NP-MRD: Showing NP-Card for 12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate (NP0219225)

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Record Information

Version

2.0

Created at

2022-09-05 20:09:07 UTC

Updated at

2022-09-05 20:09:07 UTC

NP-MRD ID

NP0219225

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate

Description

12-Ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]Henicosan-17-yl acetate belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. 12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate is found in Aconitum japonicum. 12-Ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]Henicosan-17-yl acetate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171520452D          

 30 36  0  0  0  0            999 V2000
    1.7039   -1.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9766   -0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4387    0.4021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247    0.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0346   -0.1580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7239    0.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361    1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750    1.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895    1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878    0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670    2.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9976    2.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6880    2.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241    1.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9069    1.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972    1.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051    2.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0063    2.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518    3.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734    3.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5190    4.4797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6494    3.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4437    2.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528    1.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4835    1.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156    1.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7311    0.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0670    1.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8860    1.8087    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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 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
  7 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
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 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
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 21 23  1  0  0  0  0
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 24 25  1  0  0  0  0
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 14 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 65 71  0  0  0  0  0  0  0  0999 V2000
    4.1335   -2.2095    1.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1224    0.3593   -0.5881 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0897    0.8240    0.3429 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2136    1.5425   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2371    2.0300    0.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3363    1.7762   -1.2627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597    0.5541   -0.0061 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.5929    2.7034    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8963   -0.0326    1.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850    0.1163    1.2145 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3371   -1.3941    1.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985   -1.7025   -0.0394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0432   -0.5634   -0.9478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4663   -0.8320   -0.9698 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8863   -1.3654   -2.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038   -1.8740   -2.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    0.3017   -0.5344 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1781    1.4083   -1.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508    1.9255   -1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6846   -1.8959    1.1885 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.0908    2.5213   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8993    2.5923    1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6802    3.7610    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1386    2.3462    2.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895    2.5390    0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4973    0.0610    2.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8134    0.6327    1.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2299   -1.0252    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0957    0.5692    2.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3313   -1.8861    1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8494   -1.6983    2.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6706   -2.6768   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551   -0.5375   -1.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191   -0.5958   -3.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2558   -2.2240   -2.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  2  3
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  1 31  1  0
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M  END


  Mrv1533004171520452D          

 30 36  0  0  0  0            999 V2000
    1.7039   -1.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9766   -0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4387    0.4021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247    0.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0346   -0.1580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7239    0.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361    1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750    1.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895    1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878    0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670    2.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9976    2.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6880    2.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241    1.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9069    1.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972    1.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051    2.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0063    2.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518    3.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734    3.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5190    4.4797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6494    3.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4437    2.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528    1.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4835    1.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156    1.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7311    0.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0670    1.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8860    1.8087    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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 12 16  1  0  0  0  0
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 14 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0219225

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C2C3CC4C2(C2CC(OC(C)=O)C5CC32C(O)C5=C)C2CCC4(C)C1OC2

> <INCHI_IDENTIFIER>
InChI=1S/C25H35NO4/c1-5-26-20-16-8-18-23(4)7-6-14(11-29-22(23)26)25(18,20)19-9-17(30-13(3)27)15-10-24(16,19)21(28)12(15)2/h14-22,28H,2,5-11H2,1,3-4H3

> <INCHI_KEY>
WLJTWHMJXOXZAE-UHFFFAOYSA-N

> <FORMULA>
C25H35NO4

> <MOLECULAR_WEIGHT>
413.558

> <EXACT_MASS>
413.256608611

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.086992274491486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
1.9285966046666672

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.127909833604694

> <JCHEM_PKA_STRONGEST_BASIC>
8.133746250653163

> <JCHEM_POLAR_SURFACE_AREA>
59.0

> <JCHEM_REFRACTIVITY>
111.24469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       3.181  -1.870   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.690  -0.417   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.685   0.751   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.166   0.646   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.065  -0.295   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.351   0.563   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.441   2.323   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.865   2.349   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.887   3.398   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.727   2.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.537   1.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.872   3.835   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.862   4.973   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.151   4.118   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.032   2.306   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.693   2.947   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.728   3.618   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.116   5.185   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.612   5.425   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.257   6.823   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.790   6.964   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.435   8.362   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.679   5.706   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.428   4.085   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.699   2.414   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.636   2.646   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.562   1.903   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.965   0.416   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.592   3.191   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.121   3.376   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15    7   12   17                                             
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   14   17   27                                             
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   24   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   72    0
END

View in JSmol

Synonyms

Value	Source
12-Ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0,.0,.0,.0,.0,]henicosan-17-yl acetic acid	Generator
12-Ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₅NO₄

Average Mass

413.5580 Da

Monoisotopic Mass

413.25661 Da

IUPAC Name

12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate

Traditional Name

12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate

CAS Registry Number

Not Available

SMILES

CCN1C2C3CC4C2(C2CC(OC(C)=O)C5CC32C(O)C5=C)C2CCC4(C)C1OC2

InChI Identifier

InChI=1S/C25H35NO4/c1-5-26-20-16-8-18-23(4)7-6-14(11-29-22(23)26)25(18,20)19-9-17(30-13(3)27)15-10-24(16,19)21(28)12(15)2/h14-22,28H,2,5-11H2,1,3-4H3

InChI Key

WLJTWHMJXOXZAE-UHFFFAOYSA-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 japonicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Meta-oxazepine
Azepane
Oxepane
Piperidine
Cyclic alcohol
Carboxylic acid ester
Hemiaminal
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen 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	2.22	ALOGPS
logP	1.93	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.13	ChemAxon
pKa (Strongest Basic)	8.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.24 m³·mol⁻¹	ChemAxon
Polarizability	46.09 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate (NP0219225)

MOL for NP0219225 (12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate)

3D MOL for NP0219225 (12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate)

3D SDF for NP0219225 (12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate)

3D-SDF for NP0219225 (12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate)

PDB for NP0219225 (12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate)

3D PDB for NP0219225 (12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate)

SMILES for NP0219225 (12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate)

INCHI for NP0219225 (12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate)

Structure for NP0219225 (12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate)

3D Structure for NP0219225 (12-ethyl-20-hydroxy-5-methyl-19-methylidene-10-oxa-12-azaheptacyclo[16.2.1.0¹,¹⁵.0²,¹³.0⁴,¹⁴.0⁵,¹¹.0⁸,¹⁴]henicosan-17-yl acetate)