NP-MRD: Showing NP-Card for n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid (NP0196382)

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Record Information

Version

2.0

Created at

2022-09-04 14:27:56 UTC

Updated at

2022-09-04 14:27:57 UTC

NP-MRD ID

NP0196382

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid

Description

N-[(6S,7R,8R,11R,12S,14R,15S,16R)-7-[(acetyloxy)methyl]-15-[(1S)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]Octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid 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-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid is found in Buxus sempervirens. Based on a literature review very few articles have been published on N-[(6S,7R,8R,11R,12S,14R,15S,16R)-7-[(acetyloxy)methyl]-15-[(1S)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]Octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042216272D          

 41 45  0  0  1  0            999 V2000
    0.7465   -4.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565   -3.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3573   -3.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9805   -3.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905   -2.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -1.9441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7511   -2.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959   -1.5388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.9330   -1.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9413   -0.7282    0.0000 O   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
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
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 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
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 12 17  1  0  0  0  0
  8 18  1  0  0  0  0
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 27 33  1  0  0  0  0
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 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 20  1  1  0  0  0
  6 41  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309042216272D          

 41 45  0  0  1  0            999 V2000
    0.7465   -4.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565   -3.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3573   -3.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9805   -3.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905   -2.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -1.9441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7511   -2.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959   -1.5388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2144   -1.9585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9330   -1.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9413   -0.7282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -1.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350   -2.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3453   -3.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0639   -2.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722   -1.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3619   -1.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979   -0.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9164   -0.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5563   -0.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3624   -0.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202    0.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6435    0.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089   -0.4609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5360    0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8031   -0.6843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4506   -0.1731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3317    0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2171   -0.4783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8646    0.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3361   -1.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8361   -1.5086    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5223   -1.9665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623   -1.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5510   -1.1472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1674   -1.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7278   -1.0938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3773   -1.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5749   -2.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9247   -1.5244    0.0000 C   0  0  1  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
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
 10 11  1  4  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 25 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 22  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 20  1  1  0  0  0
  6 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196382

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC[C@@H]4C(CC[C@H](N=C(O)C5=CC=CC=C5)[C@]4(C)COC(C)=O)=CC3=CC[C@]12C)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C35H50N2O4/c1-22(37(6)7)31-29(39)20-35(5)28-15-14-27-25(19-26(28)17-18-34(31,35)4)13-16-30(33(27,3)21-41-23(2)38)36-32(40)24-11-9-8-10-12-24/h8-12,17,19,22,27-31,39H,13-16,18,20-21H2,1-7H3,(H,36,40)/t22-,27+,28+,29+,30-,31-,33+,34+,35-/m0/s1

> <INCHI_KEY>
DNYDYJVMCPIMMQ-BZTLBABMSA-N

> <FORMULA>
C35H50N2O4

> <MOLECULAR_WEIGHT>
562.795

> <EXACT_MASS>
562.377058098

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
67.28611909196219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(6S,7R,8R,11R,12S,14R,15S,16R)-7-[(acetyloxy)methyl]-15-[(1S)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0^{3,8}.0^{12,16}]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid

> <JCHEM_LOGP>
3.583542367393944

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.864348256782108

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.425343721245229

> <JCHEM_PKA_STRONGEST_BASIC>
9.789783934714675

> <JCHEM_POLAR_SURFACE_AREA>
82.36

> <JCHEM_REFRACTIVITY>
165.6227

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[(6S,7R,8R,11R,12S,14R,15S,16R)-7-[(acetyloxy)methyl]-15-[(1S)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0^{3,8}.0^{12,16}]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.393  -8.892   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.852  -7.450   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.667  -7.198   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.830  -6.260   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.289  -4.819   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.267  -3.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.269  -4.799   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.926  -2.872   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.400  -3.656   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.742  -2.899   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.757  -1.359   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.067  -3.683   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.052  -5.223   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.378  -6.006   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.719  -5.249   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.735  -3.709   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.409  -2.926   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.910  -1.333   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.236  -0.549   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.577  -1.306   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.772  -0.333   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.276  -0.661   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.131   0.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.668   0.520   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.350  -0.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.334   0.324   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.832  -1.277   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.041  -0.323   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.819   1.201   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      13.472  -0.893   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      14.681   0.061   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.694  -2.417   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.894  -2.816   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.175  -3.671   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.450  -3.350   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.495  -2.141   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.779  -3.505   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.959  -2.042   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.304  -3.436   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.806  -3.794   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.593  -2.846   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                                                       
CONECT    6    5    7    8   41                                             
CONECT    7    6                                                            
CONECT    8    6    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    8   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   41                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   38                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   36                                             
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   27   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   25   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   22   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   20    6                                                  
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
N-[(6S,7R,8R,11R,12S,14R,15S,16R)-7-[(Acetyloxy)methyl]-15-[(1S)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0,.0,]octadeca-1(18),2-dien-6-yl]benzenecarboximidate	Generator

Chemical Formula

C₃₅H₅₀N₂O₄

Average Mass

562.7950 Da

Monoisotopic Mass

562.37706 Da

IUPAC Name

N-[(6S,7R,8R,11R,12S,14R,15S,16R)-7-[(acetyloxy)methyl]-15-[(1S)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0^{3,8}.0^{12,16}]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC[C@@H]4C(CC[C@H](N=C(O)C5=CC=CC=C5)[C@]4(C)COC(C)=O)=CC3=CC[C@]12C)N(C)C

InChI Identifier

InChI=1S/C35H50N2O4/c1-22(37(6)7)31-29(39)20-35(5)28-15-14-27-25(19-26(28)17-18-34(31,35)4)13-16-30(33(27,3)21-41-23(2)38)36-32(40)24-11-9-8-10-12-24/h8-12,17,19,22,27-31,39H,13-16,18,20-21H2,1-7H3,(H,36,40)/t22-,27+,28+,29+,30-,31-,33+,34+,35-/m0/s1

InChI Key

DNYDYJVMCPIMMQ-BZTLBABMSA-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 sempervirens	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
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Organic oxide
Organic nitrogen compound
Amine
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.58	ChemAxon
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	9.79	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	165.62 m³·mol⁻¹	ChemAxon
Polarizability	67.29 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

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KEGG Compound ID

Not Available

BioCyc ID

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BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

162980789

PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid (NP0196382)

MOL for NP0196382 (n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

3D MOL for NP0196382 (n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

3D SDF for NP0196382 (n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

3D-SDF for NP0196382 (n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

PDB for NP0196382 (n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

3D PDB for NP0196382 (n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

SMILES for NP0196382 (n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

INCHI for NP0196382 (n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

Structure for NP0196382 (n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

3D Structure for NP0196382 (n-[(6s,7r,8r,11r,12s,14r,15s,16r)-7-[(acetyloxy)methyl]-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,12,16-trimethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)