NP-MRD: Showing NP-Card for methyl 12-ethyl-16-{12-ethyl-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-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 (NP0264449)

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Record Information

Version

2.0

Created at

2022-09-08 07:58:43 UTC

Updated at

2022-09-08 07:58:43 UTC

NP-MRD ID

NP0264449

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 12-ethyl-16-{12-ethyl-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-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-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-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-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-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-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-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


  Mrv1533004251506572D          

 55 65  0  0  0  0            999 V2000
    4.0048   -7.5022    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
    6.1014   -5.3922    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
    5.2536   -6.8077    0.0000 O   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
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  1  0  0  0  0
  3 24  1  0  0  0  0
 15 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  2  0  0  0  0
 36 46  1  0  0  0  0
 46 47  1  0  0  0  0
 34 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 25 50  1  0  0  0  0
 50 51  1  0  0  0  0
 29 51  1  0  0  0  0
 47 51  1  0  0  0  0
 33 52  1  0  0  0  0
 52 53  2  0  0  0  0
 52 54  1  0  0  0  0
 54 55  1  0  0  0  0
M  END

     RDKit          3D

109119  0  0  0  0  0  0  0  0999 V2000
    2.3966   -3.3696    2.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8696   -1.9990    1.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1966   -1.5354    0.6539 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5612   -2.5294   -0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0483   -2.5749   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7348   -3.8514   -0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195   -4.9302   -0.6609 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1104   -3.8558   -0.8309 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8804   -5.0391   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6380   -1.3921   -0.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0096   -1.0562   -0.7686 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1816    0.3333   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537    0.8393   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7796    2.1289    0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8677    2.9416    0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7260    4.2597    0.9953 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1181    2.4422    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2104    3.2789    0.4004 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7304    4.1405   -0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2846    1.1406   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5656    0.6975   -0.5471 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3637    0.0529    0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9047   -0.1273   -0.5507 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4351    0.3728   -1.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1802    1.2041   -1.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5738    0.4124   -0.6053 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6591    0.9430    0.3631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6042    1.4900   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130    2.3870   -1.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9519    2.8736   -1.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1053    2.4655   -0.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0499    1.5717    0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928    1.1027    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4358    1.2826    0.5855 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3834    1.1048    2.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3330   -0.4158    2.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4546   -0.9722    1.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8172   -2.3069    0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9660   -2.6124   -0.0586 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6520   -3.6750   -0.9412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5003   -1.5068   -0.8862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7612   -1.7591   -1.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3888   -0.1738   -0.1314 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2062   -0.3428    1.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6521   -0.5570    0.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8354    0.9955   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6370    2.2389   -0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1979    2.4759    0.0938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5150    2.7678   -1.1376 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0806    3.2750   -2.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9212   -0.0191    0.0844 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5479   -0.0658    1.4413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1485   -1.1692    1.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7311   -1.4176    0.6919 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6793   -0.1299    0.2192 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0185   -4.1808    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3368   -3.5550    1.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4420   -3.5105    3.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453   -1.3520    2.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9703   -2.0430    1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1174   -2.2065   -1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1282   -3.4906   -0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3101   -5.8932   -1.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7882   -4.8351   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2594   -5.2398    0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8040   -1.6711   -1.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8043    2.5500    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8113    4.5819    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3180    3.9714   -1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8470    4.0217   -0.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5732    5.2257   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0767    0.7994    0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7471   -0.4452    1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9766   -0.7023   -0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1557    1.0506   -2.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1984   -0.4538   -2.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4481    2.2346   -1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.1200   -2.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    1.8405    0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623    2.7521   -1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    3.5704   -2.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477    0.4170    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4112    1.5074    2.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1695    1.5903    2.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3214   -0.7223    2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500   -0.7253    3.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0041   -2.7672    1.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004251506572D          

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M  END
> <DATABASE_ID>
NP0264449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC12CC(C(=O)OC)=C3NC4=C(OC)C(OC)=C(O)C=C4C33CCN(C13)C(C1OC21)C1=CC=C2N(C)C3CCC4(CC)C5N(CCC35C2=C1)CC(O)C4O

> <INCHI_IDENTIFIER>
InChI=1S/C43H54N4O8/c1-7-40-12-11-28-42(13-15-46(38(40)42)20-27(49)35(40)50)23-17-21(9-10-25(23)45(28)3)30-33-36(55-33)41(8-2)19-22(37(51)54-6)34-43(14-16-47(30)39(41)43)24-18-26(48)31(52-4)32(53-5)29(24)44-34/h9-10,17-18,27-28,30,33,35-36,38-39,44,48-50H,7-8,11-16,19-20H2,1-6H3

> <INCHI_KEY>
UDHOVDFGQKBCOZ-UHFFFAOYSA-N

> <FORMULA>
C43H54N4O8

> <MOLECULAR_WEIGHT>
754.925

> <EXACT_MASS>
754.394164715

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
83.8089516339825

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 12-ethyl-16-{12-ethyl-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-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>
4.20

> <JCHEM_LOGP>
2.8507876384026027

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
13.330617100484488

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.914096573997789

> <JCHEM_PKA_STRONGEST_BASIC>
9.73121605774896

> <JCHEM_POLAR_SURFACE_AREA>
139.73

> <JCHEM_REFRACTIVITY>
207.30349999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 12-ethyl-16-{12-ethyl-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-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                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       7.476 -14.004   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      11.389 -10.065   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  O   UNK     0       9.807 -12.708   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.770  -9.991   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.358  -4.823   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.127  -3.898   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.896  -2.973   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.312  -2.369   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.729  -1.765   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.498  -0.840   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.683   0.688   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.915  -0.237   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.331   0.367   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.563  -0.558   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       8.074  -0.262   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       8.822  -1.608   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.323  -1.952   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.372  -0.824   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.873  -1.169   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.776  -3.424   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      12.277  -3.769   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      13.325  -2.641   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.727  -4.552   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      10.179  -6.024   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       8.226  -4.208   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       7.774  -2.736   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.377  -2.087   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.389  -3.248   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.598  -4.569   0.000  0.00  0.00           C+0
HETATM   50  N   UNK     0       4.775  -4.219   0.000  0.00  0.00           N+0
HETATM   51  C   UNK     0       4.960  -2.691   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.517   1.896   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       6.934   2.500   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       4.286   2.821   0.000  0.00  0.00           O+0
HETATM   55  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   24                                             
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   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14    6   16   24                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    3   23                                                  
CONECT   23   22                                                            
CONECT   24   18    3   15                                                  
CONECT   25   12   26   50                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   28                                                       
CONECT   28   27   26   29                                                  
CONECT   29   28   30   32   51                                             
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34   52                                                  
CONECT   34   33   35   47                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   46                                                  
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   36   47                                                  
CONECT   47   46   34   48   51                                             
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   25   51                                                  
CONECT   51   50   29   47                                                  
CONECT   52   33   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  130    0
END

View in JSmol

Synonyms

Value	Source
Methyl 12-ethyl-16-{12-ethyl-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-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-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-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

C₄₃H₅₄N₄O₈

Average Mass

754.9250 Da

Monoisotopic Mass

754.39416 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC12CC(C(=O)OC)=C3NC4=C(OC)C(OC)=C(O)C=C4C33CCN(C13)C(C1OC21)C1=CC=C2N(C)C3CCC4(CC)C5N(CCC35C2=C1)CC(O)C4O

InChI Identifier

InChI=1S/C43H54N4O8/c1-7-40-12-11-28-42(13-15-46(38(40)42)20-27(49)35(40)50)23-17-21(9-10-25(23)45(28)3)30-33-36(55-33)41(8-2)19-22(37(51)54-6)34-43(14-16-47(30)39(41)43)24-18-26(48)31(52-4)32(53-5)29(24)44-34/h9-10,17-18,27-28,30,33,35-36,38-39,44,48-50H,7-8,11-16,19-20H2,1-6H3

InChI Key

UDHOVDFGQKBCOZ-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
Dihydroindole
Indole or derivatives
Dialkylarylamine
Anisole
Tertiary aliphatic/aromatic amine
Para-oxazepine
Alkyl aryl ether
Aralkylamine
Epoxypiperidine
Secondary aliphatic/aromatic amine
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Piperidine
N-alkylpyrrolidine
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Pyrrolidine
Enoate ester
Methyl ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
1,2-aminoalcohol
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Carboxylic acid derivative
Dialkyl ether
Enamine
Oxirane
Ether
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen 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	4.2	ALOGPS
logP	2.85	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	10.91	ChemAxon
pKa (Strongest Basic)	9.73	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	139.73 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	207.3 m³·mol⁻¹	ChemAxon
Polarizability	83.81 Å³	ChemAxon
Number of Rings	11	ChemAxon
Bioavailability	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

MOL for NP0264449 (methyl 12-ethyl-16-{12-ethyl-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-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 NP0264449 (methyl 12-ethyl-16-{12-ethyl-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-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 NP0264449 (methyl 12-ethyl-16-{12-ethyl-13,14-dihydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-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)