NP-MRD: Showing NP-Card for n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid (NP0242554)

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Record Information

Version

2.0

Created at

2022-09-07 02:53:52 UTC

Updated at

2022-09-07 02:53:52 UTC

NP-MRD ID

NP0242554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid

Description

Buxalongifolamidine belongs to the class of organic compounds known as buxus alkaloids. These are alkaloids with a triterpenoid-steroid pregnane type structure with C-4 methyl groups, a 9beta,10beta-cycloartenol system, and a degraded C-20 side chain. Structurally, they are derivatives of either a 9beta,10beta-cyclo-4,4,14alpha-trimethyl-5alpha-pregnane or a 9(10->19)abeo 4,4,14alpha-trimethyl-5alpha-pregnane system. n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid is found in Buxus balearica. n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid was first documented in 2010 (PMID: 20954721). Based on a literature review very few articles have been published on Buxalongifolamidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204532D          

 42 46  0  0  1  0            999 V2000
   -0.2108    0.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505   -0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6368    0.1372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0039   -1.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3176   -1.6018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4562   -1.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9674   -1.9632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3511   -1.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7907   -2.0166    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1412   -1.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9436   -1.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938   -1.5860    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3040   -1.1663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7674   -0.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8280   -0.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380    0.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0226   -1.5716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7329   -1.1520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4515   -1.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8132   -3.7537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0467   -4.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
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 17 18  1  1  0  0  0
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  9 32  1  6  0  0  0
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  7 35  1  0  0  0  0
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 37 38  1  1  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
M  END

     RDKit          3D

 92 96  0  0  0  0  0  0  0  0999 V2000
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   -4.8007    2.0124    0.8755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2520    0.7635    1.1675 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.1484    0.3236    0.1912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2712    1.2762   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1447    0.5440    1.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3690    0.5506   -0.0435 C   0  0  1  0  0  0  0  0  0  0  0  0
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   10.1332   -0.6585   -1.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309072204532D          

 42 46  0  0  1  0            999 V2000
   -0.2108    0.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505   -0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6368    0.1372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0039   -1.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3176   -1.6018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4562   -1.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9674   -1.9632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3511   -1.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7907   -2.0166    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1412   -1.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9436   -1.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938   -1.5860    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3040   -1.1663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7674   -0.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8280   -0.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380    0.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0226   -1.5716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7329   -1.1520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4515   -1.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1618   -1.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4598   -2.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1784   -2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1867   -3.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4764   -4.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7578   -3.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7495   -2.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309   -2.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3206   -2.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.4109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6720   -3.2330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9622   -2.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561   -2.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983   -3.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750   -3.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5096   -2.6495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0175   -3.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846   -2.4261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9321   -2.9373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6986   -2.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132   -3.7537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0467   -4.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4607   -4.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  6  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC[C@H]4[C@](C)(CO)[C@H](C=C[C@]4(O)CC3=CC[C@]12C)N=C(O)C1=CC=CC=C1)OC(C)=O)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C35H50N2O5/c1-22(37(6)7)30-27(42-23(2)39)20-34(5)26-13-14-28-32(3,21-38)29(36-31(40)24-11-9-8-10-12-24)16-18-35(28,41)19-25(26)15-17-33(30,34)4/h8-12,15-16,18,22,26-30,38,41H,13-14,17,19-21H2,1-7H3,(H,36,40)/t22-,26+,27+,28-,29-,30-,32-,33+,34-,35-/m0/s1

> <INCHI_KEY>
SQULXMOMDPJQNT-QCFSPYGNSA-N

> <FORMULA>
C35H50N2O5

> <MOLECULAR_WEIGHT>
578.794

> <EXACT_MASS>
578.371972718

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
67.69410896336154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(3R,6S,7S,8S,11R,12S,14R,15S,16R)-14-(acetyloxy)-15-[(1S)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0^{3,8}.0^{12,16}]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid

> <JCHEM_LOGP>
2.4306220943311847

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.030938918839649

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.404931747465875

> <JCHEM_PKA_STRONGEST_BASIC>
10.077903076729104

> <JCHEM_POLAR_SURFACE_AREA>
102.59

> <JCHEM_REFRACTIVITY>
167.1864

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[(3R,6S,7S,8S,11R,12S,14R,15S,16R)-14-(acetyloxy)-15-[(1S)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0^{3,8}.0^{12,16}]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid

> <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      -0.394   0.084   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.774  -0.599   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.055   0.256   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.874  -2.135   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.593  -2.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.852  -2.456   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.806  -3.665   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.522  -2.301   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.343  -3.764   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.997  -2.370   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.495  -2.012   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.708  -2.961   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.034  -2.177   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.033  -1.007   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.012  -0.988   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.471   0.454   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.376  -2.934   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      10.701  -2.150   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      12.043  -2.907   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.369  -2.124   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.058  -4.447   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.400  -5.203   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.415  -6.743   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.089  -7.527   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.748  -6.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.732  -5.230   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.391  -4.474   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.065  -5.257   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.724  -4.500   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.854  -6.035   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.530  -5.473   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.025  -5.145   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.170  -6.426   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.633  -6.326   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.951  -4.946   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.033  -6.130   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.531  -4.529   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.740  -5.483   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.171  -4.913   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      -1.518  -7.007   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      -0.087  -7.577   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.727  -7.961   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   35                                             
CONECT    8    7                                                            
CONECT    9    7   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14   15   17                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   13   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   17   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   12   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    9   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    7   36   37                                             
CONECT   36   35                                                            
CONECT   37   35    5   38                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₅₀N₂O₅

Average Mass

578.7940 Da

Monoisotopic Mass

578.37197 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC[C@H]4[C@](C)(CO)[C@H](C=C[C@]4(O)CC3=CC[C@]12C)N=C(O)C1=CC=CC=C1)OC(C)=O)N(C)C

InChI Identifier

InChI=1S/C35H50N2O5/c1-22(37(6)7)30-27(42-23(2)39)20-34(5)26-13-14-28-32(3,21-38)29(36-31(40)24-11-9-8-10-12-24)16-18-35(28,41)19-25(26)15-17-33(30,34)4/h8-12,15-16,18,22,26-30,38,41H,13-14,17,19-21H2,1-7H3,(H,36,40)/t22-,26+,27+,28-,29-,30-,32-,33+,34-,35-/m0/s1

InChI Key

SQULXMOMDPJQNT-QCFSPYGNSA-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
Buxus balearica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as buxus alkaloids. These are alkaloids with a triterpenoid-steroid pregnane type structure with C-4 methyl groups, a 9beta,10beta-cycloartenol system, and a degraded C-20 side chain. Structurally, they are derivatives of either a 9beta,10beta-cyclo-4,4,14alpha-trimethyl-5alpha-pregnane or a 9(10->19)abeo 4,4,14alpha-trimethyl-5alpha-pregnane system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Buxus alkaloids

Alternative Parents

Substituents

Abeo-9(10->19)-4,4-14(alpha)-trimethyl-5(alpha)-pregnane-skeleton
Abeoabietane diterpenoid
Diterpenoid
Benzamide
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Primary alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Alcohol
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

steroid alkaloid (CHEBI:70427 )

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

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

26389585

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53324854

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Matochko WL, James A, Lam CW, Kozera DJ, Ata A, Gengan RM: Triterpenoidal alkaloids from Buxus natalensis and their acetylcholinesterase inhibitory activity. J Nat Prod. 2010 Nov 29;73(11):1858-62. doi: 10.1021/np100494u. Epub 2010 Oct 18. [PubMed:20954721 ]
LOTUS database [Link]

Showing NP-Card for n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid (NP0242554)

MOL for NP0242554 (n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid)

3D MOL for NP0242554 (n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid)

3D SDF for NP0242554 (n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid)

3D-SDF for NP0242554 (n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid)

PDB for NP0242554 (n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid)

3D PDB for NP0242554 (n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid)

SMILES for NP0242554 (n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid)

INCHI for NP0242554 (n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid)

Structure for NP0242554 (n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid)

3D Structure for NP0242554 (n-[(3r,6s,7s,8s,11r,12s,14r,15s,16r)-14-(acetyloxy)-15-[(1s)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),4-dien-6-yl]benzenecarboximidic acid)