NP-MRD: Showing NP-Card for methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate (NP0165236)

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Record Information

Version

1.0

Created at

2022-09-03 00:18:22 UTC

Updated at

2022-09-03 00:18:22 UTC

NP-MRD ID

NP0165236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate

Description

160523-76-2, Also known as menoxymycin b, belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. Based on a literature review very few articles have been published on 160523-76-2.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032202182D          

 35 38  0  0  1  0            999 V2000
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  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  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 16 26  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 14 31  1  0  0  0  0
 31 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  2  0  0  0  0
 11 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END

     RDKit          3D

 66 69  0  0  0  0  0  0  0  0999 V2000
    5.1397   -0.0995    2.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2407    1.0014    1.9485 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0492    1.6415    1.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9767    1.1930    2.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1041    2.8068    0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796    2.4498   -0.7845 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7885    1.5538   -1.2741 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4962    0.2322   -1.1777 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8282   -0.3844   -2.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030   -0.1300   -0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1312    0.7415   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304    0.3679   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1574    1.2460   -0.5941 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4172   -1.0239   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625   -1.4318   -0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835   -0.4424   -0.0644 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2879   -1.1480    0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4163   -0.1588    0.4671 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5640    0.3306    1.7951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9050   -0.7682    2.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5119    1.3784    1.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2442    0.9026   -0.5726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4847    1.9360   -0.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4491    0.3115   -1.7169 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4707    1.2209   -2.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1547   -0.0359   -1.3809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1443   -2.7759    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1387   -3.6847    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2016   -3.3306   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1366   -4.3049   -0.1216 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -1.9935   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8139   -1.5578   -0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432   -2.3931   -0.6572 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    2.1621   -1.1360 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6129    2.9906   -0.4152 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0352   -0.7676    2.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -0.6653    2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1233    0.3276    3.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382    3.5504    1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0840    3.2985    0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1035    3.4224   -1.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -0.3278   -0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217   -1.4264   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3826    0.2658   -3.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9301   -0.2769   -2.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171    0.4379    0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5275   -1.8342   -0.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1916   -1.6225    1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502   -0.7293    0.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8154   -0.5308    3.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0547   -1.7080    2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0529   -0.9314    3.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0687    1.2144    2.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2760    1.4300    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0218    2.3875    2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2172    1.2791   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8445    2.8249   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9630   -0.6265   -2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7692    0.7875   -3.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4769    1.2194   -3.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835    2.2602   -2.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1617   -3.0429    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038   -4.7593    0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -4.4056   -0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3134    2.3550   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359    2.6637    0.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 34  1  0
 34 35  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 34  6  1  0
 31 14  1  0
 26 16  1  0
 32 10  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  6
  8 42  1  1
  9 43  1  0
  9 44  1  0
  9 45  1  0
 34 65  1  6
 35 66  1  0
 27 62  1  0
 28 63  1  0
 30 64  1  0
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  6
 22 56  1  6
 23 57  1  0
 24 58  1  6
 25 59  1  0
 25 60  1  0
 25 61  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 21 55  1  0
M  END


  Mrv1652309032202182D          

 35 38  0  0  1  0            999 V2000
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  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  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 16 26  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 14 31  1  0  0  0  0
 31 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  2  0  0  0  0
 11 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0165236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1O[C@H](C)C2=C([C@H]1O)C(=O)C1=C(C=CC(O)=C1C2=O)C1C[C@H](C(O)[C@@H](C)O1)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO9/c1-10-18-21(23(30)16(34-10)9-17(28)33-5)25(32)19-12(6-7-14(27)20(19)24(18)31)15-8-13(26(3)4)22(29)11(2)35-15/h6-7,10-11,13,15-16,22-23,27,29-30H,8-9H2,1-5H3/t10-,11-,13-,15?,16-,22?,23+/m1/s1

> <INCHI_KEY>
RHBRKICJOIFBBF-GIZPJETISA-N

> <FORMULA>
C25H31NO9

> <MOLECULAR_WEIGHT>
489.521

> <EXACT_MASS>
489.199881582

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.962701841186835

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R,3R,4R)-6-[(4R,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-3-yl]acetate

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
0.23251385136971456

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.135911493949468

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.298602167862628

> <JCHEM_PKA_STRONGEST_BASIC>
7.540915923156341

> <JCHEM_POLAR_SURFACE_AREA>
142.83

> <JCHEM_REFRACTIVITY>
124.7265

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,3R,4R)-6-[(4R,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1H,3H,4H-naphtho[2,3-c]pyran-3-yl]acetate

> <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      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   32                                                  
CONECT   11   10   12   34                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   31                                                  
CONECT   15   14   16   27                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   16                                                       
CONECT   27   15   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   14   32                                                  
CONECT   32   31   10   33                                                  
CONECT   33   32                                                            
CONECT   34   11    6   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Menoxymycin b	MeSH

Chemical Formula

C₂₅H₃₁NO₉

Average Mass

489.5210 Da

Monoisotopic Mass

489.19988 Da

IUPAC Name

methyl 2-[(1R,3R,4R)-6-[(4R,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-3-yl]acetate

Traditional Name

methyl [(1R,3R,4R)-6-[(4R,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1H,3H,4H-naphtho[2,3-c]pyran-3-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1O[C@H](C)C2=C([C@H]1O)C(=O)C1=C(C=CC(O)=C1C2=O)C1C[C@H](C(O)[C@@H](C)O1)N(C)C

InChI Identifier

InChI=1S/C25H31NO9/c1-10-18-21(23(30)16(34-10)9-17(28)33-5)25(32)19-12(6-7-14(27)20(19)24(18)31)15-8-13(26(3)4)22(29)11(2)35-15/h6-7,10-11,13,15-16,22-23,27,29-30H,8-9H2,1-5H3/t10-,11-,13-,15?,16-,22?,23+/m1/s1

InChI Key

RHBRKICJOIFBBF-GIZPJETISA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Benzoisochromanequinones

Direct Parent

Benzoisochromanequinones

Alternative Parents

Substituents

Benzoisochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Naphthalene
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Pyranone
Benzenoid
Pyran
Oxane
Vinylogous acid
Methyl ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	1.44	ALOGPS
logP	0.23	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	7.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	142.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.73 m³·mol⁻¹	ChemAxon
Polarizability	50.96 Å³	ChemAxon
Number of Rings	4	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

C00016703

Chemspider ID

138869

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157829

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate (NP0165236)

MOL for NP0165236 (methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate)

3D MOL for NP0165236 (methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate)

3D SDF for NP0165236 (methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate)

3D-SDF for NP0165236 (methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate)

PDB for NP0165236 (methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate)

3D PDB for NP0165236 (methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate)

SMILES for NP0165236 (methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate)

INCHI for NP0165236 (methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate)

Structure for NP0165236 (methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate)

3D Structure for NP0165236 (methyl 2-[(1r,3r,4r)-6-[(4r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetate)