NP-MRD: Showing NP-Card for 5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium (NP0210231)

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Record Information

Version

2.0

Created at

2022-09-05 07:57:14 UTC

Updated at

2022-09-05 07:57:14 UTC

NP-MRD ID

NP0210231

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium

Description

98296-22-1, Also known as plastatin, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. 5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium is found in Penicillium chermesinum. Based on a literature review very few articles have been published on 98296-22-1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052209572D          

 37 40  0  0  1  0            999 V2000
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    1.4289   -4.1250    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9293   -5.2049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4143   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9293   -3.8701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1843   -3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6993   -2.4180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1843   -1.7506    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9293   -0.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4814   -0.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2264    0.4318    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.9715    1.2164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0110    0.6867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4418    0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9689   -2.0055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6363   -1.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9689   -2.8305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6363   -3.3154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5501   -4.1359    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.7296   -4.0497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3706   -4.2221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4639   -4.9564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2587   -6.1695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4382   -6.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1027   -5.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
 10 11  2  0  0  0  0
 11 12  1  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
 11 15  1  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  6  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
 21 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 12 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
  9 37  2  0  0  0  0
 33 37  1  0  0  0  0
M  CHG  1  37   1
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    6.8955   -3.6520   -0.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3052   -3.1980    0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9559   -3.2588    1.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8842   -2.5312    3.2089 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.9832   -2.6192    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3594   -2.1584    1.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334   -2.5625   -1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471   -1.8668   -1.0941 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339   -0.1810   -0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0894    0.1735   -0.8087 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7097    1.4239   -0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6959    2.3673   -0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0180    3.5261   -0.1923 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2994    3.2960   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5258    1.9982   -0.5344 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7591    1.2939   -0.7165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6795   -0.0483   -0.3593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9758   -0.4681   -0.0837 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4096   -1.5955   -0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7120   -1.9613   -0.6639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1578   -3.2224   -1.7017 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.3337   -3.1234   -2.9548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8781   -4.6717   -0.8847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7848   -3.1349   -2.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8885    0.7107   -0.1155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8823    0.6966    0.8276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8731    1.8522    0.1343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4645    1.8233    1.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8108    3.2162    2.3188 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5847    3.6172    3.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0256    2.8519    3.4737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3280    4.4956    1.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0203    2.0161   -0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396    2.7364   -0.2316 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2049    1.9548   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7493    0.6758   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834    0.7426   -0.6198 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.9303   -2.6878    1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1934   -4.3413    2.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437   -3.6941   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181   -2.1341   -1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1028    4.0282   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1322    1.3250   -1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9667   -0.8856    0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7213   -2.4505   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3315   -1.3469   -2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7567   -5.0768   -0.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2659   -2.4423   -1.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2688    0.9287   -1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6903    1.1651    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2846    2.8033   -0.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9213    3.1055    3.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3058    4.6496    1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2045    3.7645   -0.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2432    2.2516   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3794   -0.1771   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 23  1  0
 21 24  1  0
 21 22  2  0
 18 17  1  0
 17 16  1  0
 16 27  1  0
 27 28  1  0
 28 29  1  0
 29 31  1  0
 29 32  1  0
 29 30  2  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37  9  2  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  9 10  1  0
 10 11  2  0
 27 25  1  0
 11 15  1  0
 11 12  1  0
 37 33  1  0
 26 50  1  0
 25 49  1  6
 18 44  1  1
 19 45  1  0
 19 46  1  0
 23 47  1  0
 24 48  1  0
 16 43  1  6
 27 51  1  6
 31 52  1  0
 32 53  1  0
 14 42  1  0
 34 54  1  0
 35 55  1  0
 36 56  1  0
  7 40  1  0
  7 41  1  0
  3 38  1  0
  3 39  1  0
M  CHG  1  37   1
M  END


  Mrv1652309052209572D          

 37 40  0  0  1  0            999 V2000
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    1.4289   -4.1250    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9293   -5.2049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4143   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9293   -3.8701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1843   -3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6993   -2.4180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1843   -1.7506    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9293   -0.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4814   -0.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2264    0.4318    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.9715    1.2164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0110    0.6867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4418    0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9689   -2.0055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6363   -1.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9689   -2.8305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6363   -3.3154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5501   -4.1359    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.7296   -4.0497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3706   -4.2221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4639   -4.9564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2587   -6.1695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4382   -6.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1027   -5.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  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
 21 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 12 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
  9 37  2  0  0  0  0
 33 37  1  0  0  0  0
M  CHG  1  37   1
M  END
> <DATABASE_ID>
NP0210231

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COP(O)(O)=O)OC([C@@H]1OP(O)(O)=O)N1C=NC2=C3NC=C[N+]3=C(SCC(=O)C(=O)CBr)N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H18BrN5O12P2S/c17-3-7(23)8(24)5-37-16-20-14-10(13-18-1-2-21(13)16)19-6-22(14)15-12(34-36(29,30)31)11(25)9(33-15)4-32-35(26,27)28/h1-2,6,9,11-12,15,25H,3-5H2,(H4,26,27,28,29,30,31)/p+1/t9-,11-,12-,15?/m1/s1

> <INCHI_KEY>
UFGRPFGLXVTQEE-FJFSNTMWSA-O

> <FORMULA>
C16H19BrN5O12P2S

> <MOLECULAR_WEIGHT>
647.26

> <EXACT_MASS>
645.940406

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
51.660095895706526

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3R,4R,5R)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-3H,9H-6lambda5-imidazo[2,1-f]purin-6-ylium

> <JCHEM_LOGP>
-2.4080980240990706

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
1.4296936254027752

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.34108299736812997

> <JCHEM_PKA_STRONGEST_BASIC>
0.8610490068290113

> <JCHEM_POLAR_SURFACE_AREA>
247.71999999999994

> <JCHEM_REFRACTIVITY>
126.75979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3R,4R,5R)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9H-6lambda5-imidazo[2,1-f]purin-6-ylium

> <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  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4 Br   UNK     0       2.667  -7.700   0.000  0.00  0.00          Br+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       9.336  -6.930   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      12.003  -6.930   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      14.801  -9.716   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      15.707  -8.470   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      14.801  -7.224   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      15.277  -5.759   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.372  -4.514   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      15.277  -3.268   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.801  -1.803   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.832  -0.659   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0      15.356   0.806   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0      14.880   2.271   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      16.821   1.282   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.891   0.330   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      16.742  -3.744   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      17.988  -2.838   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      16.742  -5.284   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      17.988  -6.189   0.000  0.00  0.00           O+0
HETATM   29  P   UNK     0      17.827  -7.720   0.000  0.00  0.00           P+0
HETATM   30  O   UNK     0      16.295  -7.559   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      19.358  -7.881   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      17.666  -9.252   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      11.683 -11.516   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      10.151 -11.677   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.525 -10.270   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      10.669  -9.240   0.000  0.00  0.00           N+1
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   37                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   18   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   16   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33   12   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    9   33                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
Plastatin	MeSH

Chemical Formula

C₁₆H₁₉BrN₅O₁₂P₂S

Average Mass

647.2600 Da

Monoisotopic Mass

645.94041 Da

IUPAC Name

5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3R,4R,5R)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-3H,9H-6lambda5-imidazo[2,1-f]purin-6-ylium

Traditional Name

5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3R,4R,5R)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9H-6lambda5-imidazo[2,1-f]purin-6-ylium

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COP(O)(O)=O)OC([C@@H]1OP(O)(O)=O)N1C=NC2=C3NC=C[N+]3=C(SCC(=O)C(=O)CBr)N=C12

InChI Identifier

InChI=1S/C16H18BrN5O12P2S/c17-3-7(23)8(24)5-37-16-20-14-10(13-18-1-2-21(13)16)19-6-22(14)15-12(34-36(29,30)31)11(25)9(33-15)4-32-35(26,27)28/h1-2,6,9,11-12,15,25H,3-5H2,(H4,26,27,28,29,30,31)/p+1/t9-,11-,12-,15?/m1/s1

InChI Key

UFGRPFGLXVTQEE-FJFSNTMWSA-O

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
Penicillium chermesinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside monophosphates

Alternative Parents

Substituents

Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Aryl thioether
Monoalkyl phosphate
Alkylarylthioether
Organic phosphoric acid derivative
Alpha-diketone
Alkyl phosphate
N-substituted imidazole
Monosaccharide
Phosphoric acid ester
Pyrimidine
Imidazole
Oxolane
Alpha-haloketone
Azole
Heteroaromatic compound
Ketone
Secondary alcohol
Thioether
Sulfenyl compound
Organoheterocyclic compound
Oxacycle
Azacycle
Aldehyde
Alkyl bromide
Organohalogen compound
Organobromide
Organonitrogen compound
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Organosulfur compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Alkyl halide
Organic cation
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	-2.4	ChemAxon
pKa (Strongest Acidic)	0.34	ChemAxon
pKa (Strongest Basic)	0.86	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	247.72 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	126.76 m³·mol⁻¹	ChemAxon
Polarizability	51.66 Å³	ChemAxon
Number of Rings	4	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

C00018643

Chemspider ID

4589184

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127078

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium (NP0210231)

MOL for NP0210231 (5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium)

3D MOL for NP0210231 (5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium)

3D SDF for NP0210231 (5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium)

3D-SDF for NP0210231 (5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium)

PDB for NP0210231 (5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium)

3D PDB for NP0210231 (5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium)

SMILES for NP0210231 (5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium)

INCHI for NP0210231 (5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium)

Structure for NP0210231 (5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium)

3D Structure for NP0210231 (5-[(4-bromo-2,3-dioxobutyl)sulfanyl]-3-[(3r,4r,5r)-4-hydroxy-3-(phosphonooxy)-5-[(phosphonooxy)methyl]oxolan-2-yl]-9h-6λ⁵-imidazo[2,1-f]purin-6-ylium)