NP-MRD: Showing NP-Card for 3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate (NP0329583)

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Record Information

Version

2.0

Created at

2022-09-12 14:06:26 UTC

Updated at

2022-09-12 14:06:27 UTC

NP-MRD ID

NP0329583

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate

Description

3,5-Bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]Icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids. 3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate is found in Clivia miniata. 3,5-Bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]Icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514012D          

 58 68  0  0  0  0            999 V2000
    1.0237   -8.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064   -8.3707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652   -8.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076   -8.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9948   -7.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5266   -7.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2463   -6.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781   -5.7511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5902   -5.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8705   -6.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220   -5.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9342   -5.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4660   -4.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2781   -4.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5584   -5.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8099   -4.2946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6220   -4.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1539   -3.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9660   -3.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6173   -3.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3002   -3.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0708   -4.7034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5772   -5.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2463   -4.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7145   -5.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9023   -5.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3705   -5.8465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6508   -6.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1190   -7.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4629   -6.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7432   -7.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5554   -7.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9909   -8.3894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7918   -8.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8514   -7.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0872   -7.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8069   -6.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9948   -6.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1857   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7175   -3.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736   -3.8590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -4.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296   -4.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342   -6.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1539   -5.4607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -5.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385   -4.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -5.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0022   -5.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5340   -6.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586   -6.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -7.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050   -7.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2537   -7.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4416   -7.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098   -6.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0976   -6.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1827   -7.6432    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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 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
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 32 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 25 38  1  0  0  0  0
 30 38  1  0  0  0  0
 13 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 11 42  1  0  0  0  0
 42 43  1  0  0  0  0
  7 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 50 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 48 56  1  0  0  0  0
 56 57  1  0  0  0  0
 44 57  1  0  0  0  0
 57 58  1  0  0  0  0
  2 58  1  0  0  0  0
  5 58  1  0  0  0  0
M  END

     RDKit          3D

101111  0  0  0  0  0  0  0  0999 V2000
   -2.1221    5.8784    1.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9179    5.1029    1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3115    5.5786    1.5487 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3566    4.8409    1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7095    5.4255    1.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951    3.6109    0.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3332    2.8529    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613    3.3869   -0.0287 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646    1.5259   -0.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3715    0.8275   -0.8386 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2083    0.2383   -2.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815   -0.3997   -2.7040 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2310   -1.6616   -3.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4156   -2.5191   -3.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2003   -1.8295   -2.1541 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4841   -1.3936   -2.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4214   -0.7635   -1.5979 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7188   -1.2438   -0.3498 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7393   -1.7374    0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4100   -2.9100    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3990   -3.3786    1.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7252   -2.7177    2.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0496   -1.5669    2.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575   -1.0700    1.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3141    0.1327    2.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6238    0.7441    3.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3310    0.5718    1.2622 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005   -0.1974    0.2169 C   0  0  1  0  0  0  0  0  0  0  0  0
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    9.3076   -4.3150    1.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2036   -4.5298    1.0459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1041    3.1053    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1479    3.8731    0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5077    3.3580    0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5409    3.9138    1.1254 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9806    1.5804   -0.1967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3838    1.5358   -1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8674    1.2717   -1.7621 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6847    2.5051   -1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2900    2.2553   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8181    0.9960    0.3261 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7389    0.3410    1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3347    0.2051   -0.7580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1235   -0.6007   -0.4342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3823   -1.9029    0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5854   -2.5419    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7385   -3.7694    0.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6967   -4.3870    1.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4825   -3.7408    1.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3312   -2.5095    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -1.7892    0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1012   -2.3775    1.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9395   -0.5316    0.3906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1734    0.2141    0.4095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1408   -5.6033    1.9354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3283   -5.9643    1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8125   -4.6598    0.9047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102    6.1218    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6449    5.3546    2.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7805    6.8511    2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1032    5.6372    0.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4052    4.7542    1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    6.4052    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2358    1.5571   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4426   -0.5831   -2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    1.0187   -2.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9784    0.3350   -3.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2818   -2.1679   -3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595   -1.3879   -4.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1165   -3.5348   -2.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0282   -2.6034   -4.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2914   -1.8690   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5337   -0.3042   -2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5576   -1.8100   -3.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1532    0.0539   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0884   -2.1373   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2028   -3.4925   -0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2637   -0.9958    3.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6888   -5.2457    2.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0636   -3.7655    1.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291    2.1279   -0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7286    2.2644    0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8612    0.7886   -2.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2116    2.5653   -2.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0691    0.9377   -2.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0863    3.4429   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004161514012D          

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M  END
> <DATABASE_ID>
NP0329583

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2CC(OC(=O)C3=CC(C(=O)OC4CC5CCN(C)C5C5C4OC(=O)C4=CC6=C(OCO6)C=C54)=C(C)N=C3C)C3OC(=O)C4=CC5=C(OCO5)C=C4C3C12

> <INCHI_IDENTIFIER>
InChI=1S/C43H43N3O12/c1-18-22(40(47)55-32-9-20-5-7-45(3)36(20)34-24-12-28-30(53-16-51-28)14-26(24)42(49)57-38(32)34)11-23(19(2)44-18)41(48)56-33-10-21-6-8-46(4)37(21)35-25-13-29-31(54-17-52-29)15-27(25)43(50)58-39(33)35/h11-15,20-21,32-39H,5-10,16-17H2,1-4H3

> <INCHI_KEY>
CJYOGPFDNAEALZ-UHFFFAOYSA-N

> <FORMULA>
C43H43N3O12

> <MOLECULAR_WEIGHT>
793.826

> <EXACT_MASS>
793.284673837

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
84.38300483681711

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
3.8721794583333344

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.29853786452141

> <JCHEM_POLAR_SURFACE_AREA>
161.48999999999998

> <JCHEM_REFRACTIVITY>
202.15609999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.911 -15.836   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.385 -15.625   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.682 -16.736   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.068 -16.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.857 -14.538   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.850 -13.361   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.326 -11.913   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.319 -10.735   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.835 -11.006   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.358 -12.455   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.828  -9.829   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.344 -10.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.337  -8.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.852  -9.194   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.376 -10.642   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0     -10.845  -8.017   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -12.361  -8.288   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -13.354  -7.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -14.870  -7.381   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -16.086  -6.436   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -17.360  -7.300   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0     -16.932  -8.780   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0     -17.877  -9.996   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -15.393  -8.830   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.400 -10.007   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.884  -9.736   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -11.892 -10.913   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -12.415 -12.362   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -11.422 -13.539   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -13.931 -12.633   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -14.454 -14.081   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -15.970 -14.352   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -16.783 -15.660   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -18.278 -15.291   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -18.389 -13.755   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -16.963 -13.175   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -16.440 -11.727   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -14.924 -11.456   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.813  -7.474   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -8.806  -6.297   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0      -6.297  -7.203   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0      -5.305  -8.381   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -3.789  -8.110   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.810 -11.642   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -0.287 -10.193   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       1.229  -9.922   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       1.752  -8.474   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       2.221 -11.099   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       3.737 -10.828   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.730 -12.006   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       6.269 -12.056   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       6.697 -13.535   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       5.423 -14.399   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       4.207 -13.454   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       2.691 -13.725   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       1.698 -12.548   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       0.182 -12.819   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -0.341 -14.267   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   58                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   58                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   44                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   42                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   39                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   19   25                                                  
CONECT   25   24   26   38                                                  
CONECT   26   25   17   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   32   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   25   30                                                  
CONECT   39   13   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   11   43                                                  
CONECT   43   42                                                            
CONECT   44    7   45   57                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   56                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   54                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   50   55                                                  
CONECT   55   54   56                                                       
CONECT   56   55   48   57                                                  
CONECT   57   56   44   58                                                  
CONECT   58   57    2    5                                                  
MASTER        0    0    0    0    0    0    0    0   58    0  136    0
END

View in JSmol

Synonyms

Value	Source
3,5-Bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0,.0,.0,]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylic acid	Generator
3,5-Bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylic acid	Generator

Chemical Formula

C₄₃H₄₃N₃O₁₂

Average Mass

793.8260 Da

Monoisotopic Mass

793.28467 Da

IUPAC Name

3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate

Traditional Name

3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate

CAS Registry Number

Not Available

SMILES

CN1CCC2CC(OC(=O)C3=CC(C(=O)OC4CC5CCN(C)C5C5C4OC(=O)C4=CC6=C(OCO6)C=C54)=C(C)N=C3C)C3OC(=O)C4=CC5=C(OCO5)C=C4C3C12

InChI Identifier

InChI=1S/C43H43N3O12/c1-18-22(40(47)55-32-9-20-5-7-45(3)36(20)34-24-12-28-30(53-16-51-28)14-26(24)42(49)57-38(32)34)11-23(19(2)44-18)41(48)56-33-10-21-6-8-46(4)37(21)35-25-13-29-31(54-17-52-29)15-27(25)43(50)58-39(33)35/h11-15,20-21,32-39H,5-10,16-17H2,1-4H3

InChI Key

CJYOGPFDNAEALZ-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
Clivia miniata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Homolycorine-type amaryllidaceae alkaloids

Direct Parent

Homolycorine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Homolycorine skeleton
Tetracarboxylic acid or derivatives
Benzopyran
Isochromane
2-benzopyran
Benzodioxole
Indole or derivatives
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Methylpyridine
Aralkylamine
Pyridine
Benzenoid
N-alkylpyrrolidine
Heteroaromatic compound
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Amine
Organopnictogen compound
Organic oxygen 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	3.42	ALOGPS
logP	3.87	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	9.3	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	161.49 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	202.16 m³·mol⁻¹	ChemAxon
Polarizability	84.38 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

74258238

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate (NP0329583)

MOL for NP0329583 (3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate)

3D MOL for NP0329583 (3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate)

3D SDF for NP0329583 (3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate)

3D-SDF for NP0329583 (3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate)

PDB for NP0329583 (3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate)

3D PDB for NP0329583 (3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate)

SMILES for NP0329583 (3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate)

INCHI for NP0329583 (3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate)

Structure for NP0329583 (3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate)

3D Structure for NP0329583 (3,5-bis({4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0²,¹⁰.0³,⁷.0¹⁵,¹⁹]icosa-1(20),13,15(19)-trien-9-yl}) 2,6-dimethylpyridine-3,5-dicarboxylate)