NP-MRD: Showing NP-Card for (-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside (NP0033671)

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Record Information

Version

2.0

Created at

2021-06-20 17:37:30 UTC

Updated at

2021-06-30 00:03:36 UTC

NP-MRD ID

NP0033671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside

Provided By

JEOL Database JEOL Logo

Description

(1R,2S)-1-(3,5-Dimethoxy-4-hydroxyphenyl)-2-(beta-D-glucopyranosyloxy)-1,3-propanediol belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside is found in Iodes cirrhosa. (-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside was first documented in 2008 (Gan, M., et al.). Based on a literature review very few articles have been published on (1R,2S)-1-(3,5-Dimethoxy-4-hydroxyphenyl)-2-(beta-D-glucopyranosyloxy)-1,3-propanediol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119373D          

 54 55  0  0  0  0            999 V2000
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   -1.5738   -0.0861   -4.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781   -0.8018   -3.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.7226   -2.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006   -1.5124   -1.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0039   -1.4078   -0.9672 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9446   -1.5756   -2.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1574    2.5442    2.1687 C   0  0  2  0  0  0  0  0  0  0  0  0
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 10 38  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652306202119373D          

 54 55  0  0  0  0            999 V2000
   -0.6727    0.7996   -4.8658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738   -0.0861   -4.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1746    1.5160    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2307    1.5496   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083    3.8510    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182    4.3078    2.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608    5.5977    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566    3.6049    0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018    3.4159    3.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5421    4.7626    3.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228    2.8342    1.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6741    1.7011    3.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    0.7996    2.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0448   -0.5510    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -2.9913   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999   -4.8227   -0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1850   -4.6841    0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173   -3.5023    1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2876   -1.1181   -3.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0  0  0  0
  3 27  2  0  0  0  0
 17 14  1  0  0  0  0
 27 24  1  0  0  0  0
 14 13  1  0  0  0  0
 24 23  2  0  0  0  0
 13 12  1  0  0  0  0
 23  5  1  0  0  0  0
  5  4  2  0  0  0  0
  3  2  1  0  0  0  0
 17 18  1  0  0  0  0
  2  1  1  0  0  0  0
 19 20  1  0  0  0  0
 27 28  1  0  0  0  0
 21 22  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5  6  1  0  0  0  0
 15 16  1  0  0  0  0
  6  7  1  0  0  0  0
 12 21  1  0  0  0  0
  6  8  1  0  0  0  0
  8 11  1  0  0  0  0
 21 19  1  0  0  0  0
  8  9  1  0  0  0  0
  4  3  1  0  0  0  0
  9 10  1  0  0  0  0
 14 15  1  0  0  0  0
 12 11  1  0  0  0  0
 12 39  1  6  0  0  0
 17 44  1  1  0  0  0
 18 45  1  0  0  0  0
 19 46  1  6  0  0  0
 20 47  1  0  0  0  0
 21 48  1  1  0  0  0
 22 49  1  0  0  0  0
 15 41  1  0  0  0  0
 15 42  1  0  0  0  0
 14 40  1  6  0  0  0
 16 43  1  0  0  0  0
  4 32  1  0  0  0  0
 23 50  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 28 54  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
  6 33  1  1  0  0  0
  7 34  1  0  0  0  0
  8 35  1  6  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1OC([H])([H])[H])[C@@]([H])(O[H])[C@@]([H])(O[C@]1([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O11/c1-25-8-3-7(4-9(26-2)13(8)21)12(20)10(5-18)27-17-16(24)15(23)14(22)11(6-19)28-17/h3-4,10-12,14-24H,5-6H2,1-2H3/t10-,11+,12+,14+,15-,16+,17+/m0/s1

> <INCHI_KEY>
AAZJIDQNEUWCEO-LFWJNILXSA-N

> <FORMULA>
C17H26O11

> <MOLECULAR_WEIGHT>
406.384

> <EXACT_MASS>
406.147511657

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.22646091055734

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.48

> <JCHEM_LOGP>
-2.444517334

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.183822352743082

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.300413362903827

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083565317106

> <JCHEM_POLAR_SURFACE_AREA>
178.52999999999997

> <JCHEM_REFRACTIVITY>
92.1195

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
   -0.6727    0.7996   -4.8658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738   -0.0861   -4.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781   -0.8018   -3.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.7226   -2.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006   -1.5124   -1.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0039   -1.4078   -0.9672 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9446   -1.5756   -2.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2303   -0.0633   -0.2341 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6632    0.0055    0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9434    1.2970    0.8752 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890    0.0223    0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371    1.2957    0.9423 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5781    2.2720    1.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0001    3.5895    1.4477 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1289    4.5698    1.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1252    4.5247    0.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1126    3.6141    2.5025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7493    4.8903    2.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1574    2.5442    2.1687 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1220    2.4848    3.2312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5049    1.1762    1.9685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5149    0.2513    1.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3338   -2.3887   -0.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6366   -2.4781   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6159   -3.2918   -0.9532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -4.1097    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9912   -1.6789   -2.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2682   -1.7492   -3.0526 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1721    0.2537   -5.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305    1.5870   -4.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    1.2798   -5.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533   -0.0558   -3.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1645   -2.2342   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174   -2.2973   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    0.7750   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8003   -0.7242    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4099   -0.1822   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1746    1.5160    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2307    1.5496   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083    3.8510    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182    4.3078    2.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608    5.5977    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566    3.6049    0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018    3.4159    3.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5421    4.7626    3.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228    2.8342    1.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6741    1.7011    3.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    0.7996    2.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0448   -0.5510    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -2.9913   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999   -4.8227   -0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1850   -4.6841    0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173   -3.5023    1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2876   -1.1181   -3.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0
  3 27  2  0
 17 14  1  0
 27 24  1  0
 14 13  1  0
 24 23  2  0
 13 12  1  0
 23  5  1  0
  5  4  2  0
  3  2  1  0
 17 18  1  0
  2  1  1  0
 19 20  1  0
 27 28  1  0
 21 22  1  0
 24 25  1  0
 25 26  1  0
  5  6  1  0
 15 16  1  0
  6  7  1  0
 12 21  1  0
  6  8  1  0
  8 11  1  0
 21 19  1  0
  8  9  1  0
  4  3  1  0
  9 10  1  0
 14 15  1  0
 12 11  1  0
 12 39  1  6
 17 44  1  1
 18 45  1  0
 19 46  1  6
 20 47  1  0
 21 48  1  1
 22 49  1  0
 15 41  1  0
 15 42  1  0
 14 40  1  6
 16 43  1  0
  4 32  1  0
 23 50  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 28 54  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
  6 33  1  1
  7 34  1  0
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.673   0.800  -4.866  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.574  -0.086  -4.210  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.078  -0.802  -3.150  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.217  -0.723  -2.643  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.601  -1.512  -1.543  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.004  -1.408  -0.967  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.945  -1.576  -2.027  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.230  -0.063  -0.234  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.663   0.006   0.328  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.943   1.297   0.875  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.289   0.022   0.863  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.637   1.296   0.942  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.578   2.272   1.377  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.000   3.590   1.448  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.129   4.570   1.781  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.125   4.525   0.755  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.113   3.614   2.502  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.749   4.890   2.554  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.157   2.544   2.169  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.122   2.485   3.231  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.505   1.176   1.968  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.515   0.251   1.541  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.334  -2.389  -0.960  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.637  -2.478  -1.455  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.616  -3.292  -0.953  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.292  -4.110   0.161  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.991  -1.679  -2.548  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.268  -1.749  -3.053  0.00  0.00           O+0
HETATM   29  H   UNK     0       0.172   0.254  -5.298  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.331   1.587  -4.186  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.215   1.280  -5.686  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.953  -0.056  -3.083  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.164  -2.234  -0.264  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.617  -2.297  -2.594  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.093   0.775  -0.930  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.800  -0.724   1.133  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.410  -0.182  -0.448  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.175   1.516   1.441  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.231   1.550  -0.046  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.608   3.851   0.456  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.618   4.308   2.725  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.761   5.598   1.846  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.457   3.605   0.719  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.302   3.416   3.499  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.542   4.763   3.114  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.723   2.834   1.274  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.674   1.701   3.031  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.123   0.800   2.925  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.045  -0.551   1.242  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.021  -2.991  -0.112  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.500  -4.823  -0.090  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.185  -4.684   0.426  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.017  -3.502   1.030  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.288  -1.118  -3.796  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3   27    2    4                                                  
CONECT    4    5    3   32                                                  
CONECT    5   23    4    6                                                  
CONECT    6    5    7    8   33                                             
CONECT    7    6   34                                                       
CONECT    8    6   11    9   35                                             
CONECT    9    8   10   36   37                                             
CONECT   10    9   38                                                       
CONECT   11    8   12                                                       
CONECT   12   13   21   11   39                                             
CONECT   13   14   12                                                       
CONECT   14   17   13   15   40                                             
CONECT   15   16   14   41   42                                             
CONECT   16   15   43                                                       
CONECT   17   19   14   18   44                                             
CONECT   18   17   45                                                       
CONECT   19   17   20   21   46                                             
CONECT   20   19   47                                                       
CONECT   21   22   12   19   48                                             
CONECT   22   21   49                                                       
CONECT   23   24    5   50                                                  
CONECT   24   27   23   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   51   52   53                                             
CONECT   27    3   24   28                                                  
CONECT   28   27   54                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    4                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   12                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   26                                                            
CONECT   52   26                                                            
CONECT   53   26                                                            
CONECT   54   28                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  110    0
END

RDKit          3D

54 55  0  0  0  0  0  0  0  0999 V2000
   -0.6727    0.7996   -4.8658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738   -0.0861   -4.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781   -0.8018   -3.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.7226   -2.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006   -1.5124   -1.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0039   -1.4078   -0.9672 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9446   -1.5756   -2.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2303   -0.0633   -0.2341 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6632    0.0055    0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9434    1.2970    0.8752 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890    0.0223    0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371    1.2957    0.9423 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5781    2.2720    1.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0001    3.5895    1.4477 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1289    4.5698    1.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1252    4.5247    0.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1126    3.6141    2.5025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7493    4.8903    2.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1574    2.5442    2.1687 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1220    2.4848    3.2312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5049    1.1762    1.9685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5149    0.2513    1.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3338   -2.3887   -0.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6366   -2.4781   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6159   -3.2918   -0.9532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -4.1097    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9912   -1.6789   -2.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2682   -1.7492   -3.0526 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1721    0.2537   -5.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305    1.5870   -4.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    1.2798   -5.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533   -0.0558   -3.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1645   -2.2342   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174   -2.2973   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    0.7750   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8003   -0.7242    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4099   -0.1822   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1746    1.5160    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2307    1.5496   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083    3.8510    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182    4.3078    2.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608    5.5977    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566    3.6049    0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018    3.4159    3.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5421    4.7626    3.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228    2.8342    1.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6741    1.7011    3.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    0.7996    2.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0448   -0.5510    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -2.9913   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999   -4.8227   -0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1850   -4.6841    0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173   -3.5023    1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2876   -1.1181   -3.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0
  3 27  2  0
 17 14  1  0
 27 24  1  0
 14 13  1  0
 24 23  2  0
 13 12  1  0
 23  5  1  0
  5  4  2  0
  3  2  1  0
 17 18  1  0
  2  1  1  0
 19 20  1  0
 27 28  1  0
 21 22  1  0
 24 25  1  0
 25 26  1  0
  5  6  1  0
 15 16  1  0
  6  7  1  0
 12 21  1  0
  6  8  1  0
  8 11  1  0
 21 19  1  0
  8  9  1  0
  4  3  1  0
  9 10  1  0
 14 15  1  0
 12 11  1  0
 12 39  1  6
 17 44  1  1
 18 45  1  0
 19 46  1  6
 20 47  1  0
 21 48  1  1
 22 49  1  0
 15 41  1  0
 15 42  1  0
 14 40  1  6
 16 43  1  0
  4 32  1  0
 23 50  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 28 54  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
  6 33  1  1
  7 34  1  0
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1R,2S)-1-(3,5-Dimethoxy-4-hydroxyphenyl)-2-(b-D-glucopyranosyloxy)-1,3-propanediol	Generator
(1R,2S)-1-(3,5-Dimethoxy-4-hydroxyphenyl)-2-(β-D-glucopyranosyloxy)-1,3-propanediol	Generator

Chemical Formula

C₁₇H₂₆O₁₁

Average Mass

406.3840 Da

Monoisotopic Mass

406.14751 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1OC([H])([H])[H])[C@@]([H])(O[H])[C@@]([H])(O[C@]1([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C17H26O11/c1-25-8-3-7(4-9(26-2)13(8)21)12(20)10(5-18)27-17-16(24)15(23)14(22)11(6-19)28-17/h3-4,10-12,14-24H,5-6H2,1-2H3/t10-,11+,12+,14+,15-,16+,17+/m0/s1

InChI Key

AAZJIDQNEUWCEO-LFWJNILXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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

Species Name	Source	Reference
Iodes cirrhosa	JEOL database	Gan, M., et al, J. Nat. Prod. 71, 647 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Hydrocarbon derivative
Alcohol
Aromatic alcohol
Primary alcohol
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	-1.5	ALOGPS
logP	-2.4	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	92.12 m³·mol⁻¹	ChemAxon
Polarizability	39.23 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

101865086

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gan, M., et al. (2008). Gan, M., et al, J. Nat. Prod. 71, 647 (2008) . J. Nat. Prod..

Showing NP-Card for (-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside (NP0033671)

MOL for NP0033671 ((-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside)

3D MOL for NP0033671 ((-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside)

3D SDF for NP0033671 ((-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside)

3D-SDF for NP0033671 ((-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside)

PDB for NP0033671 ((-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside)

3D PDB for NP0033671 ((-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside)

SMILES for NP0033671 ((-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside)

INCHI for NP0033671 ((-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside)

Structure for NP0033671 ((-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside)

3D Structure for NP0033671 ((-)-(7R,8S)-syringylglycerol 8-O-beta-D-glucopyranoside)