NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0148877)

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Record Information

Version

2.0

Created at

2022-09-02 04:41:18 UTC

Updated at

2022-09-02 04:41:18 UTC

NP-MRD ID

NP0148877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Epiafzelechin 3-o-beta-d-glucopyranoside belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Thus, epiafzelechin 3-O-beta-D-glucopyranoside is considered to be a flavonoid. (2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Cassia fistula. Based on a literature review very few articles have been published on Epiafzelechin 3-o-beta-d-glucopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206412D          

 31 34  0  0  1  0            999 V2000
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -0.6313    0.6312    3.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3754   -0.1894    2.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4661    0.6009    1.4618 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9803    1.6176    0.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5879    1.2977   -0.5775 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5820    0.3784   -0.5832 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5936    0.7280   -1.1889 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7450   -0.2309   -2.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525   -1.5553   -1.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138   -2.5630   -2.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170   -2.3774   -4.2078 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -3.8499   -2.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1915   -4.1313   -1.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -5.3733   -1.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228   -3.1098   -0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7559   -1.8232   -0.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7954   -0.8102    0.1858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8293    0.5275   -0.3546 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0391    1.4645    0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375    1.1627    1.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1720    2.0334    2.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5095    3.2393    2.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7504    4.1242    3.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6162    3.5527    1.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3981    2.6711    0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8259    0.8012   -1.3379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8352    1.7395   -1.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200   -0.4992   -0.6727 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2547   -1.4703   -0.9096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227   -0.3242    0.7858 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7501    0.1078    0.9846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.8586    3.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6774   -0.6774    1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036   -0.9162    2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0482    1.0895    2.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3192    2.2585   -1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150    1.7495   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    0.2488   -3.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2678   -0.4065   -2.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3778   -1.4633   -4.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6383   -4.6253   -3.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200   -6.0486   -0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192   -3.3145    0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7039    0.5988   -1.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812    0.2286    1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8835    1.7951    3.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4127    3.8405    4.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1003    4.5021    1.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6896    2.9203    0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668    0.6240   -2.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2477    1.8668   -2.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580   -0.8354   -1.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133   -1.8397   -1.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515   -1.3399    1.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8844    0.5156    1.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
  5 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30  3  1  0
 18  7  1  0
 25 19  1  0
 16  9  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  1
  5 36  1  6
  7 37  1  6
  8 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 18 44  1  6
 20 45  1  0
 21 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  6
 27 51  1  0
 28 52  1  6
 29 53  1  0
 30 54  1  1
 31 55  1  0
M  END


  Mrv1652309022206412D          

 31 34  0  0  1  0            999 V2000
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0148877

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O10/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9/h1-6,15-28H,7-8H2/t15-,16-,17-,18+,19-,20-,21-/m1/s1

> <INCHI_KEY>
XWMNERHJDTUVJN-UGUVDVTISA-N

> <FORMULA>
C21H24O10

> <MOLECULAR_WEIGHT>
436.413

> <EXACT_MASS>
436.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.83777387111097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
0.3278366913333333

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.730403638567623

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.148488323137016

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083556126551

> <JCHEM_POLAR_SURFACE_AREA>
169.29999999999998

> <JCHEM_REFRACTIVITY>
104.4321

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+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       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    7   19                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19                                                       
CONECT   26    5   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    3   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Epiafzelechin 3-O-b-D-glucopyranoside	Generator
Epiafzelechin 3-O-β-D-glucopyranoside	Generator

Chemical Formula

C₂₁H₂₄O₁₀

Average Mass

436.4130 Da

Monoisotopic Mass

436.13695 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H24O10/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9/h1-6,15-28H,7-8H2/t15-,16-,17-,18+,19-,20-,21-/m1/s1

InChI Key

XWMNERHJDTUVJN-UGUVDVTISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cassia fistula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.02	ALOGPS
logP	0.33	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	169.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.43 m³·mol⁻¹	ChemAxon
Polarizability	41.84 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00008833

Chemspider ID

10252039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14015956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0148877)

MOL for NP0148877 ((2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0148877 ((2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0148877 ((2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0148877 ((2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0148877 ((2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0148877 ((2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0148877 ((2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0148877 ((2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0148877 ((2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0148877 ((2r,3r,4s,5s,6r)-2-{[(2r,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)