R,19S)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecane-8,13,19-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206322D          

 24 30  0  0  1  0            999 V2000
   -1.2190   -0.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4128   -0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584    0.6269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6154    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549    0.5120    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0919   -0.4598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9328   -0.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -0.4453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3892    0.2224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5450    0.0292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4520   -0.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3277   -0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941    0.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0151    0.8559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3800    1.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2723    1.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8263    0.5259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607    0.7838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0606    1.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6528    0.0097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7059    0.2106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6731   -0.6138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361   -0.6801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0513   -1.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  1  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 10  1  1  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  1  0  0  0
  6 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  6  0  0  0
M  END

     RDKit          3D

 51 57  0  0  0  0  0  0  0  0999 V2000
    4.7792   -0.7382    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4696   -0.6965    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224   -1.6464   -0.4538 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6040   -2.1196    0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946   -1.0396    1.2762 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3690    0.2977    0.7989 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6783    1.3676    1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7962    1.2755    1.3969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1807    1.2481   -0.0928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5437   -0.0590   -0.4951 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1258   -0.6950   -1.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753   -0.5383   -1.8920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417    0.5828   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6545    1.0305    0.0703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3595    2.2927    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6967    0.0259    1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271   -0.0520    1.7277 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -0.9073    0.7641 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3104   -2.0528    0.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522    0.2508   -0.6537 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6818   -0.7993   -1.4078 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6124   -0.2406   -2.3163 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    0.3707    1.0128 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3323    1.6218    0.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3796   -0.0029    0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2850   -1.4945   -0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947   -2.4973   -0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745   -3.0113    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -2.4799    1.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786   -1.0041    2.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9950    2.3846    1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899    1.1741    2.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3307    2.0700    1.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8714    2.1161   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5397   -0.3481   -2.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9052   -1.8031   -1.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345   -1.4852   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7590   -0.4329   -3.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3250    0.3264   -1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    1.4570   -1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3474    2.3618    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4162    2.2194    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014    3.1979    0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4006    0.3144    1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9669   -0.9684    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381   -2.7851    0.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0849    1.2224   -1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0770   -1.4912   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008   -0.1092   -3.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0300    0.1270    2.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819    2.1629    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17  8  1  0
  8  7  1  0
  6  7  1  1
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3 21  1  0
 21 22  1  0
 21 20  1  0
 20 10  1  0
 10 11  1  6
 11 12  1  0
 12 13  1  0
 10  9  1  0
 10 18  1  0
 18 19  1  6
  3  2  1  0
  2  1  2  3
  2 23  1  0
 23 24  1  0
 13 14  1  0
  9 14  1  0
 18 17  1  0
  9  8  1  0
 20  6  1  0
 23  6  1  0
 18  5  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
  8 33  1  1
  7 31  1  0
  7 32  1  0
  5 30  1  1
  4 28  1  0
  4 29  1  0
  3 27  1  6
 21 48  1  6
 22 49  1  0
 20 47  1  6
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
  9 34  1  6
 19 46  1  0
  1 25  1  0
  1 26  1  0
 23 50  1  1
 24 51  1  0
M  END


  Mrv1652309072206322D          

 24 30  0  0  1  0            999 V2000
   -1.2190   -0.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4128   -0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584    0.6269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6154    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549    0.5120    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0919   -0.4598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9328   -0.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -0.4453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3892    0.2224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5450    0.0292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4520   -0.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3277   -0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941    0.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0151    0.8559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3800    1.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2723    1.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8263    0.5259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607    0.7838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0606    1.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6528    0.0097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7059    0.2106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6731   -0.6138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361   -0.6801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0513   -1.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  1  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 10  1  1  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  1  0  0  0
  6 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0243892

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CN3[C@H]4C[C@@]56[C@@H]7C[C@@H]([C@H](O)[C@H]5[C@](CCC1)([C@@H]24)[C@]37O)C(=C)[C@H]6O

> <INCHI_IDENTIFIER>
InChI=1S/C20H27NO3/c1-9-10-6-12-18(16(9)23)7-11-14-17(2)4-3-5-19(14,15(18)13(10)22)20(12,24)21(11)8-17/h10-16,22-24H,1,3-8H2,2H3/t10-,11+,12+,13+,14-,15-,16-,17+,18-,19+,20+/m1/s1

> <INCHI_KEY>
FNTVGWXTYMQJSO-LLBLNAJSSA-N

> <FORMULA>
C20H27NO3

> <MOLECULAR_WEIGHT>
329.44

> <EXACT_MASS>
329.199093733

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.893951630014364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,8S,9S,11R,13R,14S,16S,17R,18R,19S)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecane-8,13,19-triol

> <JCHEM_LOGP>
0.38862062633333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.009156649192217

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.62076653286963

> <JCHEM_PKA_STRONGEST_BASIC>
8.006923024796572

> <JCHEM_POLAR_SURFACE_AREA>
63.93000000000001

> <JCHEM_REFRACTIVITY>
88.20120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,8S,9S,11R,13R,14S,16S,17R,18R,19S)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecane-8,13,19-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.275  -0.569   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.771  -0.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.109   1.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.149   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.342   0.956   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.038  -0.858   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.608  -1.586   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.163  -0.831   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.327   0.415   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.751   0.054   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.444  -0.764   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.078  -0.420   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.949   0.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.495   1.598   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.176   2.979   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.108   2.346   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.276   0.982   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.847   1.463   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.846   3.003   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.085   0.018   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.318   0.393   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.256  -1.146   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.441  -1.270   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.096  -2.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   20   23                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   18   20                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17    5   10   19                                             
CONECT   19   18                                                            
CONECT   20   10    6   21                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21                                                            
CONECT   23    6    2   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₇NO₃

Average Mass

329.4400 Da

Monoisotopic Mass

329.19909 Da

IUPAC Name

(1S,5R,8S,9S,11R,13R,14S,16S,17R,18R,19S)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecane-8,13,19-triol

Traditional Name

(1S,5R,8S,9S,11R,13R,14S,16S,17R,18R,19S)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecane-8,13,19-triol

CAS Registry Number

Not Available

SMILES

C[C@@]12CN3[C@H]4C[C@@]56[C@@H]7C[C@@H]([C@H](O)[C@H]5[C@](CCC1)([C@@H]24)[C@]37O)C(=C)[C@H]6O

InChI Identifier

InChI=1S/C20H27NO3/c1-9-10-6-12-18(16(9)23)7-11-14-17(2)4-3-5-19(14,15(18)13(10)22)20(12,24)21(11)8-17/h10-16,22-24H,1,3-8H2,2H3/t10-,11+,12+,13+,14-,15-,16-,17+,18-,19+,20+/m1/s1

InChI Key

FNTVGWXTYMQJSO-LLBLNAJSSA-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 orientale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hetisine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetisine skeleton, which is a heptacyclic compound with an additional N-C-6 bond as compared with the hetidine-type, and thus, is one of most complex entries in the atisane-class.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Hetisine-type diterpenoid alkaloids

Alternative Parents

Substituents

Hetisine-type diterpenoid alkaloid
Azaspirodecane
Quinolizidine
Indole or derivatives
Indolizidine
Isoindoline
Alkaloid or derivatives
Isoindole or derivatives
Azepane
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Cyclic alcohol
Hemiaminal
Secondary alcohol
Polyol
Organoheterocyclic compound
Azacycle
Alkanolamine
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
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	0.39	ChemAxon
pKa (Strongest Acidic)	12.62	ChemAxon
pKa (Strongest Basic)	8.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	63.93 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.2 m³·mol⁻¹	ChemAxon
Polarizability	35.89 Å³	ChemAxon
Number of Rings	7	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163027023

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol (NP0243892)

MOL for NP0243892 ((1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol)

3D MOL for NP0243892 ((1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol)

3D SDF for NP0243892 ((1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol)

3D-SDF for NP0243892 ((1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol)

PDB for NP0243892 ((1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol)

3D PDB for NP0243892 ((1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol)

SMILES for NP0243892 ((1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol)

INCHI for NP0243892 ((1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol)

Structure for NP0243892 ((1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol)

3D Structure for NP0243892 ((1s,5r,8s,9s,11r,13r,14s,16s,17r,18r,19s)-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecane-8,13,19-triol)