NP-MRD: Showing NP-Card for (2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid (NP0146993)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 02:30:04 UTC

Updated at

2022-09-02 02:30:04 UTC

NP-MRD ID

NP0146993

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid

Description

Puromycin A belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. Purine 3'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3. (2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid is found in Streptomyces alboniger. (2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid was first documented in 1985 (PMID: 3888269). Based on a literature review very few articles have been published on puromycin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204302D          

 35 38  0  0  1  0            999 V2000
    2.1163   -9.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094   -9.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544   -8.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2474   -8.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075   -7.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -7.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -6.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -5.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486   -5.8387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -4.8826    0.0000 C   0  0  0  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
    1.1387   -4.2695    0.0000 N   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  1  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  1  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
    1.9233    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   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
    1.3515   -7.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6064   -8.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4134   -8.1926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  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  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 22 30  1  0  0  0  0
 19 30  1  0  0  0  0
 18 31  1  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  6  0  0  0
  6 33  1  0  0  0  0
 33 34  2  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
   -9.8890    1.3684   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8072    1.6795    0.8429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5117    1.2454    0.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1318    0.4637   -0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8024    0.0601   -0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8875    0.4470    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794    0.0926    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337    0.1263   -0.8202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5360    0.5138   -1.9854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3994   -0.2353   -0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7682   -0.1795   -2.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -0.5837    0.2143 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5825   -0.9286    0.1481 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8552   -2.4179    0.1760 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4296   -3.1308   -1.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9670   -3.1005   -1.1121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2497   -2.3905    0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5035   -1.5120    1.3470 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7528   -0.7808    1.1989 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4948   -0.1885    2.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5775    0.3808    1.5899 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4888    0.1232    0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3394    0.4794   -0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5181    1.2351   -0.4968 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3846    1.6075   -1.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8401    1.6208    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0154    0.0962   -2.0216 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8787   -0.6264   -2.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0537   -0.9729   -1.2603 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3501   -0.6042   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3320   -0.5348    1.4309 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5043   -0.8985    2.4905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2608    1.2472    1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5766    1.6344    1.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9418    2.4231    2.6594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7197    0.3333   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8178    1.4440    0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8856    2.0988   -0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8427    0.1488   -1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5174   -0.5635   -1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9506   -0.2025    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1752    1.3196   -2.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3935   -0.0604   -2.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539    0.7050   -2.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691   -0.4336   -0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4168   -2.8164    1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824   -2.7158   -1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7058   -4.1984   -0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3869   -3.0786   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5494   -2.0639    2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2046   -0.2010    3.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0269    0.7679   -1.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7470    1.8367   -2.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9736    2.5259   -1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9316    0.7329    1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0072    2.2461    1.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7702    2.1974    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6752   -0.9047   -3.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407    0.5062    1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8985   -1.6614    3.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5269    1.5554    2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2883    2.7229    3.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 31  1  0
 31 32  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
  6 33  1  0
 33 34  2  0
 34 35  1  0
 34  3  1  0
 31 13  1  0
 30 19  1  0
 30 22  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  5 40  1  0
  7 41  1  0
  9 42  1  0
  9 43  1  0
 11 44  1  0
 13 45  1  6
 14 46  1  1
 15 47  1  0
 15 48  1  0
 16 49  1  0
 18 50  1  1
 31 59  1  6
 32 60  1  0
 20 51  1  0
 28 58  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 33 61  1  0
 35 62  1  0
M  END


  Mrv1652309022204302D          

 35 38  0  0  1  0            999 V2000
    2.1163   -9.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094   -9.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544   -8.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2474   -8.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075   -7.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -7.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -6.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -5.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486   -5.8387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -4.8826    0.0000 C   0  0  0  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
    1.1387   -4.2695    0.0000 N   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  1  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  1  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
    1.9233    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   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
    1.3515   -7.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6064   -8.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4134   -8.1926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  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  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 22 30  1  0  0  0  0
 19 30  1  0  0  0  0
 18 31  1  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  6  0  0  0
  6 33  1  0  0  0  0
 33 34  2  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146993

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(\C=C(/N)C(O)=N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C(N=CN=C23)N(C)C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H27N7O6/c1-28(2)19-17-20(25-9-24-19)29(10-26-17)22-18(32)16(15(8-30)35-22)27-21(33)12(23)6-11-4-5-14(34-3)13(31)7-11/h4-7,9-10,15-16,18,22,30-32H,8,23H2,1-3H3,(H,27,33)/b12-6-/t15-,16-,18-,22-/m1/s1

> <INCHI_KEY>
UKSNPQPAROIFBP-NDHCZCPUSA-N

> <FORMULA>
C22H27N7O6

> <MOLECULAR_WEIGHT>
485.501

> <EXACT_MASS>
485.202281617

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.25282588328623

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid

> <ALOGPS_LOGP>
0.27

> <JCHEM_LOGP>
0.1199316690000009

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.813116401300087

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.83291634581095

> <JCHEM_PKA_STRONGEST_BASIC>
3.7295406442393855

> <JCHEM_POLAR_SURFACE_AREA>
184.59999999999997

> <JCHEM_REFRACTIVITY>
127.032

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.950 -17.902   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.444 -17.582   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.968 -16.117   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.462 -15.797   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.014 -14.332   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.016 -13.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.541 -11.723   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.571 -10.579   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.077 -10.899   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.095  -9.114   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.411  -8.794   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       2.126  -7.970   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.650  -6.505   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.185  -6.029   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.061  -6.934   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.468  -6.308   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.185  -4.489   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       4.924   1.777   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.590   2.547   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       6.258  -0.533   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       4.924  -2.843   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.555  -5.259   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.095  -5.259   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.523 -13.508   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.999 -14.973   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.505 -15.293   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   31                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   22   19                                                  
CONECT   31   18   13   32                                                  
CONECT   32   31                                                            
CONECT   33    6   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇N₇O₆

Average Mass

485.5010 Da

Monoisotopic Mass

485.20228 Da

IUPAC Name

(2Z)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid

Traditional Name

(2Z)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(\C=C(/N)C(O)=N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C(N=CN=C23)N(C)C)C=C1O

InChI Identifier

InChI=1S/C22H27N7O6/c1-28(2)19-17-20(25-9-24-19)29(10-26-17)22-18(32)16(15(8-30)35-22)27-21(33)12(23)6-11-4-5-14(34-3)13(31)7-11/h4-7,9-10,15-16,18,22,30-32H,8,23H2,1-3H3,(H,27,33)/b12-6-/t15-,16-,18-,22-/m1/s1

InChI Key

UKSNPQPAROIFBP-NDHCZCPUSA-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
Streptomyces alboniger	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. Purine 3'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 3'-deoxyribonucleosides

Direct Parent

Purine 3'-deoxyribonucleosides

Alternative Parents

Substituents

Purine 3'-deoxyribonucleoside
Cinnamic acid amide
Cinnamic acid or derivatives
Alpha-amino acid amide
Hydroxycinnamic acid or derivatives
6-alkylaminopurine
N-glycosyl compound
Glycosyl compound
Alpha-amino acid or derivatives
Methoxyphenol
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Phenol ether
Methoxybenzene
Dialkylarylamine
Anisole
Phenoxy compound
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aminopyrimidine
Phenol
Benzenoid
Imidolactam
N-substituted imidazole
Monosaccharide
Monocyclic benzene moiety
Pyrimidine
Oxolane
Imidazole
Heteroaromatic compound
Azole
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Enamine
Ether
Carbonyl group
Primary alcohol
Primary amine
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organooxygen compound
Organic oxide
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Amine
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	0.27	ALOGPS
logP	0.12	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.83	ChemAxon
pKa (Strongest Basic)	3.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	184.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.03 m³·mol⁻¹	ChemAxon
Polarizability	50.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

58837491

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90658294

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Weitzmann C, Cooperman BS: On the structural specificity of puromycin binding to Escherichia coli ribosomes. Biochemistry. 1985 Apr 23;24(9):2268-74. doi: 10.1021/bi00330a022. [PubMed:3888269 ]
LOTUS database [Link]

Showing NP-Card for (2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid (NP0146993)

MOL for NP0146993 ((2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid)

3D MOL for NP0146993 ((2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid)

3D SDF for NP0146993 ((2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid)

3D-SDF for NP0146993 ((2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid)

PDB for NP0146993 ((2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid)

3D PDB for NP0146993 ((2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid)

SMILES for NP0146993 ((2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid)

INCHI for NP0146993 ((2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid)

Structure for NP0146993 ((2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid)

3D Structure for NP0146993 ((2z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enimidic acid)