NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0294363)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 02:52:01 UTC

Updated at

2022-09-10 02:52:01 UTC

NP-MRD ID

NP0294363

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Ent-catechin 7-o-beta-d-glucopyranoside belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. (2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Pseudotsuga menziesii. Based on a literature review very few articles have been published on Ent-catechin 7-o-beta-d-glucopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102204522D          

 32 35  0  0  1  0            999 V2000
   -5.0013   -0.4125    0.0000 O   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
   -3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    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  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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  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 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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
   -2.1434   -1.2375    0.0000 C   0  0  2  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
   -2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  2  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
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 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
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 11 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -7.4228   -0.2903   -2.0479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1481   -0.7657   -1.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5070   -0.1483   -0.6031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2403   -0.6815   -0.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5796   -0.2579    0.6780 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2955    0.1072    0.2960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0885   -0.4243    0.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983   -1.5113    1.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2795   -2.0099    1.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3431   -3.1143    2.5925 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4195   -1.4490    1.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3268   -0.3584    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0947    0.1296    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    0.2116   -0.1529 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6994   -0.1099    0.5568 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8870    0.4688   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8381    1.0980    0.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9772    1.6613    0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1901    1.6067   -1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3347    2.1709   -1.8364 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2435    0.9789   -2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4726    0.9324   -3.4022 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001    0.4144   -1.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518   -1.6231    0.5957 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3098   -2.0674   -0.6672 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -2.0785    1.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2076    0.9138    1.3640 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1486    0.4246    2.2708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    1.9019    0.4802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0512    3.0362    0.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3242    1.3389   -0.8305 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4985    1.9444   -1.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9452   -0.4314   -1.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1249   -1.8606   -1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5154   -0.4695   -2.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1538   -0.2718    0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5284   -1.1305    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603   -1.9924    1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964   -3.5552    2.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038    0.9812   -0.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5631    0.2492    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6739    1.1434    1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7290    2.1570    0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4697    2.1207   -2.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7726    0.4693   -3.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3734   -0.0701   -2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7602   -2.0019    0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -2.9872   -0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6834   -3.1858    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0644   -1.7312    2.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4445    1.4597    1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9285   -0.4823    2.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7858    2.3071    0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2572    3.0335    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5030    1.4518   -1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9919    2.3472   -0.4874 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  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 26  1  0
 26 24  1  0
 24 25  1  0
 24 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
  5 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31  3  1  0
 13  7  1  0
 23 16  1  0
 12 11  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  5 37  1  1
  8 38  1  0
 10 39  1  0
 26 49  1  0
 26 50  1  0
 24 47  1  1
 25 48  1  0
 15 41  1  1
 13 40  1  0
 17 42  1  0
 18 43  1  0
 20 44  1  0
 22 45  1  0
 23 46  1  0
 27 51  1  1
 28 52  1  0
 29 53  1  1
 30 54  1  0
 31 55  1  6
 32 56  1  0
M  END


  Mrv1652309102204522D          

 32 35  0  0  1  0            999 V2000
   -5.0013   -0.4125    0.0000 O   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
   -3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    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  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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  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 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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
   -2.1434   -1.2375    0.0000 C   0  0  2  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
   -2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  2  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
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 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
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 11 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0294363

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=C3C[C@@H](O)[C@H](OC3=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O11/c22-7-16-17(27)18(28)19(29)21(32-16)30-9-4-12(24)10-6-14(26)20(31-15(10)5-9)8-1-2-11(23)13(25)3-8/h1-5,14,16-29H,6-7H2/t14-,16-,17-,18+,19-,20-,21-/m1/s1

> <INCHI_KEY>
VLFIBROLAXKPQK-PSZFZNCLSA-N

> <FORMULA>
C21H24O11

> <MOLECULAR_WEIGHT>
452.412

> <EXACT_MASS>
452.131861593

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.61234477801072

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.47296107800000037

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.703922093275128

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.041107632548306

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343758645

> <JCHEM_POLAR_SURFACE_AREA>
189.52999999999997

> <JCHEM_REFRACTIVITY>
106.14410000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

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

View in JSmol

Synonyms

Value	Source
ent-Catechin 7-O-b-D-glucopyranoside	Generator
ent-Catechin 7-O-β-D-glucopyranoside	Generator

Chemical Formula

C₂₁H₂₄O₁₁

Average Mass

452.4120 Da

Monoisotopic Mass

452.13186 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=C3C[C@@H](O)[C@H](OC3=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H24O11/c22-7-16-17(27)18(28)19(29)21(32-16)30-9-4-12(24)10-6-14(26)20(31-15(10)5-9)8-1-2-11(23)13(25)3-8/h1-5,14,16-29H,6-7H2/t14-,16-,17-,18+,19-,20-,21-/m1/s1

InChI Key

VLFIBROLAXKPQK-PSZFZNCLSA-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
Pseudotsuga menziesii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Catechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Phenolic glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Catechol
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Secondary alcohol
Oxacycle
Polyol
Ether
Organoheterocyclic compound
Acetal
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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	-0.47	ChemAxon
pKa (Strongest Acidic)	9.04	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.14 m³·mol⁻¹	ChemAxon
Polarizability	43.61 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

C00008853

Chemspider ID

10290171

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14282768

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0294363)

MOL for NP0294363 ((2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0294363 ((2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0294363 ((2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0294363 ((2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0294363 ((2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0294363 ((2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0294363 ((2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0294363 ((2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0294363 ((2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0294363 ((2s,3r,4s,5s,6r)-2-{[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2h-1-benzopyran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)