NP-MRD: Showing NP-Card for (11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione (NP0219989)

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Record Information

Version

1.0

Created at

2022-09-05 21:10:30 UTC

Updated at

2022-09-05 21:10:30 UTC

NP-MRD ID

NP0219989

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione

Description

Mederrhodin A belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is 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 Mederrhodin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052223102D          

 34 38  0  0  1  0            999 V2000
    1.3727   -0.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1232   -1.5221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3174   -1.6992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678   -2.4855    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6835   -2.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5917   -3.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010   -4.2023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2165   -3.8121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241   -3.0948    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4298   -2.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861   -3.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365   -4.3134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7918   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0414   -2.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4852   -1.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7347   -1.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794   -2.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8472   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967   -1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034   -2.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092   -2.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587   -2.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2645   -1.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5141   -1.0691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9578   -0.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3198   -0.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8207   -2.4647    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6265   -2.2877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5712   -3.2511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1274   -3.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7654   -3.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1538   -3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3481   -3.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985   -4.7456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  2 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 21 31  1  0  0  0  0
 20 32  2  0  0  0  0
 32 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
    4.8673   -2.1214    1.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936   -0.6713    1.9307 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5684    0.1811    1.8788 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2118    0.2032    0.6558 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1344    1.3995    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8794    2.0429   -0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6772    2.7767   -1.3439 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5851    1.6827   -1.0422 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3340    0.3837   -0.5252 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9118    0.1346   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932    0.4218   -1.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4877    0.9188   -2.4519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6348    0.2069   -1.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2269   -0.3142    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248   -0.6036    1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824   -1.1077    2.3293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778   -0.3666    0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008   -0.5449    0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6070   -1.0085    1.4057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -0.2528   -0.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439   -0.4824   -0.5255 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0987    0.4671    0.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5852    0.4587    0.7187 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2698    1.6249    0.2820 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9019    2.7544    1.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0420    1.9725   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0820   -0.8246    0.0369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3341   -1.1384    0.5258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1059   -1.9038    0.4913 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7357   -3.2747    0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8847   -1.8073   -0.1611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7671    0.2333   -1.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6410    0.4943   -2.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0030    0.9583   -3.2554 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6232   -2.4046    2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1712   -2.3914    0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9523   -2.7195    2.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9936   -0.5494    2.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8528   -0.7028    0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9190    2.1155    1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2172    1.0864    0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -0.3272   -1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0764    1.1922   -3.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0010   -1.3754    2.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724   -0.2298   -1.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6725    1.4541    0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5819    0.1704    1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8035    0.2659    1.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144    2.7577    1.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1189    3.6785    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4673    2.7885    2.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8885    2.6630   -1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1086    1.1411   -1.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1287    2.5961   -1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1257   -0.7375   -1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0054   -1.1617   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9254   -1.6991    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9835   -4.0792    0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4832   -3.3405   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3108   -3.5417    1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4832    0.4573   -2.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 31  1  0
 31 21  1  0
 21 22  1  0
 22 23  1  0
 23 27  1  0
 27 28  1  0
 23 24  1  0
 24 25  1  0
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 21 20  1  0
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 32 33  1  0
 33 34  2  0
 33 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17  2  1  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 14 18  1  0
 18 19  2  0
 27 29  1  0
 18 20  1  0
 11 13  1  0
 10 17  1  0
  9  4  1  0
 30 58  1  0
 30 59  1  0
 30 60  1  0
 29 57  1  1
 21 45  1  6
 22 46  1  0
 22 47  1  0
 23 48  1  1
 27 55  1  6
 28 56  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
 32 61  1  0
 16 44  1  0
  2 38  1  1
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 39  1  6
  5 40  1  0
  5 41  1  0
  9 42  1  6
 12 43  1  0
M  END


  Mrv1652309052223102D          

 34 38  0  0  1  0            999 V2000
    1.3727   -0.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1232   -1.5221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3174   -1.6992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678   -2.4855    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6835   -2.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5917   -3.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010   -4.2023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2165   -3.8121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241   -3.0948    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4298   -2.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861   -3.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365   -4.3134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7918   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0414   -2.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4852   -1.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7347   -1.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794   -2.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8472   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967   -1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034   -2.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092   -2.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587   -2.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2645   -1.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5141   -1.0691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9578   -0.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3198   -0.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8207   -2.4647    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6265   -2.2877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5712   -3.2511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1274   -3.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7654   -3.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1538   -3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3481   -3.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985   -4.7456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  2 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 21 31  1  0  0  0  0
 20 32  2  0  0  0  0
 32 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0219989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(CC([C@@H]1O)N(C)C)C1=CC(=O)C2=C(C(O)=C3[C@@H](C)O[C@@H]4CC(=O)O[C@@H]4C3=C2O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H27NO9/c1-8-16-19(24-14(32-8)7-15(27)34-24)23(31)17-12(26)5-10(21(29)18(17)22(16)30)13-6-11(25(3)4)20(28)9(2)33-13/h5,8-9,11,13-14,20,24,28,30-31H,6-7H2,1-4H3/t8-,9-,11?,13?,14-,20-,24+/m1/s1

> <INCHI_KEY>
YKHPVCQWMSOJBO-AJHFTWGYSA-N

> <FORMULA>
C24H27NO9

> <MOLECULAR_WEIGHT>
473.478

> <EXACT_MASS>
473.168581453

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
48.434886869574065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11R,15R,17R)-5-[(5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione

> <JCHEM_LOGP>
0.9808546244906567

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.66417635933041

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.24380859914486

> <JCHEM_PKA_STRONGEST_BASIC>
7.645309099578489

> <JCHEM_POLAR_SURFACE_AREA>
142.83

> <JCHEM_REFRACTIVITY>
119.13019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(11R,15R,17R)-5-[(5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.562  -1.373   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.097  -2.841   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.592  -3.172   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.127  -4.640   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.276  -5.276   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.104  -6.806   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.242  -7.844   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.404  -7.116   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.165  -5.777   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.669  -5.446   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.707  -6.584   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.241  -8.052   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.211  -6.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.677  -4.785   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.639  -3.648   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.105  -2.180   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.135  -3.979   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.181  -4.455   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.647  -2.987   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.220  -5.592   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.724  -5.262   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.190  -3.794   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.694  -3.463   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      12.160  -1.996   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      11.121  -0.858   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.664  -1.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.732  -4.601   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.236  -4.270   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.266  -6.069   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.304  -7.206   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.762  -6.399   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.754  -7.060   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.250  -7.391   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.784  -8.859   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   33                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10    2                                                  
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   32                                                  
CONECT   21   20   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   21                                                       
CONECT   32   20   33                                                       
CONECT   33   32   13   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxymedermycin	MeSH

Chemical Formula

C₂₄H₂₇NO₉

Average Mass

473.4780 Da

Monoisotopic Mass

473.16858 Da

IUPAC Name

(11R,15R,17R)-5-[(5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione

Traditional Name

(11R,15R,17R)-5-[(5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(CC([C@@H]1O)N(C)C)C1=CC(=O)C2=C(C(O)=C3[C@@H](C)O[C@@H]4CC(=O)O[C@@H]4C3=C2O)C1=O

InChI Identifier

InChI=1S/C24H27NO9/c1-8-16-19(24-14(32-8)7-15(27)34-24)23(31)17-12(26)5-10(21(29)18(17)22(16)30)13-6-11(25(3)4)20(28)9(2)33-13/h5,8-9,11,13-14,20,24,28,30-31H,6-7H2,1-4H3/t8-,9-,11?,13?,14-,20-,24+/m1/s1

InChI Key

YKHPVCQWMSOJBO-AJHFTWGYSA-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 isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is 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

Not Available

Direct Parent

Isochromanequinones

Alternative Parents

Substituents

Isochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Naphthalene
Benzopyran
Isochromane
2-benzopyran
Aryl ketone
Quinone
Phenol
Pyranone
Gamma butyrolactone
Benzenoid
Oxane
Pyran
Vinylogous acid
Oxolane
Tertiary amine
Tertiary aliphatic amine
Ketone
Lactone
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen 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	0.98	ChemAxon
pKa (Strongest Acidic)	8.24	ChemAxon
pKa (Strongest Basic)	7.65	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	2	ChemAxon
Refractivity	119.13 m³·mol⁻¹	ChemAxon
Polarizability	48.43 Å³	ChemAxon
Number of Rings	5	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

2343070

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3086448

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione (NP0219989)

MOL for NP0219989 ((11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione)

3D MOL for NP0219989 ((11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione)

3D SDF for NP0219989 ((11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione)

3D-SDF for NP0219989 ((11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione)

PDB for NP0219989 ((11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione)

3D PDB for NP0219989 ((11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione)

SMILES for NP0219989 ((11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione)

INCHI for NP0219989 ((11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione)

Structure for NP0219989 ((11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione)

3D Structure for NP0219989 ((11r,15r,17r)-5-[(5s,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-2,9-dihydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1,3(8),5,9-tetraene-4,7,13-trione)