NP-MRD: Showing NP-Card for n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid (NP0327666)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-12 10:27:29 UTC

Updated at

2022-09-12 10:27:29 UTC

NP-MRD ID

NP0327666

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Benzoylbuxidienine 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,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid is found in Buxus sempervirens. It was first documented in 1993 (PMID: 36137062). Based on a literature review a significant number of articles have been published on Benzoylbuxidienine (PMID: 17049575) (PMID: 36137063) (PMID: 36137748) (PMID: 36137747).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122212272D          

 37 41  0  0  1  0            999 V2000
   -0.8132   -3.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9321   -2.9373    0.0000 C   0  0  1  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
   -0.3176   -1.6018    0.0000 C   0  0  2  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
    0.4562   -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  2  0  0  0  0  0  0  0  0  0
    3.6020   -2.4109    0.0000 C   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  2  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
    4.3206   -2.8162    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
    5.0226   -1.5716    0.0000 C   0  0  2  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
    6.4598   -2.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1618   -1.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1535   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8638    0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5824   -0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5907   -1.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8804   -1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3040   -1.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6840   -0.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9094   -0.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986   -2.6322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461   -3.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8176   -1.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  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
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  4  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 22 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
M  END

     RDKit          3D

 85 89  0  0  0  0  0  0  0  0999 V2000
   -6.3485   -1.9044   -0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0056   -0.6983    0.3331 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8958    0.1548   -0.2253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7519    1.3228    0.7592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0049    2.5317    0.0882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3183    1.2615    1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443    0.6834    0.0377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5813    1.6519   -1.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    0.1237    0.2785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3930    1.2406    0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9203    0.6654    1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9246    0.8490    0.1416 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6412    0.1943   -1.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310   -0.2779   -1.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209   -0.3142   -1.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7219   -0.7851   -1.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1619   -0.9410   -1.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5642   -0.4965   -0.3121 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3389   -1.6428    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814    0.0116   -2.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8842    1.0025   -1.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3123    1.0086   -0.3530 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6403    0.6428   -0.1155 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5655    0.0542   -0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4814   -0.5044   -1.9159 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8518   -0.0695    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0242    0.4601    1.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2113    0.3508    1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2659   -0.3025    1.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1456   -0.8474    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9290   -0.7194   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119    0.3535    0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404    0.9005    1.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3479   -1.1212    0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1506    0.1631    0.5561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7296    0.7142   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0575   -0.3382    1.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3908   -1.8238   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6930   -2.1057   -1.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4577   -2.7908    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6784   -0.9881    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1898    0.5713   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3890    1.2325    1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2296    2.3199   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289    2.2756    1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2680    0.6042    2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8254    2.6665   -0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820    1.4292   -1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437    1.7209   -1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2244   -0.6845    1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2339    2.0352    0.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262    1.7274    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2657    1.2573    2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476   -0.4055    1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0600    1.9608    0.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731   -0.7397   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525   -1.0951   -2.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7818   -0.5039   -2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3586   -2.0528   -1.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981   -2.1589    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012   -1.3744    1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1289   -2.3931    0.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3855    0.2310   -3.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1265   -1.0403   -2.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195    0.8056   -2.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4801    2.0045   -2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2465    2.1036   -0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6209   -1.4966   -2.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1808    0.9849    1.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2633    0.7947    2.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1925   -0.3777    1.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9756   -1.3624   -0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8187   -1.1509   -1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1720    1.9572    2.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064    0.8404    2.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9689    0.2812    2.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3606   -1.5116    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1742   -1.6071    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3971   -1.5524    0.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8107    0.4629   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5644    1.8226   -0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1929    0.3289   -1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4911    0.5368    2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8782   -0.9441    1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4482   -0.8691    2.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 22 32  1  0
 32 33  1  0
 32 34  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
  2 35  1  0
 35 36  1  0
 35 37  1  0
 18  3  1  0
 18  7  1  0
 15  9  1  0
 32 12  1  0
 31 26  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  1
  3 42  1  6
  4 43  1  1
  5 44  1  0
  6 45  1  0
  6 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  1
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  6
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  1
 25 68  1  0
 27 69  1  0
 28 70  1  0
 29 71  1  0
 30 72  1  0
 31 73  1  0
 33 74  1  0
 33 75  1  0
 33 76  1  0
 34 77  1  0
 34 78  1  0
 34 79  1  0
 14 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 19 60  1  0
 19 61  1  0
 19 62  1  0
 36 80  1  0
 36 81  1  0
 36 82  1  0
 37 83  1  0
 37 84  1  0
 37 85  1  0
M  END


  Mrv1652309122212272D          

 37 41  0  0  1  0            999 V2000
   -0.8132   -3.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9321   -2.9373    0.0000 C   0  0  1  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
   -0.3176   -1.6018    0.0000 C   0  0  2  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
    0.4562   -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  2  0  0  0  0  0  0  0  0  0
    3.6020   -2.4109    0.0000 C   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  2  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
    4.3206   -2.8162    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
    5.0226   -1.5716    0.0000 C   0  0  2  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
    6.4598   -2.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1618   -1.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1535   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8638    0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5824   -0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5907   -1.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8804   -1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3040   -1.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6840   -0.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9094   -0.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986   -2.6322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461   -3.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8176   -1.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  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
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  4  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 22 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327666

> <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)C4(C)C)=CC3=CC[C@]12C)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H48N2O2/c1-21(35(6)7)29-27(36)20-33(5)26-15-14-25-23(19-24(26)17-18-32(29,33)4)13-16-28(31(25,2)3)34-30(37)22-11-9-8-10-12-22/h8-12,17,19,21,25-29,36H,13-16,18,20H2,1-7H3,(H,34,37)/t21-,25+,26+,27+,28-,29-,32+,33-/m0/s1

> <INCHI_KEY>
BBFKBCLCNWMEAC-YWVLQBNOSA-N

> <FORMULA>
C33H48N2O2

> <MOLECULAR_WEIGHT>
504.759

> <EXACT_MASS>
504.371578794

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
60.906077491505386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
4.513706003365357

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.864348312286634

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.544385164143184

> <JCHEM_PKA_STRONGEST_BASIC>
9.796324479096652

> <JCHEM_POLAR_SURFACE_AREA>
56.06000000000001

> <JCHEM_REFRACTIVITY>
154.69650000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.518  -7.007   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.740  -5.483   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.531  -4.529   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.593  -2.990   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.874  -2.135   0.000  0.00  0.00           O+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       6.724  -4.500   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.530  -5.473   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.025  -5.145   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.170  -6.426   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.633  -6.326   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.951  -4.946   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.033  -6.130   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.065  -5.257   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.391  -4.474   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.376  -2.934   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      10.701  -2.150   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      12.043  -2.907   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.058  -4.447   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.369  -2.124   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.353  -0.584   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.679   0.200   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.020  -0.557   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.036  -2.097   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.710  -2.880   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.034  -2.177   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.744  -0.810   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.298  -0.825   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -3.171  -4.913   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      -4.379  -5.868   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.393  -3.389   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   18                                             
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    3    7   19                                             
CONECT   19   18                                                            
CONECT   20   13   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   22   12   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    2   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₈N₂O₂

Average Mass

504.7590 Da

Monoisotopic Mass

504.37158 Da

IUPAC Name

Not Available

Traditional Name

Not Available

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)C4(C)C)=CC3=CC[C@]12C)N(C)C

InChI Identifier

InChI=1S/C33H48N2O2/c1-21(35(6)7)29-27(36)20-33(5)26-15-14-25-23(19-24(26)17-18-32(29,33)4)13-16-28(31(25,2)3)34-30(37)22-11-9-8-10-12-22/h8-12,17,19,21,25-29,36H,13-16,18,20H2,1-7H3,(H,34,37)/t21-,25+,26+,27+,28-,29-,32+,33-/m0/s1

InChI Key

BBFKBCLCNWMEAC-YWVLQBNOSA-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
Benzamide
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Carboxamide group
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Amine
Organonitrogen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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

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

101600043

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Babar ZU, Ata A, Meshkatalsadat MH: New bioactive steroidal alkaloids from Buxus hyrcana. Steroids. 2006 Dec;71(13-14):1045-51. doi: 10.1016/j.steroids.2006.09.002. Epub 2006 Oct 17. [PubMed:17049575 ]
Salisbury L, Baraitser L: Depressing time: Waiting, melancholia, and the psychoanalytic practice of care. 2020. [PubMed:36137063 ]
Heimer G, Neuser S, Ben-Zeev B, Ebrahimi-Fakhari D: TECPR2-Related Hereditary Sensory and Autonomic Neuropathy with Intellectual Disability. 1993. [PubMed:36137062 ]
Tibbe D, Ferle P, Krisp C, Nampoothiri S, Mirzaa G, Assaf M, Parikh S, Kutsche K, Kreienkamp HJ: Regulation of Liprin-alpha phase separation by CASK is disrupted by a mutation in its CaM kinase domain. Life Sci Alliance. 2022 Sep 22;5(10). pii: 5/10/e202201512. doi: 10.26508/lsa.202201512. Print 2022 Oct. [PubMed:36137748 ]
Sengupta R, Mihelc EM, Angel S, Lanman JK, Kuhn RJ, Stahelin RV: Contribution of the Golgi apparatus in morphogenesis of a virus-induced cytopathic vacuolar system. Life Sci Alliance. 2022 Sep 22;5(10). pii: 5/10/e202000887. doi: 10.26508/lsa.202000887. Print 2022 Oct. [PubMed:36137747 ]
LOTUS database [Link]

Showing NP-Card for n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid (NP0327666)

MOL for NP0327666 (n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

3D MOL for NP0327666 (n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

3D SDF for NP0327666 (n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

3D-SDF for NP0327666 (n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

PDB for NP0327666 (n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

3D PDB for NP0327666 (n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

SMILES for NP0327666 (n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

INCHI for NP0327666 (n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

Structure for NP0327666 (n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)

3D Structure for NP0327666 (n-[(6s,8r,11r,12s,14r,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-6-yl]benzenecarboximidic acid)