NP-MRD: Showing NP-Card for 2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid (NP0183180)

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Record Information

Version

2.0

Created at

2022-09-03 22:02:29 UTC

Updated at

2022-09-03 22:02:29 UTC

NP-MRD ID

NP0183180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid

Description

4-[(2-O,3-O,4-O,6-O-Tetraacetyl-beta-D-glucopyranosyl)oxy]-2,6-dihydroxybenzoic acid belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. 2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid is found in Phegopteris connectilis. Based on a literature review very few articles have been published on 4-[(2-O,3-O,4-O,6-O-Tetraacetyl-beta-D-glucopyranosyl)oxy]-2,6-dihydroxybenzoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200022D          

 35 36  0  0  1  0            999 V2000
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 10 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
M  END

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
   -3.5977    4.4365   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440    3.4912   -0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628    3.0242   -1.8884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4897    3.1003   -0.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6743    2.2271   -1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2367    0.8345   -1.2799 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2688    0.1794   -2.0297 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130   -0.5798   -1.2877 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2223    0.0491   -0.2458 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5561    0.2032    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -0.3020   -0.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794   -0.1397   -0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8359   -0.6558   -1.4405 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2996    0.5304    0.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7113    0.6969    0.8062 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5693    0.2327    0.0297 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1088    1.3769    1.9359 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3406    1.0387    1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7841    1.7182    2.5145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099    0.8846    1.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355   -1.7963   -0.8510 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6316   -2.3747   -2.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455   -3.5873   -2.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6020   -4.1493   -3.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6866   -4.1883   -1.8307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3967   -1.3760   -0.0604 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4934   -1.7583    1.2648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4888   -2.4304    1.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -2.8135    3.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4271   -2.7233    1.1280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5889    0.1600   -0.0115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9340    0.4493    0.3211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2878    1.1136    1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    1.4051    1.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3230    1.4305    2.2531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2421    4.3879    1.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724    5.4478   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6634    4.2245   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3647    2.1754   -0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456    2.6379   -2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1184    0.9476   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -1.0143   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2726   -0.8465   -1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189   -1.1505   -2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6864    0.9717    2.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1210    2.1026    3.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808    1.2930    1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726   -2.4855   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1349   -3.7675   -4.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6682   -5.2396   -3.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5626   -3.6494   -4.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3228   -1.7278   -0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3882   -2.3978    3.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6290   -3.9250    3.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213   -2.5219    3.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700    0.5771    0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8875    1.4739    2.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2879    0.5129    1.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0450    2.2656    1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 14 18  1  0
 18 19  1  0
 18 20  2  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 26 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 31  6  1  0
 20 10  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  6
  8 42  1  6
 11 43  1  0
 13 44  1  0
 17 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  1
 24 49  1  0
 24 50  1  0
 24 51  1  0
 26 52  1  6
 29 53  1  0
 29 54  1  0
 29 55  1  0
 31 56  1  1
 34 57  1  0
 34 58  1  0
 34 59  1  0
M  END


  Mrv1652309042200022D          

 35 36  0  0  1  0            999 V2000
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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  1  0  0  0
  9 10  1  0  0  0  0
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 11 12  1  0  0  0  0
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 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 10 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0183180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](OC2=CC(O)=C(C(O)=O)C(O)=C2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O14/c1-8(22)30-7-15-17(31-9(2)23)18(32-10(3)24)19(33-11(4)25)21(35-15)34-12-5-13(26)16(20(28)29)14(27)6-12/h5-6,15,17-19,21,26-27H,7H2,1-4H3,(H,28,29)/t15-,17-,18+,19-,21-/m1/s1

> <INCHI_KEY>
KLJIMBOVPMSFMM-PEVLUNPASA-N

> <FORMULA>
C21H24O14

> <MOLECULAR_WEIGHT>
500.409

> <EXACT_MASS>
500.116605453

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.52990202468755

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6-dihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid

> <JCHEM_LOGP>
1.5165663069999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.544400892133972

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.764084177742565

> <JCHEM_PKA_STRONGEST_BASIC>
-4.304215766388083

> <JCHEM_POLAR_SURFACE_AREA>
201.41999999999996

> <JCHEM_REFRACTIVITY>
108.0073

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid

> <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       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   10                                                       
CONECT   21    8   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26    6   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
4-[(2-O,3-O,4-O,6-O-Tetraacetyl-b-D-glucopyranosyl)oxy]-2,6-dihydroxybenzoate	Generator
4-[(2-O,3-O,4-O,6-O-Tetraacetyl-b-D-glucopyranosyl)oxy]-2,6-dihydroxybenzoic acid	Generator
4-[(2-O,3-O,4-O,6-O-Tetraacetyl-beta-D-glucopyranosyl)oxy]-2,6-dihydroxybenzoate	Generator
4-[(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyl)oxy]-2,6-dihydroxybenzoate	Generator
4-[(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyl)oxy]-2,6-dihydroxybenzoic acid	Generator

Chemical Formula

C₂₁H₂₄O₁₄

Average Mass

500.4090 Da

Monoisotopic Mass

500.11661 Da

IUPAC Name

2,6-dihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid

Traditional Name

2,6-dihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](OC2=CC(O)=C(C(O)=O)C(O)=C2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C21H24O14/c1-8(22)30-7-15-17(31-9(2)23)18(32-10(3)24)19(33-11(4)25)21(35-15)34-12-5-13(26)16(20(28)29)14(27)6-12/h5-6,15,17-19,21,26-27H,7H2,1-4H3,(H,28,29)/t15-,17-,18+,19-,21-/m1/s1

InChI Key

KLJIMBOVPMSFMM-PEVLUNPASA-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
Phegopteris connectilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Hydroxybenzoic acid
Salicylic acid or derivatives
Salicylic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Phenoxy compound
Phenol ether
Resorcinol
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Sugar acid
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Vinylogous acid
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.52	ChemAxon
pKa (Strongest Acidic)	1.76	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	201.42 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	108.01 m³·mol⁻¹	ChemAxon
Polarizability	46.53 Å³	ChemAxon
Number of Rings	2	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

100998032

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid (NP0183180)

MOL for NP0183180 (2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid)

3D MOL for NP0183180 (2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid)

3D SDF for NP0183180 (2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid)

3D-SDF for NP0183180 (2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid)

PDB for NP0183180 (2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid)

3D PDB for NP0183180 (2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid)

SMILES for NP0183180 (2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid)

INCHI for NP0183180 (2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid)

Structure for NP0183180 (2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid)

3D Structure for NP0183180 (2,6-dihydroxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoic acid)