NP-MRD: Showing NP-Card for (2r,3s,4r,5r,6s)-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 (NP0193540)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 11:00:48 UTC

Updated at

2022-09-04 11:00:49 UTC

NP-MRD ID

NP0193540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,5r,6s)-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

(2R,3S,4R,5R,6S)-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 hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. (2r,3s,4r,5r,6s)-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. Based on a literature review very few articles have been published on (2R,3S,4R,5R,6S)-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.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042213002D          

 45 50  0  0  1  0            999 V2000
    2.7219    1.1671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732    1.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049    2.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2860    3.1766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1102    3.2125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5534    2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724    1.7849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4912    3.9443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0480    4.6401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4290    5.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237    4.6042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7805    5.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8427    3.8724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0185    3.8365    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
    5.9926    2.7741    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
    6.8163    1.2525    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
    6.2512    0.0545    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
    5.5355   -1.2057    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
    4.7014   -2.3049    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
    1.8471   -3.0297    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
   -0.2451   -0.7561    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
    0.5010    0.6106    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
    3.7367    1.0776    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  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  6  0  0  0
  2 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
 39 45  2  0  0  0  0
 33 45  1  0  0  0  0
M  END

     RDKit          3D

 65 70  0  0  0  0  0  0  0  0999 V2000
   -0.3037   -0.7771   -0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9300   -0.1447   -1.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885   -0.0334   -0.9047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0616   -0.6004    0.1638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1352   -1.5138   -0.3815 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2874   -2.7628    0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0054   -3.2927    0.6513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3224   -0.8800   -0.6504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0062   -0.4287    0.4505 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9653    0.4994   -0.0192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0787    0.2067    1.4385 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6712    1.4282    1.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7458    0.5712    0.8357 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9477    1.1675    1.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2413    0.4784   -2.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9279    1.1714   -3.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597    1.7461   -4.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9475    2.4573   -5.1724 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1163    1.6507   -4.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7359    2.2544   -5.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040    0.9597   -3.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1947    0.8450   -3.4403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    0.3818   -2.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120   -0.3408   -1.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302   -1.6849   -1.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334   -2.3738   -2.5600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8772   -2.3642   -0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1038   -3.7198   -0.6431 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3868   -1.7220    0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0910   -2.3370    1.5662 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5773   -1.7177    2.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2506   -2.3487    3.5015 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3877   -0.3702    2.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8921    0.2943    3.9675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724    1.6418    4.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1635    2.3388    5.2454 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324    2.3026    3.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7073    3.6566    3.3416 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4249    1.6423    2.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7202    2.2589    1.1266 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323    1.6565    0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5582    2.2832   -0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4139    0.3103   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585   -0.3723    0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6536    0.2942    1.8959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3855   -1.1306    0.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7413   -1.8775   -1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9597   -3.4884   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7041   -2.5698    1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060   -3.8587   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6311   -1.2423    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1791    1.1676    0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9662   -0.3735    2.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2247    1.3212    2.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9643    1.3742    0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903    0.4942    2.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011    1.2588   -3.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9518    2.5348   -5.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7118    2.2444   -5.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7488    1.2267   -4.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323   -3.3625   -2.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6401   -4.2124    0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4632   -0.2445    4.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6943    1.8863    5.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1699    4.1400    2.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13  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  5  1  0
 23 15  1  0
 43 24  1  0
 44 29  1  0
 45 33  1  0
 40 39  1  0
  7 50  1  0
  6 48  1  0
  6 49  1  0
  5 47  1  6
  9 51  1  1
 10 52  1  0
 11 53  1  1
 12 54  1  0
 13 55  1  6
 14 56  1  0
  4 46  1  1
 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


  Mrv1652309042213002D          

 45 50  0  0  1  0            999 V2000
    2.7219    1.1671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732    1.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049    2.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2860    3.1766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1102    3.2125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5534    2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724    1.7849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4912    3.9443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0480    4.6401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4290    5.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237    4.6042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7805    5.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8427    3.8724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0185    3.8365    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
    5.9926    2.7741    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
    6.8163    1.2525    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
    6.2512    0.0545    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
    5.5355   -1.2057    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
    4.7014   -2.3049    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
    1.8471   -3.0297    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
   -0.2451   -0.7561    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
    0.5010    0.6106    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
    3.7367    1.0776    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  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  6  0  0  0
  2 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
 39 45  2  0  0  0  0
 33 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1OC(=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/t8-,19-,20-,21-,27+/m1/s1

> <INCHI_KEY>
KLGPORNWEXMEEM-MZMJHEIMSA-N

> <FORMULA>
C27H20O18

> <MOLECULAR_WEIGHT>
632.439

> <EXACT_MASS>
632.064963804

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
56.62174458395107

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6S)-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^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl}benzoate

> <JCHEM_LOGP>
0.6419666296666665

> <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>
141.37389999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6S)-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^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl}benzoate

> <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  O   UNK     0       5.081   2.179   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.297   3.192   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.423   4.564   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.134   5.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.672   5.997   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.500   4.698   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.788   3.332   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.384   7.363   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.556   8.661   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.267  10.027   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.018   8.594   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.190   9.893   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.306   7.229   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.768   7.161   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      11.186   5.178   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      12.724   2.338   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      11.669   0.102   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      10.333  -2.251   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       8.776  -4.303   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       3.448  -5.656   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      -0.458  -1.411   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       0.935   1.140   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       6.975   2.011   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   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    4   14                                                  
CONECT   14   13                                                            
CONECT   15    2   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   39   33                                                  
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S,4R,5R,6S)-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

Chemical Formula

C₂₇H₂₀O₁₈

Average Mass

632.4390 Da

Monoisotopic Mass

632.06496 Da

IUPAC Name

(2R,3S,4R,5R,6S)-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^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl}benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1OC(=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/t8-,19-,20-,21-,27+/m1/s1

InChI Key

KLGPORNWEXMEEM-MZMJHEIMSA-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 hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Ellagic_acid
Biphenol
7,8-dihydroxycoumarin
Galloyl ester
Hexose monosaccharide
Gallic acid or derivatives
P-hydroxybenzoic acid ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
Coumarin
Isocoumarin
Benzoate ester
Benzopyran
1-benzopyran
2-benzopyran
Pyrogallol derivative
Benzoic acid or derivatives
Benzenetriol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Lactone
Hemiacetal
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen 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
logP	0.64	ChemAxon
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	56.62 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

162950715

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4r,5r,6s)-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 (NP0193540)

MOL for NP0193540 ((2r,3s,4r,5r,6s)-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 NP0193540 ((2r,3s,4r,5r,6s)-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 NP0193540 ((2r,3s,4r,5r,6s)-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 NP0193540 ((2r,3s,4r,5r,6s)-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 NP0193540 ((2r,3s,4r,5r,6s)-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 NP0193540 ((2r,3s,4r,5r,6s)-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 NP0193540 ((2r,3s,4r,5r,6s)-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 NP0193540 ((2r,3s,4r,5r,6s)-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 NP0193540 ((2r,3s,4r,5r,6s)-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 NP0193540 ((2r,3s,4r,5r,6s)-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)