NP-MRD: Showing NP-Card for 4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate (NP0176980)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 14:44:18 UTC

Updated at

2022-09-03 14:44:18 UTC

NP-MRD ID

NP0176980

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate

Description

4,5,6-Trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]Hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}benzoate belongs to the class of organic compounds known as ubiquinols. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methylbenzene-1,4-diol moiety to which an isoprenyl group is attached at ring position 2(or 6). 4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate is found in Terminalia chebula. 4,5,6-Trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]Hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151519412D          

 45 50  0  0  0  0            999 V2000
    5.3589    2.6615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5372    2.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629    3.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4104    4.0116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362    4.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2836    5.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1144    4.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6402    5.2885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    3.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9452    3.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412    3.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937    2.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3925    1.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7385    1.1728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0388    2.7623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8441    1.2998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2796    0.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341   -1.1864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6985   -2.3043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8496   -3.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427   -0.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967    0.6031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7124    1.0989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 24 43  1  0  0  0  0
 43 44  2  0  0  0  0
 29 44  1  0  0  0  0
 44 45  1  0  0  0  0
 33 45  1  0  0  0  0
 39 45  2  0  0  0  0
M  END

     RDKit          3D

 65 70  0  0  0  0  0  0  0  0999 V2000
    0.4367   -0.2835   -0.6399 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0939   -1.0885    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4494   -0.7511    0.2327 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107    0.4232   -0.3263 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4750    1.2623    0.8727 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2230    0.4047    1.6781 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973    2.4345    0.4563 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5333    3.5957    0.3406 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0045    2.1698   -0.8376 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3173    2.7761   -1.8867 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2791    0.8456   -1.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1877    0.0275   -1.1525 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8445   -0.0755   -2.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9974   -0.6254   -3.2451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5403   -2.2979    0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170   -3.1652    1.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399   -4.3050    1.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5006   -5.1732    2.6778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5897   -4.5940    1.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1426   -5.7235    2.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3577   -3.7106    0.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6940   -3.9736    0.7213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908   -2.5720    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -1.6453   -0.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6970   -1.7557   -1.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0509   -2.7943   -2.3793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484   -0.8577   -2.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5703   -0.9757   -3.8717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0960    0.1827   -1.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8133    1.0424   -2.5711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4293    2.0320   -1.9771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0989    2.8245   -2.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3632    2.2240   -0.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0016    3.2574    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9096    3.4162    1.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5621    4.4651    2.0293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    2.5197    2.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706    2.6804    3.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5160    1.4815    1.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871    0.6007    2.1751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1651   -0.3928    1.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750   -1.2166    2.2903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2229   -0.6007    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9811    0.3085   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6220    1.3442    0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533    1.0020   -0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5800    1.6512    1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.9805    2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394    2.6467    1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1623    4.3546    0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970    2.7006   -0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388    3.2728   -2.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304   -1.0098   -0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -0.7707   -2.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6182    0.8955   -3.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1447   -1.4877   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -2.9216    1.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4770   -5.0366    2.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103   -5.9777    2.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -3.3582    0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1277   -2.8961   -3.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1229   -0.3049   -4.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5885    3.9622   -0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1100    5.1206    1.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5405    3.4358    3.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  1  0
  9  7  1  0
  7  8  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 37 38  1  0
 37 39  1  0
 39 45  2  0
 45 44  1  0
 44 43  2  0
 43 41  1  0
 41 42  2  0
 41 40  1  0
  4 12  1  0
 23 15  1  0
 43 24  1  0
 44 29  1  0
 45 33  1  0
 40 39  1  0
 14 56  1  0
 13 54  1  0
 13 55  1  0
 12 53  1  1
  9 51  1  1
 10 52  1  0
  7 49  1  1
  8 50  1  0
  5 47  1  1
  6 48  1  0
  4 46  1  6
 16 57  1  0
 18 58  1  0
 20 59  1  0
 22 60  1  0
 26 61  1  0
 28 62  1  0
 34 63  1  0
 36 64  1  0
 38 65  1  0
M  END


  Mrv1533004151519412D          

 45 50  0  0  0  0            999 V2000
    5.3589    2.6615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5372    2.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629    3.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4104    4.0116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362    4.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2836    5.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1144    4.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6402    5.2885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    3.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9452    3.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412    3.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937    2.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3925    1.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7385    1.1728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0388    2.7623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8441    1.2998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2796    0.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341   -1.1864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6985   -2.3043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8496   -3.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427   -0.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967    0.6031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7124    1.0989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 24 43  1  0  0  0  0
 43 44  2  0  0  0  0
 29 44  1  0  0  0  0
 44 45  1  0  0  0  0
 33 45  1  0  0  0  0
 39 45  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0176980

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(O)C(O)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1C1=C(O)C(O)=C2OC(=O)C3=CC(O)=C(O)C4=C3C2=C1C(=O)O4

> <INCHI_IDENTIFIER>
InChI=1S/C27H20O18/c28-3-8-21(19(36)20(37)27(41)42-8)43-24(38)4-1-6(29)14(31)16(33)9(4)11-13-12-10-5(25(39)44-23(12)18(35)17(11)34)2-7(30)15(32)22(10)45-26(13)40/h1-2,8,19-21,27-37,41H,3H2

> <INCHI_KEY>
KLGPORNWEXMEEM-UHFFFAOYSA-N

> <FORMULA>
C27H20O18

> <MOLECULAR_WEIGHT>
632.439

> <EXACT_MASS>
632.064963804

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
56.950409368815805

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl}benzoate

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
0.6419666296666665

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.051118624274855

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.285019816228574

> <JCHEM_PKA_STRONGEST_BASIC>
-4.393567561804159

> <JCHEM_POLAR_SURFACE_AREA>
310.65999999999997

> <JCHEM_REFRACTIVITY>
141.3739

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl}benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  O   UNK     0      10.003   4.968   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.469   4.831   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.584   6.092   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.233   7.488   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.347   8.748   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.996  10.145   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.814   8.612   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.928   9.872   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.165   7.215   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.631   7.078   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.050   5.955   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.402   4.558   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.333   3.233   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.112   2.189   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.057   2.461   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.827   3.795   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.367   3.795   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.272   5.156   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.137   2.461   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.776   2.426   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.367   1.127   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.722   0.171   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.827   1.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.330  -2.215   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.770  -4.301   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.747  -4.207   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.207  -4.207   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.453  -5.652   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.453  -1.404   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.927   1.126   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.207   1.127   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.747   1.127   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       6.930   2.051   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   15   24                                                  
CONECT   24   23   25   43                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   44                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   45                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   45                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   24   44                                                  
CONECT   44   43   29   45                                                  
CONECT   45   44   33   39                                                  
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
4,5,6-Trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0,.0,]hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}benzoic acid	Generator
4,5,6-Trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}benzoic acid	Generator

Chemical Formula

C₂₇H₂₀O₁₈

Average Mass

632.4390 Da

Monoisotopic Mass

632.06496 Da

IUPAC Name

4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl}benzoate

Traditional Name

4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl}benzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(O)C(O)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1C1=C(O)C(O)=C2OC(=O)C3=CC(O)=C(O)C4=C3C2=C1C(=O)O4

InChI Identifier

InChI=1S/C27H20O18/c28-3-8-21(19(36)20(37)27(41)42-8)43-24(38)4-1-6(29)14(31)16(33)9(4)11-13-12-10-5(25(39)44-23(12)18(35)17(11)34)2-7(30)15(32)22(10)45-26(13)40/h1-2,8,19-21,27-37,41H,3H2

InChI Key

KLGPORNWEXMEEM-UHFFFAOYSA-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
Terminalia chebula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ubiquinols. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methylbenzene-1,4-diol moiety to which an isoprenyl group is attached at ring position 2(or 6).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Ubiquinols

Alternative Parents

Substituents

Ubiquinol skeleton
5-unsubstituted pyrrogallol
M-cresol
O-cresol
P-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Monocyclic benzene moiety
Benzenoid
Polyol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.27	ALOGPS
logP	0.64	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	5.29	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	310.66 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.37 m³·mol⁻¹	ChemAxon
Polarizability	56.95 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14886033

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate (NP0176980)

MOL for NP0176980 (4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate)

3D MOL for NP0176980 (4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate)

3D SDF for NP0176980 (4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate)

3D-SDF for NP0176980 (4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate)

PDB for NP0176980 (4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate)

3D PDB for NP0176980 (4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate)

SMILES for NP0176980 (4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate)

INCHI for NP0176980 (4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate)

Structure for NP0176980 (4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate)

3D Structure for NP0176980 (4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxy-2-{6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl}benzoate)