NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0194358)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 12:00:09 UTC

Updated at

2022-09-04 12:00:10 UTC

NP-MRD ID

NP0194358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(2S,3R,4S,5S,6R)-2-{[(1S,3aS,4R,6aR)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. (2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Carex distachya. Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-2-{[(1S,3aS,4R,6aR)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214002D          

 39 43  0  0  1  0            999 V2000
   -1.1092   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -2.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0542    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3397    1.3951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6252    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0892    1.3951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8037    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5182    1.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0892    2.2201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8037    2.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6252    2.6326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6252    3.4576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3397    2.2201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0542    2.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0937    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    1.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966    2.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036    2.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8585    3.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3065    4.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1556    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626    2.3248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007    1.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5666   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498   -4.0609    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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
  9 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 23 32  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  6  0  0  0
  6 35  1  0  0  0  0
  9 35  1  0  0  0  0
  5 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
   -2.9289    6.3216    2.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375    6.7185    0.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9342    5.7663   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9126    4.4487    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4332    3.4227   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4668    2.0529   -0.0134 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9110    1.1421   -0.9429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8823    0.2636   -1.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1425    0.1425    0.0126 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1266   -0.3201   -0.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077    0.1601   -0.9207 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3741   -0.8849   -1.7680 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4884   -1.5621   -1.3828 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3356   -3.0128   -1.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4607   -3.7651   -1.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435   -1.6107    0.0843 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9126   -2.3576    0.2884 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904   -0.2002    0.5693 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6007   -0.1025    1.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635    0.7560   -0.3377 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1097    1.0619   -1.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0153   -0.4556    1.0815 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1925   -1.8972    1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2413   -2.8319    1.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648   -4.1886    1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6798   -4.6498    0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225   -6.0228    0.7464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200   -6.9280    1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6707   -3.7621    0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982   -4.2392    0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9563   -3.4172   -0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3961   -2.4146    0.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4207    0.0113    2.2308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1451    1.3387    2.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404    1.5728    0.5146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9504    3.7954   -1.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9614    5.1356   -2.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430    6.1103   -1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605    7.4557   -1.7185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7463    5.5857    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2418    7.2430    2.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1395    5.8572    2.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110    4.2081    1.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520    2.0513    0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3409    0.7095   -2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -0.7093   -1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    0.9386   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4323   -1.2043   -1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939   -3.0240   -2.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4628   -3.4856   -1.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3017   -3.3409   -1.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259   -2.1178    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319   -1.8785    0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0821   -0.0021    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319    0.8275    2.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923    1.6895    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6435    1.4815   -2.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    0.0363    0.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6997   -2.4972    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3344   -4.8719    1.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2471   -7.9576    0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346   -6.7082    0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -6.8566    2.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9008   -4.0186   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457   -3.1612   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0768   -2.5016    0.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1879   -1.7333    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8155    2.0327    2.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038    1.5382    2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7157    2.1529    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5687    3.0535   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5782    5.4327   -3.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8197    8.1769   -1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 26  1  0
 26 25  2  0
 25 24  1  0
 24 23  2  0
 23 32  1  0
 32 29  2  0
 29 30  1  0
 30 31  1  0
 23 22  1  0
 22 33  1  0
 33 34  1  0
 34 35  1  0
 35  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  6  5  1  0
  5 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 38  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
 29 26  1  0
  9 22  1  0
 20 11  1  0
  4  5  1  0
  9 35  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 25 60  1  0
 24 59  1  0
 32 67  1  0
 31 64  1  0
 31 65  1  0
 31 66  1  0
 22 58  1  6
 34 68  1  0
 34 69  1  0
 35 70  1  1
  6 44  1  1
  8 45  1  0
  8 46  1  0
 11 47  1  6
 13 48  1  6
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  1
 17 53  1  0
 18 54  1  1
 19 55  1  0
 20 56  1  1
 21 57  1  0
 36 71  1  0
 37 72  1  0
 39 73  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
M  END


  Mrv1652309042214002D          

 39 43  0  0  1  0            999 V2000
   -1.1092   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -2.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0542    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3397    1.3951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6252    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0892    1.3951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8037    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5182    1.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0892    2.2201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8037    2.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6252    2.6326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6252    3.4576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3397    2.2201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0542    2.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0937    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    1.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966    2.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036    2.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8585    3.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3065    4.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1556    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626    2.3248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007    1.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5666   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498   -4.0609    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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
  9 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 23 32  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  6  0  0  0
  6 35  1  0  0  0  0
  9 35  1  0  0  0  0
  5 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194358

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)[C@H]1OC[C@@H]2[C@H](OC[C@]12O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O12/c1-33-17-7-5-14(9-19(17)35-3)25-27(39-26-23(32)22(31)21(30)20(10-28)38-26)12-37-24(15(27)11-36-25)13-4-6-16(29)18(8-13)34-2/h4-9,15,20-26,28-32H,10-12H2,1-3H3/t15-,20-,21-,22+,23-,24-,25-,26+,27-/m1/s1

> <INCHI_KEY>
HOFGXNLBZBHYMH-DPZCMJKASA-N

> <FORMULA>
C27H34O12

> <MOLECULAR_WEIGHT>
550.557

> <EXACT_MASS>
550.205026535

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.960546173790284

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(1S,3aS,4R,6aR)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
0.10280926666666658

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.211835049887924

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908490798597231

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083698723456

> <JCHEM_POLAR_SURFACE_AREA>
165.76

> <JCHEM_REFRACTIVITY>
132.87690000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(1S,3aS,4R,6aR)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1H-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.071  -6.756   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.595  -5.291   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.088  -4.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.388  -3.507   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.834   1.834   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.501   2.604   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.167   1.834   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.167   2.604   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.500   1.834   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.834   2.604   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.167   4.144   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.500   4.914   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.167   4.914   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.167   6.454   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.501   4.144   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.834   4.914   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.775   2.235   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.744   3.379   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.220   4.844   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.727   5.164   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.203   6.629   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.172   7.773   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.757   4.019   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.264   4.340   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.294   3.195   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.281   2.555   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.204  -0.476   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.924  -4.331   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.449  -5.795   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.942  -6.116   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.466  -7.580   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22   35                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20                                                            
CONECT   22    9   23   33                                                  
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   23                                                       
CONECT   33   22   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    6    9                                                  
CONECT   36    5   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37    3   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₂

Average Mass

550.5570 Da

Monoisotopic Mass

550.20503 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)[C@H]1OC[C@@H]2[C@H](OC[C@]12O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C27H34O12/c1-33-17-7-5-14(9-19(17)35-3)25-27(39-26-23(32)22(31)21(30)20(10-28)38-26)12-37-24(15(27)11-36-25)13-4-6-16(29)18(8-13)34-2/h4-9,15,20-26,28-32H,10-12H2,1-3H3/t15-,20-,21-,22+,23-,24-,25-,26+,27-/m1/s1

InChI Key

HOFGXNLBZBHYMH-DPZCMJKASA-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
Carex distachya	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Furanoid lignan
Furofuran lignan skeleton
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
O-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Anisole
Methoxybenzene
Phenoxy compound
Furofuran
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Tetrahydrofuran
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Ether
Acetal
Polyol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Alcohol
Organooxygen compound
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

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

162869344

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,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0194358)

MOL for NP0194358 ((2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0194358 ((2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0194358 ((2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0194358 ((2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0194358 ((2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0194358 ((2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0194358 ((2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0194358 ((2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0194358 ((2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0194358 ((2s,3r,4s,5s,6r)-2-{[(1s,3as,4r,6ar)-4-(3,4-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)