NP-MRD: Showing NP-Card for Ophioglonol 4'-O-beta-D-glucopyranoside (NP0001561)

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Record Information

Version

2.0

Created at

2020-09-21 21:51:00 UTC

Updated at

2021-08-10 02:55:15 UTC

NP-MRD ID

NP0001561

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ophioglonol 4'-O-beta-D-glucopyranoside

Description

Ophioglonol 4'-O-beta-D-glucopyranoside belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Ophioglonol 4'-O-beta-D-glucopyranoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Ophioglonol 4'-O-beta-D-glucopyranoside was first documented in 2005 (PMID: 15787440). Based on a literature review a small amount of articles have been published on ophioglonol 4'-O-beta-D-glucopyranoside.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309212023512D          

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M  END

NP0001561
     RDKit          3D

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M  END


  Mrv1652309212023512D          

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    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 H   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
    4.2868   -5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6571    0.7372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    0.7372    0.0000 H   0  0  0  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
    5.7158   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  2  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
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 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
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  6  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  1  0  0  0
 38 39  1  0  0  0  0
 36 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  6  0  0  0
 42 43  1  0  0  0  0
 40 44  1  0  0  0  0
 26 44  1  0  0  0  0
 44 45  1  6  0  0  0
 44 46  1  6  0  0  0
 46 47  1  0  0  0  0
 24 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
 18 50  1  0  0  0  0
 50 51  1  0  0  0  0
 12 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 52 55  1  0  0  0  0
 55 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001561

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C(=C(OC2=C1[H])C1=C([H])C(O[H])=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])C([H])=C1[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O12/c23-6-10-17(28)16-12(27)4-9(25)5-14(16)32-21(10)8-1-2-13(11(26)3-8)33-22-20(31)19(30)18(29)15(7-24)34-22/h1-5,15,18-20,22-27,29-31H,6-7H2/t15-,18-,19+,20-,22-/m1/s1

> <INCHI_KEY>
XTPXAOSAGWJNDB-VQIXPAPJSA-N

> <FORMULA>
C22H22O12

> <MOLECULAR_WEIGHT>
478.406

> <EXACT_MASS>
478.111126148

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
46.12270893160411

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(hydroxymethyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
0.14

> <JCHEM_LOGP>
-0.7501649486666664

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.105574335340718

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.525418612426447

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8668099680165477

> <JCHEM_POLAR_SURFACE_AREA>
206.6

> <JCHEM_REFRACTIVITY>
113.17100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(hydroxymethyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001561
     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -6.1779    2.2242    0.1254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3757    1.2654    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816    1.5271    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6176    2.9598    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016    3.2466    0.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1039    0.5014    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6476    0.6127    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8346   -0.0845   -0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5369   -0.1435   -0.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1993    0.4866    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5749    0.4413    0.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5367   -0.1620   -0.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2963   -1.1234    0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4129   -1.3632   -0.2457 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0416   -2.6493    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0737   -3.6447    0.1510 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4496   -0.2673   -0.0629 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1900   -0.0552   -1.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6562    1.0191    0.1941 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3274    1.1575    1.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296    0.9434   -0.6897 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7824    0.7039   -1.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4021    1.1711    1.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369    1.8151    2.4484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9812    1.2304    1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914   -0.7262   -0.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8485   -1.0161   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2887   -2.3241   -0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6187   -2.6500   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0176   -3.9859   -0.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5505   -1.6387   -0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1444   -0.3405   -0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0462    0.7163   -0.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7923   -0.0088   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881    3.4557   -0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762    3.4269    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808    3.6277   -0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3548   -0.5839   -1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286   -0.7042   -1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1078   -0.6801   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1382   -1.5027   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9890   -2.8922   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1798   -2.4811    1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419   -3.9033   -0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0939   -0.4334    0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7807    0.7227   -1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2680    1.8747   -0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133    1.4523    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8954    1.9214   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9085    1.5152   -2.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5857    2.3414    3.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5638    1.7420    2.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5718   -3.1320   -0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0933   -4.3431   -1.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5925   -1.8937   -0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0362    0.6309   -0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10 23  1  0
 23 24  1  0
 23 25  2  0
  6 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 34  2  1  0
 25  7  1  0
 34 27  1  0
 21 12  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  6
 14 41  1  6
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 19 47  1  6
 20 48  1  0
 21 49  1  6
 22 50  1  0
 24 51  1  0
 25 52  1  0
 28 53  1  0
 30 54  1  0
 31 55  1  0
 33 56  1  0
M  END

HEADER    PROTEIN                                 21-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-SEP-20         0                                  
HETATM    1  H   UNK     0      -1.334  -2.310   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0       4.001   2.310   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       2.667  -4.620   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       8.002  -1.540   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      13.337  -3.080   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      10.669  -6.160   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      13.337 -10.780   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      14.938 -11.527   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      15.850 -11.000   0.000  0.00  0.00           H+0
HETATM   34  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   35  H   UNK     0      16.832  -7.941   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0      10.669 -10.780   0.000  0.00  0.00           H+0
HETATM   38  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   39  H   UNK     0      12.003 -13.090   0.000  0.00  0.00           H+0
HETATM   40  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   41  H   UNK     0       9.336  -8.470   0.000  0.00  0.00           H+0
HETATM   42  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   43  H   UNK     0       8.002 -10.780   0.000  0.00  0.00           H+0
HETATM   44  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   45  H   UNK     0      12.003  -8.470   0.000  0.00  0.00           H+0
HETATM   46  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   47  H   UNK     0       7.796  -6.930   0.000  0.00  0.00           H+0
HETATM   48  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   49  H   UNK     0       8.002  -6.160   0.000  0.00  0.00           H+0
HETATM   50  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   51  H   UNK     0       6.462  -4.620   0.000  0.00  0.00           H+0
HETATM   52  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   53  H   UNK     0       8.693   1.376   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       7.311   1.376   0.000  0.00  0.00           H+0
HETATM   55  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   56  H   UNK     0      10.669  -0.000   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   52                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15    3   17                                                  
CONECT   17   16                                                            
CONECT   18   13   19   50                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   48                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28   44                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31   36                                             
CONECT   30   29                                                            
CONECT   31   29   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35                                                       
CONECT   35   34                                                            
CONECT   36   29   37   38   40                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   36   41   42   44                                             
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42                                                            
CONECT   44   40   26   45   46                                             
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46                                                            
CONECT   48   24   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   18   51                                                  
CONECT   51   50                                                            
CONECT   52   12   53   54   55                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   52   56                                                       
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  118    0
END

COMPND    NP0001561
HETATM    1  O1  UNL     1      -6.178   2.224   0.125  1.00  0.00           O  
HETATM    2  C1  UNL     1      -5.376   1.265   0.053  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.982   1.527   0.192  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.618   2.960   0.298  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.302   3.247   0.325  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.104   0.501   0.124  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.648   0.613   0.259  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.835  -0.084  -0.650  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.537  -0.143  -0.530  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.199   0.487   0.503  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.575   0.441   0.641  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.537  -0.162  -0.105  1.00  0.00           C  
HETATM   13  O4  UNL     1       4.296  -1.123   0.557  1.00  0.00           O  
HETATM   14  C10 UNL     1       5.413  -1.363  -0.246  1.00  0.00           C  
HETATM   15  C11 UNL     1       6.042  -2.649   0.277  1.00  0.00           C  
HETATM   16  O5  UNL     1       5.074  -3.645   0.151  1.00  0.00           O  
HETATM   17  C12 UNL     1       6.450  -0.267  -0.063  1.00  0.00           C  
HETATM   18  O6  UNL     1       7.190  -0.055  -1.214  1.00  0.00           O  
HETATM   19  C13 UNL     1       5.656   1.019   0.194  1.00  0.00           C  
HETATM   20  O7  UNL     1       5.327   1.158   1.521  1.00  0.00           O  
HETATM   21  C14 UNL     1       4.430   0.943  -0.690  1.00  0.00           C  
HETATM   22  O8  UNL     1       4.782   0.704  -1.997  1.00  0.00           O  
HETATM   23  C15 UNL     1       0.402   1.171   1.398  1.00  0.00           C  
HETATM   24  O9  UNL     1       1.037   1.815   2.448  1.00  0.00           O  
HETATM   25  C16 UNL     1      -0.981   1.230   1.279  1.00  0.00           C  
HETATM   26  O10 UNL     1      -3.591  -0.726  -0.085  1.00  0.00           O  
HETATM   27  C17 UNL     1      -4.848  -1.016  -0.223  1.00  0.00           C  
HETATM   28  C18 UNL     1      -5.289  -2.324  -0.439  1.00  0.00           C  
HETATM   29  C19 UNL     1      -6.619  -2.650  -0.587  1.00  0.00           C  
HETATM   30  O11 UNL     1      -7.018  -3.986  -0.804  1.00  0.00           O  
HETATM   31  C20 UNL     1      -7.550  -1.639  -0.517  1.00  0.00           C  
HETATM   32  C21 UNL     1      -7.144  -0.341  -0.304  1.00  0.00           C  
HETATM   33  O12 UNL     1      -8.046   0.716  -0.225  1.00  0.00           O  
HETATM   34  C22 UNL     1      -5.792  -0.009  -0.154  1.00  0.00           C  
HETATM   35  H1  UNL     1      -4.088   3.456  -0.600  1.00  0.00           H  
HETATM   36  H2  UNL     1      -4.176   3.427   1.178  1.00  0.00           H  
HETATM   37  H3  UNL     1      -1.981   3.628  -0.549  1.00  0.00           H  
HETATM   38  H4  UNL     1      -1.355  -0.584  -1.468  1.00  0.00           H  
HETATM   39  H5  UNL     1       1.129  -0.704  -1.270  1.00  0.00           H  
HETATM   40  H6  UNL     1       3.108  -0.680  -0.983  1.00  0.00           H  
HETATM   41  H7  UNL     1       5.138  -1.503  -1.318  1.00  0.00           H  
HETATM   42  H8  UNL     1       6.989  -2.892  -0.205  1.00  0.00           H  
HETATM   43  H9  UNL     1       6.180  -2.481   1.380  1.00  0.00           H  
HETATM   44  H10 UNL     1       4.942  -3.903  -0.779  1.00  0.00           H  
HETATM   45  H11 UNL     1       7.094  -0.433   0.798  1.00  0.00           H  
HETATM   46  H12 UNL     1       7.781   0.723  -1.024  1.00  0.00           H  
HETATM   47  H13 UNL     1       6.268   1.875  -0.178  1.00  0.00           H  
HETATM   48  H14 UNL     1       4.413   1.452   1.699  1.00  0.00           H  
HETATM   49  H15 UNL     1       3.895   1.921  -0.652  1.00  0.00           H  
HETATM   50  H16 UNL     1       4.909   1.515  -2.526  1.00  0.00           H  
HETATM   51  H17 UNL     1       0.586   2.341   3.161  1.00  0.00           H  
HETATM   52  H18 UNL     1      -1.564   1.742   2.067  1.00  0.00           H  
HETATM   53  H19 UNL     1      -4.572  -3.132  -0.497  1.00  0.00           H  
HETATM   54  H20 UNL     1      -7.093  -4.343  -1.767  1.00  0.00           H  
HETATM   55  H21 UNL     1      -8.593  -1.894  -0.632  1.00  0.00           H  
HETATM   56  H22 UNL     1      -9.036   0.631  -0.313  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   34
CONECT    3    4    6    6
CONECT    4    5   35   36
CONECT    5   37
CONECT    6    7   26
CONECT    7    8    8   25
CONECT    8    9   38
CONECT    9   10   10   39
CONECT   10   11   23
CONECT   11   12
CONECT   12   13   21   40
CONECT   13   14
CONECT   14   15   17   41
CONECT   15   16   42   43
CONECT   16   44
CONECT   17   18   19   45
CONECT   18   46
CONECT   19   20   21   47
CONECT   20   48
CONECT   21   22   49
CONECT   22   50
CONECT   23   24   25   25
CONECT   24   51
CONECT   25   52
CONECT   26   27
CONECT   27   28   28   34
CONECT   28   29   53
CONECT   29   30   31   31
CONECT   30   54
CONECT   31   32   55
CONECT   32   33   34   34
CONECT   33   56
END

NP0001561
     RDKit          3D

56 59  0  0  0  0  0  0  0  0999 V2000
   -6.1779    2.2242    0.1254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3757    1.2654    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816    1.5271    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6176    2.9598    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016    3.2466    0.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1039    0.5014    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6476    0.6127    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8346   -0.0845   -0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5369   -0.1435   -0.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1993    0.4866    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5749    0.4413    0.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5367   -0.1620   -0.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2963   -1.1234    0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4129   -1.3632   -0.2457 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0416   -2.6493    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0737   -3.6447    0.1510 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4496   -0.2673   -0.0629 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1900   -0.0552   -1.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6562    1.0191    0.1941 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3274    1.1575    1.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296    0.9434   -0.6897 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7824    0.7039   -1.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4021    1.1711    1.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369    1.8151    2.4484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9812    1.2304    1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914   -0.7262   -0.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8485   -1.0161   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2887   -2.3241   -0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6187   -2.6500   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0176   -3.9859   -0.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5505   -1.6387   -0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1444   -0.3405   -0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0462    0.7163   -0.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7923   -0.0088   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881    3.4557   -0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762    3.4269    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808    3.6277   -0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3548   -0.5839   -1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286   -0.7042   -1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1078   -0.6801   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1382   -1.5027   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9890   -2.8922   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1798   -2.4811    1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419   -3.9033   -0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0939   -0.4334    0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7807    0.7227   -1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2680    1.8747   -0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133    1.4523    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8954    1.9214   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9085    1.5152   -2.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5857    2.3414    3.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5638    1.7420    2.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5718   -3.1320   -0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0933   -4.3431   -1.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5925   -1.8937   -0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0362    0.6309   -0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10 23  1  0
 23 24  1  0
 23 25  2  0
  6 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 34  2  1  0
 25  7  1  0
 34 27  1  0
 21 12  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  6
 14 41  1  6
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 19 47  1  6
 20 48  1  0
 21 49  1  6
 22 50  1  0
 24 51  1  0
 25 52  1  0
 28 53  1  0
 30 54  1  0
 31 55  1  0
 33 56  1  0
M  END

View in JSmol

Synonyms

Value	Source
Ophioglonol 4'-O-b-D-glucopyranoside	Generator
Ophioglonol 4'-O-β-D-glucopyranoside	Generator

Chemical Formula

C₂₂H₂₂O₁₂

Average Mass

478.4060 Da

Monoisotopic Mass

478.11113 Da

IUPAC Name

5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(hydroxymethyl)-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(hydroxymethyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(=O)C(=C(OC2=C1[H])C1=C([H])C(O[H])=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])C([H])=C1[H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C22H22O12/c23-6-10-17(28)16-12(27)4-9(25)5-14(16)32-21(10)8-1-2-13(11(26)3-8)33-22-20(31)19(30)18(29)15(7-24)34-22/h1-5,15,18-20,22-27,29-31H,6-7H2/t15-,18-,19+,20-,22-/m1/s1

InChI Key

XTPXAOSAGWJNDB-VQIXPAPJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500MHz, H₂O, simulated)	mb1@ualberta.ca	Not Available	Not Available	2021-03-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500Mz, DMSO, simulated)	rgf8b@missouri.edu	Not Available	Not Available	2020-09-21	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Ophioglossum petiolatum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid-4p-o-glycoside
Flavonoid o-glycoside
3'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:67935 )
monosaccharide derivative (CHEBI:67935 )
hydroxy homoflavonoid (CHEBI:67935 )
homoflavonoid glycoside (CHEBI:67935 )

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	0.14	ALOGPS
logP	-0.75	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.53	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.17 m³·mol⁻¹	ChemAxon
Polarizability	46.12 Å³	ChemAxon
Number of Rings	4	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

C00042808

Chemspider ID

26348377

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

67935

Good Scents ID

Not Available

References

General References

Lin YL, Shen CC, Huang YJ, Chang YY: Homoflavonoids from Ophioglossum petiolatum. J Nat Prod. 2005 Mar;68(3):381-4. doi: 10.1021/np0401819. [PubMed:15787440 ]

Showing NP-Card for Ophioglonol 4'-O-beta-D-glucopyranoside (NP0001561)

MOL for NP0001561 (Ophioglonol 4'-O-beta-D-glucopyranoside)

3D MOL for NP0001561 (Ophioglonol 4'-O-beta-D-glucopyranoside)

3D SDF for NP0001561 (Ophioglonol 4'-O-beta-D-glucopyranoside)

3D-SDF for NP0001561 (Ophioglonol 4'-O-beta-D-glucopyranoside)

PDB for NP0001561 (Ophioglonol 4'-O-beta-D-glucopyranoside)

3D PDB for NP0001561 (Ophioglonol 4'-O-beta-D-glucopyranoside)

SMILES for NP0001561 (Ophioglonol 4'-O-beta-D-glucopyranoside)

INCHI for NP0001561 (Ophioglonol 4'-O-beta-D-glucopyranoside)

Structure for NP0001561 (Ophioglonol 4'-O-beta-D-glucopyranoside)

3D Structure for NP0001561 (Ophioglonol 4'-O-beta-D-glucopyranoside)