NP-MRD: Showing NP-Card for (2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid (NP0306722)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 23:23:16 UTC

Updated at

2022-09-10 23:23:17 UTC

NP-MRD ID

NP0306722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid

Description

HYGROMYCIN, also known as hygromycin a, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid is found in Streptomyces noboritoensis. (2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid was first documented in 2022 (PMID: 36082708). Based on a literature review a small amount of articles have been published on HYGROMYCIN (PMID: 36077399) (PMID: 36006545) (PMID: 36005449) (PMID: 35968963).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201232D          

 36 39  0  0  1  0            999 V2000
    9.8351    0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0146    0.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5297    1.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6790   -0.3725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8721   -0.5441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7858   -1.3646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0714   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0714   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5395   -1.7001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7110   -2.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0915   -1.0870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9120   -1.1733    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  4  0  0  0
 15 17  2  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  6  0  0  0
 11 30  1  0  0  0  0
 30 31  2  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  4 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    9.6960    2.3628    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2124    2.2910    0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6024    3.3351    0.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6046    0.9925    0.7347 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2114    1.0742    0.8378 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8014   -0.2736    0.9542 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5503   -0.5292    0.7837 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.7875    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5704   -0.5189   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460   -0.8092   -0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557   -1.3873    0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697   -1.6983    0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794   -0.8739   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3843    0.4840   -0.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -1.2605   -0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5939   -2.5040    0.1513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0460   -0.4450   -0.7563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4523   -0.6318   -0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1712   -1.0755    0.3319 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3005   -1.8511    0.0052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6893    0.0977    1.1470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6821    1.0349    1.3593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3546    2.2354    1.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5369    2.1723    0.8779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7187    0.8980    0.3955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5233    0.7741   -1.0939 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9906    1.9642   -1.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0942    0.6171   -1.5079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0500    0.5109   -2.8844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2183   -1.6756    1.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5355   -1.3842    1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -1.6723    2.8243 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6898   -1.0269   -0.0318 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9568   -1.4480   -1.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7294   -0.0051   -0.3913 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0084   -0.5540   -0.4578 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1608    1.5264    0.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9567    2.1277   -0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1118    3.3322    0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9968    0.5161    1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1524   -0.5565    1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1232   -0.0573   -1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7093   -0.5942   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2446   -2.6630    0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3701    0.5091   -1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5021    0.8632   -0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    1.1858   -0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3762   -2.8684    1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5927   -1.4555   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5761   -1.6809    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1889   -2.2742   -0.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1080   -0.3026    2.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7626    3.0780    1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4946    2.3166    2.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7596    0.5276    0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0906   -0.1034   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8794    2.7171   -1.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4940    1.5148   -1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2979    0.9958   -3.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597   -2.1405    2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1587   -1.4688    2.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1742   -1.8511    0.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6246   -1.8911   -1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4438    0.4586   -1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4354   -0.1939   -1.2750 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 11 30  1  0
 30 31  2  0
 31 32  1  0
  6 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35  4  1  0
 31  8  1  0
 28 18  1  0
 25 21  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  1
  6 41  1  1
  9 42  1  0
 10 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 18 49  1  6
 19 50  1  1
 20 51  1  0
 21 52  1  1
 23 53  1  0
 23 54  1  0
 25 55  1  6
 26 56  1  6
 27 57  1  0
 28 58  1  6
 29 59  1  0
 30 60  1  0
 32 61  1  0
 33 62  1  1
 34 63  1  0
 35 64  1  6
 36 65  1  0
M  END


  Mrv1652309112201232D          

 36 39  0  0  1  0            999 V2000
    9.8351    0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0146    0.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5297    1.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6790   -0.3725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8721   -0.5441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7858   -1.3646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0714   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0714   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5395   -1.7001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7110   -2.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0915   -1.0870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9120   -1.1733    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  4  0  0  0
 15 17  2  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  6  0  0  0
 11 30  1  0  0  0  0
 30 31  2  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  4 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0306722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)[C@H]1O[C@@H](OC2=CC=C(\C=C(/C)C(O)=N[C@H]3[C@H](O)[C@H]4OCO[C@H]4[C@@H](O)[C@@H]3O)C=C2O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO12/c1-8(22(32)24-13-14(27)16(29)21-20(15(13)28)33-7-34-21)5-10-3-4-12(11(26)6-10)35-23-18(31)17(30)19(36-23)9(2)25/h3-6,13-21,23,26-31H,7H2,1-2H3,(H,24,32)/b8-5+/t13-,14-,15+,16+,17+,18+,19-,20-,21+,23-/m1/s1

> <INCHI_KEY>
YQYJSBFKSSDGFO-YYVVTDTASA-N

> <FORMULA>
C23H29NO12

> <MOLECULAR_WEIGHT>
511.48

> <EXACT_MASS>
511.168975378

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.61460793008473

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-N-[(3aR,4S,5R,6R,7S,7aS)-4,6,7-trihydroxy-hexahydro-2H-1,3-benzodioxol-5-yl]-3-(4-{[(2S,3S,4S,5S)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid

> <JCHEM_LOGP>
-0.8655929826666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.690241466462705

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.475665084718228

> <JCHEM_PKA_STRONGEST_BASIC>
2.130199191519818

> <JCHEM_POLAR_SURFACE_AREA>
207.95999999999998

> <JCHEM_REFRACTIVITY>
118.07640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-[(3aR,4S,5R,6R,7S,7aS)-4,6,7-trihydroxy-hexahydro-2H-1,3-benzodioxol-5-yl]-3-(4-{[(2S,3S,4S,5S)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic 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      18.359   0.872   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.827   0.711   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      15.922   1.957   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      16.201  -0.695   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      14.695  -1.016   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      14.534  -2.547   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.200  -3.317   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.866  -2.547   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.533  -3.317   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.199  -2.547   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.199  -1.007   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.865  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.865   1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.199   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.531   3.613   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       5.198   1.303   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.530  -0.237   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.533  -0.237   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.866  -1.007   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.200  -0.237   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      15.940  -3.174   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      16.261  -4.680   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      16.971  -2.029   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      18.502  -2.190   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   35                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   18   29                                                  
CONECT   29   28                                                            
CONECT   30   11   31                                                       
CONECT   31   30    8   32                                                  
CONECT   32   31                                                            
CONECT   33    6   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    4   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Hygromycin a	MeSH

Chemical Formula

C₂₃H₂₉NO₁₂

Average Mass

511.4800 Da

Monoisotopic Mass

511.16898 Da

IUPAC Name

(2E)-N-[(3aR,4S,5R,6R,7S,7aS)-4,6,7-trihydroxy-hexahydro-2H-1,3-benzodioxol-5-yl]-3-(4-{[(2S,3S,4S,5S)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid

Traditional Name

(2E)-N-[(3aR,4S,5R,6R,7S,7aS)-4,6,7-trihydroxy-hexahydro-2H-1,3-benzodioxol-5-yl]-3-(4-{[(2S,3S,4S,5S)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid

CAS Registry Number

Not Available

SMILES

CC(=O)[C@H]1O[C@@H](OC2=CC=C(\C=C(/C)C(O)=N[C@H]3[C@H](O)[C@H]4OCO[C@H]4[C@@H](O)[C@@H]3O)C=C2O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C23H29NO12/c1-8(22(32)24-13-14(27)16(29)21-20(15(13)28)33-7-34-21)5-10-3-4-12(11(26)6-10)35-23-18(31)17(30)19(36-23)9(2)25/h3-6,13-21,23,26-31H,7H2,1-2H3,(H,24,32)/b8-5+/t13-,14-,15+,16+,17+,18+,19-,20-,21+,23-/m1/s1

InChI Key

YQYJSBFKSSDGFO-YYVVTDTASA-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 noboritoensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Pentose monosaccharide
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Cyclitol or derivatives
Tetrahydrofuran
Cyclic alcohol
Meta-dioxolane
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
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	-0.87	ChemAxon
pKa (Strongest Acidic)	5.48	ChemAxon
pKa (Strongest Basic)	2.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	207.96 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	118.08 m³·mol⁻¹	ChemAxon
Polarizability	50.61 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

C00018293

Chemspider ID

35035444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129628308

PDB ID

4L4

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li M, Wang C, Yuan M, Lu S, Qian Z, Li B, Xu T, Wang H: [Establishment of a THP-1 macrophage model infected by recombinant Mycobacterium smegmatis expressing green fluorescent protein]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2022 Sep;38(9):789-793. [PubMed:36082708 ]
Li Y, Xiao F, Zhai C, Li X, Wu Y, Gao H, Li J, Zhai S, Liu B, Wu G: Qualitative and Quantitative Real-Time PCR Methods for Assessing False-Positive Rates in Genetically Modified Organisms Based on the Microbial-Infection-Linked HPT Gene. Int J Mol Sci. 2022 Sep 2;23(17):10000. doi: 10.3390/ijms231710000. [PubMed:36077399 ]
Gupta V, Khan S, Verma RK, Shanker K, Singh SV, Rahman LU: Overexpression of chrysanthemyl diphosphate synthase (CDS) gene in Tagetes erecta leads to the overproduction of pyrethrin. Transgenic Res. 2022 Dec;31(6):625-635. doi: 10.1007/s11248-022-00323-9. Epub 2022 Aug 25. [PubMed:36006545 ]
de Castro RJA, Rego MTAM, Brandao FS, Perez ALA, De Marco JL, Pocas-Fonseca MJ, Nichols C, Alspaugh JA, Felipe MSS, Alanio A, Bocca AL, Fernandes L: Engineered Fluorescent Strains of Cryptococcus neoformans: a Versatile Toolbox for Studies of Host-Pathogen Interactions and Fungal Biology, Including the Viable but Nonculturable State. Microbiol Spectr. 2022 Oct 26;10(5):e0150422. doi: 10.1128/spectrum.01504-22. Epub 2022 Aug 25. [PubMed:36005449 ]
Park SO, Frazer C, Bennett RJ: An Adjuvant-Based Approach Enables the Use of Dominant HYG and KAN Selectable Markers in Candida albicans. mSphere. 2022 Aug 31;7(4):e0034722. doi: 10.1128/msphere.00347-22. Epub 2022 Aug 15. [PubMed:35968963 ]
LOTUS database [Link]

Showing NP-Card for (2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid (NP0306722)

MOL for NP0306722 ((2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid)

3D MOL for NP0306722 ((2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid)

3D SDF for NP0306722 ((2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid)

3D-SDF for NP0306722 ((2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid)

PDB for NP0306722 ((2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid)

3D PDB for NP0306722 ((2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid)

SMILES for NP0306722 ((2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid)

INCHI for NP0306722 ((2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid)

Structure for NP0306722 ((2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid)

3D Structure for NP0306722 ((2e)-n-[(3ar,4s,5r,6r,7s,7as)-4,6,7-trihydroxy-hexahydro-2h-1,3-benzodioxol-5-yl]-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methylprop-2-enimidic acid)