NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one (NP0177180)

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Record Information

Version

2.0

Created at

2022-09-03 14:59:15 UTC

Updated at

2022-09-03 14:59:15 UTC

NP-MRD ID

NP0177180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one

Description

Quercetin 3-beta-l-arabinopyranoside 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, quercetin 3-beta-L-arabinopyranoside is considered to be a flavonoid. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one is found in Amelanchier spicata, Aster koraiensis, Hydrocotyle leucocephala, Hypericum perforatum, Hypericum scabrum, Phoebe formosana, Pilularia globulifera, Dasiphora fruticosa, Quercus suber and Tephrosia vogelii. Based on a literature review very few articles have been published on Quercetin 3-beta-l-arabinopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309032216592D          

 31 34  0  0  1  0            999 V2000
    1.4289   -2.4750    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
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
    0.7145   -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
   -0.7145   -0.4125    0.0000 C   0  0  0  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
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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  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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
  3 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  2 31  1  0  0  0  0
 24 31  1  0  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -0.1088   -2.6052   -1.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210   -1.8812   -0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -0.5294   -0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328   -0.1033   -0.8866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178   -0.1849    0.0639 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3074    1.0609    0.2660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3158    1.0172    1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5279    0.4531    0.5105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6345    0.4507    1.3847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2291   -0.9348    0.0754 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5762   -1.7900    1.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396   -1.1930   -0.3951 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8675   -1.3394   -1.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5075    0.2898   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3963    1.7208    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678    2.3716    0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.7276    1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    4.5216    0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3950    5.9033    0.7394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207    3.9278   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6149    4.6800   -0.8243 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349    2.5408   -0.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7172   -0.2455    0.1373 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124   -1.4859    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3025   -1.8987    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6024   -3.2202    0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8870   -3.6867    0.4893 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6596   -4.0976   -0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633   -3.6986   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5094   -4.6428   -1.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0726   -2.3748   -0.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -0.5514    1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750    0.2905    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725    2.0094    1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7407    1.1109   -0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4154    0.2188    0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9793   -1.1979   -0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8636   -1.7696    1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5353   -2.1789    0.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2230   -0.7562   -2.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1676    1.7787    1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1288    4.1951    1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1268    6.3119    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6276    5.6641   -0.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3268    2.1060   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0383   -1.1913    0.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5795   -3.0543    0.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038   -5.1267   -0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944   -4.6122   -1.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3 14  2  0
 14 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31  2  1  0
  2  1  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
  5 12  1  0
 12 13  1  0
 12 10  1  0
 10 11  1  0
 10  8  1  0
  2  3  1  0
 22 15  1  0
 31 24  1  0
  9 36  1  0
  8 35  1  6
  7 33  1  0
  7 34  1  0
  5 32  1  1
 25 46  1  0
 27 47  1  0
 28 48  1  0
 30 49  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 12 39  1  1
 13 40  1  0
 10 37  1  6
 11 38  1  0
M  END

  Mrv1652309032216592D          

 31 34  0  0  1  0            999 V2000
    1.4289   -2.4750    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
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
    0.7145   -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
   -0.7145   -0.4125    0.0000 C   0  0  0  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
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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  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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
  3 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  2 31  1  0  0  0  0
 24 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0177180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CO[C@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15-,17+,20+/m0/s1

> <INCHI_KEY>
PZZRDJXEMZMZFD-JNEVDQRJSA-N

> <FORMULA>
C20H18O11

> <MOLECULAR_WEIGHT>
434.353

> <EXACT_MASS>
434.0849114

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.34507161156431

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-4H-chromen-4-one

> <JCHEM_LOGP>
0.4854996460000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.872523508792614

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372406805937166

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265985532894106

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
103.313

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+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       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12                                                            
CONECT   14    3   15   23                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
CONECT   23   14   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2   24                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Quercetin 3-b-L-arabinopyranoside	Generator
Quercetin 3-β-L-arabinopyranoside	Generator

Chemical Formula

C₂₀H₁₈O₁₁

Average Mass

434.3530 Da

Monoisotopic Mass

434.08491 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

O[C@H]1CO[C@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15-,17+,20+/m0/s1

InChI Key

PZZRDJXEMZMZFD-JNEVDQRJSA-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
Amelanchier spicata	LOTUS Database	35616633
Aster koraiensis	LOTUS Database	35616633
Hydrocotyle leucocephala	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Hypericum scabrum	LOTUS Database	35616633
Phoebe formosana	LOTUS Database	35616633
Pilularia globulifera	LOTUS Database	35616633
Potentilla fruticosa	LOTUS Database	35616633
Quercus suber	LOTUS Database	35616633
Tephrosia vogelii	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
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen 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	0.49	ChemAxon
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.31 m³·mol⁻¹	ChemAxon
Polarizability	40.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

C00005369

Chemspider ID

4476578

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one (NP0177180)

MOL for NP0177180 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0177180 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0177180 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0177180 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

PDB for NP0177180 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0177180 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

SMILES for NP0177180 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

INCHI for NP0177180 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

Structure for NP0177180 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0177180 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2r,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)