NP-MRD: Showing NP-Card for [(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid (NP0312431)

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Record Information

Version

2.0

Created at

2022-09-11 09:12:47 UTC

Updated at

2022-09-11 09:12:47 UTC

NP-MRD ID

NP0312431

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid

Description

{[(2S,3R,4R,5S)-4-{[(2R,3S,4R,5R,6S)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. [(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid is found in Penicillium brevicompactum. Based on a literature review very few articles have been published on {[(2S,3R,4R,5S)-4-{[(2R,3S,4R,5R,6S)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112211122D          

 45 48  0  0  1  0            999 V2000
   -3.1932   -4.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412   -4.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -3.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -4.3680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -5.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7723   -5.3242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2203   -4.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -4.8826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0992   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5683   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -3.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1937   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062   -3.5319    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -3.9444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3207   -3.1194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -4.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -5.6672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6486   -5.8387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -6.2803    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5445   -7.0649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075   -7.6780    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6206   -7.1260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6056   -8.2301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5595   -8.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5174   -6.1088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0694   -6.7219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -6.5504    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479   -7.3573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834   -6.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7049   -5.7434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  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  6  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 16 25  1  0  0  0  0
 15 26  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 34 40  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 42 45  1  0  0  0  0
M  END

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
   -7.6800    0.2103   -1.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1881   -0.0775   -1.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8266   -1.0956   -1.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906    0.7094   -2.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9450    0.6716   -2.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0374    0.9968   -1.3902 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6893    0.8287   -1.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8933    0.2615   -0.7985 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4075    0.0502   -1.3441 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    0.8138   -0.7576 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1009    1.7193   -1.7341 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5001    1.6356   -3.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554    0.3795   -3.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4425    1.3587   -1.7218 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291    1.0673   -0.3521 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9266    0.6008   -0.0329 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6966   -0.2222   -0.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8578   -0.4299   -0.1241 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8805    0.2459    1.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8102    0.3793    2.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0646   -0.2842    1.9922 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4608    1.1728    3.0759 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2613    1.8020    3.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3639    1.6642    2.1215 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6486    0.8974    1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5299    0.0362   -0.1662 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7862   -1.1222   -0.8919 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8133   -2.5104    0.0385 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4642   -3.1101    0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7450   -3.7170   -0.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5197   -2.2143    1.5680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3701   -0.9550   -0.0951 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6561   -1.0151    1.1269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187   -0.8731    0.2404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0013   -1.2312    1.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9077   -2.6246    1.7634 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.1327   -3.5757    2.6603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2228   -3.4007    0.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3611   -2.2684    2.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3098    0.5441   -0.0118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5289    0.8461    0.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4381    1.8970    1.7795 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.0260    3.2976    1.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9602    1.9757    2.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3392    1.3640    2.9583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9825    0.7427   -0.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8911    0.8532   -2.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2038   -0.7572   -1.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6514   -0.3554   -2.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868    1.3320   -3.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0955    2.1526   -1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6956    1.0462   -0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899    1.4755    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0559    2.7838   -1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325    2.4005   -3.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4533    1.9604   -3.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289   -0.1268   -3.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3072    1.9679    0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3831   -0.6404   -1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6967   -0.3161    1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0101    2.4276    3.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -0.2214    0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0739   -3.4068   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9275   -3.0738    1.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -1.9049   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8243   -1.8692    1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3395   -1.6276   -0.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4020   -4.3493    0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1064   -1.8404    3.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5755    1.1527    0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5557    2.4391    1.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5415    1.8389    3.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  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
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 12 13  1  0
 11 14  1  0
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 15 26  1  0
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 28 30  1  0
 28 31  1  0
 28 29  2  0
 15 16  1  0
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 17 18  2  0
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  8 32  1  0
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 36 37  2  0
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 26 10  1  0
 25 16  1  0
 25 19  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  5 49  1  0
  5 50  1  0
  6 51  1  1
  8 52  1  1
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 26 63  1  1
 30 64  1  0
 31 65  1  0
 17 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  0
 32 66  1  6
 33 67  1  0
 34 68  1  6
 38 69  1  0
 39 70  1  0
 40 71  1  1
 44 72  1  0
 45 73  1  0
M  END


  Mrv1652309112211122D          

 45 48  0  0  1  0            999 V2000
   -3.1932   -4.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412   -4.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -3.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -4.3680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -5.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7723   -5.3242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2203   -4.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -4.8826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0992   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5683   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -3.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1937   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062   -3.5319    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -3.9444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3207   -3.1194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -4.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -5.6672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6486   -5.8387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -6.2803    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5445   -7.0649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075   -7.6780    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6206   -7.1260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6056   -8.2301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5595   -8.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5174   -6.1088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0694   -6.7219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -6.5504    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479   -7.3573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834   -6.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7049   -5.7434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  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  6  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 16 25  1  0  0  0  0
 15 26  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 34 40  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 42 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312431

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@H]1O[C@H](O[C@@H]2[C@H](CO)O[C@@H]([C@@H]2OP(O)(O)=O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H28N5O19P3/c1-6(25)36-3-8-12(40-43(27,28)29)13(41-44(30,31)32)10(26)18(38-8)39-11-7(2-24)37-17(14(11)42-45(33,34)35)23-5-22-9-15(19)20-4-21-16(9)23/h4-5,7-8,10-14,17-18,24,26H,2-3H2,1H3,(H2,19,20,21)(H2,27,28,29)(H2,30,31,32)(H2,33,34,35)/t7-,8-,10-,11+,12+,13+,14+,17-,18+/m0/s1

> <INCHI_KEY>
ZYMMXLQDBUGSID-XQLDYHJTSA-N

> <FORMULA>
C18H28N5O19P3

> <MOLECULAR_WEIGHT>
711.359

> <EXACT_MASS>
711.059134696

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.40400901862805

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2S,3R,4R,5S)-4-{[(2R,3S,4R,5R,6S)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid

> <JCHEM_LOGP>
-6.02457461598259

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-6

> <JCHEM_PKA>
0.6744050055742923

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.14700845493964732

> <JCHEM_PKA_STRONGEST_BASIC>
3.897422915316907

> <JCHEM_POLAR_SURFACE_AREA>
364.35

> <JCHEM_REFRACTIVITY>
137.37910000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3R,4R,5S)-4-{[(2R,3S,4R,5R,6S)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.961  -8.978   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.930  -7.833   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.406  -6.369   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -3.424  -8.154   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.948  -9.618   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.442  -9.938   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.411  -8.794   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.095  -9.114   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.126  -7.970   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.650  -6.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.185  -6.029   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.061  -6.934   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.468  -6.308   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.185  -4.489   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       4.924   1.777   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       6.258  -0.533   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       4.924  -2.843   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.555  -5.259   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.095  -5.259   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0       4.865  -6.593   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0       3.531  -7.363   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.199  -5.823   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.635  -7.927   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.571 -10.579   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.077 -10.899   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.541 -11.723   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.016 -13.188   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      -0.014 -14.332   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      -1.158 -13.302   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       1.130 -15.363   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -1.044 -15.477   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.966 -11.403   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.996 -12.548   0.000  0.00  0.00           O+0
HETATM   42  P   UNK     0      -3.503 -12.227   0.000  0.00  0.00           P+0
HETATM   43  O   UNK     0      -3.823 -13.734   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -5.009 -11.907   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -3.182 -10.721   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   40                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19   16                                                  
CONECT   26   15   10   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32    8   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
CONECT   40   34    6   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44   45                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   42                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Value	Source
{[(2S,3R,4R,5S)-4-{[(2R,3S,4R,5R,6S)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonate	Generator

Chemical Formula

C₁₈H₂₈N₅O₁₉P₃

Average Mass

711.3590 Da

Monoisotopic Mass

711.05913 Da

IUPAC Name

{[(2S,3R,4R,5S)-4-{[(2R,3S,4R,5R,6S)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2S,3R,4R,5S)-4-{[(2R,3S,4R,5R,6S)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@H]1O[C@H](O[C@@H]2[C@H](CO)O[C@@H]([C@@H]2OP(O)(O)=O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O

InChI Identifier

InChI=1S/C18H28N5O19P3/c1-6(25)36-3-8-12(40-43(27,28)29)13(41-44(30,31)32)10(26)18(38-8)39-11-7(2-24)37-17(14(11)42-45(33,34)35)23-5-22-9-15(19)20-4-21-16(9)23/h4-5,7-8,10-14,17-18,24,26H,2-3H2,1H3,(H2,19,20,21)(H2,27,28,29)(H2,30,31,32)(H2,33,34,35)/t7-,8-,10-,11+,12+,13+,14+,17-,18+/m0/s1

InChI Key

ZYMMXLQDBUGSID-XQLDYHJTSA-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
Penicillium brevicompactum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents

Substituents

Pentose phosphate
Hexose phosphate
O-glycosyl compound
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
6-aminopurine
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
N-substituted imidazole
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Azole
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Primary alcohol
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	-6	ChemAxon
pKa (Strongest Acidic)	0.15	ChemAxon
pKa (Strongest Basic)	3.9	ChemAxon
Physiological Charge	-6	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	364.35 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	137.38 m³·mol⁻¹	ChemAxon
Polarizability	57.4 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

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

162944267

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid (NP0312431)

MOL for NP0312431 ([(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid)

3D MOL for NP0312431 ([(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid)

3D SDF for NP0312431 ([(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid)

3D-SDF for NP0312431 ([(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid)

PDB for NP0312431 ([(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid)

3D PDB for NP0312431 ([(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid)

SMILES for NP0312431 ([(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid)

INCHI for NP0312431 ([(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid)

Structure for NP0312431 ([(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid)

3D Structure for NP0312431 ([(2s,3r,4r,5s)-4-{[(2r,3s,4r,5r,6s)-6-[(acetyloxy)methyl]-3-hydroxy-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid)