NP-MRD: Showing NP-Card for methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate (NP0170704)

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Record Information

Version

2.0

Created at

2022-09-03 06:56:25 UTC

Updated at

2022-09-03 06:56:25 UTC

NP-MRD ID

NP0170704

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate

Description

Pyrifoline belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond. methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate is found in Aspidosperma pyrifolium. Based on a literature review very few articles have been published on Pyrifoline.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032208562D          

 32 37  0  0  1  0            999 V2000
    2.1702   -1.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719   -1.5308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414   -0.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3431   -1.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3092   -0.1422    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3823   -0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1050    0.8351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7556    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3933    0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0361    0.4267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8508    0.1240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1420   -0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191   -1.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9561   -0.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2531    0.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0468    1.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6385    0.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4322    0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2488    1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571    2.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8634    2.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613    1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7822    1.3477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8205    2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2641    2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    2.3256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615    2.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.0596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6403    0.5127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422    0.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193    1.4584    0.0000 C   0  0  1  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  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
 23 22  1  1  0  0  0
 10 23  1  0  0  0  0
 23 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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 32 26  1  6  0  0  0
  7 32  1  0  0  0  0
 23 32  1  0  0  0  0
M  END

     RDKit          3D

 64 69  0  0  0  0  0  0  0  0999 V2000
    0.5549    2.2579    4.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5523    2.1199    2.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5399    1.8025    2.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6073    1.6332    2.7799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6506    1.6388    0.6275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0861    1.1294    0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0867   -0.0285   -0.6158 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5128    0.4920   -1.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1142    0.8837   -1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315    0.7548   -0.1076 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6591    1.0160   -0.1681 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3073    2.1743    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432    2.3999    0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6152    3.2582    0.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1818   -0.1880   -0.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -0.4040   -1.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916    0.6307   -1.5839 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4812    0.3667   -2.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6598   -1.6846   -1.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750   -2.7131   -1.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5932   -2.4941   -0.9864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2928   -1.2379   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -0.6863    0.2341 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3167   -1.1254    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -2.2823    1.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184   -1.6461    1.0582 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -2.5224    0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5548   -2.0596   -0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4729   -0.5906   -0.7897 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3475    0.1813   -0.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2628    0.8924   -0.8062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043   -1.1660   -0.1648 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2416    2.9170    4.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255    2.7167    4.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391    1.2457    4.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6216    2.6741    0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553    0.7716    1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7310    1.9430   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349   -0.2887   -2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138    1.3853   -2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6196    0.2588   -2.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0803    1.9352   -1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870    2.9467   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    3.1303    1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2607    1.5035    0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1249   -0.3807   -1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0860    1.2848   -2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080   -0.0836   -3.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6030   -1.8173   -2.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0392   -3.6963   -2.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8796   -3.2850   -0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565   -0.4807    2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3186   -1.6190    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405   -3.1784    1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0023   -2.4442    2.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4294   -3.5489    0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072   -2.6840    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0648   -2.5713   -1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6227   -2.3529   -0.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7322   -0.4448   -1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8918    1.4606   -0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8117    1.6501   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9492    0.2002   -1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780   -1.9505   -0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 23 24  1  1
 23 32  1  0
 32  7  1  0
  7  8  1  6
  8  9  1  0
  9 10  1  0
 10  5  1  0
  5  6  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
 10 11  1  6
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  7 29  1  0
  6  7  1  0
 22 15  1  0
 32 26  1  0
 10 23  1  0
 22 23  1  0
 31 61  1  0
 31 62  1  0
 31 63  1  0
 29 60  1  6
 28 58  1  0
 28 59  1  0
 27 56  1  0
 27 57  1  0
 25 54  1  0
 25 55  1  0
 24 52  1  0
 24 53  1  0
 32 64  1  6
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
  5 36  1  6
  6 37  1  0
  6 38  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
M  END


  Mrv1652309032208562D          

 32 37  0  0  1  0            999 V2000
    2.1702   -1.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719   -1.5308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414   -0.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3431   -1.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3092   -0.1422    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3823   -0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1050    0.8351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7556    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3933    0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0361    0.4267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8508    0.1240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1420   -0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191   -1.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9561   -0.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2531    0.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0468    1.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6385    0.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4322    0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2488    1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571    2.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8634    2.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613    1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7822    1.3477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8205    2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2641    2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    2.3256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615    2.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.0596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6403    0.5127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422    0.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193    1.4584    0.0000 C   0  0  1  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  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
 23 22  1  1  0  0  0
 10 23  1  0  0  0  0
 23 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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 32 26  1  6  0  0  0
  7 32  1  0  0  0  0
 23 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0170704

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1CCN2CC[C@@]34[C@@H]2[C@@]11CC[C@]3([C@@H](C1)C(=O)OC)N(C(C)=O)C1=C(OC)C=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C25H32N2O5/c1-15(28)27-20-16(6-5-7-18(20)30-2)24-11-13-26-12-8-19(31-3)23(22(24)26)9-10-25(24,27)17(14-23)21(29)32-4/h5-7,17,19,22H,8-14H2,1-4H3/t17-,19+,22-,23+,24+,25+/m0/s1

> <INCHI_KEY>
GNRCMQYGBOTWCN-PMSRPSIBSA-N

> <FORMULA>
C25H32N2O5

> <MOLECULAR_WEIGHT>
440.54

> <EXACT_MASS>
440.231122138

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.46496075922636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,9R,15R,16S,18R,21R)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7-triene-18-carboxylate

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
1.0974373493333323

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.481062082038624

> <JCHEM_POLAR_SURFACE_AREA>
68.31

> <JCHEM_REFRACTIVITY>
117.50789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,9R,15R,16S,18R,21R)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7-triene-18-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       4.051  -2.494   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.548  -2.857   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.611  -1.743   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.107  -2.107   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.177  -0.265   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.447  -0.103   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.929   1.559   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.144   0.774   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.334   1.536   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.534   0.797   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.055   0.231   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.598  -1.209   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.622  -2.401   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.118  -1.459   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.806   1.627   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.287   2.047   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.392   0.974   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.873   1.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.664   3.541   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.560   4.614   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.078   4.194   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.701   2.701   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.060   2.516   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.132   4.122   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.093   5.297   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       4.843   4.341   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       3.288   4.589   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.132   3.534   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.348   1.978   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.195   0.957   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.265   1.445   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.263   2.722   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29   32                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11   23                                             
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   22                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   15   23                                                  
CONECT   23   22   10   24   32                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    7   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   26    7   23                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂N₂O₅

Average Mass

440.5400 Da

Monoisotopic Mass

440.23112 Da

IUPAC Name

methyl (1R,9R,15R,16S,18R,21R)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7-triene-18-carboxylate

Traditional Name

methyl (1R,9R,15R,16S,18R,21R)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7-triene-18-carboxylate

CAS Registry Number

Not Available

SMILES

CO[C@@H]1CCN2CC[C@@]34[C@@H]2[C@@]11CC[C@]3([C@@H](C1)C(=O)OC)N(C(C)=O)C1=C(OC)C=CC=C41

InChI Identifier

InChI=1S/C25H32N2O5/c1-15(28)27-20-16(6-5-7-18(20)30-2)24-11-13-26-12-8-19(31-3)23(22(24)26)9-10-25(24,27)17(14-23)21(29)32-4/h5-7,17,19,22H,8-14H2,1-4H3/t17-,19+,22-,23+,24+,25+/m0/s1

InChI Key

GNRCMQYGBOTWCN-PMSRPSIBSA-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
Aspidosperma pyrifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidofractine alkaloids

Sub Class

Not Available

Direct Parent

Aspidofractine alkaloids

Alternative Parents

Substituents

Aspidofractine skeleton
Aspidosperma alkaloid
Carbazole
Azaspirodecane
Quinolidine
Indole or derivatives
Indolizidine
Anisole
Phenol ether
Alkyl aryl ether
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Piperidine
Acetamide
Methyl ester
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Carboxylic acid ester
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Dialkyl ether
Ether
Organoheterocyclic compound
Amine
Carbonyl group
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen 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	2.09	ALOGPS
logP	1.1	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	9.48	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	68.31 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	117.51 m³·mol⁻¹	ChemAxon
Polarizability	47.46 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

101287836

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate (NP0170704)

MOL for NP0170704 (methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate)

3D MOL for NP0170704 (methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate)

3D SDF for NP0170704 (methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate)

3D-SDF for NP0170704 (methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate)

PDB for NP0170704 (methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate)

3D PDB for NP0170704 (methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate)

SMILES for NP0170704 (methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate)

INCHI for NP0170704 (methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate)

Structure for NP0170704 (methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate)

3D Structure for NP0170704 (methyl (1r,9r,15r,16s,18r,21r)-2-acetyl-4,15-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylate)