NP-MRD: Showing NP-Card for Litseaefoloside B (NP0044062)

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Record Information

Version

1.0

Created at

2021-11-12 23:47:59 UTC

Updated at

2021-11-26 17:45:00 UTC

NP-MRD ID

NP0044062

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Litseaefoloside B

Description

Litseaefoloside B 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. It was first documented in 2005 (PMID: 16252920). Based on a literature review a significant number of articles have been published on Litseaefoloside B (PMID: 34756847) (PMID: 34758548) (PMID: 34758547) (PMID: 34758546).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100482D          

 33 35  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    3.5724   -5.3625    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  2  0  0  0  0
  2 22  1  0  0  0  0
 23  1  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    7.2533   -0.4496   -3.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1625   -1.3865   -2.1149 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2967   -1.3491   -1.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601   -0.3605   -0.8397 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5248   -0.3922    0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5618    0.6715    0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7998    0.6374    1.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4422    1.7371   -0.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4702    2.7174   -0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    2.0167   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8404    1.0758   -1.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    0.4187   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446    0.6754   -0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591    0.0515   -0.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807   -0.9094   -0.9819 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2546   -0.4183   -1.5422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2973   -0.2857   -0.6713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9638    1.0847   -0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0118    1.1395    0.0964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9713   -0.4867    0.7679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2005   -0.5723    1.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2956   -1.8190    0.9373 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6787   -1.9485    2.1855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -2.1670   -0.1724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8038   -3.2012   -0.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0129    1.6276    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556    1.9001    1.7493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6904    2.8552    2.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2005    2.2811    0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5934   -1.4098    1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5309   -2.4187    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3703   -2.3851   -0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2857   -3.4111   -0.2855 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4133   -0.9349   -4.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3663    0.1969   -3.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1444    0.2293   -3.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883    0.4553   -1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4952    3.5649   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666    3.1377    0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5699    0.8499   -1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172   -0.3256   -1.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298   -1.2305   -1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1074   -1.0226   -0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2058    1.8695   -0.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3308    1.1468   -1.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7983    1.6283   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264    0.3521    1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3246    0.1477    2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1095   -2.6014    0.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3225   -1.8500    2.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3796   -2.4612    0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9582   -2.9432   -1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6953    2.6054    3.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4751    2.8497    3.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6336    3.8828    2.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    3.0266    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9387   -1.4627    2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5815   -3.2255    1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9092   -3.4043   -1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 26  2  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 10  2  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 32  2  0
 32 33  1  0
 32 31  1  0
 31 30  2  0
 10 11  1  0
 11 12  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 12 13  1  0
 30  5  1  0
 24 15  1  0
 28 53  1  0
 28 54  1  0
 28 55  1  0
 29 56  1  0
  9 38  1  0
  9 39  1  0
  4 37  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 33 59  1  0
 31 58  1  0
 30 57  1  0
 11 40  1  0
 12 41  1  0
 15 42  1  6
 17 43  1  6
 18 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  1
 21 48  1  0
 22 49  1  1
 23 50  1  0
 24 51  1  1
 25 52  1  0
M  END


  Mrv1652311132100482D          

 33 35  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    3.5724   -5.3625    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  2  0  0  0  0
  2 22  1  0  0  0  0
 23  1  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044062

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C(=O)OCC1=CC(OC)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O11/c1-29-15-8-12(4-5-13(15)24)21(28)31-10-11-3-6-14(16(7-11)30-2)32-22-20(27)19(26)18(25)17(9-23)33-22/h3-8,17-20,22-27H,9-10H2,1-2H3/t17-,18-,19+,20-,22-/m1/s1

> <INCHI_KEY>
JUCQVFMGZWICMA-OUUKCGNVSA-N

> <FORMULA>
C22H26O11

> <MOLECULAR_WEIGHT>
466.439

> <EXACT_MASS>
466.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.46065195092598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
0.64

> <JCHEM_LOGP>
0.5106546293333336

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200255432477116

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.98948559297739

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
111.72850000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2   23                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   12                                                       
CONECT   21    7   22                                                       
CONECT   22   21    2                                                       
CONECT   23    1   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₁₁

Average Mass

466.4390 Da

Monoisotopic Mass

466.14751 Da

IUPAC Name

(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 4-hydroxy-3-methoxybenzoate

Traditional Name

(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C(=O)OCC1=CC(OC)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

InChI Identifier

InChI=1S/C22H26O11/c1-29-15-8-12(4-5-13(15)24)21(28)31-10-11-3-6-14(16(7-11)30-2)32-22-20(27)19(26)18(25)17(9-23)33-22/h3-8,17-20,22-27H,9-10H2,1-2H3/t17-,18-,19+,20-,22-/m1/s1

InChI Key

JUCQVFMGZWICMA-OUUKCGNVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Ilex litseaefolia

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
Phenolic glycoside
Hexose monosaccharide
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Glycosyl compound
M-methoxybenzoic acid or derivatives
O-glycosyl compound
Benzoate ester
Benzyloxycarbonyl
Methoxyphenol
Benzoic acid or derivatives
Anisole
Phenoxy compound
Benzoyl
Methoxybenzene
Phenol ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Oxane
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Carboxylic acid ester
Ether
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Oxacycle
Organic oxide
Primary alcohol
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
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	0.64	ALOGPS
logP	0.51	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	111.73 m³·mol⁻¹	ChemAxon
Polarizability	46.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9887147

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11712425

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang AL, Ye Q, Li BG, Qi HY, Zhang GL: Phenolic and triterpene glycosides from the stems of Ilex litseaefolia. J Nat Prod. 2005 Oct;68(10):1531-5. doi: 10.1021/np050285z. [PubMed:16252920 ]
McDonagh MS, Wagner J, Ahmed AY, Morasco B, Kansagara D, Chou R: Living Systematic Review on Cannabis and Other Plant-Based Treatments for Chronic Pain - Quarterly Progress Report/Addendum: September 2021. 2020 Dec. [PubMed:34756847 ]
Zhang WB, Yang QB, Wu SF, Lu SH, Cheng M, Sheng Y, Zhang QC, Yang LF, Yu L, Yan SX: [Application of diffusion-weighted magnetic resonance imaging in evaluating the efficacy of radiotherapy and chemotherapy for esophageal cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3427-3430. doi: 10.3760/cma.j.cn112137-20210709-01544. [PubMed:34758548 ]
Sun Y, Wang DM, Yu H, Liu C, Ji TY, Wang S, Wu Y, Liu XY, Jiang YW, Cai LX, Liu QZ: [The screening of potential biological markers of seizure onset zone in focal cortical dysplasia based on bioinformatics analysis]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3422-3426. doi: 10.3760/cma.j.cn112137-20210331-00779. [PubMed:34758547 ]
Dong HH, Cai YS, Liang XN, Miao JB, Chen QS, Gao YD, Li H: [Analysis of incidence and risk factors for postoperative venous thromboembolism in patients with stage a non-small-cell lung cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3417-3421. doi: 10.3760/cma.j.cn112137-20210418-00929. [PubMed:34758546 ]

Showing NP-Card for Litseaefoloside B (NP0044062)

MOL for NP0044062 (Litseaefoloside B)

3D MOL for NP0044062 (Litseaefoloside B)

3D SDF for NP0044062 (Litseaefoloside B)

3D-SDF for NP0044062 (Litseaefoloside B)

PDB for NP0044062 (Litseaefoloside B)

3D PDB for NP0044062 (Litseaefoloside B)

SMILES for NP0044062 (Litseaefoloside B)

INCHI for NP0044062 (Litseaefoloside B)

Structure for NP0044062 (Litseaefoloside B)

3D Structure for NP0044062 (Litseaefoloside B)