NP-MRD: Showing NP-Card for methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate (NP0252501)

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Record Information

Version

2.0

Created at

2022-09-07 16:02:21 UTC

Updated at

2022-09-07 16:02:21 UTC

NP-MRD ID

NP0252501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate

Description

Methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2(7),3,5-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2,4,6,9-tetraene-10-carboxylate belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate is found in Tabernaemontana divaricata. Methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2(7),3,5-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2,4,6,9-tetraene-10-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518272D          

 54 65  0  0  0  0            999 V2000
    5.2536   -6.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4287   -6.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0277   -6.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6038   -6.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789   -6.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -6.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5738   -5.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9519   -6.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5007   -5.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412   -4.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9406   -3.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995   -3.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591   -3.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2597   -4.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8018   -5.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595   -4.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2347   -4.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0506   -4.6447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8755   -4.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -5.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6775   -6.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8526   -6.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267   -5.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7989   -2.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1394   -2.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -1.5926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -1.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977   -0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381   -0.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375    0.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0971   -0.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8561    0.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156   -0.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253   -0.1404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0922   -0.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8963   -0.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7727   -1.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768   -2.0189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1386   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2109   -2.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -3.2272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4067   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644   -1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4162   -1.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9584   -1.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5345   -2.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -2.2603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6573   -1.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144    1.3390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959    1.5112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3953    2.3302    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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
  3 23  1  0  0  0  0
 15 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 39 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 35 45  1  0  0  0  0
 45 46  1  0  0  0  0
 33 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 24 49  1  0  0  0  0
 49 50  1  0  0  0  0
 28 50  1  0  0  0  0
 46 50  1  0  0  0  0
 32 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END

     RDKit          3D

106117  0  0  0  0  0  0  0  0999 V2000
    3.0622   -1.8027   -3.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1797   -0.3157   -3.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141    0.4879   -2.9765 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5207    1.9799   -3.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7540    2.2953   -2.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7338    3.1531   -3.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5510    3.6311   -4.3299 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8920    3.4825   -2.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9111    4.3058   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9989    1.8348   -1.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781    1.9707   -0.3851 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0316    0.7988    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    0.0335    0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7882   -1.2404    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7179   -1.7422    1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5502   -3.0487    1.9763 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7922   -0.9950    1.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6927   -1.5437    2.8063 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5751   -1.4346    4.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9442    0.2899    1.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0195    1.0508    1.7897 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8475    1.8753    2.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0916    0.9555   -0.6733 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1664    1.5367    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1482    0.3626    0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3854   -0.4410   -0.7335 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261   -1.0118   -1.3507 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8202   -1.4484   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3560   -2.1474    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2815   -2.5813    1.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -2.3285    1.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153   -1.6364    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1588   -1.1981   -0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -1.5603    0.4894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1504   -2.7175   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5349   -2.2219   -0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5968   -0.8457   -0.2761 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2115    0.0023   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2765    1.3910   -0.7255 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7073    1.4899    0.6022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3224    1.8191    0.2147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2838    0.8467    0.7313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9617    1.5944    0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0489    2.8574    1.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7013    0.4636    2.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7381   -0.5525    2.7176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8696   -1.8041    1.9151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7511   -2.6851    2.2893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7803   -3.7014    3.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2105   -0.3743   -0.1241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2412   -0.3096   -2.5595 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2109   -0.9488   -3.8388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7168    0.2544   -3.4719 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0016    0.5436   -1.5282 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9274   -2.2522   -3.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1676   -2.1859   -3.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329   -2.1712   -2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1551    0.0812   -3.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1294   -0.1212   -4.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099    2.1326   -4.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    2.5740   -2.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167    5.1321   -2.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6227    4.6185   -4.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8273    3.6649   -3.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7629    2.7503   -0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9818   -1.8700    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2202   -3.4121    2.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6118   -0.9813    4.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5477   -2.4905    4.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4485   -0.9450    4.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2938    1.4091    3.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7615    2.0691    3.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3640    2.8567    2.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397    2.4421    0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6680    1.7066    1.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274   -0.1652    1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683    0.8352    0.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175   -2.0339   -1.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154   -2.3608    0.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180   -3.1365    2.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5506   -0.6565   -1.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1591   -3.6457    0.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5292   -2.9230   -1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7921   -2.3781   -1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2461   -2.8732   -0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5682   -0.0844   -2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231518272D          

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M  END
> <DATABASE_ID>
NP0252501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC12CCC3N(C)C4=CC=C(C=C4C33CCN(CC4OC14)C23)C1C2OC2C2(CC)CC(C(=O)OC)=C3NC4=C(OC)C(OC)=C(O)C=C4C33CCN1C23

> <INCHI_IDENTIFIER>
InChI=1S/C43H52N4O7/c1-7-40-12-11-28-42(13-15-46(38(40)42)20-27-35(40)53-27)23-17-21(9-10-25(23)45(28)3)30-33-36(54-33)41(8-2)19-22(37(49)52-6)34-43(14-16-47(30)39(41)43)24-18-26(48)31(50-4)32(51-5)29(24)44-34/h9-10,17-18,27-28,30,33,35-36,38-39,44,48H,7-8,11-16,19-20H2,1-6H3

> <INCHI_KEY>
AXBZVPIBJWOFHO-UHFFFAOYSA-N

> <FORMULA>
C43H52N4O7

> <MOLECULAR_WEIGHT>
736.91

> <EXACT_MASS>
736.38360003

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
81.0318354339377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate

> <ALOGPS_LOGP>
4.93

> <JCHEM_LOGP>
4.268598574666669

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
13.970371812189565

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.88663682695562

> <JCHEM_PKA_STRONGEST_BASIC>
8.701320983440114

> <JCHEM_POLAR_SURFACE_AREA>
111.8

> <JCHEM_REFRACTIVITY>
203.79339999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       9.807 -12.708   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.267 -12.683   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.518 -11.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.727 -12.658   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.187 -12.634   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.439 -11.288   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.938 -10.943   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.777 -11.955   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.801  -9.409   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.570  -8.484   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.756  -6.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.172  -6.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.404  -7.277   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.218  -8.806   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.230  -9.966   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.778  -8.494   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.038  -7.609   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.561  -8.670   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       9.101  -8.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.849 -10.041   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.598 -11.387   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.058 -11.362   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.770  -9.991   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.358  -4.823   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.127  -3.898   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.896  -2.973   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.312  -2.369   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.729  -1.765   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.498  -0.840   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.683   0.688   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.915  -0.237   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.331   0.367   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.563  -0.558   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       8.074  -0.262   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       8.822  -1.608   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.323  -1.952   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.372  -0.824   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.873  -1.169   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.776  -3.424   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.277  -3.769   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      13.325  -2.641   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.727  -4.552   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      10.179  -6.024   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.226  -4.208   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.774  -2.736   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       6.377  -2.087   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.389  -3.248   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.598  -4.569   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0       4.775  -4.219   0.000  0.00  0.00           N+0
HETATM   50  C   UNK     0       4.960  -2.691   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       5.517   1.896   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       6.934   2.500   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       4.286   2.821   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       4.471   4.350   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22   23                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14    6   16   23                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   21    3   20                                                  
CONECT   23   18    3   15                                                  
CONECT   24   12   25   49                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   27                                                       
CONECT   27   26   25   28                                                  
CONECT   28   27   29   31   50                                             
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32                                                       
CONECT   32   31   33   51                                                  
CONECT   33   32   34   46                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   45                                                  
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   39   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   35   46                                                  
CONECT   46   45   33   47   50                                             
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   24   50                                                  
CONECT   50   49   28   46                                                  
CONECT   51   32   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54                                                       
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  130    0
END

View in JSmol

Synonyms

Value	Source
Methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0,.0,.0,.0,]icosa-2(7),3,5-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0,.0,.0,.0,]icosa-2,4,6,9-tetraene-10-carboxylic acid	Generator
Methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylic acid	Generator

Chemical Formula

C₄₃H₅₂N₄O₇

Average Mass

736.9100 Da

Monoisotopic Mass

736.38360 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC12CCC3N(C)C4=CC=C(C=C4C33CCN(CC4OC14)C23)C1C2OC2C2(CC)CC(C(=O)OC)=C3NC4=C(OC)C(OC)=C(O)C=C4C33CCN1C23

InChI Identifier

InChI=1S/C43H52N4O7/c1-7-40-12-11-28-42(13-15-46(38(40)42)20-27-35(40)53-27)23-17-21(9-10-25(23)45(28)3)30-33-36(54-33)41(8-2)19-22(37(49)52-6)34-43(14-16-47(30)39(41)43)24-18-26(48)31(50-4)32(51-5)29(24)44-34/h9-10,17-18,27-28,30,33,35-36,38-39,44,48H,7-8,11-16,19-20H2,1-6H3

InChI Key

AXBZVPIBJWOFHO-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
Ervatamia coronaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Substituents

Aspidosperma alkaloid
Plumeran-type alkaloid
Carbazole
Quinolidine
Indolizidine
Indole or derivatives
Dihydroindole
Tertiary aliphatic/aromatic amine
Anisole
Dialkylarylamine
Para-oxazepine
Secondary aliphatic/aromatic amine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Epoxypiperidine
Alkyl aryl ether
N-alkylpyrrolidine
Piperidine
Benzenoid
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrolidine
Methyl ester
Tertiary amine
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Ether
Oxacycle
Oxirane
Enamine
Dialkyl ether
Amine
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.93	ALOGPS
logP	4.27	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	10.89	ChemAxon
pKa (Strongest Basic)	8.7	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.8 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	203.79 m³·mol⁻¹	ChemAxon
Polarizability	81.03 Å³	ChemAxon
Number of Rings	12	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

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

85043184

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

MOL for NP0252501 (methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate)

3D MOL for NP0252501 (methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate)

3D SDF for NP0252501 (methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate)

3D-SDF for NP0252501 (methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate)

PDB for NP0252501 (methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate)

3D PDB for NP0252501 (methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate)

SMILES for NP0252501 (methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate)

INCHI for NP0252501 (methyl 12-ethyl-16-{12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6-trien-4-yl}-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2(7),3,5,9-tetraene-10-carboxylate)