NP-MRD: Showing NP-Card for 2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one (NP0184503)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 23:39:13 UTC

Updated at

2022-09-03 23:39:13 UTC

NP-MRD ID

NP0184503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one

Description

2-Hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]Trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]Heptadecan-6-one belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. 2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one is found in Maackia amurensis. 2-Hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]Trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]Heptadecan-6-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171504582D          

 34 40  0  0  0  0            999 V2000
    5.0191    0.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404   -0.4406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2327   -1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7349   -1.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405   -0.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8128   -0.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9949    0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3151   -0.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0773   -0.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7318   -0.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6241   -1.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619   -2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -2.8387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2074   -1.5185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5529   -2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    3.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    2.0344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281    2.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    2.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646    1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281    0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197    1.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197    2.0344    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  1  0  0  0  0
  5 10  1  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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 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
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  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
 25 34  1  0  0  0  0
 29 34  1  0  0  0  0
M  END

     RDKit          3D

 72 78  0  0  0  0  0  0  0  0999 V2000
    3.6215   -2.3608   -1.4950 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081   -2.0326   -0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1413   -2.9415    0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566   -2.8909    0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0413   -1.5364    0.2855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2475   -1.6395   -0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0954   -0.5166   -0.4607 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7593   -0.2770    0.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0621   -1.0391    0.9123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5885   -1.5113   -0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3597   -0.3611   -1.3900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8837   -0.2591   -1.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9261    0.8799   -0.7694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0793    1.9975   -1.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5872    3.1642   -1.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9620    3.2516    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7985    2.1366    1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1350    2.1960    2.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2912    0.9865    0.5133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1621   -0.1499    1.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753   -0.3929   -0.1170 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1590    0.3433   -1.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2126    0.6057    0.9623 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6036    1.8838    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8537    1.5997   -0.5684 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7721    0.3728   -1.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1303   -0.7356   -0.7488 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407    1.3328    0.4627 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3011    1.4269   -0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3482    0.5874    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8661   -0.7151    1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6597   -0.3965    1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195    0.0552    1.0638 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3959    0.2012    1.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667   -3.9729    0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5304   -2.7629    1.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4089   -3.3672   -0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1850   -3.5379    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990   -1.3689    1.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791   -1.7147   -1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6881   -2.6176   -0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -0.5350    1.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0176    0.8026    0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568   -1.8910    1.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0134   -2.3837   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6741   -1.7304   -0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8372   -0.5581   -2.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6901    0.7687   -2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6336   -1.0185   -2.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7718    1.8890   -2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6843    4.0025   -1.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3551    4.1866    0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9593    0.2064    2.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1086   -0.7067    1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2434   -0.0360   -1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3811    0.8247    1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7599    2.2063   -0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8770    2.6687    0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1428    2.4490   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807    0.6305   -2.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7617    0.0606   -1.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7579    2.0935    1.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2968    1.2819   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6281    2.5056   -0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0916    0.3123   -0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9052    1.1392    1.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5008   -1.3596    0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6916   -1.1484    1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3268   -1.3358    2.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000    0.3712    2.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1182   -0.6698    2.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653    1.0506    2.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  6
 21  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 34  1  0
 34 33  1  0
 33 32  1  0
 32 31  1  0
 31 30  1  0
 30 29  1  0
 29 28  1  0
 27 21  1  0
 28 25  1  0
 23 21  1  0
 28 33  1  0
 12  7  1  0
 19 13  1  0
 20  9  1  0
 22 55  1  0
  5 39  1  1
  6 40  1  0
  6 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 10 45  1  0
 10 46  1  0
 11 47  1  6
 12 48  1  0
 12 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 20 53  1  0
 20 54  1  0
  4 37  1  0
  4 38  1  0
  3 35  1  0
  3 36  1  0
 26 60  1  0
 26 61  1  0
 25 59  1  6
 24 57  1  0
 24 58  1  0
 23 56  1  1
 34 71  1  0
 34 72  1  0
 32 69  1  0
 32 70  1  0
 31 67  1  0
 31 68  1  0
 30 65  1  0
 30 66  1  0
 29 63  1  0
 29 64  1  0
 28 62  1  1
M  END


  Mrv1533004171504582D          

 34 40  0  0  0  0            999 V2000
    5.0191    0.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404   -0.4406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2327   -1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7349   -1.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405   -0.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8128   -0.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9949    0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3151   -0.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0773   -0.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7318   -0.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6241   -1.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619   -2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -2.8387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2074   -1.5185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5529   -2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    3.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    2.0344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281    2.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    2.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646    1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281    0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197    1.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197    2.0344    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  1  0  0  0  0
  5 10  1  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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 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
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  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
 25 34  1  0  0  0  0
 29 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184503

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC12C(CN3CC4CC(C3)C3=CC=CC(=O)N3C4)CCC(=O)N1CC1CC2CN2CCCCC12

> <INCHI_IDENTIFIER>
InChI=1S/C27H38N4O3/c32-25-6-3-5-24-19-10-18(13-30(24)25)12-28(14-19)16-21-7-8-26(33)31-15-20-11-22(27(21,31)34)17-29-9-2-1-4-23(20)29/h3,5-6,18-23,34H,1-2,4,7-17H2

> <INCHI_KEY>
YCYPSQCECLHIAW-UHFFFAOYSA-N

> <FORMULA>
C27H38N4O3

> <MOLECULAR_WEIGHT>
466.626

> <EXACT_MASS>
466.2943911

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.29624589314986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
0.6882089879999982

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.659717698003757

> <JCHEM_PKA_STRONGEST_BASIC>
9.51697831995485

> <JCHEM_POLAR_SURFACE_AREA>
67.33

> <JCHEM_REFRACTIVITY>
132.76539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       9.369   0.731   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.168   2.258   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.502   1.488   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.502  -0.052   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      11.835  -0.822   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.634  -2.349   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.572  -3.571   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.142  -1.577   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.584  -0.086   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.057   0.115   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.521  -1.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.944  -0.718   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.166  -1.656   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.965  -3.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.542  -3.772   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.341  -5.299   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      15.320  -2.835   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      14.099  -3.772   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.835   2.258   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.835   3.798   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.502   4.568   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.502   6.108   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       9.168   3.798   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       8.079   4.886   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.539   4.886   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.774   3.220   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.079   1.169   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.539   1.169   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       5.450   2.258   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       4.116   1.488   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.783   2.258   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.783   3.798   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.116   4.568   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.450   3.798   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23   27                                             
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17    7                                                       
CONECT   19    3   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26    2   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   25   29                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈N₄O₃

Average Mass

466.6260 Da

Monoisotopic Mass

466.29439 Da

IUPAC Name

2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one

Traditional Name

2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one

CAS Registry Number

Not Available

SMILES

OC12C(CN3CC4CC(C3)C3=CC=CC(=O)N3C4)CCC(=O)N1CC1CC2CN2CCCCC12

InChI Identifier

InChI=1S/C27H38N4O3/c32-25-6-3-5-24-19-10-18(13-30(24)25)12-28(14-19)16-21-7-8-26(33)31-15-20-11-22(27(21,31)34)17-29-9-2-1-4-23(20)29/h3,5-6,18-23,34H,1-2,4,7-17H2

InChI Key

YCYPSQCECLHIAW-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
Maackia amurensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Sparteine, lupanine, and related alkaloids

Direct Parent

Sparteine, lupanine, and related alkaloids

Alternative Parents

Substituents

Sparteine-lupanine skeleton
Cytisine
Quinolizidinone
Quinolizidine
Delta-lactam
Piperidinone
Pyridinone
Aralkylamine
Pyridine
Piperidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxamide group
Lactam
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Alkanolamine
Hydrocarbon derivative
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Amine
Carbonyl group
Organic oxygen compound
Organic oxide
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	2.18	ALOGPS
logP	0.69	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.66	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.77 m³·mol⁻¹	ChemAxon
Polarizability	50.3 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

73200985

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one (NP0184503)

MOL for NP0184503 (2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one)

3D MOL for NP0184503 (2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one)

3D SDF for NP0184503 (2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one)

3D-SDF for NP0184503 (2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one)

PDB for NP0184503 (2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one)

3D PDB for NP0184503 (2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one)

SMILES for NP0184503 (2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one)

INCHI for NP0184503 (2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one)

Structure for NP0184503 (2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one)

3D Structure for NP0184503 (2-hydroxy-3-({6-oxo-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-11-yl}methyl)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one)