NP-MRD: Showing NP-Card for 3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside (NP0031048)

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Record Information

Version

2.0

Created at

2021-06-19 22:14:29 UTC

Updated at

2021-06-29 23:59:24 UTC

NP-MRD ID

NP0031048

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside

Provided By

JEOL Database JEOL Logo

Description

[(2R,3S,4S,5R,6S)-6-{4-[3-(3,4-dihydroxyphenyl)propanoyl]-3,5-dihydroxyphenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate 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. 3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside is found in Balanophora harlandii and Balanophora tobiracola. 3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside was first documented in 2005 (Tanaka, T., et al.). Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-6-{4-[3-(3,4-dihydroxyphenyl)propanoyl]-3,5-dihydroxyphenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100143D          

 71 74  0  0  0  0            999 V2000
   -6.2812    0.9411   -1.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5270    0.6200   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3914    1.2848   -0.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1466    2.5190   -1.1173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2143    2.3410   -2.3295 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9106    1.9511   -1.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222    1.9558   -2.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3636    1.5714   -2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8603    2.3329   -1.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6948    1.6548   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473    2.2902    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299    1.6030    1.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801    3.6114    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0428   -2.5403    0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1361   -3.3192    0.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0122    2.6392    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0003    4.2651   -1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8059    0.4269   -5.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0603    0.3654   -5.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8252    0.3207   -2.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6772    1.4579   -3.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
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  5  4  1  0  0  0  0
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  7 47  1  6  0  0  0
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  4 44  1  0  0  0  0
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 12 49  1  0  0  0  0
 27 59  1  0  0  0  0
 22 56  1  0  0  0  0
 24 57  1  0  0  0  0
 38 68  1  0  0  0  0
 40 69  1  0  0  0  0
 42 70  1  0  0  0  0
M  END

     RDKit          3D

 71 74  0  0  0  0  0  0  0  0999 V2000
   -6.2812    0.9411   -1.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5270    0.6200   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3914    1.2848   -0.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1466    2.5190   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143    2.3410   -2.3295 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.9222    1.9558   -2.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
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 41 42  1  0
  5  4  1  0
  7  8  1  0
 43 71  1  0
 36 67  1  0
  7 47  1  6
 33 65  1  1
 34 66  1  0
 31 63  1  6
 32 64  1  0
 29 61  1  1
 30 62  1  0
  4 44  1  0
  4 45  1  0
  5 46  1  6
 19 54  1  0
 25 58  1  0
 20 55  1  0
 10 48  1  0
 28 60  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 12 49  1  0
 27 59  1  0
 22 56  1  0
 24 57  1  0
 38 68  1  0
 40 69  1  0
 42 70  1  0
M  END


  Mrv1652306202100143D          

 71 74  0  0  0  0            999 V2000
   -6.2812    0.9411   -1.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5270    0.6200   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3914    1.2848   -0.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1466    2.5190   -1.1173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2143    2.3410   -2.3295 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9106    1.9511   -1.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222    1.9558   -2.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3636    1.5714   -2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8603    2.3329   -1.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6948    1.6548   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473    2.2902    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299    1.6030    1.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801    3.6114    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0091    4.2734    2.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3117    5.4694    2.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882    3.5407    3.5412 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1786    3.3405    3.7289 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3090    1.9792    3.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1699    0.8713    4.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5739   -0.4020    3.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0769   -0.5690    2.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704   -1.8103    2.0353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021    0.5118    1.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6521    0.2445    0.3231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8679    1.7923    2.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0513    4.3190   -0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    5.6382    0.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5852    3.6844   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3080    0.9415   -4.0069 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4082    1.0054   -5.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7202    1.2334   -4.5124 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1130    0.1975   -5.4275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7217    1.3208   -3.3590 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9844    1.6988   -3.9116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7176   -0.5894    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8101   -0.9482    1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0205   -2.1127    1.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1544   -2.5343    2.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1392   -2.8989    1.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3599   -4.0395    2.3237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0428   -2.5403    0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1361   -3.3192    0.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8410   -1.3939   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0870    3.0018   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6626    3.1814   -0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1269    3.3306   -2.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8438    2.9531   -3.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361    0.6135   -0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0474    0.6895    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626    2.6166    3.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506    4.1923    4.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3926    4.1253    3.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638    3.4466    4.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553    0.9974    5.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4748   -1.2516    4.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746   -1.7128    1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6154    1.0629   -0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0122    2.6392    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2742    6.0152    0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    4.2651   -1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -0.0806   -3.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8059    0.4269   -5.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7282    2.1610   -5.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0603    0.3654   -5.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8252    0.3207   -2.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6772    1.4579   -3.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551   -0.3203    1.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046   -2.0533    2.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6093   -4.0731    2.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0660   -4.0544    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5566   -1.1338   -0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 25  2  0  0  0  0
 37 39  2  0  0  0  0
 25 23  1  0  0  0  0
 39 41  1  0  0  0  0
 23 21  2  0  0  0  0
 35  2  1  0  0  0  0
 21 20  1  0  0  0  0
 20 19  2  0  0  0  0
 43 35  1  0  0  0  0
  2  3  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  2  1  2  0  0  0  0
 11 13  2  0  0  0  0
  7 29  1  0  0  0  0
 13 26  1  0  0  0  0
 29 31  1  0  0  0  0
 26 28  2  0  0  0  0
 28  9  1  0  0  0  0
 31 33  1  0  0  0  0
 13 14  1  0  0  0  0
 33  5  1  0  0  0  0
 14 16  1  0  0  0  0
  5  6  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 33 34  1  0  0  0  0
 26 27  1  0  0  0  0
 31 32  1  0  0  0  0
 14 15  2  0  0  0  0
 29 30  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 35 36  2  0  0  0  0
  9  8  1  0  0  0  0
  4  3  1  0  0  0  0
 41 43  2  0  0  0  0
 37 38  1  0  0  0  0
 19 18  1  0  0  0  0
 39 40  1  0  0  0  0
 36 37  1  0  0  0  0
 41 42  1  0  0  0  0
  5  4  1  0  0  0  0
  7  8  1  0  0  0  0
 43 71  1  0  0  0  0
 36 67  1  0  0  0  0
  7 47  1  6  0  0  0
 33 65  1  1  0  0  0
 34 66  1  0  0  0  0
 31 63  1  6  0  0  0
 32 64  1  0  0  0  0
 29 61  1  1  0  0  0
 30 62  1  0  0  0  0
  4 44  1  0  0  0  0
  4 45  1  0  0  0  0
  5 46  1  6  0  0  0
 19 54  1  0  0  0  0
 25 58  1  0  0  0  0
 20 55  1  0  0  0  0
 10 48  1  0  0  0  0
 28 60  1  0  0  0  0
 16 50  1  0  0  0  0
 16 51  1  0  0  0  0
 17 52  1  0  0  0  0
 17 53  1  0  0  0  0
 12 49  1  0  0  0  0
 27 59  1  0  0  0  0
 22 56  1  0  0  0  0
 24 57  1  0  0  0  0
 38 68  1  0  0  0  0
 40 69  1  0  0  0  0
 42 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031048

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C([H])C(O[H])=C1O[H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])C(O[H])=C(C(=O)C([H])([H])C([H])([H])C3=C([H])C(O[H])=C(O[H])C([H])=C3[H])C(O[H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O15/c29-14-3-1-11(5-16(14)31)2-4-15(30)22-17(32)8-13(9-18(22)33)42-28-26(39)25(38)24(37)21(43-28)10-41-27(40)12-6-19(34)23(36)20(35)7-12/h1,3,5-9,21,24-26,28-29,31-39H,2,4,10H2/t21-,24-,25+,26-,28-/m1/s1

> <INCHI_KEY>
HELQISLFMHRLML-ZKPBLSLZSA-N

> <FORMULA>
C28H28O15

> <MOLECULAR_WEIGHT>
604.517

> <EXACT_MASS>
604.142820202

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
56.71160535287484

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-{4-[3-(3,4-dihydroxyphenyl)propanoyl]-3,5-dihydroxyphenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
2.9085110013333324

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.776303586473631

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.009488139813643

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9540586213537603

> <JCHEM_POLAR_SURFACE_AREA>
264.12999999999994

> <JCHEM_REFRACTIVITY>
143.59730000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{4-[3-(3,4-dihydroxyphenyl)propanoyl]-3,5-dihydroxyphenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 74  0  0  0  0  0  0  0  0999 V2000
   -6.2812    0.9411   -1.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5270    0.6200   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3914    1.2848   -0.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1466    2.5190   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143    2.3410   -2.3295 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9106    1.9511   -1.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222    1.9558   -2.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3636    1.5714   -2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8603    2.3329   -1.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6948    1.6548   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473    2.2902    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299    1.6030    1.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801    3.6114    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0091    4.2734    2.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3117    5.4694    2.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882    3.5407    3.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786    3.3405    3.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3090    1.9792    3.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1699    0.8713    4.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5739   -0.4020    3.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0769   -0.5690    2.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704   -1.8103    2.0353 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8679    1.7923    2.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0513    4.3190   -0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5852    3.6844   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3080    0.9415   -4.0069 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4082    1.0054   -5.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7202    1.2334   -4.5124 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1130    0.1975   -5.4275 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7176   -0.5894    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8101   -0.9482    1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0205   -2.1127    1.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1544   -2.5343    2.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3599   -4.0395    2.3237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0428   -2.5403    0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1361   -3.3192    0.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8410   -1.3939   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0870    3.0018   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6626    3.1814   -0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1269    3.3306   -2.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9361    0.6135   -0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0474    0.6895    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626    2.6166    3.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506    4.1923    4.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3926    4.1253    3.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638    3.4466    4.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553    0.9974    5.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4748   -1.2516    4.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5746   -1.7128    1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6154    1.0629   -0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0122    2.6392    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2742    6.0152    0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    4.2651   -1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -0.0806   -3.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8059    0.4269   -5.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7282    2.1610   -5.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0603    0.3654   -5.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8252    0.3207   -2.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6772    1.4579   -3.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551   -0.3203    1.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6093   -4.0731    2.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0660   -4.0544    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5566   -1.1338   -0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 25  2  0
 37 39  2  0
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 42 70  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  O   UNK     0      -6.281   0.941  -1.649  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.527   0.620  -0.742  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.391   1.285  -0.413  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.147   2.519  -1.117  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.214   2.341  -2.329  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.911   1.951  -1.855  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.922   1.956  -2.910  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.364   1.571  -2.389  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.860   2.333  -1.368  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.695   1.655  -0.473  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.147   2.290   0.686  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.930   1.603   1.568  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.780   3.611   0.946  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.009   4.273   2.250  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.312   5.469   2.240  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.688   3.541   3.541  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.179   3.341   3.729  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.309   1.979   3.281  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.170   0.871   4.137  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.574  -0.402   3.731  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.077  -0.569   2.452  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.470  -1.810   2.035  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.202   0.512   1.586  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.652   0.245   0.323  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.868   1.792   2.006  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.051   4.319  -0.021  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.709   5.638   0.128  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.585   3.684  -1.169  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.308   0.942  -4.007  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.408   1.005  -5.124  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.720   1.233  -4.512  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.113   0.198  -5.428  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.722   1.321  -3.359  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.984   1.699  -3.912  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.718  -0.589   0.103  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.810  -0.948   1.116  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.021  -2.113   1.848  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.154  -2.534   2.818  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.139  -2.899   1.601  0.00  0.00           C+0
HETATM   40  O   UNK     0      -6.360  -4.040   2.324  0.00  0.00           O+0
HETATM   41  C   UNK     0      -7.043  -2.540   0.610  0.00  0.00           C+0
HETATM   42  O   UNK     0      -8.136  -3.319   0.368  0.00  0.00           O+0
HETATM   43  C   UNK     0      -6.841  -1.394  -0.147  0.00  0.00           C+0
HETATM   44  H   UNK     0      -5.087   3.002  -1.408  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.663   3.181  -0.391  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.127   3.331  -2.799  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.844   2.953  -3.362  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.936   0.614  -0.670  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.047   0.690   1.253  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.263   2.617   3.634  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.051   4.192   4.348  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.393   4.125   3.217  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.064   3.447   4.795  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.255   0.997   5.132  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.475  -1.252   4.399  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.575  -1.713   1.064  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.615   1.063  -0.217  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.012   2.639   1.343  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.274   6.015   0.842  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.000   4.265  -1.874  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.248  -0.081  -3.613  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.806   0.427  -5.806  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.728   2.161  -5.099  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.060   0.365  -5.611  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.825   0.321  -2.921  0.00  0.00           H+0
HETATM   66  H   UNK     0      -5.677   1.458  -3.254  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.955  -0.320   1.335  0.00  0.00           H+0
HETATM   68  H   UNK     0      -3.305  -2.053   2.728  0.00  0.00           H+0
HETATM   69  H   UNK     0      -5.609  -4.073   2.953  0.00  0.00           H+0
HETATM   70  H   UNK     0      -8.066  -4.054   1.011  0.00  0.00           H+0
HETATM   71  H   UNK     0      -7.557  -1.134  -0.923  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   35    3    1                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   44   45                                             
CONECT    5   33    6    4   46                                             
CONECT    6    5    7                                                       
CONECT    7   29    6    8   47                                             
CONECT    8    9    7                                                       
CONECT    9   10   28    8                                                  
CONECT   10    9   11   48                                                  
CONECT   11   10   13   12                                                  
CONECT   12   11   49                                                       
CONECT   13   11   26   14                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14                                                            
CONECT   16   14   17   50   51                                             
CONECT   17   16   18   52   53                                             
CONECT   18   25   17   19                                                  
CONECT   19   20   18   54                                                  
CONECT   20   21   19   55                                                  
CONECT   21   23   20   22                                                  
CONECT   22   21   56                                                       
CONECT   23   25   21   24                                                  
CONECT   24   23   57                                                       
CONECT   25   18   23   58                                                  
CONECT   26   13   28   27                                                  
CONECT   27   26   59                                                       
CONECT   28   26    9   60                                                  
CONECT   29    7   31   30   61                                             
CONECT   30   29   62                                                       
CONECT   31   29   33   32   63                                             
CONECT   32   31   64                                                       
CONECT   33   31    5   34   65                                             
CONECT   34   33   66                                                       
CONECT   35    2   43   36                                                  
CONECT   36   35   37   67                                                  
CONECT   37   39   38   36                                                  
CONECT   38   37   68                                                       
CONECT   39   37   41   40                                                  
CONECT   40   39   69                                                       
CONECT   41   39   43   42                                                  
CONECT   42   41   70                                                       
CONECT   43   35   41   71                                                  
CONECT   44    4                                                            
CONECT   45    4                                                            
CONECT   46    5                                                            
CONECT   47    7                                                            
CONECT   48   10                                                            
CONECT   49   12                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   19                                                            
CONECT   55   20                                                            
CONECT   56   22                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   27                                                            
CONECT   60   28                                                            
CONECT   61   29                                                            
CONECT   62   30                                                            
CONECT   63   31                                                            
CONECT   64   32                                                            
CONECT   65   33                                                            
CONECT   66   34                                                            
CONECT   67   36                                                            
CONECT   68   38                                                            
CONECT   69   40                                                            
CONECT   70   42                                                            
CONECT   71   43                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  148    0
END

RDKit          3D

71 74  0  0  0  0  0  0  0  0999 V2000
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   -6.3599   -4.0395    2.3237 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.1361   -3.3192    0.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0870    3.0018   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3046   -2.0533    2.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6093   -4.0731    2.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0660   -4.0544    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5566   -1.1338   -0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 25  2  0
 37 39  2  0
 25 23  1  0
 39 41  1  0
 23 21  2  0
 35  2  1  0
 21 20  1  0
 20 19  2  0
 43 35  1  0
  2  3  1  0
  9 10  2  0
 10 11  1  0
  2  1  2  0
 11 13  2  0
  7 29  1  0
 13 26  1  0
 29 31  1  0
 26 28  2  0
 28  9  1  0
 31 33  1  0
 13 14  1  0
 33  5  1  0
 14 16  1  0
  5  6  1  0
 16 17  1  0
 17 18  1  0
  6  7  1  0
 11 12  1  0
 33 34  1  0
 26 27  1  0
 31 32  1  0
 14 15  2  0
 29 30  1  0
 21 22  1  0
 23 24  1  0
 35 36  2  0
  9  8  1  0
  4  3  1  0
 41 43  2  0
 37 38  1  0
 19 18  1  0
 39 40  1  0
 36 37  1  0
 41 42  1  0
  5  4  1  0
  7  8  1  0
 43 71  1  0
 36 67  1  0
  7 47  1  6
 33 65  1  1
 34 66  1  0
 31 63  1  6
 32 64  1  0
 29 61  1  1
 30 62  1  0
  4 44  1  0
  4 45  1  0
  5 46  1  6
 19 54  1  0
 25 58  1  0
 20 55  1  0
 10 48  1  0
 28 60  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 12 49  1  0
 27 59  1  0
 22 56  1  0
 24 57  1  0
 38 68  1  0
 40 69  1  0
 42 70  1  0
M  END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-6-{4-[3-(3,4-dihydroxyphenyl)propanoyl]-3,5-dihydroxyphenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₈H₂₈O₁₅

Average Mass

604.5170 Da

Monoisotopic Mass

604.14282 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-{4-[3-(3,4-dihydroxyphenyl)propanoyl]-3,5-dihydroxyphenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Traditional Name

[(2R,3S,4S,5R,6S)-6-{4-[3-(3,4-dihydroxyphenyl)propanoyl]-3,5-dihydroxyphenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C([H])C(O[H])=C1O[H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])C(O[H])=C(C(=O)C([H])([H])C([H])([H])C3=C([H])C(O[H])=C(O[H])C([H])=C3[H])C(O[H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C28H28O15/c29-14-3-1-11(5-16(14)31)2-4-15(30)22-17(32)8-13(9-18(22)33)42-28-26(39)25(38)24(37)21(43-28)10-41-27(40)12-6-19(34)23(36)20(35)7-12/h1,3,5-9,21,24-26,28-29,31-39H,2,4,10H2/t21-,24-,25+,26-,28-/m1/s1

InChI Key

HELQISLFMHRLML-ZKPBLSLZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Balanophora harlandii	LOTUS Database	35616633
Balanophora tobiracola	JEOL database	Tanaka, T., et al, Phytochemistry 66, 675 (2005)

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 o-glycoside
2'-hydroxy-dihydrochalcone
Fatty acyl glycoside
Cinnamylphenol
Linear 1,3-diarylpropanoid
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Galloyl ester
Alkyl-phenylketone
Gallic acid or derivatives
Alkyl glycoside
Glycosyl compound
P-hydroxybenzoic acid ester
M-hydroxybenzoic acid ester
Butyrophenone
P-hydroxybenzoic acid alkyl ester
O-glycosyl compound
Benzoate ester
Benzenetriol
Pyrogallol derivative
Phenylketone
Benzoic acid or derivatives
Phenol ether
Resorcinol
Phenoxy compound
Benzoyl
Catechol
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Ketone
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Aldehyde
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	1.61	ALOGPS
logP	2.91	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	264.13 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	143.6 m³·mol⁻¹	ChemAxon
Polarizability	56.71 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	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

10193267

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21580528

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tanaka, T., et al. (2005). Tanaka, T., et al, Phytochemistry 66, 675 (2005) . Phytochem..

Showing NP-Card for 3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside (NP0031048)

MOL for NP0031048 (3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside)

3D MOL for NP0031048 (3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside)

3D SDF for NP0031048 (3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside)

3D-SDF for NP0031048 (3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside)

PDB for NP0031048 (3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside)

3D PDB for NP0031048 (3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside)

SMILES for NP0031048 (3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside)

INCHI for NP0031048 (3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside)

Structure for NP0031048 (3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside)

3D Structure for NP0031048 (3-hydroxyphloretin 4'-O-(6''-O-galloyl)-beta-D-glucoside)